8-Bromo-3-methyl-xanthine supplier

Name
8-Bromo-3-methyl-xanthine
EINECS 819-117-0
CAS No. 93703-24-3
Article Data25
CAS DataBase
Density 1.975 g/cm³
Solubility
Melting Point 300°C(lit.)
Formula C₆H₅BrN₄O₂
Boiling Point
Molecular Weight 245.035
Flash Point
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 22
Molecular Structure
Hazard Symbols
Synonyms 1H-Purine-2,6-dione,8-bromo-3,7-dihydro-3-methyl- (9CI);3-Methyl-8-bromoxanthine;8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione;8-Bromo-3-methylxanthine;
PSA 83.54000
LogP -0.28760

Synthetic route

: C6H7BrN4O2

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
With N-Bromosuccinimide; potassium carbonate In 1,2-dichloro-ethane at 60℃; for 5h; Reagent/catalyst; Solvent; Temperature;	97%

: 1076-22-8
3-methylxanthine

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
With bromine; sodium acetate In acetic acid at 50 - 65℃; for 3h;	96.6%
With bromine; acetic acid at 100℃; for 6h;	95%
With bromine; sodium acetate; acetic acid at 65℃; for 3h;	94.17%

: 64-18-6
formic acid

: 6972-82-3
5,6-diamino-1-methyluracil

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
Stage #1: formic acid; 5,6-diamino-1-methyluracil In water for 2h; Reflux; Stage #2: With sodium hydroxide In water at 100℃; for 16h; Stage #3: With bromine; sodium acetate; acetic acid at 66℃; for 3h;	84%

: 93703-23-2
3-methyl-8-nitroxanthine

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
With potassium bromate; hydrogen bromide In acetic acid at 80 - 95℃; for 12h;	83%
With hydrogen bromide for 4h; Heating;	64%

: 6972-82-3
5,6-diamino-1-methyluracil

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water / 3 h / 105 °C 1.2: 1 h / 105 °C 2.1: sodium acetate; bromine; acetic acid / water / 2 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1.1: water / 3 h / Reflux; Inert atmosphere 1.2: 1 h / Reflux; Inert atmosphere 2.1: acetic acid; sodium acetate; bromine / water / 2 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide 2: hydrogen bromide; sodium chlorate View Scheme

: 2434-53-9
6-amino-1-methyluracil

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetic acid; sodium nitrite / water / 1.5 h / 20 - 50 °C 2.1: ammonium hydroxide; sodium dithionite / 7 h / 25 - 60 °C 3.1: water / 3 h / 105 °C 3.2: 1 h / 105 °C 4.1: sodium acetate; bromine; acetic acid / water / 2 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium dithionite; ammonium hydroxide / 1 h / 50 °C 2.1: water / 3 h / Reflux; Inert atmosphere 2.2: 1 h / Reflux; Inert atmosphere 3.1: acetic acid; sodium acetate; bromine / water / 2 h / 65 °C View Scheme
Multi-step reaction with 4 steps 1: sodium nitrite / Acidic conditions 2: sodium dithionite 3: sodium hydroxide 4: hydrogen bromide; sodium chlorate View Scheme

: 6972-78-7
6-amino-1-methyl-5-nitrosouracil

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium hydroxide; sodium dithionite / 7 h / 25 - 60 °C 2.1: water / 3 h / 105 °C 2.2: 1 h / 105 °C 3.1: sodium acetate; bromine; acetic acid / water / 2 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1: sodium dithionite 2: sodium hydroxide 3: hydrogen bromide; sodium chlorate View Scheme
Multi-step reaction with 3 steps 1: sodium dithionite / water / 1 h / 70 °C 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3.5 h / 70 °C / Inert atmosphere 3: acetic acid; bromine; sodium acetate / 3 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1.1: ammonium hydroxide; sodium dithionite / 1 h / 35 - 60 °C 2.1: water / 3 h / 105 °C 2.2: 1 h / 105 °C 3.1: acetic acid; sodium acetate; bromine / 2 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium dithionite; ammonia / 1 h / 50 °C 2.1: water / 3 h / Reflux; Inert atmosphere 3.1: acetic acid; sodium acetate / 25 - 30 °C 3.2: 10 - 65 °C View Scheme

: 90801-87-9
4-(N-methylamino)-1H-imidazole-5-carboxamide

: 93703-24-3
3-methyl-8-bromoxanthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid adsorbed on silica gel; formic acid / ethanol / 0.33 h / 20 °C 2: sodium acetate; acetic acid; bromine / 3 h / 65 °C View Scheme

: 93703-24-3
3-methyl-8-bromoxanthine

: 3355-28-0
1-Bromo-2-butyne

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With sodium carbonate In acetone at 40℃; for 4h; Temperature; Reagent/catalyst; Solvent;	98%
With N-ethyl-N,N-diisopropylamine In acetone Solvent; Reflux; Further stages;	97.4%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 10h;	95.68%

: 93703-24-3
3-methyl-8-bromoxanthine

: 70404-40-9
8-mercapto-3-methylxanthine

Conditions

Conditions	Yield
With potassium hydrosulfide In methanol at 170 - 175℃; for 8h; sealed ampoule;	96.5%

: 503-17-3
dimethylacetylene

: 93703-24-3
3-methyl-8-bromoxanthine

: 8-bromo-3,7-dihydro-3-methyl-9-(2-butynyl)-1H-purine-2,6-dione

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; copper(II) perchlorate In N,N-dimethyl-formamide at 50℃; for 4h; Temperature; Inert atmosphere;	95.1%

: 3221-15-6
2-(chloromethyl)thiirane

: 93703-24-3
3-methyl-8-bromoxanthine

: 1005482-51-8
8-bromo-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione

Conditions

Conditions	Yield
With potassium hydroxide In water; N,N-dimethyl-formamide at 0 - 20℃;	94.3%

: 93703-24-3
3-methyl-8-bromoxanthine

: 74-88-4
methyl iodide

: 15371-15-0
8-bromo-3,7-dimethylxanthine

Conditions

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; water	93%
With potassium carbonate In N-methyl-acetamide; water	93%
With potassium carbonate In N-methyl-acetamide; water	93%

: 93703-24-3
3-methyl-8-bromoxanthine

: 74-88-4
methyl iodide

: 10381-82-5
8-bromocaffeine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h;	92%

: 93703-24-3
3-methyl-8-bromoxanthine

: 870-63-3
prenyl bromide

: 313273-69-7
8-bromo-3-methyl-7-(3-methyl-but-2-enyl)-3,7-dihydro-purine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.166667h; Stage #2: prenyl bromide In N,N-dimethyl-formamide at 20℃;	91.1%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 4h;	86%
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h;	80%

: 503-17-3
dimethylacetylene

: 93703-24-3
3-methyl-8-bromoxanthine

: 8-bromo-3,9-dihydro-3-methyl-9-(2-butynyl)-1H-purine-2,6-dione

Conditions

Conditions	Yield
With 1,10-Phenanthroline; copper dichloride In N,N-dimethyl-formamide at 50℃; for 6h; Reagent/catalyst; Concentration; Solvent; Inert atmosphere;	91.1%

: 93703-24-3
3-methyl-8-bromoxanthine

: 22115-41-9
2-(bromomethyl)benzonitrile

: 485821-27-0
2-((8-bromo-3-methyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)methyl)benzonitrile

Conditions

Conditions	Yield
	91%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

: 446-48-0
o-fluorobenzyl bromide

: 93703-24-3
3-methyl-8-bromoxanthine

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

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 4h;	90%

: 100-39-0
benzyl bromide

: 93703-24-3
3-methyl-8-bromoxanthine

: 93703-26-5
7-benzyl-8-bromo-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N-methyl-acetamide	89%
With potassium carbonate In N-methyl-acetamide	89%
With potassium carbonate In N-methyl-acetamide	89%

: 93703-24-3
3-methyl-8-bromoxanthine

: 106-95-6
allyl bromide

: 7-allyl-8-bromo-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	86%

: 69966-55-8
3-picolyl bromide

: 93703-24-3
3-methyl-8-bromoxanthine

: 8-bromo-3-methyl-7-(pyridin-3-ylmethyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With hydrogen bromide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 4h;	86%

: 93703-24-3
3-methyl-8-bromoxanthine

: 824-94-2
p-methoxybenzyl chloride

: 8-bromo-7-(4-methoxybenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 2.5h;	85%

: 128577-47-9
methyl 4-(bromomethyl)-3-fluorobenzoate

: 93703-24-3
3-methyl-8-bromoxanthine

: methyl 4-((8-amino-3-methyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)methyl)-3-fluorobenzoate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 4h;	84%

: 93703-24-3
3-methyl-8-bromoxanthine

: 89-92-9
2-methylbenzyl bromide

: 485821-36-1
8-Bromo-3-methyl-7-(2-methylbenzyl)-3,7-dihydropurine-2,6-dione

Conditions

Conditions	Yield
	79%

: 20099-89-2
4-Cyanophenacyl bromide

: 93703-24-3
3-methyl-8-bromoxanthine

: 1192215-85-2
8-bromo-7-[2-(4-cyanophenyl)-2-oxoethyl]-3,7-dihydro-3-methyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-Cyanophenacyl bromide In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	79%

: 93703-24-3
3-methyl-8-bromoxanthine

: 1699-59-8
3,4-dibenzyloxybenzyl chloride

: 8-bromo-3-methyl-7-(3',4'-dibenzyloxy)benzyl xanthine

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 60℃; for 12h;	78%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 60℃; for 12h;	78%

: 93703-24-3
3-methyl-8-bromoxanthine

: 107-82-4
i-pentyl bromide

: 8-bromo-7-isopentyl-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 15h;	78%

: 2270-59-9
1-bromo-4-methylpent-3-ene

: 93703-24-3
3-methyl-8-bromoxanthine

: 8-bromo-3-methyl-7-(4-methylpent-3-enyl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 4h; Reagent/catalyst;	78%

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

: 93703-24-3
3-methyl-8-bromoxanthine

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

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 2h;	76%

: 41011-01-2
2-bromo-1-(3-chloro-phenyl)-ethanone

: 93703-24-3
3-methyl-8-bromoxanthine

: 1415838-41-3
8-bromo-7-(2-(3-chlorophenyl)-2-oxoethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: 2-bromo-1-(3-chloro-phenyl)-ethanone In N,N-dimethyl-formamide at 25℃; for 15h; Inert atmosphere; Schlenk technique;	76%

: 31949-21-0
bromomethyl 2-methoxyphenyl ketone

: 93703-24-3
3-methyl-8-bromoxanthine

: 1192215-75-0
8-bromo-3,7-dihydro-7-[2-(2-methoxyphenyl)-2-oxoethyl]-3-methyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: bromomethyl 2-methoxyphenyl ketone In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	75%

: 2491-37-4
2-bromo-1-(3-hydroxyphenyl)ethanone

: 93703-24-3
3-methyl-8-bromoxanthine

: 1192215-80-7
8-bromo-3,7-dihydro-7-[2-(3-hydroxyphenyl)-2-oxoethyl]-3-methyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-1-(3-hydroxyphenyl)ethanone In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	75%

: 93703-24-3
3-methyl-8-bromoxanthine

: 51012-64-7
2-bromo-3'-methylacetophenone

: 1192215-78-3
8-bromo-3,7-dihydro-3-methyl-7-[2-(3-methylphenyl)-2-oxoethyl]-1H-purine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-3'-methylacetophenone In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	75%

: 93703-24-3
3-methyl-8-bromoxanthine

: 5000-65-7
2-bromo-3'-methoxyacetophenone

: 1192215-76-1
8-bromo-3,7-dihydro-7-[2-(3-methoxyphenyl)-2-oxoethyl]-3-methyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 3-methyl-8-bromoxanthine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-3'-methoxyacetophenone In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	75%

8-Bromo-3-methyl-xanthine Specification

The 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-3-methyl-, with the CAS registry number 93703-24-3, is also known as 8-Bromo-3-methylxanthine. This chemical's molecular formula is C₆H₅BrN₄O₂ and molecular weight is 245.03. What's more, its IUPAC name is called 8-Bromo-3-methyl-xanthine.

Physical properties about 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-3-methyl- are: (1)ACD/LogP: -0.632; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.63; (4)ACD/LogD (pH 7.4): -0.68; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 10.78; (8) ACD/KOC (pH 7.4): 9.62; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 78.09 Å²; (13)Index of Refraction: 1.662; (14)Molar Refractivity: 45.914 cm³; (15)Molar Volume: 124.076 cm³; (16)Polarizability: 18.202×10^-24cm³; (17)Surface Tension: 75.226 dyne/cm; (18)Density: 1.975 g/cm³.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2N(c1nc(Br)nc1C(=O)N2)C
(2) InChI: InChI=1S/C6H5BrN4O2/c1-11-3-2(8-5(7)9-3)4(12)10-6(11)13/h1H3,(H,8,9)(H,10,12,13)
(3) InChIKey: QTEQVEJOXGBDGI-UHFFFAOYSA-N

Product Name

8-Bromo-3-methyl-xanthine

Synthetic route

8-Bromo-3-methyl-xanthine Specification

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