939-52-6

Basic information

• Product Name: GAMMA-CHLOROBUTYROPHENONE
• Synonyms: 1-Butanone, 4-chloro-1-phenyl-;omega-Chlorobutyrophenone;GAMMA-CHLOROBUTYROPHENONE;4-CHLORO-1-PHENYL-1-BUTANONE;4-CHLORO-1-OXO-1-PHENYLBUTANE;4-CHLORO-1-PHENYLBUTANONE;4-CHLOROBUTYROPHENONE;4-CHLOROBUTYROPHENONE, TECH.
• CAS NO: 939-52-6
• Molecular Formula: C₁₀H₁₁ClO
• Molecular Weight: 182.65
• EINECS: 213-362-1
• Mol File: 939-52-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: 19-20 °C(lit.)
• Boiling Point: 130-133 °C4 mm Hg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.137 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.544(lit.)
• BRN: 878974
• CAS DataBase Reference: GAMMA-CHLOROBUTYROPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: GAMMA-CHLOROBUTYROPHENONE(939-52-6)
• EPA Substance Registry System: GAMMA-CHLOROBUTYROPHENONE(939-52-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• RIDADR: UN 2927 6.1/PG 1
• WGK Germany: 3
• Hazardous Substances Data: 939-52-6(Hazardous Substances Data)

Usage

Uses

4-Chlorobutyrophenone may be used in the preparation of silyl enol ether, Z-4-chloro-1-phenyl-1-trimethylsilyloxybut-1-ene. It may be used as starting material in the preparation of 8-arylimidazopyridines.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 1455, 1957 DOI: 10.1021/ja01563a049

General Description

4-Chlorobutyrophenone is a chloro ketone. Preparation of 4-chlorobutyrophenone is reported.

Purification Methods

Fractionate the ketone several times using a short column. It recrystallises from pet ether at -20o as glistening white rosettes and is filtered at 0o, and dried in a vacuum desiccator over H2SO4. The semicarbazone has m 136-137o. [Conant et al. J Am Chem Soc 46 1882 1924, Cloke J Chem Soc 1174 1929, Hart & Curtis J Am Chem Soc 79 931 1957, Beilstein 7 IV 711.]

InChI:InChI=1/C10H11ClO/c1-2-3-10(12)8-4-6-9(11)7-5-8/h4-7H,2-3H2,1H3

Upstream product

• 628-20-6 4-Chlorobutyronitrile 
• 60-29-7 diethyl ether 
• 98-88-4 benzoyl chloride 
• 75-19-4 cyclopropane 
• 7647-01-0 hydrogenchloride 
• 98-80-6 phenylboronic acid 
• 65488-05-3 4-iodobutyrophenone 
• 2051-95-8 succinylbenzene 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 109-70-6 1.3-chlorobromopropane 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 71-43-2 benzene 
• 1501-05-9 5-oxo-5-phenylvaleric acid 

Downstream Products

• 59995-69-6 4-(4-hydroxy-4-p-tolyl-piperidino)-1-phenyl-butan-1-one 
• 31293-75-1 4-piperidinobutyrophenone hydrochloride 
• 848785-33-1 [2-(4-chlorophenyl)-tetrahydrofuran-3-yl]phenylmethanone 
• 144667-63-0 trans-3-benzoyl-2-(p-chlorophenyl)tetrahydrofuran 
• 144667-63-0 cis-3-benzoyl-2-(p-chlorophenyl)tetrahydrofuran 
• 3481-02-5 cyclopropyl phenyl ketone 
• 144667-61-8 trans-3-benzoyl-2-phenyltetrahydrofuran 
• 144667-61-8 cis-3-benzoyl-2-phenyloxolane 
• 38111-75-0 (S)-1-Cyclopropyl-2-methanesulfinyl-1-phenyl-ethanol 
• 87696-87-5 1,2,3,3a-Tetrahydro-3a-phenylpyrrolo<2,1-b>benzothiazole 
• 76293-51-1 3,4-dihydro-5-phenyl-2H-1,6-benzothiazocine 
• 439579-50-7 3-(3-chloropropyl)-3-phenyl-4,5,6,7-tetrahydro-3H-isobenzofuran-2-one 
• 10413-00-0 5-oxo-5-phenylpentanenitrile 

Relevant articles and documents

Copper-catalyzed radical ring-opening halogenation with HX

An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) is described. This protocol features redox-neutral conditions, green halogen sources, and a broad substrate scope, providing practical access to distally chlorinated, brominated and iodinated alkyl ketones and alkyl nitriles with moderate to good yields. This journal is

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.

Visible-light-enhanced ring opening of cycloalkanols enabled by br?nsted base-tethered acyloxy radical induced hydrogen atom transfer-electron transfer

A metal-free ring opening/halogenation of cycloalkanols, which combines both PPO/TBAX oxidant system and blue LEDs irradiation, is presented. This method produces diverse γ, α, and even more remotely halogenated ketones in moderate to excellent yields under mild conditions. Interestingly, experimental and computational studies demonstrate the novel ring size-dependent concerted/stepwise (four-/five- to eight-membered rings) hydrogen atom transfer-electron transfer induced by Br?nsted base-tethered acyloxy radical, which indicates distinct advantages brought by the cyclic structure of diacyl peroxides.