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

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

Uses

Used in Pharmaceutical Industry:
3-Buten-2-one, 1-chlorois utilized as a chemical intermediate for the production of various pharmaceuticals. Its reactivity and functional groups make it a valuable component in the synthesis of a range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Pesticide Industry:
In the pesticide sector, 3-Buten-2-one, 1-chloroserves as a key intermediate in the formulation of different types of pesticides. Its chemical properties allow for the creation of effective pest control agents, enhancing agricultural productivity and crop protection.
Used in Organic Synthesis:
3-Buten-2-one, 1-chlorois employed as a reagent in organic synthesis, where it participates in various chemical reactions to form a multitude of organic compounds. Its versatility in organic chemistry makes it an essential tool for researchers and chemists in the synthesis of complex organic molecules.
Used in Manufacturing of Other Organic Compounds:
As a precursor, 3-Buten-2-one, 1-chlorois instrumental in the manufacturing process of a variety of other organic compounds. Its role in the synthesis of these compounds is critical, as it provides the necessary building blocks for the creation of a wide array of chemical products.

Upstream product

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

Downstream Products

• 99417-86-4 1-chloro-4-formyloxy-butan-2-one 
• 38982-28-4 1-acetoxybut-3-en-2-one 
• 10469-98-4 1-Chloracetyl-4-methylcyclohex-3-en 
• 61955-91-7 1-chloro-4-(phenylthio)butan-2-one 
• 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 
• 99187-89-0 1-bicyclo[2.2.2]oct-5-en-2-yl-2-chloro-ethanone 
• 61955-88-2 4-Acetoxy-1-chloro-2-butanon 
• 90972-96-6 2-chloro-1-(3,4-dimethyl-cyclohex-3-enyl)-ethanone 
• 1614-91-1 1-Chloracetyl-cyclohex-3-en 

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.

Alcohol dehydrogenase- and rat liver cytosol-dependent bioactivation of 1-chloro-2-hydroxy-3-butene to 1-chloro-3-buten-2-one, a bifunctional alkylating agent

1,3-Butadiene (BD) is an air pollutant whose toxicity and carcinogenicity have been considered primarily mediated by its reactive metabolites, 3,4-epoxy-1-butene and 1,2,3,4-diepoxybutane, formed in liver and extrahepatic tissues by cytochromes P450s. A possible alternative metabolic pathway in bone marrow and immune cells is the conversion of BD to the chlorinated allylic alcohol 1-chloro-2-hydroxy-3-butene (CHB) by myeloperoxidase in the presence of hydrogen peroxide and chloride ion. In the present study, we investigated the in vitro bioactivation of CHB by alcohol dehydrogenases (ADH) under in vitro physiological conditions (pH 7.4, 37 °C). The results provide clear evidence for CHB being converted to 1-chloro-3-buten-2-one (CBO) by purified horse liver ADH and rat liver cytosol. CBO readily reacted with glutathione (GSH) under assay conditions to form three products: two CBO-mono-GSH conjugates [1-chloro-4-(S-glutathionyl)butan-2-one (3) and 1-(S-glutathionyl)-3-buten-2-one (4)] and one CBO-di-GSH conjugate [1,4-bis(S-glutathionyl)butan-2-one (5)]. CHB bioactivation and the ratios of the three GSH conjugates formed were dependent upon incubation time, GSH and CHB concentrations, and the presence of ADH or rat liver cytosol. The ADH enzymatic reaction followed Michaelis-Menten kinetics with a Km at 3.5 mM and a kcat at 0.033 s-1. After CBO was incubated with freshly isolated mouse erythrocytes, globin dimers were detected using SDS-PAGE and silver staining, providing evidence that CBO can act as a protein cross-linking agent. Collectively, the results provide clear evidence for CHB bioactivation by ADH and rat liver cytosol to yield CBO. The bifunctional alkylating ability of CBO suggests that it may play a role in BD toxicity and/or carcinogenicity.