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254584

Sigma-Aldrich

Crotyl chloride, predominantly trans

95%

Synonym(s):

1-Chloro-2-butene

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About This Item

Linear Formula:
CH3CH=CHCH2Cl
CAS Number:
4894-61-5
Molecular Weight:
90.55
EC Number:
225-516-5
MDL number:
MFCD00000987
UNSPSC Code:
12352100
PubChem Substance ID:
24855394
NACRES:
NA.22

Quality Level

100

assay

95%

form

liquid

impurities

4% 3-chloro-1-butene

refractive index

n20/D 1.436 (lit.)

bp

84-85 °C (lit.)

density

0.929 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]\C(C)=C(\[H])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 salt to give the corresponding allyltrichlorosilane.

Application

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.

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

23.0 °F

flash_point_c

-5 °C

Certificates of Analysis (COA)

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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)
Stereohomogeneous synthesis of (E)-and (Z)-crotyltrifluorosilanes and highly stereoselective allylation of aldehydes.
Kira M, et al.
Tetrahedron Letters, 30(9), 1099-1102 (1989)

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