67289-05-8

Basic information

• Product Name: 2-bromo-5-methyl-benzene-1,4-diol
• Synonyms: 2-bromo-5-methyl-benzene-1,4-diol;2-BROMO-5-METHYLHYDROQUINONE
• CAS NO: 67289-05-8
• Molecular Formula: C₇H₇BrO₂
• Molecular Weight: 203.0333
• Mol File: 67289-05-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 289.9°Cat760mmHg
• Flash Point: 129.1°C
• Appearance: /
• Density: 1.709g/cm³
• Vapor Pressure: 0.00123mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 2-bromo-5-methyl-benzene-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-5-methyl-benzene-1,4-diol(67289-05-8)
• EPA Substance Registry System: 2-bromo-5-methyl-benzene-1,4-diol(67289-05-8)

Safety Data

• Hazardous Substances Data: 67289-05-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 3078, 1978 DOI: 10.1021/jo00409a039

InChI:InChI=1/C7H7BrO2/c1-4-2-7(10)5(8)3-6(4)9/h2-3,9-10H,1H3

Upstream product

• 95-71-6 2-methylbenzene-1,4-diol 
• 13070-25-2 2-bromo-5-methyl-[1,4]benzoquinone 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 10035-10-6 hydrogen bromide 
• 24599-58-4 2,5-dimethoxy toluene 
• 13070-29-6 5,6-dibromo-2-methyl-cyclohex-2-ene-1,4-dione 
• 106-51-4 p-benzoquinone 
• 13321-74-9 1-bromo-2,5-dimethoxy-4-methylbenzene 

Downstream Products

• 13070-25-2 2-bromo-5-methyl-[1,4]benzoquinone 
• 98277-68-0 2-mercapto-5-methyl-hydroquinone 
• 13321-72-7 2-bromo-5-methylhydroquinone dibenzyl ether 
• 13321-74-9 1-bromo-2,5-dimethoxy-4-methylbenzene 
• 3899-19-2 2,5-dihydroxy-4-methylbenzoic acid methyl ester 
• 681473-22-3 2,5-bis(methoxymethoxy)-4-bromotoluene 
• 916843-99-7 1,4-Dimethoxy-2-methyl-5-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-benzene 
• 57402-26-3 5-methyl-2-[(2'E,6'E)-3',7',11'-trimethyl-2',6',10'-dodecatrienyl]-2,5-cyclohexadiene-1,4-dione 
• 79644-43-2 4-methyl-3,6-dioxocyclohexa-1,4-dienecarboxylic acid methyl ester 
• 187809-40-1 2-bromo-3-chloro-5-methyl-[1,4]benzoquinone 
• 187809-44-5 2-bromo-3-chloro-5-methyl-hydroquinone 
• 35458-39-0 4-bromo-2,5-dimethoxybenzoic acid 
• 873420-96-3 4-bromo-2,5-dihydroxybenzoic acid 
• 408340-52-3 (2,5-dihydroxy-4-methyl-phenylsulfanyl)-acetic acid 

Relevant articles and documents

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus

Two triprenylated toluquinone and toluhydroquinone marine fungal metabolites, 5-methyl-2-[(2′E,6′E)-3′,7′,11′-trimethyl-2′,6′,10′-dodecatrienyl]-2,5-cyclohexadiene-1,4-dione and 5-methyl-2-[(2′E,6′E)-3,7,11-trimethyl-2′,6′,10′-dodecatrienyl]-1,4-benzenediol, were synthesized in four and five steps, respectively, from 2-methyl-1,4-benzoquinone. The synthesis extends the applicability of the oxidative ether cleavage of hydroquinone dimethyl ethers with argentic oxide under acidic conditions to include the oxidative demethylation of polyprenylated-1,4-dimethoxy-toluhydroquinones with a quantitative survival of the oxidation- and acid-sensitive polyprenyl side chain.