Product Name

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  • Name

    Caffeine

  • EINECS 200-362-1
  • CAS No. 58-08-2
  • Article Data142
  • CAS DataBase
  • Density 1.45 g/cm3
  • Solubility 20 g/L (20 °C) in water
  • Melting Point 234-236.5 °C(lit.)
  • Formula C8H10N4O2
  • Boiling Point 416.789 °C at 760 mmHg
  • Molecular Weight 194.193
  • Flash Point 205.867 °C
  • Transport Information UN 1544 6.1/PG 3
  • Appearance white to light yellow crystal powder
  • Safety 16-36/37-45
  • Risk Codes 22-25
  • Molecular Structure Molecular Structure of 58-08-2 (Caffeine)
  • Hazard Symbols HarmfulXn, ToxicT
  • Synonyms 1H-Purine-2,6-dione,3,7-dihydro-1,3,7-trimethyl-;1,3,7-Trimethyl-2,6-dioxopurine;1,3,7-Trimethylxanthine;3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione;7-Methyltheophylline;Alert-Pep;Asia migrine;DHCplus;Durvitan;Guaranine;Koffein;Mateina;Methyltheobromine;Midron extra;Miudol;Phensal;Refresh'n;SK 65 Compound;Shape Plus;StayAlert;Theine;
  • PSA 61.82000
  • LogP -1.02930

Synthetic route

methyl bromide
74-83-9

methyl bromide

xanthin
69-89-6

xanthin

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)room temp. 12h 2)reflux 3h;100%
2,6-dimethoxy-7,9-dimethylpurinium iodide

2,6-dimethoxy-7,9-dimethylpurinium iodide

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In xylene at 140℃; for 0.75h; Rearrangement;100%
theophylline sodium salt
3485-82-3

theophylline sodium salt

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; ethylene glycol at 135℃; for 4h; Autoclave; Green chemistry;98.4%
With PEG 400 In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 12h; Solvent; Concentration; Temperature; Reagent/catalyst;94.9%
With NaY (Y-type sodium zeolite catalyst); turkey red oil In water for 5h; Reflux;
methyl bromide
74-83-9

methyl bromide

theophylline
58-55-9

theophylline

A

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

B

3-benzyladenine
7280-81-1

3-benzyladenine

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h;A 98%
B n/a
...Expand
Methyl formate
107-31-3

Methyl formate

1,3-Dimethylxanthine potassium salt
57533-87-6

1,3-Dimethylxanthine potassium salt

A

theophylline
58-55-9

theophylline

B

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In methanolA 97.5%
B n/a
...Expand
methanol
67-56-1

methanol

1,3-Dimethylxanthine potassium salt
57533-87-6

1,3-Dimethylxanthine potassium salt

A

Methyl formate
107-31-3

Methyl formate

B

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With carbon monoxide at 140℃; under 37503 Torr; for 20h;A n/a
B 97%
...Expand
theophylline
58-55-9

theophylline

methyl iodide
74-88-4

methyl iodide

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide for 0.75h;95%
With sodium hydride In dimethyl sulfoxide at 20℃; for 24h; Reagent/catalyst;90%
methyl bromide
74-83-9

methyl bromide

theobromine /
83-67-0

theobromine /

A

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

B

3-benzyladenine
7280-81-1

3-benzyladenine

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h;A 94%
B n/a
...Expand
3-methylxanthine
1076-22-8

3-methylxanthine

dimethyl sulfate
77-78-1

dimethyl sulfate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With tetramethyl ammoniumhydroxide; potassium carbonate In methanol; water at 65 - 70℃;92.5%
theobromine /
83-67-0

theobromine /

dimethyl sulfate
77-78-1

dimethyl sulfate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
potassium fluoride on basic alumina In acetonitrile for 24h; Ambient temperature;92%
With sodium hydroxide
theophylline
58-55-9

theophylline

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With cetyltrimethylammonium bromide; N-ethyl-N,N-diisopropylamine In toluene at 140℃; for 9h; Solvent; Concentration; Reagent/catalyst; Temperature;90.7%
With 18-crown-6 ether In N,N-dimethyl-formamide at 90℃; for 12h;67%
With DABCO-NaY (1:1 DABCO Y-type sodium zeolite catalyst); turkey red oil In water for 5h; Reagent/catalyst; Reflux;
theophylline
58-55-9

theophylline

methyl iodide
74-88-4

methyl iodide

A

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

B

3-benzyladenine
7280-81-1

3-benzyladenine

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h;A 90%
B n/a
...Expand
theophylline
58-55-9

theophylline

dimethyl sulfate
77-78-1

dimethyl sulfate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
potassium fluoride on basic alumina In acetonitrile for 24h; Ambient temperature;88%
With sodium hydroxide
With sodium hydroxide
With potassium hydroxide; Aliquat 336 1.) 20 deg C, 2 h, 2.) 1 h; Yield given. Multistep reaction;
theophylline
58-55-9

theophylline

diphenylmethylsulfonium tetrafluoroborate
10504-60-6

diphenylmethylsulfonium tetrafluoroborate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 3h;88%
Trimethylsulfonium Fluoride
353-39-9

Trimethylsulfonium Fluoride

Theophylline
58-55-9

Theophylline

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 1h;86%
xanthin
69-89-6

xanthin

N,N'-dicyclohexyl-O-methyl isourea
6257-10-9

N,N'-dicyclohexyl-O-methyl isourea

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 48h;85%
theophylline
58-55-9

theophylline

acetic acid
64-19-7

acetic acid

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; bathophenanthroline; iodomesitylene diacetate In 1,4-dioxane at 20℃; for 1h; Inert atmosphere; Irradiation; regioselective reaction;82%
4--1-methyl-5-methylaminocarbonylimidazole
107605-83-4

4--1-methyl-5-methylaminocarbonylimidazole

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With sodium hydride In ethanol for 1.5h; Heating;81%
theobromine /
83-67-0

theobromine /

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With 18-crown-6 ether In N,N-dimethyl-formamide at 90℃; for 12h;78%
1-methyl-9-aminoxanthine potassium salt
113613-79-9

1-methyl-9-aminoxanthine potassium salt

methyl iodide
74-88-4

methyl iodide

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 3h;76%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

xanthin
69-89-6

xanthin

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With 18-crown-6 ether In N,N-dimethyl-formamide at 90℃; for 12h;74%
8-bromocaffeine
10381-82-5

8-bromocaffeine

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide for 2h; Heating;72%
1-methyl-9-aminoxanthine
113613-76-6

1-methyl-9-aminoxanthine

methyl iodide
74-88-4

methyl iodide

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 1h;71%
4-(N-trichloroacetyl-N-methylamino)-1-methyl-5-methylaminocarbonylimidazole
107605-87-8

4-(N-trichloroacetyl-N-methylamino)-1-methyl-5-methylaminocarbonylimidazole

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With sodium hydride In ethanol for 2h; Heating;66%
7-(2-hydroxyethyl)theophylline
519-37-9

7-(2-hydroxyethyl)theophylline

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With cerium(III) chloride; 9,10-diphenylanthracene; 1,2-bis(2,4,6-triisopropylphenyl)disulfane; tetrabutyl-ammonium chloride In acetonitrile for 168h; Irradiation; Inert atmosphere;63%
dimethyl sulfate
77-78-1

dimethyl sulfate

xanthin
69-89-6

xanthin

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
potassium fluoride on basic alumina In acetonitrile for 24h; Ambient temperature;61%
With alkaline solution
With sodium hydroxide
theobromine /
83-67-0

theobromine /

methyl iodide
74-88-4

methyl iodide

A

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

B

3-benzyladenine
7280-81-1

3-benzyladenine

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h;A 56%
B n/a
...Expand
1,3,7,9-tetramethylxanthinium methyl sulfate
18623-34-2

1,3,7,9-tetramethylxanthinium methyl sulfate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
at 260℃; for 15h;25%
theophylline
58-55-9

theophylline

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
With sodium hydroxide
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

8-chlorocaffeine
4921-49-7

8-chlorocaffeine

Conditions
ConditionsYield
With chlorine In chloroform100%
With chlorine In chloroform at 50℃; for 2h;100%
With trichloroisocyanuric acid; brilliant green carbocation In acetonitrile at 20℃; for 2h; Irradiation; regioselective reaction;78%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

8-bromocaffeine
10381-82-5

8-bromocaffeine

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane; water for 120h;100%
With N-Bromosuccinimide In dichloromethane; water for 120h;99%
With N-Bromosuccinimide In dichloromethane; water for 120h;99%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

8-deuterio-1,3,7-trimethylxanthine

8-deuterio-1,3,7-trimethylxanthine

Conditions
ConditionsYield
With [(N,N’-bis(1R,2R,3R,5S)-(−)-isopinocampheyl-1,2-ethanediimine-radical)NiI(μ2-H)]2; deuterium In tetrahydrofuran at -196 - 45℃; under 760.051 Torr; for 24h; Sealed tube;100%
With deuteromethanol; silver carbonate; johnphos In dichloromethane at 50 - 80℃;98%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;92%
With palladium 10% on activated carbon; hydrogen; water-d2 at 90℃; for 1.5h;86.9%
With water-d2 at 150℃; for 0.25h; Microwave irradiation;
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

para-chlorotoluene
106-43-4

para-chlorotoluene

1,3,7-trimethyl-8-(4-methylphenyl)-1H-purine-3,7-dihydro-2,6-dione

1,3,7-trimethyl-8-(4-methylphenyl)-1H-purine-3,7-dihydro-2,6-dione

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 20 - 130℃; for 24h; Inert atmosphere;99%
With potassium phosphate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 125℃; for 24h;86%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

1,3,7-trimethyl-8-(p-methoxyphenyl)-xanthine
439927-43-2

1,3,7-trimethyl-8-(p-methoxyphenyl)-xanthine

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;99%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction;98%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

diphenyl acetylene
501-65-5

diphenyl acetylene

(E)-8-(1,2-Diphenylethenyl)-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion
99765-12-5

(E)-8-(1,2-Diphenylethenyl)-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; cesium acetate; 1,2-bis-(diphenylphosphino)ethane In toluene at 120℃; for 24h; Sealed vial; optical yield given as %de; stereoselective reaction;99%
With bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 14h; Inert atmosphere; Glovebox; stereoselective reaction;69%
tert-butyl N-(thiophen-2-ylmethyl)carbamate
401485-19-6

tert-butyl N-(thiophen-2-ylmethyl)carbamate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

tert-butyl N-((5-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl) thiophen-2-yl)methyl)carbamate
1403938-43-1

tert-butyl N-((5-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl) thiophen-2-yl)methyl)carbamate

Conditions
ConditionsYield
With pyridine; palladium diacetate; copper(II) acetate monohydrate; copper(l) chloride In 1,4-dioxane at 120℃; for 20h; Schlenk technique; Inert atmosphere;99%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

2-iodonaphthalene
612-55-5

2-iodonaphthalene

1,3,7-trimethyl-8-(naphthalen-2-yl)-xanthine
1257390-78-5

1,3,7-trimethyl-8-(naphthalen-2-yl)-xanthine

Conditions
ConditionsYield
With (1-(2-(tert-butylamino)ethyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)copper(I) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 8h; Glovebox;99%
NH-pyrazole
288-13-1

NH-pyrazole

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

1,3,7-trimethyl-4,5,8-tri(1H-pyrazol-1-yl)-3,4,5,7-tetrahydro-1H-purine-2,6-dione

1,3,7-trimethyl-4,5,8-tri(1H-pyrazol-1-yl)-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Temperature; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction;99%
4-bromo-1H-pyrazole
2075-45-8

4-bromo-1H-pyrazole

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

4,5,8-tris(4-bromo-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

4,5,8-tris(4-bromo-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction;99%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

4-bromo-3-methyl-1H-pyrazole
13808-64-5

4-bromo-3-methyl-1H-pyrazole

4,5,8-tris(4-bromo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

4,5,8-tris(4-bromo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction;99%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

oxalic acid
144-62-7

oxalic acid

oxalic acid caffeine, oxalic acid

oxalic acid caffeine, oxalic acid

Conditions
ConditionsYield
In methanol; cyclohexane at 17 - 22℃; under 724.572 - 782.178 Torr; for 0.5h;98.3%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

2,6-dithiocaffeine
32061-73-7

2,6-dithiocaffeine

Conditions
ConditionsYield
With Lawessons reagent; aluminum oxide for 0.1h; microwave irradiation;98%
With Lawessons reagent In toluene for 25h; Reflux;75%
With bis(1,5-cyclooctadiylboryl)sulfide In 1,3,5-trimethyl-benzene for 336h; Heating;62%
With kerosine
d6-dimethyl sulfate
15199-43-6

d6-dimethyl sulfate

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

C9H10(2)H3N4O2(1+)*C(2)H3O4S(1-)

C9H10(2)H3N4O2(1+)*C(2)H3O4S(1-)

Conditions
ConditionsYield
In nitrobenzene at 90 - 100℃; for 25h;98%
ethanol
64-17-5

ethanol

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

8-(1-hydroxyethyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
32086-89-8

8-(1-hydroxyethyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide In decane at 120℃; for 0.333333h; Reagent/catalyst; Solvent; Temperature; Time; Microwave irradiation; Green chemistry;98%
With di-tert-butyl peroxide In water at 20℃; Inert atmosphere; UV-irradiation;96%
With benzophenone Ambient temperature; Irradiation;
bromobenzene
108-86-1

bromobenzene

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

1,3,7-trimethyl-8-phenylxanthine
6439-88-9

1,3,7-trimethyl-8-phenylxanthine

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;98%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction;93%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

9-bromophenanthrene
573-17-1

9-bromophenanthrene

3,7-Dihydro-1,3,7-trimethyl-8-(9-phenanthryl)-1H-purin-2,6-dion
99765-06-7

3,7-Dihydro-1,3,7-trimethyl-8-(9-phenanthryl)-1H-purin-2,6-dion

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;98%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction;95%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

8-deuterio-1,3,7-tris(trideuteriomethyl)xanthine
1220356-33-1

8-deuterio-1,3,7-tris(trideuteriomethyl)xanthine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; water-d2 at 160℃; for 24h;98%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

1,3,7,9-tetramethylxanthinium tetrafluoroborate

1,3,7,9-tetramethylxanthinium tetrafluoroborate

Conditions
ConditionsYield
Stage #1: 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; trimethoxonium tetrafluoroborate In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: With sodium carbonate In acetonitrile at 20℃; for 0.916667h;		97%
In 1,2-dichloro-ethane at 100℃; for 1h;66%
In 1,2-dichloro-ethane Inert atmosphere; Schlenk technique; Reflux;
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

para-iodoanisole
696-62-8

para-iodoanisole

1,3,7-trimethyl-8-(p-methoxyphenyl)-xanthine
439927-43-2

1,3,7-trimethyl-8-(p-methoxyphenyl)-xanthine

Conditions
ConditionsYield
With (1-(2-(tert-butylamino)ethyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)copper(I) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 8h; Glovebox;97%
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;92%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

4-iodo-3-methyl-1H-pyrazole
15802-75-2

4-iodo-3-methyl-1H-pyrazole

4,5,8-tris(4-iodo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

4,5,8-tris(4-iodo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction;97%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

para-bromotoluene
106-38-7

para-bromotoluene

1,3,7-trimethyl-8-(4-methylphenyl)-1H-purine-3,7-dihydro-2,6-dione

1,3,7-trimethyl-8-(4-methylphenyl)-1H-purine-3,7-dihydro-2,6-dione

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;96%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction;96%
With 2-ethyl-[1,2,4] triazolo[4,3-a]pyridin-2-ium tetrafluoroborate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 115℃; for 22h; Inert atmosphere;94%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

1,3,7-trimethyl-8-(o-tolyl)-xanthine
1137486-72-6

1,3,7-trimethyl-8-(o-tolyl)-xanthine

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;96%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction;88%
2-Methylthiophene
554-14-3

2-Methylthiophene

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

1,3,7-trimethyl-8-(5-methylthiophen-2-yl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
1207995-92-3

1,3,7-trimethyl-8-(5-methylthiophen-2-yl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Conditions
ConditionsYield
Stage #1: 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione With pyridine; palladium diacetate; copper(II) acetate monohydrate In 1,4-dioxane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 2-Methylthiophene In 1,4-dioxane at 120℃; for 20h; Inert atmosphere;		96%
With pyridine; palladium diacetate; copper(II) acetate monohydrate In 1,4-dioxane at 120℃; for 24h; Schlenk technique; Inert atmosphere;92%
With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; oxygen; copper(II) acetate monohydrate In 1,4-dioxane at 140℃; under 760.051 Torr; for 30h; Schlenk technique; Green chemistry;89%

Caffeine Chemical Properties


IUPAC Name: 1,3,7-Trimethylpurine-2,6-dione
Molecular Formula: C8H10N4O2
Molecular Weight: 194.19 g/mol
EINECS: 200-362-1
Classification Code: Central Nervous System Agents; Central nervous system stimulants; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Mutation data; Natural Product; Phosphodiesterase inhibitors; Reproductive Effect; Stimulant [central]; Tumor data
Melting Point: 234-236.5 °C(lit.)
storage temp.: 2-8 °C
Water Solubility: 20 g/L (20 °C)
Sublimation: 178 °C
Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, iodine, silver salts, tannins. Weakly light sensitive in solution.
Index of Refraction: 1.679 
Molar Refractivity: 50.38 cm3 
Molar Volume: 133.3 cm3 
Surface Tension: 55.7 dyne/cm 
Density: 1.45 g/cm3 
Flash Point: 205.9 °C 
Enthalpy of Vaporization: 67.01 kJ/mol 
Boiling Point: 416.8 °C at 760 mmHg 
Vapour Pressure of Caffeine (CAS NO.58-08-2): 3.72E-07 mmHg at 25 °C

Caffeine Uses

Common sources of Caffeine are coffee, tea, and to a lesser extent chocolate derived from cocoa beans. Less commonly used sources of Caffeine include the yerba maté and guarana plants, which are sometimes used in the preparation of teas and energy drinks.

Caffeine Production

 Caffeine (CAS NO.58-08-2) has been isolated from waste tea and from the decaffeinization of coffee by extraction at 70 ℃, using rotating countercurrent drums and an organic solvent, frequently trichloroethylene. The solvent is drained off, and the beans steamed to remove residual solvent. The extraction solvent is evaporated, and the caffeine is hot-water-extracted from the wax, decolorized with carbon, and recrystallized.
 Caffeine (CAS NO.58-08-2) is also manufactured synthetically by, for instance, the methylation of theobromine and also total synthesis by methylation and other reactions based upon urea.

Caffeine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 316mg/kg (316mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LDLo intraperitoneal 180mg/kg (180mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
cat LDLo intravenous 80mg/kg (80mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
cat LDLo oral 100mg/kg (100mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
cat LDLo subcutaneous 150mg/kg (150mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
child LDLo oral 320mg/kg (320mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Forensic Science. Vol. 3, Pg. 275, 1974.
child TDLo oral 140mg/kg (140mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BLOOD: HEMORRHAGE		 Pediatric Emergency Care. Vol. 10, Pg. 349, 1994.
dog LD50 oral 140mg/kg (140mg/kg)   Drugs in Japan Vol. 6, Pg. 174, 1982.
dog LD50 subcutaneous 100mg/kg (100mg/kg)   Drugs in Japan Vol. 6, Pg. 174, 1982.
dog LDLo intravenous 4mg/kg (4mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
frog LDLo parenteral 120mg/kg (120mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: STIFFNESS

CARDIAC: OTHER CHANGES		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
frog LDLo subcutaneous 120mg/kg (120mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959.
guinea pig LD50 oral 230mg/kg (230mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Toxicology and Applied Pharmacology. Vol. 2, Pg. 23, 1960.
guinea pig LDLo intraperitoneal 220mg/kg (220mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
guinea pig LDLo subcutaneous 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
hamster LD50 oral 230mg/kg (230mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 44, Pg. 1, 1978.
human LDLo oral 192mg/kg (192mg/kg)   Journal of New Drugs. Vol. 5, Pg. 252, 1965.
human TDLo intravenous 7mg/kg (7mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959.
infant TDLo intramuscular 36mg/kg (36mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA		 American Journal of Diseases of Children. Vol. 134, Pg. 495, 1980.
infant TDLo intravenous 68mg/kg (68mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA		 American Journal of Diseases of Children. Vol. 134, Pg. 495, 1980.
infant TDLo oral 14700ug/kg (14.7mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Clinical Biochemistry Vol. 10, Pg. 148, 1977.
man TDLo oral 13mg/kg (13mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS American Journal of Psychiatry. Vol. 143, Pg. 1320, 1986.
man TDLo oral 51mg/kg (51mg/kg) CARDIAC: CHANGE IN RATE

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

MUSCULOSKELETAL: TUMORS		 Annals of Emergency Medicine. Vol. 18, Pg. 94, 1989.
mouse LD50 intraperitoneal 168mg/kg (168mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: AGGRESSION

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED		 Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1459, 1974.
mouse LD50 intravenous 62mg/kg (62mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Toxicology Letters. Vol. 29, Pg. 25, 1985.
mouse LD50 oral 127mg/kg (127mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 44, Pg. 1, 1978.
mouse LD50 subcutaneous 242mg/kg (242mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 601, 1956.
mouse LD50 unreported 251mg/kg (251mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
pigeon LDLo subcutaneous 140mg/kg (140mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 1, Pg. 572, 1910.
rabbit LD50 intravenous 58mg/kg (58mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 13, Pg. 791, 1979.
rabbit LD50 oral 224mg/kg (224mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 44, Pg. 1, 1978.
rabbit LDLo intramuscular 200mg/kg (200mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 1, Pg. 572, 1910.
rabbit LDLo intraperitoneal 150mg/kg (150mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935.
rabbit LDLo subcutaneous 275mg/kg (275mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 1, Pg. 572, 1910.
rat LD50 intraperitoneal 240mg/kg (240mg/kg)   Zeitschrift fuer Ernaehrungswissenschaft. Vol. 15, Pg. 64, 1976.
rat LD50 intravenous 105mg/kg (105mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER		 Journal of Pharmacology and Experimental Therapeutics. Vol. 82, Pg. 89, 1944.
rat LD50 oral 192mg/kg (192mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

BEHAVIORAL: WITHDRAWAL

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS		 Journal of New Drugs. Vol. 5, Pg. 252, 1965.
rat LD50 rectal 300mg/kg (300mg/kg)   Journal of Clinical Pharmacology and Journal of New Drugs. Vol. 7, Pg. 131, 1967.
rat LD50 subcutaneous 170mg/kg (170mg/kg)   Journal of Clinical Pharmacology and Journal of New Drugs. Vol. 7, Pg. 131, 1967.
women LDLo intravenous 57mg/kg (57mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION		 Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959.
women LDLo oral 400mg/kg (400mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER		 Veterinary and Human Toxicology. Vol. 39, Pg. 228, 1997.
women LDLo oral 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Bulletin of the International Association of Forensic Toxicologists.Vol. -, Pg. 6, 1973.
women TDLo oral 96mg/kg/1D-I (96mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Journal of Pediatrics. Vol. 105, Pg. 493, 1984.

Caffeine Safety Profile

Hazard Codes: HarmfulXn,ToxicT
Risk Statements : 22-25
R22:  Harmful if swallowed 
R25:  Toxic if swallowed 
Safety Statements : 16-36/37-45
S16:  Keep away from sources of ignition - No smoking 
S36/37:  Wear suitable protective clothing and gloves 
S45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
RIDADR : UN 1544 6.1/PG 3
WGK Germany : 1
F 10: Keep under argon.
HazardClass : 6.1
PackingGroup : III
RTECS : EV6475000

Caffeine Specification

  Caffeine (CAS NO.58-08-2), its Synonyms are 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl- ; 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione ; 1,3,7-Trimethyl-2,6-dioxopurine ; 1,3,7-Trimethylxanthine ; Alert-pep ; Anhydrous caffeine ; Vivarin ; Wigraine ; Xanthine, 1,3,7-trimethyl . It is white to light yellow crystal powder.

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