25476-89-5

Basic information

• Product Name: 3-Buten-2-one, 1-chloro-
• CAS NO: 25476-89-5
• Molecular Formula: C4H5ClO
• Molecular Weight: 104.536
• Mol File: 25476-89-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Buten-2-one, 1-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-2-one, 1-chloro-(25476-89-5)
• EPA Substance Registry System: 3-Buten-2-one, 1-chloro-(25476-89-5)

Safety Data

• Hazardous Substances Data: 25476-89-5(Hazardous Substances Data)

Usage

General Description

3-Buten-2-one, 1-chloro-, also known as chloroacetyl ketone, is a chemical compound with the molecular formula C4H5ClO. It is a colorless liquid with a pungent and irritating odor. 3-Buten-2-one, 1-chloro- is primarily used as a chemical intermediate in the production of various pharmaceuticals and pesticides. It is also used as a reagent in organic synthesis and as a precursor in the manufacturing of other organic compounds. Due to its potentially hazardous properties, including its irritant and corrosive effects, handling and use of 3-Buten-2-one, 1-chloro- should be conducted with proper safety precautions and in accordance with applicable regulations.

Upstream product

• 671-56-7 1-chloro-2-hydroxy-3-butene 
• 126-99-8 chloroprene 

Downstream Products

• 10469-98-4 1-Chloracetyl-4-methylcyclohex-3-en 
• 619333-09-4 1-chloro-4-(S-glutathionyl)butan-2-one 
• 1407494-96-5 1-(S-glutathionyl)-3-buten-2-one 
• 144692-22-8 1-Benzyl-3a-(3,4-dimethoxy-phenyl)-1,2,3,3a,4,5-hexahydro-indol-6-one 
• 61955-91-7 1-chloro-4-(phenylthio)butan-2-one 
• 61955-88-2 4-Acetoxy-1-chloro-2-butanon 
• 38982-28-4 1-acetoxybut-3-en-2-one 
• 90972-96-6 2-chloro-1-(3,4-dimethyl-cyclohex-3-enyl)-ethanone 
• 1614-91-1 1-Chloracetyl-cyclohex-3-en 
• 99187-89-0 1-bicyclo[2.2.2]oct-5-en-2-yl-2-chloro-ethanone 
• 99417-86-4 1-chloro-4-formyloxy-butan-2-one 

Relevant articles and documents

In vitro metabolism of chloroprene: Species differences, epoxide stereochemistry and a de-chlorination pathway

Chloroprene (1) was metabolized by liver microsomes from Sprague-Dawley rats, Fischer 344 rats, B6C3F1 mice, and humans to the monoepoxides, (1-chloro-ethenyl)oxirane (5a/5b), and 2-chloro-2-ethenyloxirane (4a/4b). The formation of 4a/4b was inferred from the identification of their degradation products. With male Sprague-Dawley and Fischer 344 rat liver microsomes, there was a ca. 3:2 preference for the formation of (R)-(1-chloroethenyl)oxirane (5a) compared to the (S)-enantiomer (5b). A smaller but distinct enantioselectivity in the formation of (S)-(1-chloro-ethenyl)oxirane occurred with liver microsomes from male mouse (R:S, 0.90:1) or male human (R:S, 0.86:1). 2-Chloro-2-ethenyloxirane was very unstable in the presence of the microsomal mixture and was rapidly converted to 1-hydroxybut-3-en-2-one (11) and 1-chlorobut-3-en-2-one (12). An additional rearrangement pathway of 2-chloro-2-ethenyloxirane gave rise to 2-chlorobut-3-en-1-al (14) and 2-chlorobut-2-en-1-al (15). Further reductive metabolism of these metabolites occurred to form 1-hydroxybutan-2-one (17) and 1-chlorobutan-2-one (18). In the absence of an epoxide hydrolase inhibitor, the microsomal incubations converted (1-chloroethenyl)oxirane to 3-chlorobut-3-ene-1,2-diol (21a/21b). When microsomal incubations were supplemented with glutathione, 1-hydroxybut-3-en-2-one was not detected because of its rapid conjugation with this thiol scavenger.