873-38-1

Basic information

• Product Name: 2-Bromo-4-chloroaniline
• Synonyms: 2-BROMO-4-CHLOROANILINE;1-AMINO-2-BROMO-4-CHLOROBENZENE;Benzenamine, 2-bromo-4-chloro-;DISCONTINUED !2-Bromo-4-chloroaniline;2-Bromo-4-chloroaniline,98%;2-Bromo-4-chloroaniline 99%;4-Chloro-2-Bromoaniline;2-Bromo-4-chlorobenzenamine
• CAS NO: 873-38-1
• Molecular Formula: C₆H₅BrClN
• Molecular Weight: 206.47
• EINECS: 212-837-0
• Product Categories: Amines;blocks;Bromides;Anilines, Amides & Amines;Bromine Compounds;Chlorine Compounds;C2 to C6;Nitrogen Compounds;Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 873-38-1.mol

Chemical Properties

• Melting Point: 64-68 °C(lit.)
• Boiling Point: 127°C 14mm
• Flash Point: 127°C/20mm
• Appearance: Pale brown/Crystalline Powder
• Density: 1.722 g/cm³
• Vapor Pressure: 0.00944mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 1.90±0.10(Predicted)
• BRN: 2802563
• CAS DataBase Reference: 2-Bromo-4-chloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-chloroaniline(873-38-1)
• EPA Substance Registry System: 2-Bromo-4-chloroaniline(873-38-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 873-38-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-chloroaniline is used as a key intermediate in the synthesis of various pharmaceuticals, including:
2-bromo-4-chloro-N-tosylaniline: 2-Bromo-4-chloroaniline is used in the preparation of pharmaceuticals with potential therapeutic applications.
2-bromo-4-chlorothiophenol: 2-Bromo-4-chloroaniline can be used in the development of new drugs with specific therapeutic properties.
7-chloro-4a-methyl-4,4a,9,9a-tetrahydro-1H-carbazol-2(3H)-one: 2-Bromo-4-chloroaniline serves as a building block for the synthesis of novel pharmaceuticals with potential therapeutic benefits.

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

Upstream product

• 106-47-8 4-chloro-aniline 
• 10035-10-6 hydrogen bromide 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 57045-85-9 2-bromo-4-chloroacetanilide 
• 615-36-1 2-bromoaniline 

Downstream Products

• 71757-16-9 2-bromo-4-chloro-6-iodoaniline 
• 891779-90-1 3-(2-bromo-4-chlorophenylamino)quinoline 
• 1075-35-0 5-chloro-2-methylindole 
• 1003042-41-8 2-amino-5-chlorophenylboronic acid 
• 928782-97-2 4-chloro-2-(phenylethynyl)aniline 
• 384793-16-2 (2-bromo-4-chloro-phenyl)-carbamic acid tert-butyl ester 
• 180624-15-1 4-chloro-2-trimethylsilanylethynyl-phenylamine 
• 7033-51-4 6-chloro-2-phenyl-benzo[d][1,3]oxazin-4-one 
• 1379774-51-2 N-ethyl-2-(2-bromo-4-chlorophenylamino)-4-methylbenzamide 
• 1379773-20-2 N-(2-bromo-4-chlorophenyl)-2-iodobenzamide 
• 1379772-99-2 N-(2-bromo-5-methoxyphenyl)-7-chlorodibenz[b,f][1,4]oxazepin-11(10H)-one 
• 1426812-87-4 N-(5-chloro-3'-methoxybiphenyl-2-yl)-4-methylbenzenesulfonamide 
• 1426812-94-3 N-(4-chloro-2-(naphthalen-1-yl)phenyl)-4-methylbenzenesulfonamide 
• 1416878-99-3 (Z)-2-bromo-4-chloro-N-(1-nitroprop-1-en-2-yl)aniline 

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.

Flexible on-site halogenation paired with hydrogenation using halide electrolysis

Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.

Selective Thiocyanation and Aromatic Amination to Achieve Organized Annulation of Enaminone with Thiocyanate

A tandem insertion of thiocyanate to enamine was performed for the regioselective synthesis of multisubstituted benzoimidazo[2,1-b]thiazoles. This method was shown to be effective in addressing the issue of isomerization encountered in common strategies. With a change made to the leading group on the aniline fragment of enamine, the reaction achieved different transformations, thus enabling multisubstituted benzo[4,5]imidazo[2,1-b]thiazoles and thiazoles in satisfactory yields.

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

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.

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.

Nitromethane as a reagent for the synthesis of 3-nitroindoles from 2-haloarylamine derivatives

A new approach to the synthesis of 3-nitroindoles using palladium-catalyzed arylation of nitromethane with N-(2-bromoaryl)imidates was developed. A convenient and rapid method for cyclization of ethyl N-(2-nitromethylaryl)acetimidates to 2-methyl-3-nitro-1H-indoles was proposed.

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

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.