4628-21-1

Basic information

• Product Name: (Z)-1-chlorobut-2-ene
• Synonyms: (Z)-1-chlorobut-2-ene;(2Z)-1-Chloro-2-butene;(Z)-1-Chloro-2-butene;(Z)-2-Butenyl chloride;(Z)-3-Methylallyl chloride;cis-Crotyl chloride;2-Butene, 1-chloro-, (Z)-;Ai3-15322
• CAS NO: 4628-21-1
• Molecular Formula: C₄H₇Cl
• Molecular Weight: 90.55138
• EINECS: 225-041-3
• Mol File: 4628-21-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: -96°C (estimate)
• Boiling Point: 69.71°C (estimate)
• Flash Point: 105.4°C
• Appearance: /
• Density: 0.9366
• Vapor Pressure: 80.6mmHg at 25°C
• Refractive Index: 1.4365
• CAS DataBase Reference: (Z)-1-chlorobut-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-chlorobut-2-ene(4628-21-1)
• EPA Substance Registry System: (Z)-1-chlorobut-2-ene(4628-21-1)

Safety Data

• Hazardous Substances Data: 4628-21-1(Hazardous Substances Data)

Usage

Description

(Z)-1-chlorobut-2-ene, also known as 2-chloro-1-butene, is a chemical compound characterized by its molecular formula C4H7Cl. It is a colorless liquid with a pungent odor and is recognized for its versatile applications in the chemical industry.

Uses

Used in Polymer and Plastics Industry:
(Z)-1-chlorobut-2-ene is used as a monomer for the production of various polymers and plastics. Its chemical structure allows it to be a key component in the synthesis of these materials, contributing to their properties and performance.
Used in Solvent Applications:
(Z)-1-chlorobut-2-ene is also utilized as a solvent in various chemical processes. Its ability to dissolve other substances makes it a valuable asset in the industry, facilitating reactions and improving the efficiency of certain processes.
Used in Organic Chemical Manufacturing:
(Z)-1-chlorobut-2-ene is employed in the manufacturing of other organic chemicals, where it serves as an intermediate or a building block for more complex molecules. Its reactivity and functional groups make it a useful starting material for the synthesis of a range of chemical products.
Safety Precautions:

InChI:InChI=1/C4H7Cl/c1-2-3-4-5/h2-3H,4H2,1H3/b3-2-

Upstream product

• 106-98-9 1-butylene 
• 764-01-2 methyl propargyl alcohol 
• 4088-60-2 cis-2-buten-1-ol 
• 55538-23-3 1-[((Z)-But-2-enyl)oxy]-2,4-dinitro-benzene 
• 106-99-0 buta-1,3-diene 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 598-32-3 2-hydroxy-3-butene 
• 590-18-1 (Z)-2-Butene 

Downstream Products

• 100863-96-5 (+/-)-3-but-2c-enyl-2-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester 
• 22575-33-3 but-2c-enyl-(2,6-dimethyl-phenyl)-ether 
• 4810-09-7 3-methyl-1-heptene 
• 39761-61-0 cis-5,5-Dimethyl-hexen-(2) 
• 39782-43-9 trans-5,5-dimethyl-2-hexene 
• 16745-94-1 3,4-Dimethyl-hexen-(1) 
• 97964-94-8 (Z)-1-(phenylsulfinyl)but-2-ene 
• 28809-09-8 2-[(Z)-(2-butenyl)oxy]benzaldehyde 
• 66527-92-2 (Z)-(but-2-en-1-yloxy)benzene 

Relevant articles and documents

Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis

We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.

Regio- and Stereoselective Substitution of Hydroxy Group in Allyl Alcohols by Halogen

A preparative method for regio- and stereoselective substitution of the hydroxy group by halogen in allyl alcohols under the action of triphenylphosphine complexes with ethyl trichloroacetate or trichloroacetonitrile has been developed.The regio- and stereoselectivity of substitution of hydroxy group by halogen with triphenylphosphine complexes and compounds containing trichloromethyl group is compared.

Surface-Catalyzed Hydrochlorination of Alkenes. The Reaction of the Gases Hydrogen Chloride and 1,3-Butadiene

Mixtures of gaseous hydrogen chloride and gaseous 1,3-butadiene at total pressures less than 1 atm and at temperatures between 294 and 334 K yield mixtures of 3-chloro-1-butene and (E)- and (Z)-1-chloro-2-butene.The ratio of the product of putative 1,2-addition to those of 1,4-addition is approximately unity with only the amount of (Z)-1-chloro-2-butene increasing from ca. 2percent of the total reaction product mixture at the lower temperature to ca. 4percent at the higher temperature.Kinetic measurements have been made by observing the reaction throughout its course utilizing FT-IR spectroscopy.It is concluded that surface catalysis is required for product formation and that the reaction, which occurs at the walls, is most probably between multilayer adsorbed hydrogen chloride and gaseous or weakly adsorbed 1,3-butadiene.