5157-57-3

Basic information

• Product Name: 2,2-Dichloro-1-(4-chlorophenyl)ethanone
• Synonyms: 2,2-Dichloro-1-(4-chlorophenyl)ethanone;Acetophenone, 2,2-dichloro-4'-chloro-
• CAS NO: 5157-57-3
• Molecular Formula: C₈H₅Cl₃O
• Molecular Weight: 223.4837
• Mol File: 5157-57-3.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 907.6°C at 760 mmHg
• Flash Point: 502.7°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 1.59E-35mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 2,2-Dichloro-1-(4-chlorophenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dichloro-1-(4-chlorophenyl)ethanone(5157-57-3)
• EPA Substance Registry System: 2,2-Dichloro-1-(4-chlorophenyl)ethanone(5157-57-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5157-57-3(Hazardous Substances Data)

Usage

General Description

2,2-Dichloro-1-(4-chlorophenyl)ethanone is a chemical compound that is often used in the production of pharmaceuticals and as a reagent in organic synthesis. It is a chlorine-substituted derivative of acetophenone and is commonly used as a building block in the synthesis of various pharmaceutical drugs. The compound is a white crystalline solid at room temperature and is primarily used in laboratory settings for its reactivity and versatility in creating a wide range of chemical compounds. It is important to handle this compound with care as it can be hazardous if not properly handled and disposed of.

InChI:InChI=1/C42H56N2O13/c1-20-11-10-12-21(2)41(52)43-32-27(19-44-14-17-54-18-15-44)36(49)29-30(37(32)50)35(48)25(6)39-31(29)40(51)42(8,57-39)55-16-13-28(53-9)22(3)38(56-26(7)45)24(5)34(47)23(4)33(20)46/h10-13,16,20,22-24,28,33-34,38,46-50H,14-15,17-19H2,1-9H3,(H,43,52)

Upstream product

• 99-91-2 para-chloroacetophenone 
• 67-56-1 methanol 
• 27704-37-6 2,2,2-trichloro-1-(4-chlorophenyl)ethanone 
• 1073-67-2 4-vinylbenzyl chloride 
• 873-73-4 4-n-chlorophenylacetylene 
• 64-19-7 acetic acid 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 28587-05-5 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one 
• 18931-60-7 1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-dione 
• 74-11-3 para-chlorobenzoic acid 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 4640-66-8 p-chlorobenzoylacetonitrile 
• 5333-82-4 2,2,2-trichloro-1-(4-chloro-phenyl)-ethanol 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 3567-18-8 4-chloro-α-(4-chlorophenyl)-α-dichloromethylbenzenemethanol 
• 64654-41-7 Methyl-phosphonic acid (Z)-2-chloro-1-(4-chloro-phenyl)-vinyl ester ethyl ester 
• 4998-15-6 4-chlorophenylglyoxal 
• 201206-11-3 1-(4-chlorophenyl)-2,2-dichloroethanone oxime 
• 41521-04-4 2,2-dichloro-1-(4-chlorophenyl)ethanol 
• 1588767-03-6 (S)-2,2-dichloro-1-(4-chlorophenyl)ethanol 
• 1588766-97-5 (R)-2,2-dichloro-1-(4-chlorophenyl)ethanol 
• 183430-89-9 2,2-dichloro-1,1-bis(4-chloro-3-nitrophenyl)ethane 
• 72-54-8 1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane 
• 1022-22-6 1-chloro-2,2-bis(p-chlorophenyl)ethylene 
• 72-55-9 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene 
• 907563-65-9 N-[2,2-dichloro-1-(4-chlorophenyl)ethylidene]isopropylamine 

Relevant articles and documents

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

Switchable Synthesis of α,α-Dihalomethyl and α,α,α-Trihalomethyl Ketones by Metal-Free Decomposition of Enaminone C=C Double Bond

The novel free radical-based cleavage of the enaminone C=C double bond is realized by using N-halosuccinimides (NXS) in the presence of benzoyl peroxide (BPO) with mild heating, enabling the tunable synthesis of α,α-dihalomethyl ketones and α,α,α-trihalomethyl ketones under different reaction conditions. The formation of these divergent products involving featured C=C double bond cleavage requires no any metal reagent, and represents one more practical example on the synthesis of poly halogenated methyl ketones via the functionalization of carbon?carbon bond. (Figure presented.).