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Merck
CN

28115

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57648288
EC Number:
209-739-5
Beilstein/REAXYS Number:
605304
MDL number:
MFCD00000987
Assay:
~70% (GC)
Form:
liquid

Key Documents

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InChI key

YTKRILODNOEEPX-NSCUHMNNSA-N

InChI

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

SMILES string

C\C=C\CCl

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.)

functional group

alkyl halide, chloro

Quality Level

100

Related Categories

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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL1748
BCCJ6177
BCCD4788
BCCC4767
BCCB4895

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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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