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28115

Sigma-Aldrich

Crotyl chloride

technical, (cis+trans), mixture of cis- and trans-isomers (~1:6), ~70% (GC)

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Synonym(s):
cis,trans-1-Chloro-2-butene
Linear Formula:
CH3CH=CHCH2Cl
CAS Number:
591-97-9
Molecular Weight:
90.55
Beilstein:
605304
EC Number:
209-739-5
MDL number:
MFCD00000987
UNSPSC Code:
12352100
PubChem Substance ID:
57648288
NACRES:
NA.22

Quality Level

100

grade

technical

Assay

~70% (GC)

form

liquid

impurities

~30% 3-chloro-1-butene

refractive index

n20/D 1.430

bp

85-86 °C (lit.)

solubility

water: soluble 14 g/L at 20 °C

density

0.923 g/mL at 20 °C (lit.)

SMILES string

C\C=C\CCl

InChI

1S/C4H7Cl/c1-2-3-4-5/h2-3H,4H2,1H3/b3-2+

InChI key

YTKRILODNOEEPX-NSCUHMNNSA-N

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General description

Crotyl chloride reacts with trichlorosilane in the presence of tertiary amine and copper salts to give the corresponding allyltrichlorosilanes.

Application

Crotyl 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 relationships
  • in the preparation of (E)-crotyltrichlorosilane

Signal Word

Danger

Hazard Statements

H225,H301,H314,H317,H412

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Stereohomogeneous synthesis of (E)-and (Z)-crotyltrifluorosilanes and highly stereoselective allylation of aldehydes.
Kira M, et al.
Tetrahedron Letters, 30(9), 1099-1102 (1989)
Rate constants for the reactions of chlorine atoms with a series of unsaturated aldehydes and ketones at 298 K: structure and reactivity.
Wang W, et al.
Physical Chemistry Chemical Physics, 4(10), 1824-1831 (2002)
The condensation reaction of trichlorosilane with allylic chlorides catalyzed by copper salts in the presence of a tertiary amine.
Furuya N and Sukawa T.
Journal of Organometallic Chemistry, 96(1), C1-C3 (1975)

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