25129-61-7

Basic information

• Product Name: (Z)-2-chlorobut-2-enal
• Synonyms: (Z)-2-chlorobut-2-enal;(Z)-2-Chlorocrotonaldehyde;Crotonaldehyde, 2-chloro-, (Z)-
• CAS NO: 25129-61-7
• Molecular Formula: C₄H₅ClO
• Molecular Weight: 104.5349
• Mol File: 25129-61-7.mol

Chemical Properties

• Boiling Point: 148.5°Cat760mmHg
• Flash Point: 43.8°C
• Appearance: /
• Density: 1.081g/cm³
• CAS DataBase Reference: (Z)-2-chlorobut-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-chlorobut-2-enal(25129-61-7)
• EPA Substance Registry System: (Z)-2-chlorobut-2-enal(25129-61-7)

Safety Data

• Hazardous Substances Data: 25129-61-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-2-chlorobut-2-enal serves as an intermediate in the synthesis of a variety of pharmaceuticals, contributing to the development of new medications and therapies.
Used in Plastics Industry:
(Z)-2-chlorobut-2-enal is also utilized as an intermediate in the production of plastics, playing a role in the creation of various plastic materials and products.
Used in Agrochemicals Industry:
(Z)-2-chlorobut-2-enal is employed in the agrochemical sector as an intermediate for synthesizing different agrochemicals, which are essential for enhancing crop protection and yield.

Upstream product

• 7364-07-0 trans-2-chloro-1,1-diethoxy-2-butene 
• 63995-81-3 1-chloro-2-ethoxy-1-fluoro-3-methyl-cyclopropane 
• 18777-99-6 (Z)-2-chloro-1-(2-chloro-ethoxy)-1-ethoxy-but-2-ene 
• 123-73-9 trans-Crotonaldehyde 
• 75455-41-3 rac-2-chlorobut-3-en-1-ol 
• 56152-76-2 2-chloro-1,1-diethoxy-but-2-ene 

Downstream Products

• 4394-85-8 4-morpholinecarboxaldehyde 
• 22039-43-6 1,2-dimorpholino-ethene 
• 114746-04-2 2-morpholinobut-2-enal 
• 114745-98-1 (E)-2-Morpholino-2-butenal 
• 124974-85-2 (E)-2-Dibutylamino-but-2-enal 
• 114746-00-8 (E)-N,N,N',N'-Tetrabutyl-ethene-1,2-diamine 
• 761-65-9 N,N-dibutylformamide 
• 617-84-5 N-formyldiethylamine 
• 20155-68-4 tetra-N-ethyl-trans-ethene-1,2-diamine 
• 114746-01-9 (E)-2-Diethylamino-but-2-enal 
• 204458-18-4 5-chloro-2-pyridinyl phenyl sulfone 
• 150004-36-7 (R)-4-Benzyl-3-((Z)-(2R,3R)-4-chloro-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one 
• 2591-86-8 N-Formylpiperidine 
• 52900-92-2 2-Piperidinobut-2-enal 

Relevant articles and documents

A New Approach to Models of the 4,5-Dihydroxycyclopentenone Core of the Kodaistatins A–D: Elucidation of the Diol Configuration in Kodaistatin A

The kodaistatins A–D are strongly anti-diabetic natural products from Aspergillus terreus that hold some promise of a novel diabetes cure. However, considerations of that kind face two drawbacks: 1) The kodaistatins A–D contain a heavily substituted pulvinone/cyclopentenone combination; 2) they are 1,2-diols, the 3D structures of which have not been assigned yet. However, we can exclude two of the four possible stereostructures. We conclude that kodaistatin A is a trans-, not a cis-diol from NMR comparisons with a pair of cis, trans-isomeric kodaistatin models, which we synthesized in 11 and 12 steps, respectively. The stereocenters of the diol moiety arose from stereocomplementary, highly diastereoselective aldol additions of a lithium enolate or the corresponding silyl ketene acetal. The cyclopentenone moieties stemmed from intramolecular aldol additions and ensuing dehydrations. The requisite enolates were obtained by the reduction of α-bromoketones with samarium diiodide.

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.

A New Platinum Complex Catalyzed Reaction Involving Nucleophilic Substitution at the Central Carbon Atom of the π-Allyl Ligand

The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in the presence of a platinum-(0) complex gave furan derivatives. The key feature of this new platinum-catalyzed reaction is the nucleophilic substitution at the central carbon atom of π-allyl complexes. The regioselectivity of the nucleophilic attacks (central or terminal) is dependent on the pKa of the nucleophile. In addition, a labeling experiment revealed that a rapid syn-anti isomerization of the (π-allyl) platinum complexes occurs.

Reaction of Benzeneseleninyl Chloride with Olefins in the Presence of a Lewis Acid. A Novel One Step Vinylic Chlorination

In the presence of aluminum chloride benzeneseleninyl chloride was found to be an exellent vinylic chlorinating reagent of olefins under mild conditions.However, such olefins as styrene, trans-stilbene, and trans-1-phenylpropene afforded dichloro adducts under similar conditions.A plausible reaction mechanism involving positive chlorine intermediate is proposed.