22459-81-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-BROMO-3-CHLOROACETANILIDE is used as a key intermediate in the synthesis of various pharmaceutical and agrochemical products, contributing to the development of new drugs and pesticides.
Used in Dye and Pigment Industries:
4-BROMO-3-CHLOROACETANILIDE is utilized as a building block in the synthesis of dyes and pigments, playing a crucial role in the production of colorants for various applications.
Used in Organic Synthesis:
As a reagent, 4-BROMO-3-CHLOROACETANILIDE is employed in organic synthesis processes, facilitating the creation of a range of organic compounds for diverse uses.
Used as a Precursor in Chemical Production:
4-BROMO-3-CHLOROACETANILIDE serves as a precursor for the production of other chemical compounds, enabling the synthesis of a variety of substances for industrial and research purposes.

Upstream product

• 21402-26-6 4-bromo-3-chloroaniline 
• 108-24-7 acetic anhydride 
• 103-88-8 4-bromoacetanilide 
• 588-07-8 3-Chloroacetanilide 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 1331753-30-0 N-(11-phenyl-5H-dibenzo[b,e][1,4]diazepin-8-yl)acetamide 
• 1331753-48-0 N-(4-((2-benzoylphenyl)amino)-3-chlorophenyl)acetamide 
• 1300731-18-3 N-(3-chloro-4-(2-hydroxyethyl)phenyl)acetamide 
• 1300731-19-4 C₁₀H₁₀ClNO 
• 1187368-76-8 N-(4-bromo-3-chloro-phenyl)-N-methyl-acetamide 
• 80026-15-9 2,4-dibromo-3-chloro-aniline 
• 56978-48-4 4-bromo-2,3-dichloro-phenylamine 
• 19230-27-4 2-chloro-1,3-dibromobenzene 
• 56961-77-4 1-bromo-2,3-dichlorobenzene 
• 1940-27-8 2,5-dichloro-4-bromo-aniline 
• 1435-50-3 2-bromo-1,4-dichlorobenzene 
• 20925-27-3 4-amino-2-chlorobenzonitrile 
• 51572-25-9 2-chloro-4-isocyanatobenzonitrile 
• 22304-33-2 C₉H₇ClN₂O 

Relevant academic research and scientific papers

Crystal packing: An examination of the packing of molecules approximately isosteric with 4,5-dichlorophthalic anhydride

The crystal structures of five 5,6-disubstituted benzofurazan 1-oxides are presented and compared with five previously reported structures: three polymorphs of 5,6-dichlorobenzofurazan 1-oxide plus 4,5-dichloro- and 4,5-dibromophthalic anhydride. All but one of these compounds pack with similar two-dimensional layers. The benzofurazan oxides all show disorder about a crystallographic twofold or pseudo-twofold axis. In addition, six complexes of phthalic anhydride and benzofurazan oxides are reported. With the packing in the complexes principally directed by the π complexing, the disorder, invariably found in the uncomplexed benzofurazan oxides, is diminished, and, in two cases, eliminated.

Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids

Site-selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long-standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2?H bonds of aromatic amines occurs. Furthermore, the superacid-promoted (poly)protonation of the molecules acts as a protection, favoring the late-stage selective halogenation of natural alkaloids and active pharmaceutical ingredients.

A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents

A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives

A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.

Regioselective and efficient bromination of anilides on water using HBr and Selectfluor

A metal-, additive-, and Br2-free highly regioselective bromination of anilides using HBr and Selectfluor is presented. This reaction proceeded under mild conditions with high efficiency and good functional group tolerance, and water served as the solvent. In general, with substrates bearing no para-substituent, para-mono-bromination occurred exclusively, while ortho-mono-brominated anilides were the only products when para-positions were blocked. The incorporation of a stronger orienting group might result in a reversed regioselectivity, and the reaction was sensitive to steric hindrance.

Tandem optimization of target activity and elimination of mutagenic potential in a potent series of N-aryl bicyclic hydantoin-based selective androgen receptor modulators

Pharmacokinetic studies in cynomolgus monkeys with a novel prototype selective androgen receptor modulator revealed trace amounts of an aniline fragment released through hydrolytic metabolism. This aniline fragment was determined to be mutagenic in an Ames assay. Subsequent concurrent optimization for target activity and avoidance of mutagenicity led to the identification of a pharmacologically superior clinical candidate without mutagenic potential.

Studies on enamides. VI. An improvised methodology for orton rearrangement under neutral condition

A highly efficient methodology in neutral medium has been developed for the synthesis of bromoanilides from the corresponding anilides using N-bromosuccinimide in carbon tetrachloride under irradiation with visible light. The products are obtained in highly pure crystalline state with an excellent yield.

Treatment of influenza with 2-estersubstituted-3,4-dihydro-3-oxoquinoxalines

3,4-Dihydro-3-oxoquinoxalines carrying a carboxylic acid or ester function in the 2 position, used as antiviral agents, particularly against influenza virus, both A and B strains.

Antiviral combinations

Antiviral combinations containing a 2-ester-substituted-3,4-dihydro-3-oxoquinoxaline and a hindered amine.