Basic information
- CAS
591-97-9- Standard SMILES
CC=CCCl- InChIKey
YTKRILODNOEEPX-UHFFFAOYSA-N- Molecular formula
- C4H7Cl
- Average molar mass
- 90.55 g/mol
- Monoisotopic mass
- 90.0236279
Overview
used as a reagent in organic synthesis
Names & identifiers
- Preferred name
- Crotyl chloride
- IUPAC
- 1-chlorobut-2-ene
- English name
- 1-Chloro-2-butene
- Molecular formula
- C4H7Cl
- Molecular weight
- 90.55
Names & synonyms
2-Butene, 1-chloro-591-97-9DTXSID5052258RefChem:431467DTXCID0030829209-739-51-Chloro-2-butene2-Butenyl chlorideCrotyl chlorideG6Y5C34N83gamma-Methallyl chloridegamma-Methylallyl chloride
Show more names
CrotyLCrotylchlorid1-Chlorbut-2-en-Chloro-butylene1-chloro-2-buten2-butenylchloride
Krotylchlorid1-Chlorobut-2-ene2-Buten-1-yl Chloridechloro-2-butenechloromethylpropenemethyallyl chloride4-chloro-2-butene3-methylallyl chloride
Database identifiers
- CAS
591-97-9- PubChem CID
- 11589
- DTXSID
DTXSID5052258- EC Number
- 209-739-5
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 30.6
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Halogenated Aliphatics, Unsaturated
Flammable agents - 3rd degree
SpringerMaterials PropertiesDensity
Vapor Pressure69.0 [mmHg]
Physical Description(E)- and (Z)-forms are liquids; [Merck Index] Clear colorless liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- -65 °C · -65°C
- Boiling point
- 85 · 85-86 °C(lit.)
- Density
- 0.923 g/mL · 0.923 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.430
- Flash point
- -12 °C · -12°C
- storage temp.
- 0 · 0-6°C
- solubility
- 14 g/L · water: soluble14g/L at 20°C
- form
- clear liquid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H225 (57.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P362+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 87 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Butene, 1-chloro-
1-Chloro-2-butene: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Hazards Summary
An eye and respiratory tract irritant; [Merck Index] Contains 25-30% 3-Chloro-1-butene (CAS# 563-52-0) as residual from manufacture; Causes burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; [Sigma-Aldrich MSDS] See 3-Chloro-1-butene.
Hazard Classes and Categories
Flam. Liq. 2 (57.5%)
Flammable agents - 3rd degree, Reactive agents - 1st degree
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2-Butene, 1-chloro-: ACTIVE
Applications
Description1-Chloro-2-butene is a butenylating agent via Grignard and other organometallic reagents, organoborane compounds, other nucleophiles, and organosilane compounds.
UsesCrotyl chloride has been used:to investihgate the kinetics of the reactions of atomic chlorine with series of unsaturated aldehydes and ketones at 298K, to probe structure-reactivity relationshipsin the preparation of (E)-crotyltrichlorosilane
General DescriptionCrotyl chloride reacts with trichlorosilane in the presence of tertiary amine and copper salts to give the corresponding allyltrichlorosilanes.
Preparation methods
Preparationpure isomers of 1-Chloro-2-butene can be prepared by chloride displacement of corresponding alcohols via Ph3P in various solvents, and other chlorinating agents.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers63 total
Related reactions
66 records
Compound notes
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