1-Chloro-2-butene

Base Information

• Chemical Name: 1-Chloro-2-butene
• CAS No.: 4894-61-5
• Molecular Formula: C4H7 Cl
• Molecular Weight: 90.5526
• Hs Code.: 2903290000
• European Community (EC) Number: 225-516-5,209-739-5
• UNII: XX3QN28JUX
• DSSTox Substance ID: DTXSID10884116
• Nikkaji Number: J612B,J70.085A
• Wikipedia: Crotyl_chloride
• Wikidata: Q22829214
• Mol file: 4894-61-5.mol

Synonyms:1-chloro-2-butene;2-butenyl chloride;crotyl chloride

Chemical Property of 1-Chloro-2-butene

Chemical Property:

• Appearance/Colour: Clear Colourless liquid
• Vapor Pressure: 80.6mmHg at 25°C
• Melting Point: -65ºC
• Refractive Index: n20/D 1.430
• Boiling Point: 80-85 ºC
• Flash Point: -15 ºC
• PSA: 0.00000
• Density: 0.92
• LogP: 1.80130
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 90.0236279
• Heavy Atom Count: 5
• Complexity: 30.6

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-CrotylChloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,C
• Statements: 11-22-34-36/37
• Safety Statements: 16-26-36/37/39-45-25-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Aliphatics, Unsaturated
• Canonical SMILES: CC=CCCl
• Isomeric SMILES: C/C=C/CCl
• Uses: Crotyl Chloride is a useful intermediate used in the preparation of crotyltrichlorosilanes and in other crotylsilylation related reactions Crotyl chloride was used in kinetics measurements of reactions of atomic chlorine with series of unsaturated aldehydes and ketones at 298K. (E)Crotyl chloride was also used in the preparation of (E)-crotyltrichlorosilane.

Technology Process of 1-Chloro-2-butene

There total 36 articles about 1-Chloro-2-butene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 16.0%

2-hydroxy-3-butene (598-32-3) → 2-chloro-3-butene (563-52-0,35729-37-4) + trans-but-2-enyl chloride (4894-61-5)

Guidance literature:

With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In dichloromethane; 1.) 0 deg C; 2.) rt., 3h;

DOI:10.1016/S0040-4039(00)99407-3

Reference yield: 10.0%

(E)-but-2-enol (504-61-0,542-72-3) → 2-chloro-3-butene (563-52-0,35729-37-4) + trans-but-2-enyl chloride (4894-61-5)

Guidance literature:

With phosphorus trichloride; In pyridine;

DOI:10.1016/S0040-4039(01)80370-1

Reference yield:

trans-2-Butene (624-64-6) → 2-chloro-3-butene (563-52-0,35729-37-4) + trans-but-2-enyl chloride (4894-61-5)

Guidance literature:

With tert-butylhypochlorite; In benzene; at 70 ℃; Yield given. Yields of byproduct given; Irradiation;

DOI:10.1021/ja00286a020

upstream raw materials:

tetrahydrofuran

(+/-)-chlorocarbonic acid-(1-methyl-allyl ester)

1,4-dioxane

(E)-but-2-enol

Downstream raw materials:

but-2t-enyl-(2,6-dimethyl-phenyl)-ether

2-hydroxy-3-butene

(E/Z)-2-buten-1-ol

cis-2-hexene

Refernces

• 1、 Munyemana, Fran?ois,Patiny, Luc,Ghosez, Léon. "A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols". . . Retrieved 2021/06/07.
• 2、 Munyemana, Fran?ois,George, Isabelle,Devos, Alain,Colens, Alain,Badarau, Eduard,Frisque-Hesbain, Anne-Marie,Loudet, Aurore,Differding, Edmond,Damien, Jean-Marie,Rémion, Jeanine,Van Uytbergen, Jacqueline,Ghosez, Léon. "A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity". . p. 420 - 430. Retrieved 2015/12/31.