Product Name

  • Name

    8-BROMOTHEOPHYLLINE

  • EINECS 233-846-6
  • CAS No. 10381-75-6
  • Article Data15
  • CAS DataBase
  • Density 1.862 g/cm3
  • Solubility
  • Melting Point 295-297 °C
  • Formula C7H7BrN4O2
  • Boiling Point 469.468 °C at 760 mmHg
  • Molecular Weight 259.062
  • Flash Point 237.726 °C
  • Transport Information UN 2811
  • Appearance White crystalline powder
  • Safety 24/25-36/37
  • Risk Codes 20/21/22
  • Molecular Structure Molecular Structure of 10381-75-6 (8-BROMOTHEOPHYLLINE)
  • Hazard Symbols
  • Synonyms 1H-Purine-2,6-dione,8-bromo-3,7-dihydro-1,3-dimethyl- (9CI);Theophylline, 8-bromo- (6CI,7CI,8CI);8-Bromotheophylline;Bromotheaminum;Bromotheophylline;NSC 164940;
  • PSA 72.68000
  • LogP -0.27720

Synthetic route

8-trifluoroacetoxymercuritheophylline
86468-95-3

8-trifluoroacetoxymercuritheophylline

8-bromotheophylline
10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With bromine; sodium hydrogencarbonate; potassium bromide at 80℃; for 0.5h; pH 7;96%
theophylline
58-55-9

theophylline

8-bromotheophylline
10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With bromine In water; acetic acid at 50℃; for 4h;94.5%
With bromine at 150℃; zuletzt auf 150grad;
With ethanol; bromine
8-bromo-1,3-dimethyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
208577-20-2

8-bromo-1,3-dimethyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione

A

3-ethoxy-λ6-thietane 1,1-dioxide
82299-33-0

3-ethoxy-λ6-thietane 1,1-dioxide

B

8-bromotheophylline
10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With sodium In ethanol for 0.5h; Heating;A n/a
B 85%
8-nitrotheophylline
2099-73-2

8-nitrotheophylline

8-bromotheophylline
10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With water; hydrogen bromide
8-nitrotheophylline
2099-73-2

8-nitrotheophylline

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

8-bromotheophylline
10381-75-6

8-bromotheophylline

1,3-dimethyluric acid
944-73-0

1,3-dimethyluric acid

A

8-bromotheophylline
10381-75-6

8-bromotheophylline

B

8-chloro-theophylline

8-chloro-theophylline

Conditions
ConditionsYield
With phosphorus pentabromide; trichlorophosphate at 145 - 150℃;
piperidine
110-89-4

piperidine

8-bromotheophylline
10381-75-6

8-bromotheophylline

1,3-dimethyl-8-(1-piperidyl)-7H-purine-2,6-dione
961-48-8

1,3-dimethyl-8-(1-piperidyl)-7H-purine-2,6-dione

Conditions
ConditionsYield
for 2h; Heating;98%
8-bromotheophylline
10381-75-6

8-bromotheophylline

2,4-dichloro-1-(cyclopropylmethoxy)benzene

2,4-dichloro-1-(cyclopropylmethoxy)benzene

8-bromo-7-[2-hydroxy-3-(2,4-dichlorophenoxy)prop-1-yl]theophylline

8-bromo-7-[2-hydroxy-3-(2,4-dichlorophenoxy)prop-1-yl]theophylline

Conditions
ConditionsYield
Reflux;97.3%
1,2-epoxy-7-octene
52485-73-1, 105205-70-7, 126872-17-1, 19600-63-6

1,2-epoxy-7-octene

8-bromotheophylline
10381-75-6

8-bromotheophylline

7-hex-5-enyl-1,3-dimethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione

7-hex-5-enyl-1,3-dimethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione

Conditions
ConditionsYield
With pyridine In butan-1-ol for 2h; Heating;97%
1-bromo-2-(4'-methylphenoxy)ethane
18800-34-5

1-bromo-2-(4'-methylphenoxy)ethane

8-bromotheophylline
10381-75-6

8-bromotheophylline

7-(4'-methylphenoxy)ethyl-8-bromotheophylline
228247-62-9

7-(4'-methylphenoxy)ethyl-8-bromotheophylline

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 9h; Heating;96%
8-bromotheophylline
10381-75-6

8-bromotheophylline

benzyl bromide
100-39-0

benzyl bromide

7-benzyl-8-bromo-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
70404-23-8

7-benzyl-8-bromo-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;96%
With potassium carbonate In N,N-dimethyl-formamide90%
glycidyl isobutyl ether
3814-55-9

glycidyl isobutyl ether

8-bromotheophylline
10381-75-6

8-bromotheophylline

7-isobutoxymethyl-1,3-dimethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione

7-isobutoxymethyl-1,3-dimethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione

Conditions
ConditionsYield
With pyridine In propan-1-ol for 5h; Heating;92%
8-bromotheophylline
10381-75-6

8-bromotheophylline

meta-bromobenzyl bromide
823-78-9

meta-bromobenzyl bromide

8-bromo-7-(3-bromobenzyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione

8-bromo-7-(3-bromobenzyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;91.9%
8-bromotheophylline
10381-75-6

8-bromotheophylline

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

1,3-Dimethyl-8-m-tolylamino-3,7-dihydro-purine-2,6-dione

1,3-Dimethyl-8-m-tolylamino-3,7-dihydro-purine-2,6-dione

Conditions
ConditionsYield
In various solvent(s) for 15h; Heating;91%
2-pentyloxirane
1003-14-1

2-pentyloxirane

8-bromotheophylline
10381-75-6

8-bromotheophylline

1,3-dimethyl-7-propyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione
344455-29-4

1,3-dimethyl-7-propyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione

Conditions
ConditionsYield
With pyridine In butan-1-ol for 4h; Heating;91%
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

8-bromotheophylline
10381-75-6

8-bromotheophylline

7-(4-chlorobutyl)-8-bromo-1,3-dimethyl-3,7-dihydropurine-2,6-dione
943655-00-3

7-(4-chlorobutyl)-8-bromo-1,3-dimethyl-3,7-dihydropurine-2,6-dione

Conditions
ConditionsYield
91%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetone Reflux;
2-aminobutanol
96-20-8, 13054-87-0

2-aminobutanol

8-bromotheophylline
10381-75-6

8-bromotheophylline

(R,S)-8-(1-hydroxy-2-butyl)-aminotheophylline
88002-65-7

(R,S)-8-(1-hydroxy-2-butyl)-aminotheophylline

Conditions
ConditionsYield
In xylene for 20h; Heating;90%
8-bromotheophylline
10381-75-6

8-bromotheophylline

1-<1-(2-methoxyphenyl)-4-piperazino>-2,3-epoxypropane

1-<1-(2-methoxyphenyl)-4-piperazino>-2,3-epoxypropane

7-[4-(-2'-methoxyphenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4-(1H,3H)-dione

7-[4-(-2'-methoxyphenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4-(1H,3H)-dione

Conditions
ConditionsYield
With pyridine In propan-1-ol for 10h; Reflux;90%
8-bromotheophylline
10381-75-6

8-bromotheophylline

3[4-(3'-chlorophenyl)piperazinyl]-1,2-epoxypropane
103234-06-6

3[4-(3'-chlorophenyl)piperazinyl]-1,2-epoxypropane

7-[4-(-3'-chlorophenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4-(1H,3H)-dione

7-[4-(-3'-chlorophenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4-(1H,3H)-dione

Conditions
ConditionsYield
With pyridine In propan-1-ol for 10h; Reflux;90%
8-bromotheophylline
10381-75-6

8-bromotheophylline

3[4-(2',3'-dichlorophenyl)piperazinyl]-1,2-epoxypropane

3[4-(2',3'-dichlorophenyl)piperazinyl]-1,2-epoxypropane

7-[4-(-2',3'-dichlorophenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4-(1H,3H)-dione

7-[4-(-2',3'-dichlorophenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4-(1H,3H)-dione

Conditions
ConditionsYield
With pyridine In propan-1-ol for 10h; Reflux;90%
8-bromotheophylline
10381-75-6

8-bromotheophylline

3[4-(3',4'-dichlorophenyl)piperazinyl]-1,2-epoxypropane
335165-60-1

3[4-(3',4'-dichlorophenyl)piperazinyl]-1,2-epoxypropane

7-[4-(-3',4'-dichlorophenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4(1H,3H)-dione

7-[4-(-3',4'-dichlorophenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With pyridine In propan-1-ol for 10h; Reflux;90%
8-bromotheophylline
10381-75-6

8-bromotheophylline

2-(bromomethyl)-1-chloro-3-fluorobenzene
68220-26-8

2-(bromomethyl)-1-chloro-3-fluorobenzene

8-bromo-7-(2-chloro-6-fluorobenzyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
374921-30-9

8-bromo-7-(2-chloro-6-fluorobenzyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions
ConditionsYield
Stage #1: 8-bromotheophylline With potassium carbonate In water Heating / reflux;
Stage #2: With ethanol In water
Stage #3: 2-(bromomethyl)-1-chloro-3-fluorobenzene In water; dimethyl sulfoxide at 100℃; for 1h;		89%
8-bromotheophylline
10381-75-6

8-bromotheophylline

1-(1-phenyl-4-piperazino)-2,3-epoxypropane
72566-27-9

1-(1-phenyl-4-piperazino)-2,3-epoxypropane

7-[(4-phenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4(1H,3H)-dione

7-[(4-phenyl)-piperazin-1-yl-methylene]-1,3-dimethyl-6,7-dihydro-1,3-oxazolo[2,3-f]-purine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With pyridine In propan-1-ol for 10h; Reflux;89%
3,5-Lutidine
591-22-0

3,5-Lutidine

8-bromotheophylline
10381-75-6

8-bromotheophylline

C14H15N5O2
142954-89-0

C14H15N5O2

Conditions
ConditionsYield
With chloramine-B for 0.166667h; Ambient temperature;88%
With acetic anhydride 1.) 125-135 deg C, 2.) r.t.;71%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

tetrakis(triphenylphosphine) palladium(0)
14221-01-3

tetrakis(triphenylphosphine) palladium(0)

8-bromotheophylline
10381-75-6

8-bromotheophylline

C44H40BrN4O2P2Pd(1+)*BF4(1-)

C44H40BrN4O2P2Pd(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrakis(triphenylphosphine) palladium(0); 8-bromotheophylline In toluene at 25℃; for 24h; Inert atmosphere;
Stage #2: tetrafluoroboric acid diethyl ether In toluene at 25℃; for 48h; Inert atmosphere;		88%
...Expand
2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone
17133-48-1

2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone

8-bromotheophylline
10381-75-6

8-bromotheophylline

8-bromo-7-[2-(indolin-1-yl)-2-oxoethyl]-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione

8-bromo-7-[2-(indolin-1-yl)-2-oxoethyl]-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione

Conditions
ConditionsYield
Stage #1: 8-bromotheophylline With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;
Stage #2: 2-Chloro-1-(2,3-dihydro-1H-1-indolyl)-1-ethanone In N,N-dimethyl-formamide at 20℃; for 24h;		88%

8-Bromotheophylline Specification

The IUPAC name of 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-1,3-dimethyl- is 8-bromo-1,3-dimethyl-7H-purine-2,6-dione. With the CAS registry number 10381-75-6, it is also named as 8-Bromotheophylline. The product's categories are Pharmaceutical Raw Materials; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides. It is white crystalline powder which is used as pharmaceutical intermediate.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.18; (4)ACD/LogD (pH 7.4): -1.52; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 14.58; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.651; (13)Molar Refractivity: 50.84 cm3; (14)Molar Volume: 139 cm3; (15)Polarizability: 20.15×10-24 cm3; (16)Surface Tension: 70.8 dyne/cm; (17)Enthalpy of Vaporization: 73.18 kJ/mol; (18)Vapour Pressure: 5.49E-09 mmHg at 25°C; (19)Tautomer Count: 4; (20)Exact Mass: 257.975238; (21)MonoIsotopic Mass: 257.975238; (22)Topological Polar Surface Area: 69.3; (23)Heavy Atom Count: 14; (24)Complexity: 297.

Preparation of 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-1,3-dimethyl-: It can be obtained by 8-trifluoroacetoxymercuritheophylline. This reaction needs reagent Br2, aq. KBr, NaHCO3 at temperature of 80 °C. The reaction time is 30 min. The yield is 96%.

Uses of 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-1,3-dimethyl-: It can react with chloromethyl-thiirane to get 8-bromo-1,3-dimethyl-7-(thietanyl-3)xanthine. This reaction needs reagent KOH and solvent H2O at temperature of 60 °C. The reaction time is 3 hours. The yield is 44%.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C2N(c1nc(Br)nc1C(=O)N2C)C
2. InChI:InChI=1/C7H7BrN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)
3. InChIKey:SKTFQHRVFFOHTQ-UHFFFAOYAW

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