90259-31-7

Basic information

• Product Name: 2-Bromo-6-methylbenzoic acid
• Synonyms: 2-BROMO-6-METHYLBENZOIC ACID;6-Bromo-o-toluic acid;3-Bromo-2-carboxytoluene, 6-Bromo-o-toluic acid
• CAS NO: 90259-31-7
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Acids & Esters;Bromine Compounds;Carboxylic Acids;Phenyls & Phenyl-Het;Pharmaceutical intermediate;C8;Carbonyl Compounds
• Mol File: 90259-31-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 108-112 °C
• Boiling Point: 307.043 °C at 760 mmHg
• Flash Point: 139.495 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 2.56±0.31(Predicted)
• BRN: 2614094
• CAS DataBase Reference: 2-Bromo-6-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-methylbenzoic acid(90259-31-7)
• EPA Substance Registry System: 2-Bromo-6-methylbenzoic acid(90259-31-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 90259-31-7(Hazardous Substances Data)

Usage

Description

2-Bromo-6-methylbenzoic acid is a chemical compound with the molecular formula C8H7BrO2, belonging to the benzoic acid derivatives. It features a unique structure with a bromine atom and a methyl group, which endows it with distinctive chemical properties. 2-Bromo-6-methylbenzoic acid is widely utilized in the pharmaceutical and agrochemical industries, as well as in organic synthesis and drug development.

Uses

Used in Pharmaceutical Industry:
2-Bromo-6-methylbenzoic acid is used as an intermediate in the synthesis of various pharmaceuticals for its unique chemical properties. It contributes to the development of new drugs by serving as a building block for complex organic molecules, enhancing the therapeutic efficacy and pharmacological properties of the final products.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromo-6-methylbenzoic acid is employed as a key intermediate in the production of pesticides and other agrochemicals. Its unique structure allows for the creation of compounds with specific pesticidal properties, improving crop protection and yield.
Used in Organic Synthesis:
2-Bromo-6-methylbenzoic acid is utilized as a versatile building block in organic synthesis. Its bromine and methyl substituents facilitate various chemical reactions, enabling the synthesis of a wide range of complex organic molecules for diverse applications.
Used in Drug Development:
As a valuable intermediate, 2-Bromo-6-methylbenzoic acid plays a crucial role in drug development. Its unique chemical properties allow for the design and synthesis of novel drug candidates with improved pharmacological profiles, contributing to the advancement of medical treatments.

InChI:InChI=1/C8H7BrO2/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4H,1H3,(H,10,11)

Upstream product

• 124-38-9 carbon dioxide 
• 61563-25-5 2,3-dibromotoluene 
• 4389-50-8 2-amino-6-methylbenzoic acid 
• 7440-44-0 pyrographite 
• 1352898-58-8 2-thieno[3,2-b]pyridin-5-yl-ethylamine 
• 583-53-9 2,3-dibromobenzene 
• 912457-17-1 2-(2,3-dibromophenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 99548-56-8 methyl 2-bromo-6-methyl-benzoate 

Downstream Products

• 144727-19-5 2-Bromo-6-(3-isopropenyl-4-methyl-pent-3-enyl)-benzoic acid 
• 99548-56-8 methyl 2-bromo-6-methyl-benzoate 
• 343850-66-8 N-[(2-bromo-6-methylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 
• 220848-33-9 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[(2-bromo-6-methylphenyl)carbonyl]-L-phenylalanine methyl ester 
• 1174734-42-9 2-bromo-6-methyl-benzoyl fluoride 
• 1338235-73-6 2-(2-tert-butylphenoxy)-6-methylbenzoic acid isopropyl ester 
• 942-13-2 isopropyl 2-methylbenzoate 
• 1338235-72-5 2-bromo-6-methylbenzoic acid isopropyl ester 
• 1417188-96-5 7-(4-Fluorophenyl)-2-(2-thieno[3,2-b]pyridin-5-ylethyl)isoindolin-1-one 
• 1172117-25-7 2-methyl-6-vinylbenzoic acid 

Relevant articles and documents

Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes

We report a catalytic asymmetric synthesis of piperidines through [4 + 2] cycloaddition of 1-azadienes and nitro-alkenes. The reaction uses earth abundant Zn as catalyst and is highly diastereo- and regioselective. A novel BOPA ligand (F-BOPA) confers high reactivity and enantioselectivity in the process. The presence of ortho substitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due to limiting the undesired coordination of 1-azadiene to the Lewis acid and thus allowing the reaction to be carried out at lower temperature. A series of secondary kinetic isotope effect studies using a range of ligands implicates a stepwise mechanism for the transformation, involving an initial Michael-type addition of the imine to the nitro-alkene followed by a cyclization event. The stepwise mechanism obviates the electronic requirement inherent to a concerted mechanism, explaining the successful cycloaddition between two electron-deficient partners. (Chemical Equation Presented).

Regioselective halogen-metal exchange reaction of 3-substituted 1,2-dibromo arenes: The synthesis of 2-substituted 5-bromobenzoic acids

Regioselective halogen-metal exchange reactions using isopropylmagnesium chloride were carried out on 3-substituted 1,2-dibromo arenes. Eleven examples are given. Georg Thieme Verlag Stuttgart.

Intramolecular Anodic Carbon-Carbon Bond-Forming Reactions of Oxidized Phenol Intermediates Leading to Spirodienones. Structural Effects on Reactivity and Evidence for a Phenoxonium Ion Intermediate

Anodic oxidation of 4-phenylphenol in methanol leads to 4-methoxy-4-phenylcyclohexa-2,5-dienones whereas anodic oxidation of 4-(2-alkenylphenyl)-phenols leads to spirocyclic 2,5-cyclohexadienones in competition with methanol addition to the 4-position.Usi