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Merck
CN

195707

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24851705
EC Number:
216-021-5
Beilstein/REAXYS Number:
1719692
MDL number:
MFCD00062950

Key Documents

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Product Name

cis-1,4-Dichloro-2-butene, 95%

InChI key

FQDIANVAWVHZIR-UPHRSURJSA-N

InChI

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

SMILES string

ClC\C=C/CCl

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.)

functional group

chloro

storage temp.

2-8°C

Quality Level

200

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Application

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

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.

signalword

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

3 - Flammable liquids

wgk

WGK 3

flash_point_f

131.0 °F - closed cup

flash_point_c

55 °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
BCCN6411
BCCK1434
BCCH9856
BCCG9329
BCCG2458

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Efficient 4+ 1 Syntheses of Highly Functionalized Cyclopentenes.
Nantz MH, et al.
Synthetic Communications, 17(1), 55-69 (1987)
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)
L S Mullin et al.
Drug and chemical toxicology, 25(2), 227-230 (2002-05-25)
Rats were exposed by inhalation to either 0.5 ppm 1,4-dichlorobutene-2 (DCB) for two years or to 5.0 ppm for seven months, 2.5 ppm for five months, and no further exposure for 12 months prior to sacrifice. Malignant and non-malignant tumors
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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