1587-29-7

Basic information

• Product Name: (E)-2,3-Dichloro-2-butene
• Synonyms: (E)-2,3-Dichloro-2-butene;trans-2,3-Dichloro-2-butene
• CAS NO: 1587-29-7
• Molecular Formula: C₄H₆Cl₂
• Molecular Weight: 125
• Mol File: 1587-29-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: -27.02°C (estimate)
• Boiling Point: 118.18°C (rough estimate)
• Appearance: /
• Density: 1.1416
• Refractive Index: 1.4582
• CAS DataBase Reference: (E)-2,3-Dichloro-2-butene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2,3-Dichloro-2-butene(1587-29-7)
• EPA Substance Registry System: (E)-2,3-Dichloro-2-butene(1587-29-7)

Safety Data

• Hazardous Substances Data: 1587-29-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-2,3-Dichloro-2-butene is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its role in this industry is crucial as it aids in the production of a range of medications that cater to different health needs.
Used in Agrochemical Industry:
In the agrochemical sector, (E)-2,3-Dichloro-2-butene is employed as an intermediate in the development of chemicals that are utilized in agriculture. These chemicals can include pesticides, herbicides, and other compounds that help in enhancing crop protection and yield.
Used in Polymer Production:
(E)-2,3-Dichloro-2-butene is also used as a monomer in the manufacturing process of polymers. Polymers are large molecules composed of repeating structural units, and this compound contributes to the formation of specific types of polymers that find applications in various industries, such as plastics, textiles, and coatings.

Upstream product

• 503-17-3 dimethylacetylene 
• 10403-60-8 2,2,3-trichloro-butane 
• 7791-25-5 sulfuryl dichloride 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 4461-41-0 2-chloro-but-2-ene 
• 14499-87-7 2,2,3,3-tetrachloro-butane 

Downstream Products

• 79-20-9 acetic acid methyl ester 
• 2648-66-0 α,α-Dichloroacetophenone dimethyl acetal 
• 90584-32-0 1,1-Dichloroethyl hydroperoxide 
• 75-36-5 acetyl chloride 
• 110-22-5 diacetyl peroxide 
• 59183-18-5 Peressigsaeure-1,1-dichlorethylester 
• 55949-61-6 trans-2,3-Dichloro-2,3-dimethyloxirane 
• 90584-34-2 3,6-Dichloro-3,6-dimethyl-[1,2,4,5]tetroxane 
• 108-24-7 acetic anhydride 
• 34450-24-3 trans-1,2,3-trichloro-2-butene 
• 34581-45-8 cis-1,2,3-trichloro-2-butene 
• 14499-87-7 2,2,3,3-tetrachloro-butane 
• 83293-82-7 1,2,2,3,3-pentachlorobutane 
• 39083-23-3 2,3,3-trichloro-1-butene 

Relevant articles and documents

UNSATURATED COMPOUNDS. XV. LIQUID-PHASE LOW-TEMPERATURE CHLORINATION OF 2-CHLORO- AND 2,3-DICHLORO-2-BUTENES IN THE PRESENCE OF FERRIC CHLORIDE

The effect of anhydrous ferric chloride on the degree of normal and anomalous chlorination of 2-chloro- and 2,3-dichloro-2-butenes at low temperatures (-20 to 0 deg C) in the presence of tert-butyl pyrocatechol was investigated.It was established that the addition of ferric chloride leads to a significant decrease in the amount of anomalous chlorination products.At the same time an increase is observed in the chlorination rate of trans-2,3-dichloro-2-butene. During the chlorination of 2,3-dichloro-2-butene under the influence of ferric chloride the anomalous chlorination product 2,3,3-trichloro-1-butene isomerizes to 1,2,3-trichloro-2-butene.

INVESTIGATION IN THE FIELD OF UNSATURATED COMPOUNDS VI. LIQUID-PHASE CHLORINATION OF 2-HALOGENO-2-BUTENES

The liquid-phase chlorination of 2-halogeno-2-butenes in the presence of tert-butylpyrocatechol leads to the formation of the products from an anomalous reaction (2,3-dihalogeno-1-butenes), substitution of hydrogen at the double bond (2,3-dihalogeno-2-butenes), and normal addition (2,2,3-trihalogenobutanes).The ratios of these compounds are 70:6:24 in the case of 2-chloro-2-butene and 54:7.5:38.5 in the case of 2-bromo-2-butene.During the chlorination of 2-chloro-2-butene in the presence of sodium bicarbonate the formation of 3-chloro-2-butanol (20percent) was observed as a result of the combined addition of chlorine and water.

Vinyl Cation Intermediates in Electrophilic Additions to Triple Bonds. 2. Chlorination of Alkylacetylenes

The addition of molecular chlorine to 12 alkyl-substituted acetylenes has been studied in anhydrous acetic acid.Disubstituted acetylenes react by predominant anti addition to give both dichlorides and chloro acetates.Monosubstituted acetylenes react by exclusively syn addition and give only 1,2-dichlorides.Acetylene itself does not react at all under the same conditions.Acetylenes substituted with tert-butyl groups react by a variety of pathways to give skeletally rearranged products and none of the expected simple addition products.The rates of chlorination are very fast for the disubstituted compounds, and the second-order rate constants follow Taft's polar substituent constant scale with a ρ of -3.2.However, the rates for monosubstituted compounds are slower than would be expected from this relationship.The tert-butyl derivatives also react more slowly, and some show evidence of steric retardation.The results are consistent with bridge vinyl-cation-like intermediates and transition states only in the case of disubstituted triple bonds.Acetylenes with only one or no alkyl substituents are presumed to react via open vinyl-cation-like species, if at all.Both types of intermediate can react by a variety of pathways to give final products.These include ion-pair collapse, solvent attack, proton abstraction, and 1,2-shifts.The overall mechanisms of chlorination of both alkyl- and aryl-substituted triple bonds are summarized.