99-58-1

Basic information

• Product Name: 3-BROMO-4-METHOXYBENZOIC ACID
• Synonyms: RARECHEM AL BO 0751;TIMTEC-BB SBB009955;3-BROMO-4-METHOXYBENZOIC ACID;3-BROMO-P-ANISIC ACID;AKOS BBB/210;AKOS 211-11;3-Bromo-4-methoxybenzoic acid, 98+%;3-BROMO-P-ANISIC ACID, 98+%
• CAS NO: 99-58-1
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• EINECS: 202-768-4
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds
• Mol File: 99-58-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 220-222 °C(lit.)
• Boiling Point: 326 °C at 760 mmHg
• Flash Point: 151 °C
• Appearance: white powder
• Density: 1.625 g/cm³
• Vapor Pressure: 9.02E-05mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), methanol (Slightly)
• PKA: 4.08±0.10(Predicted)
• BRN: 2087585
• CAS DataBase Reference: 3-BROMO-4-METHOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-METHOXYBENZOIC ACID(99-58-1)
• EPA Substance Registry System: 3-BROMO-4-METHOXYBENZOIC ACID(99-58-1)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 99-58-1(Hazardous Substances Data)

Usage

Description

3-Bromo-4-methoxybenzoic acid is an organic compound characterized by the presence of a bromine atom at the 3-position and a methoxy group at the 4-position on a benzene ring, with a carboxylic acid functional group. It is a white crystalline solid and is used as a key intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-methoxybenzoic acid is used as a reagent for the preparation of benzamide compounds, which serve as ABL1, ABL2, and BCR-ABL1 inhibitors. These inhibitors are crucial in the treatment of cancer and central nervous system (CNS) disorders, as they target specific enzymes involved in the development and progression of these diseases.
In the synthesis of benzamide compounds, 3-bromo-4-methoxybenzoic acid acts as a starting material, which can be further modified and functionalized to create the desired active pharmaceutical ingredients (APIs). The benzamide class of compounds has been found to possess significant biological activity, making them valuable in the development of new therapeutic agents for various medical conditions.

InChI:InChI=1/C8H7BrO3/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4H,1H3,(H,10,11)/p-1

Upstream product

• 4374-35-0 α-bromoethyl 3-bromo-4-methoxyphenyl ketone 
• 200956-55-4 3-bromo-4-methoxybenzamide 
• 100-09-4 4-methoxybenzoic acid 
• 104689-84-1 3-bromo-4,4'-dimethoxy-benzophenone 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 356541-58-7 3-bromo-4-methoxy-benzoic acid anilide 
• 7758-19-2 sodium chlorite 
• 513-35-9 2-methyl-but-2-ene 
• 34841-06-0 3-bromo-4-methoxybenzylaldehyde 
• 874-90-8 4-methoxybenzonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 578-57-4 2-bromoanisole 

Downstream Products

• 100-09-4 4-methoxybenzoic acid 
• 5197-28-4 2-bromo-4-nitroanisole 
• 36324-64-8 2-Bromo-4,6-dinitroanisole 
• 954815-08-8 3-bromo-4-methoxy-5-nitro-benzoic acid 
• 876752-69-1 3-bromo-4-methoxybenzoic acid tert-butyl ester 
• 121789-53-5 2-(3-Brom-4-methoxyphenyl)-1H-pyrrol 
• 121789-44-4 1-(3-Brom-4-methoxyphenyl)-1,4-butandion 
• 121789-34-2 1-(3-Brom-4-methoxyphenyl)-3-(1,3-dioxan-2-yl)-1-propanon 
• 121789-59-1 2,3,4-Tribrom-5-(3-brom-4-methoxyphenyl)-1H-pyrrol 
• 213598-09-5 4-methoxy-3-(trifluoromethyl)benzoic acid 
• 22934-35-6 3-ethyl-4-methoxybenzoic acid 
• 851673-57-9 1,3-bromo-N-(4-hydroxymethyl-phenyl)-4-methoxy-benzamide 
• 1156807-51-0 (3-bromo-4-methoxyphenyl)(furan-2-yl)methanone 
• 1310849-26-3 (3-bromo-4-hydroxyphenyl)(furan-2-yl)methanone 

Relevant articles and documents

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Promising hydrogen peroxide stabilizers for large-scale application: unprecedented effect of aryl alkyl ketones

Aryl alkyl ketones with substituents in the aromatic ring taken in an amount from 0.005 to 0.5% efficiently stabilize hydrogen peroxide in an aqueous solution during storage at 22–25°C for 16–24 months.