3132-77-2

Usage

InChI:InChI=1/C4H5ClO/c1-3(5)4-2-6-4/h4H,1-2H2

Upstream product

• 3491-32-5 3,4-dichloro-1,2-epoxybutane 
• 126-99-8 chloroprene 
• 1941-84-0 sodium pentanolate 

Downstream Products

• 20967-32-2 3-Chlor-1-propylthiobuten-3-ol-2 
• 51830-18-3 3-Chloro-4-phenyl-2-butene-1-ol 
• 37428-46-9 3-chloro-2-buten-1-ol 
• 71-36-3 butan-1-ol 
• 21113-91-7 3-Chlor-1-phenylseleno-buten-⁽³⁾-ol-⁽²⁾ 

Relevant academic research and scientific papers

Preparation and reactions of 2-chloro-3,4-epoxy-1-butene: a convenient route to (Z)-3-chloroallylic alcohols.

Epoxide 2 was prepared from 3,4-dichloro-1-butene (1) by epoxidation with m-CPBA and subsequent dehydrohalogenation of the intermediate dichloroepoxide with molten KOH, affording 2 in 64% overall yield (2 steps). Catalytic CuBr/SMe(2)-mediated S(N)2' addition of sp(2)- or sp(3)-hybridized Grignard reagents to 2-chloro-3,4-epoxy-1-butene (2) afforded (Z)-3-chloroallylic alcohols such as 3 in good yields and with high regio- and stereoselectivity.

DNA interstrand cross-linking activity of (1-chloroethenyl)oxirane, a metabolite of β-chloroprene

With the goal of elucidating the molecular and cellular mechanisms of chloroprene toxicity, we examined the potential DNA cross-linking of the bifunctional chloroprene metabolite, (1-chloroethenyl)oxirane (CEO). We used denaturing polyacrylamide gel electrophoresis to monitor the possible formation of interstrand cross-links by CEO within synthetic DNA duplexes. Our data suggest interstrand cross-linking at deoxyguanosine residues within 5′-GC and 5′-GGC sites, with the rate of cross-linking depending on pH (pH 5.0 > pH 6.0 > pH 7.0). A comparison of the cross-linking efficiencies of CEO and the structurally similar cross-linkers diepoxybutane (DEB) and epichlorohydrin (ECH) revealed that DEB > CEO ≥ ECH. Furthermore, we found that cytotoxicity correlates with cross-linking efficiency, supporting a role for interstrand cross-links in the genotoxicology of chloroprene.

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.

Process for the preparation of (1-chloroethenyl-) oxirane

An improved process has been invented for the production of (1-chloroethenyl)-oxirane which comprises dehydrochlorinating (1,2-dichloroethyl)-oxirane with a solution of the sodium salt of an alcohol having at least 5 carbon atoms in said alcohol and separating the (1-chloro-ethenyl)-oxirane from the reaction mixture.