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543144

Sigma-Aldrich

6-Chloro-1-hexene

96%

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About This Item

Linear Formula:
Cl(CH2)4CH=CH2
CAS Number:
Molecular Weight:
118.60
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

refractive index

n20/D 1.438 (lit.)

bp

135-136 °C (lit.)

density

0.896 g/mL at 25 °C (lit.)

SMILES string

ClCCCCC=C

InChI

1S/C6H11Cl/c1-2-3-4-5-6-7/h2H,1,3-6H2

InChI key

BLMIXWDJHNJWDT-UHFFFAOYSA-N

Related Categories

General description

6-Chloro-1-hexene is an ω-chloro-1-alkene. It reacts with β-substituted imines in the presence of a rhodium catalyst to afford tri- and tetra-substituted imines. It undergoes cross-coupling reaction in the presence of copper(II) chloride and 1-phenylpropyne.

Application

6-Chloro-1-hexene may be used in the synthesis of 1-(5-hexen)-2,3-dimethyl-imidazolium chloride.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

84.0 °F

Flash Point(C)

28.9 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Stereoselective alkylation of a, ?-unsaturated imines via CH bond activation
Colby, Denise A., Robert G. Bergman, and Jonathan A. Ellman
Journal of the American Chemical Society, 128.17, 5604-5605 (2006)
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Aprile C, et al.
Green Chemistry, 9.12, 1328-1334 (2007)
Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents.
Kim JH and Chung YK.
Chemical Communications (Cambridge, England), 49(94), 11101-11103 (2013)
The Signs of Si29-H1 and Si29-F19 Coupling Constants
Danyluk SS.
Journal of the American Chemical Society, 86.20, 4504-4505 (1964)
Christopher L Rock et al.
Dalton transactions (Cambridge, England : 2003), 48(2), 461-467 (2018-11-30)
The phosphine-substituted α-diimine Ni precursor, (Ph2PPrDI)Ni, has been found to catalyze alkene hydrosilylation in the presence of Ph2SiH2 with turnover frequencies of up to 124 h-1 at 25 °C (990 h-1 at 60 °C). Moreover, the selective hydrosilylation of allylic

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