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28115

Sigma-Aldrich

Crotyl chloride

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

Synonym(s):

cis,trans-1-Chloro-2-butene

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About This Item

Linear Formula:
CH3CH=CHCH2Cl
CAS Number:
591-97-9
Molecular Weight:
90.55
Beilstein/REAXYS Number:
605304
EC Number:
209-739-5
MDL number:
MFCD00000987
UNSPSC Code:
12352100
PubChem Substance ID:
57648288
NACRES:
NA.22

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

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

10.4 °F - closed cup

flash_point_c

-12 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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)
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)
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)

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