38762-41-3

Basic information

• Product Name: 4-Bromo-2-chloroaniline
• Synonyms: 4-BROMO-2-CHLOROANILINE;4-Bromo-2-chloroaniline 98%;4-BROMO-2-CHLOROANILINE, 98+%;Benzenamine, 4-bromo-2-chloro-;1-Amino-4-bromo-2-chlorobenzene;4-Bromo-2-chloroaniline,99%;4-Bromo-2-chloroanilinev;4-Bromo-2-chloroanil
• CAS NO: 38762-41-3
• Molecular Formula: C₆H₅BrClN
• Molecular Weight: 206.47
• EINECS: 254-118-4
• Product Categories: Amines;blocks;Bromides;Anilines, Aromatic Amines and Nitro Compounds;Benzene series;Anilines, Amides & Amines;Bromine Compounds;Chlorine Compounds;C2 to C6;Nitrogen Compounds;Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 38762-41-3.mol

Chemical Properties

• Melting Point: 70-72 °C(lit.)
• Boiling Point: 241.8 °C at 760 mmHg
• Flash Point: 100 °C
• Appearance: Slightly yellow to light brown/Crystalline Powder
• Density: 1.6567 (rough estimate)
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.95±0.10(Predicted)
• BRN: 3117740
• CAS DataBase Reference: 4-Bromo-2-chloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-chloroaniline(38762-41-3)
• EPA Substance Registry System: 4-Bromo-2-chloroaniline(38762-41-3)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-20/21
• Safety Statements: 36-23
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 38762-41-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-chloroaniline is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
4-Bromo-2-chloroaniline is used as a starting material in the preparation of other organic compounds, such as 3,4-dichloro-α-trichloromethylbenzyl alcohol. 4-Bromo-2-chloroaniline can be further utilized in various chemical reactions to produce a wide range of products with different applications.

InChI:InChI=1/C6H5BrClN/c7-4-1-5(8)3-6(9)2-4/h1-3H,9H2

Upstream product

• 95-51-2 o-chloroaniline 
• 106-40-1 4-bromo-aniline 
• 103-84-4 Acetanilid 
• 103-88-8 4-bromoacetanilide 
• 588-07-8 3-Chloroacetanilide 
• 825-41-2 3-chloro-4-nitroaniline 
• 108-86-1 bromobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 7647-01-0 hydrogenchloride 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 89465-97-4 4-bromo-2-chloro-1-nitrobenzene 
• 80862-31-3 3-(4-bromophenyl)-1,2,3,4-oxatriazolium-5-one 

Downstream Products

• 89465-97-4 4-bromo-2-chloro-1-nitrobenzene 
• 721960-43-6 2‐chloro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)aniline 
• 536746-56-2 2-(4-Bromo-2-chloro-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 330794-09-7 tert-butyl-N-(4-bromo-2-chlorophenyl)carbamate 
• 934664-20-7 2-[(4-bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acid 
• 1030382-37-6 3-(4-bromo-2-chloro-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester 
• 1033586-53-6 N-(4-bromo-2-chlorophenyl)-2,6-dichlorobenzamidine 
• 1080521-77-2 2-chloro-4-propylaniline 
• 60197-25-3 2-chloro-4-octylaniline 
• 917980-13-3 4-amino-2-(4-bromo-2-chlorophenylamino)-3-fluoro-5-nitrobenzonitrile 
• 874-18-0 2-chloro-4,6-dibromoaniline 
• 1356928-12-5 2-(4'-bromo-2'-chloroanilino)quinoline 
• 1314987-48-8 tert-butyl-(4-bromo-2-chloro-phenyl)-N-tert-butoxycarbonyl-carbamate 
• 1386950-68-0 tert-butyl 4-(4-(bis(tert-butoxycarbonyl)amino)-3-chlorophenyl)piperazine-1-carboxylate 

Relevant articles and documents

A Practical Procedure for Regioselective Bromination of Anilines

A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

A metal-free aerobic oxidative bromination of anilines and aryl ketones with 2-methylpyridinium nitrate as a reusable ionic liquid

An aerobic oxidative bromination of anilines and aryl ketones catalyzed by recyclable 2-methylpyridinium nitrate ionic liquid is achieved in water using hydrobromic acid as the bromine source and molecular oxygen as the oxidant. The catalytic system shows good efficiency and atom economy.

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones

The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.

Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach

A simple, environmentally benign methodology has been developed to synthesize some bromoorganic compounds which have potential as antimicrobial agents. The required compounds were obtained through microwave (MW) irradiation, on-water reactions and using cetyltrimethylammonium tribromide (CTMATB) as the bromine source. The high yield of the product could be achieved within short reaction times, thus representing the main attribute of the present synthetic approach. The compounds were evaluated for in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Bacillus subtilis. Further, in silico studies were carried out to elucidate the interactions of the compounds with the bacterial proteins.

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst

A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.

Method for synthesizing monobrominated aniline compound

The invention discloses a method for synthesizing a monobrominated aniline compound. The method comprises the following steps: by taking an aniline compound as a raw material, and taking zinc aluminum hydrotalcite ZnAl-BrO3-LDHs with a bromate inserted layer and an alkali metal bromide as bromine sources in a mixed solvent of water and an organic solvent, reacting for 1-3h at 10-50 DEG C; after ending the reaction, extracting a reaction mixed solution A by using dichloromethane; adding a column chromatography silica gel into dichloromethane phase; removing the solvent in the manner of reduced pressure distillation; and acquiring a mono-bromination objective product in the manner of column chromatography separation by using an eluent composed of petroleum ether and ethyl acetate at the ratio of 10:1. The invention realizes a high-selectivity oxidative bromination method by adopting an aniline compound under the effects of ZnAl-BrO3-LDHs and potassium bromide; the monobrominated aniline compound is prepared; the reaction popularity is high and the raw material is low in cost and is easily acquired; the reaction condition is mild; the reaction yield is high; the atom utilization ratio is high; and the chemical selectivity is excellent and the environment is protected.

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.