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195707

Sigma-Aldrich

cis-1,4-Dichloro-2-butene

95%

Synonym(s):

(2Z)-1,4-Dichloro-2-butene, (2Z)-1,4-Dichlorobut-2-ene, (Z)-1,4-Dichloro-2-butene, 1,4-Dichloro-cis-2-butene, cis-1,2-Bis(chloromethyl)ethene

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About This Item

Linear Formula:
ClCH2CH=CHCH2Cl
CAS Number:
1476-11-5
Molecular Weight:
125.00
Beilstein:
1719692
EC Number:
216-021-5
MDL number:
MFCD00062950
UNSPSC Code:
12352100
PubChem Substance ID:
24851705
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.489 (lit.)

bp

152 °C/758 mmHg (lit.)

mp

−48 °C (lit.)

density

1.188 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC\C=C/CCl

InChI

1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1-

InChI key

FQDIANVAWVHZIR-UPHRSURJSA-N

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General description

cis-1,4-Dichloro-2-butene on reaction with sodium amide yields trans-1-chloro-1,3-butadiene. Mechanism of condensation of sulfone-activated methylene compounds with cis-1,4-dichloro-2-butene to yield cyclopentene has been investigated.

Application

cis-1,4-Dichloro-2-butene was used in the preparation of functionalized 3,5-disubstituted cyclopent-2-enones.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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cis-1,3-Dichloropropene 97%

Sigma-Aldrich

377414

cis-1,3-Dichloropropene

Wei-Chieh Cheng et al.
The Journal of organic chemistry, 67(13), 4387-4391 (2002-06-22)
The preparation of functionalized 3,5-disubstituted cyclopent-2-enones via a solid-phase sulfone linker strategy is described. Polystyrene/divinylbenzene sulfinate 1 underwent S-alkylation followed by alpha,alpha-dialkylation with cis-1,4-dichloro-2-butene to form polymer-bound 3-phenylsulfonylcyclopentenes 8. Subsequent epoxidation of the cyclopentene moiety in 8 was accomplished by
Reactions of cis-and trans-1, 4-dichloro-2-butene with sodium amide.
Heasley VL and Lais BR.
The Journal of Organic Chemistry, 33(6), 2571-2572 (1968)
Efficient 4+ 1 Syntheses of Highly Functionalized Cyclopentenes.
Nantz MH, et al.
Synthetic Communications, 17(1), 55-69 (1987)
trans-1,4-dichlorobutene.
IARC monographs on the evaluation of carcinogenic risks to humans, 71 Pt 3, 1389-1391 (1999-09-07)
R J Gardner et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 23(1), 87-92 (1985-01-01)
Several important chemicals, including formaldehyde, 1,4-dichloro-2-butene, bis-chloromethyl ether, hexamethylphosphoramide, and epichlorohydrin have been shown to produce nasal tumours in rats following repeated or continuous inhalation exposures. Some of these compounds are respiratory irritants. To determine whether there is a correlation
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