13319-71-6

Basic information

• Product Name: 6-BROMO-O-CRESOL
• Synonyms: 6-BROMO-O-CRESOL;2-Bromo-6-methylphenol;Phenol,2-broMo-6-Methyl-;2-Bromo-6-methylphenol 96%;3-Bromo-2-hydroxytoluene, 6-Bromo-o-cresol;6-BroMo-o-cresol,2-BroMo-6-Methylphenol;2-Bromo-6-methylphenol96%;6-Bromo-o-cresol
• CAS NO: 13319-71-6
• Molecular Formula: C₇H₇BrO
• Molecular Weight: 187.03
• Mol File: 13319-71-6.mol
• Article Data: 48

Chemical Properties

• Melting Point: 16 °C
• Boiling Point: 208 °C
• Flash Point: 79.532 °C
• Appearance: /
• Density: 1.51
• Vapor Pressure: 0.153mmHg at 25°C
• Refractive Index: 1.5680-1.5720
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.78±0.10(Predicted)
• CAS DataBase Reference: 6-BROMO-O-CRESOL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-O-CRESOL(13319-71-6)
• EPA Substance Registry System: 6-BROMO-O-CRESOL(13319-71-6)

Safety Data

• Hazardous Substances Data: 13319-71-6(Hazardous Substances Data)

Usage

General Description

6-Bromo-O-cresol, also known as 2-Bromo-6-methylphenol, is a chemical compound with the molecular formula C7H7BrO. It is a white to off-white crystalline solid that is used in the production of pharmaceuticals and chemical intermediates. 6-Bromo-O-cresol is a versatile compound that can be used as a precursor for the synthesis of various biologically active molecules. It is also used in the manufacturing of dyes, perfumes, and as a disinfectant and preservative in personal care and cosmetic products. 6-Bromo-O-cresol is a highly corrosive and irritant substance, and proper safety precautions should be taken when handling this chemical.

InChI:InChI=1/C7H7BrO/c1-5-3-2-4-6(8)7(5)9/h2-4,9H,1H3

Upstream product

• 95-48-7 ortho-cresol 
• 95-46-5 2-methylphenyl bromide 
• 7664-93-9 sulfuric acid 
• 85911-53-1 5-bromo-6-hydroxy-toluene-3-sulfonic acid 
• 861537-87-3 3-bromo-4-hydroxy-5-methyl-benzoic acid 
• 128-08-5 N-Bromosuccinimide 
• 99-66-1 valproic acid 
• 584-08-7 potassium carbonate 
• 2695-47-8 6-Bromo-1-hexene 
• 499-76-3 4-hydroxy-3-methylbenzoic acid 
• 583-60-8 2-Methylcyclohexanone 
• 100782-06-7 2-Bromo-6-methyl-phenol; compound with methylamine 
• 608-33-3 2,6-dibromophenol 
• 917-54-4 methyllithium 

Downstream Products

• 854663-35-7 2-bromo-6-methyl-4-trityl-phenol 
• 85341-61-3 6-bromo-2-methyl-4-benzylphenol 
• 17755-10-1 2-methyl-6-phenylphenol 
• 178739-07-6 ethyl trans-trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate 
• 1158430-65-9 C₁₉H₁₉BBrOP 
• 499236-68-9 2-cyclopropyl-6-methylphenol 
• 1226800-00-5 4-bromo-2-cyclopropyl-6-methyl-phenol 
• 1260248-47-2 5-bromo-1-cyclopropyl-2-methoxy-3-methyl-benzene 
• 1260248-48-3 7-(3-chloro-phenyl)-7-(3-cyclopropyl-4-methoxy-5-methyl-phenyl)-7H-pyrrolo[3,4-b]pyrazin-5-ylamine 
• 1260248-17-6 7-(3-cyclopropyl-4-methoxy-5-methyl-phenyl)-7-(3-pyrimidin-5-yl-phenyl)-7H-pyrrolo[3,4-b] pyrazin-5-ylamine 
• 1379772-90-3 N-ethyl-3,9-dimethyldibenz[b,f][1,4]oxazepin-11(10H)-one 
• 1379773-12-2 N-ethyl-2-(2-bromo-6-methylphenoxy)-4-methylbenzamide 
• 1443366-06-0 C₁₀H₁₅BrOSi 
• 556812-44-3 2-methyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant articles and documents

Aryne 1,2,3,5-Tetrasubstitution Enabled by 3-Silylaryne and Allyl Sulfoxide via an Aromatic 1,3-Silyl Migration

Although benzyne has been well-known to serve as a synthon that can conveniently prepare various 1,2-difunctionalized benzenes, the sites other than its formal triple bond remain silent in typical benzyne transformations. An unprecedented aryne 1,2,3,5-tetrasubstitution was realized from 3-silylbenzyne and aryl allyl sulfoxide, the mechanistic pathway of which includes a regioselective aryne insertion into the SO bond, a [3,6]-sigmatropic rearrangement, and a thermal aromatic 1,3-silyl migration cascade.

Chiral Phosphine–Phosphite Ligands in Asymmetric Gold Catalysis: Highly Enantioselective Synthesis of Furo[3,4-d]-Tetrahydropyridazine Derivatives through [3+3]-Cycloaddition

The AuI-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions.

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.