4559-96-0

Basic information

• Product Name: 4'-BROMO-4-CHLOROBUTYROPHENONE
• Synonyms: P-BROMO-G-CHLOROBUTYROPHENONE;4'-BROMO-4-CHLOROBUTYROPHENONE 98%;4'-Bromo-4-chlorobutyrophenone,99%;4'-Bromo-γ-chlorobutyrophenone;γ-Chloro-4'-bromobutyrophenone;1-(4-BROMOPHENYL)-4-CHLORO-1-BUTANONE;1-(4-BROMOPHENYL)-4-CHLORO-1-OXOBUTANE;4-BROMO-GAMMA-CHLOROBUTYROPHENONE
• CAS NO: 4559-96-0
• Molecular Formula: C₁₀H₁₀BrClO
• Molecular Weight: 261.54
• EINECS: 224-930-3
• Mol File: 4559-96-0.mol

Chemical Properties

• Melting Point: 35.5-38 °C(lit.)
• Boiling Point: 352.8°Cat760mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.4780 (rough estimate)
• Refractive Index: 1.5963 (estimate)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 4'-BROMO-4-CHLOROBUTYROPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-BROMO-4-CHLOROBUTYROPHENONE(4559-96-0)
• EPA Substance Registry System: 4'-BROMO-4-CHLOROBUTYROPHENONE(4559-96-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4559-96-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-BROMO-4-CHLOROBUTYROPHENONE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs and medications, contributing to the advancement of medical treatments.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4'-BROMO-4-CHLOROBUTYROPHENONE is utilized as an intermediate for creating a wide range of chemical products. Its versatility in chemical reactions makes it a valuable asset in the development of new materials and compounds for various applications.

Upstream product

• 108-86-1 bromobenzene 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 589-87-7 1,4-bromoiodobenzene 
• 19936-14-2 1-(4-bromophenyl)cyclobutan-1-ol 

Downstream Products

• 149490-99-3 [(2S,5S)-2-(4-Bromo-phenyl)-2-(3-imidazol-1-yl-propyl)-[1,3]oxathiolan-5-yl]-methanol 
• 149490-99-3 [(2S,5R)-2-(4-Bromo-phenyl)-2-(3-imidazol-1-yl-propyl)-[1,3]oxathiolan-5-yl]-methanol 
• 168907-70-8 2-{3-[2-(4-Bromo-phenyl)-[1,3]dioxolan-2-yl]-propyl}-1-methyl-1H-imidazole 
• 168907-74-2 1-(4-bromophenyl)-4-(1-methyl-2-imidazolyl)-1-butanone 
• 168907-68-4 2-(4-bromophenyl)-2-(3-iodopropyl)-1,3-dioxolane 
• 148853-54-7 1-(4-{4-[4-(2-isopropoxyphenyl)-1-piperazinyl]-4-hydroxybutyl}benzoyl)piperidine 
• 148827-13-8 1-(4-{4-[4-(2-isopropoxyphenyl)-1-piperazinyl]-4-oxobutyl}benzoyl)piperidine 
• 62403-67-2 [5-(4-bromo-phenyl)-thiophen-2-yl]-acetic acid 
• 62404-41-5 [5-(4-bromo-phenyl)-thiophen-2-yl]-acetonitrile 
• 649569-57-3 methyl 5-(4-bromophenyl)thiophene-2-carboxylate 
• 62404-13-1 2-(4-bromo-phenyl)-5-chloromethyl-thiophene 
• 344417-31-8 2-Hydroxymethyl-5-(p-bromophenyl)thiophene 
• 38401-70-6 5-(p-Bromophenyl)thiophene-2-carboxaldehyde 
• 40133-13-9 5-(4-bromo-phenyl)-thiophene-2-carboxylic acid 

Relevant articles and documents

Preparation method of fexofenadine

The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.

Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.

A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.

Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols

A novel and regioselective approach to carbonyl-containing alkyl chlorides via silver-catalyzed ring-opening chlorination of cycloalkanols is reported. Concurrent C(sp3)-C(sp3) bond cleavage and C(sp3)-Cl bond formation efficiently occur with good yields under mild conditions, and the chlorinated products are readily transformed into other useful synthetic intermediates and drugs. The reaction features complete regioselectivity, high efficiency, and excellent practicality. (Chemical Equation Presented).

The synthesis of ω-(2-aryl-1,3-dioxolan-2-yl)alkyl purine derivatives and their activity towards HIV reverse transcriptase

Novel derivatives of 6-substituted purines were synthesized by alkylation of 6-substituted purines with various 2-(chloroalkyl)-2-aryl-1,3-dioxolanes and related compounds. Their inhibitory properties toward HIV reverse transcriptase were studied. The structure-activity relationship within the synthesized compounds was found.

Azido carbonyl compounds as DNA cleaving agents

Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.

Copper(II)-catalyzed hydrosilylation of ketones using chiral dipyridylphosphane ligands: Highly enantioselective synthesis of valuable alcohols

In the presence of PhSiH3 as the reductant, the combination of enantiomeric dipyridylphosphane ligands and Cu(OAc)2·H 2O, which is an easy-to-handle and inexpensive copper salt, led to a remarkably practical and versatile chiral catalyst system. The stereoselective formation of a selection of synthetically interesting β-, γ- or δ-halo alcohols bearing high degrees of enantiopurity (up to 99.9 % enantiomeric excess (ee)) was realized with a substrate-to-ligand molar ratio (S/L) of up to 10 000. The present protocol also allowed the hydrosilylation of a diverse spectrum of alkyl aryl ketones with excellent enantioselectivities (up to 98 % ee) and exceedingly high turn-over rates (up to 50 000 S/L molar ratio in 50 min reaction time) in air, under very mild conditions, which offers great opportunities for the preparation of various physiologically active targets. The synthetic utility of the chiral products obtained was highlighted by the efficient conversion of optically enriched β-halo alcohols into the corresponding styrene oxide, β-amino alcohol, and β-azido alcohol, respectively.

Design and synthesis of selective, high-affinity inhibitors of human cytochrome P450 2J2

The active site topology, substrate specificity, and biological roles of the human cytochrome P450 CYP2J2, which is mainly expressed in the cardiovascular system, are poorly known even though recent data suggest that it could be a novel biomarker and potential target for therapy of human cancer. This paper reports a first series of high-affinity, selective CYP2J2 inhibitors that are related to terfenadine, with Ki values as low as 160 nM, that should be useful tools to determine the biological roles of CYP2J2.

Synthesis and structure-activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)-thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate (5h), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds.