56961-26-3

Basic information

• Product Name: 2-Bromo-3-chlorobenzoicacid
• Synonyms: Benzoic acid, 2-bromo-3-chloro-
• CAS NO: 56961-26-3
• Molecular Formula: C₇H₄BrClO₂
• Molecular Weight: 235.464
• Mol File: 56961-26-3.mol

Chemical Properties

• Boiling Point: 330.4 °C at 760 mmHg
• Flash Point: 153.6 °C
• Appearance: /
• Density: 1.809
• Vapor Pressure: 6.67E-05mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.48±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-3-chlorobenzoicacid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-3-chlorobenzoicacid(56961-26-3)
• EPA Substance Registry System: 2-Bromo-3-chlorobenzoicacid(56961-26-3)

Safety Data

• Hazardous Substances Data: 56961-26-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-3-chlorobenzoic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its reactivity allows for the creation of new drug molecules with specific therapeutic properties. The presence of bromine and chlorine atoms makes it a valuable building block for the development of novel medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromo-3-chlorobenzoic acid serves as an intermediate for the production of pesticides and other agrochemicals. Its chemical structure can be modified to create active ingredients that protect crops from pests and diseases, contributing to increased agricultural productivity.
Used in Dye Industry:
2-Bromo-3-chlorobenzoic acid is utilized in the synthesis of dyes due to its ability to form colored compounds. Its presence in the molecular structure of dyes can influence their color, stability, and other properties, making it an important component in the production of various dyes used in different industries.
Used in Organic Compounds Production:
Due to its reactivity and versatility, 2-Bromo-3-chlorobenzoic acid is used in the production of a wide range of organic compounds. Its halogenated nature allows for various chemical reactions, making it a valuable precursor for the synthesis of specialty chemicals, fine chemicals, and other organic compounds.
Used in Medicinal Chemistry Research:
2-Bromo-3-chlorobenzoic acid has been studied for its potential biological activities, making it of interest in medicinal chemistry. Its unique structure and reactivity offer opportunities for the development of new therapeutic agents with potential applications in treating various diseases and medical conditions.

InChI:InChI=1/C7H4BrClO2/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3H,(H,10,11)

Upstream product

• 69190-56-3 2-bromo-1-chloro-3-methylbenzene 
• 535-80-8 3-chlorobenzoate 
• 570-24-1 2-Methyl-6-nitroaniline 
• 124-38-9 carbon dioxide 
• 104514-49-0 3-chloro-1,2-dibromobenzene 
• 694-80-4 2-bromo-1-chlorobenzene 

Downstream Products

• 116529-64-7 2-bromo-3-chlorobenzoyl chloride 
• 96558-73-5 2-bromo-3-chloro-aniline 
• 1107627-14-4 2-bromo-3-chlorobenzoic acid methyl ester 
• 439117-38-1 methyl 5-chloro-2-cyanobenzoate 
• 439117-39-2 [2-(aminomethyl)-5-chlorophenyl]methanol 
• 27007-53-0 methyl-2-bromo-5-chlorobenzoate 
• 1463053-89-5 tert-butyl (2-bromo-3-chlorophenyl)carbamate 
• 1448336-70-6 (2-(aminomethyl)-3-chlorophenyl)methanol 

Relevant articles and documents

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.

Halogen-metal exchange of 3-substituted 1,2-dibromoarenes: The use of long-range JCH coupling constants to determine regiochemistry

Regioselective halogen/metal exchange reactions were carried out on a series of 3-substituted-1,2-dibromoarenes. Product mixtures were quenched with CO2 to form the corresponding benzoic acid analogs to facilitate HPLC and NMR analysis. Substitution at the 3-position could readily be assigned on the basis of 2D HMBC long-range correlations, while assignment at the 2-position was not as straightforward. The use of three-bond JCH coupling constant measurements, extracted from 1-D 1H coupled 13C experiments, were necessary to render unequivocal regio assignments. Copyright

Ortho-metalation of unprotected 3-bromo and 3-chlorobenzoic acids with hindered lithium dialkylamides

Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 °C, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of s

The acidifying effects of chlorine and bromine: Little difference

Lithium diisopropylamide deprotonates ortho- and para-bromochlorobenzene randomly at the two halogen adjacent positions. Obviously for steric reasons, the bulkier base lithium 2,2,6,6-tetramethylpiperidide favors the attack in the vicinity of the chlorine rather than the bromine atom to the extent of 2:1. At -75°C, both 2-bromo-3-chlorophenyllithium and 3-bromo-2-chlorophenyllithium isomerize to give 2-bromo-6-chlorophenyllithium. The latter species can be directly generated from 1-bromo-3-chlorobenzene.

Lithiations directed by carboxylic acid, fluorine and chlorine: The regioselective synthesis of polysubstituted benzoic acids and acetophenones

Lithiation/electrophilic quenching of ortho-lithiated benzoates allows the totally regiocontrolled synthesis of a wide range of 2,3-, 2,3,4-, and 2,3,4,5-polysubstituted benzoic acids and related acetophenones. Elsevier,.

Directed lithiation of unprotected benzoic acids

Benzoic acid gives the ortho-lithiated species 1 under standard conditions (s-BuLi-TMEDA-THF, -90 deg C).Reaction of 1 at -78 deg C with either methyl iodide, dimethyl disulfide, hexachloroethane, or 1,2-dibromotetrachloroethane gives the ortho-substituted product.Intramolecular competition between the carboxylic acid and methoxy, chloro, fluoro, or diethylamido functions in ortho- and -para-substituted benzoic acids establishes the carboxylic acid group to be of intermediate capacity in directing metallation.Complimentarity of directing effects is observed with the chloro and fluoro groups in the meta-substituted benzoic acid but not with the methoxy and trifluoromethyl groups.Electrophile introduction into meta- and para-lithiated benzoates occurs with equal efficacy and comparable scope.The 2,4-dihalogenobenzoic acids undergo hydrogen/metal exchange at the position flanked by both halogen substituents. 2,2-Difluoro-1,3-benzodioxole-4-carboxylic acid undergoes lithiation adjacent to the oxygen atom.By use of such methods, routes to benzoic acids contiguously tri- and tetra-substituted with a variety of functionalities have been developed.

Regiospecific Synthesis of Mixed 2,3-Dihalobenzoic Acids and Related Acetophenones via Ortho-Metalation Reactions

Concise general routes to mixed 2,3-dihalobenzoic acids and related acetophenones-based on directed ortho-metalation and ipso-desilylation reactions are described.