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52985

Sigma-Aldrich

cis-3-Hexene

≥95.0%

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About This Item

Empirical Formula (Hill Notation):
C6H12
CAS Number:
7642-09-3
Molecular Weight:
84.16
Beilstein/REAXYS Number:
1718858
MDL number:
MFCD00085300
UNSPSC Code:
12352100
PubChem Substance ID:
57651395
NACRES:
NA.22

assay

≥95.0%

refractive index

n20/D 1.395

bp

66-68 °C (lit.)

density

0.681 g/mL at 20 °C (lit.)

SMILES string

CC\C=C/CC

InChI

1S/C6H12/c1-3-5-6-4-2/h5-6H,3-4H2,1-2H3/b6-5-

InChI key

ZQDPJFUHLCOCRG-WAYWQWQTSA-N

General description

cis-3-Hexene is a symmetrical cis-disubstituted alkene that can be prepared by the hydroboration of 3-hexyne followed by protonolysis. The gas-phase study of its molecular structure by electron diffraction combined with molecular mechanical calculations reveals the presence of the (+ac, +ac) and the (-ac, +ac) forms. cis-3-Hexene undergoes epoxidation with dimethyldioxirane to form the corresponding epoxide.

Application

cis-3-Hexene may be used in the preparation of 3-hexanol via asymmetric hydroboration with diisopinocampheylborane (Ipc2BH).

signalword

Danger

Hazard Classifications

Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-13.0 °F - closed cup

flash_point_c

-25 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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The molecular structures of cis-3-hexene and trans-3-hexene in the gas phase by electron diffraction and molecular mechanical calculations.
Van HD, et al.
Journal of Molecular Structure, 74(1), 123-135 (1981)
Hydroboration. 61. Diisopinocampheylborane of high optical purity. Improved preparation and asymmetric hydroboration of representative cis-disubstituted alkenes.
Brown HC, et al.
The Journal of Organic Chemistry, 47(26), 5065-5069 (1982)
Hydroboration. XI. The hydroboration of acetylenes-A convenient conversion of internal acetylenes into cis-olefins and of terminal acetylenes into aldehydes
Brown HC and Zweifel G.
Journal of the American Chemical Society, 83(18), 3834-3840 (1961)
Epoxidation by dimethyldioxirane. Electronic and steric effects.
Baumstark AL and Vasquez PC.
The Journal of Organic Chemistry, 53(15), 3437-3439 (1988)
Nadhem Aissani et al.
Journal of agricultural and food chemistry, 63(27), 6120-6125 (2015-06-18)
Research on new pesticides based on plant extracts, aimed at the development of nontoxic formulates, has recently gained increased interest. This study investigated the use of the volatilome of rucola (Eruca sativa) as a powerful natural nematicidal agent against the
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