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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

Quality Level

200

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9329
BCCG2458
BCCC8100
BCBV3133
SHBH4584V

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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
Efficient 4+ 1 Syntheses of Highly Functionalized Cyclopentenes.
Nantz MH, et al.
Synthetic Communications, 17(1), 55-69 (1987)
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)
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
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
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Protocols

US EPA Method 8260: GC Analysis of Volatiles on SPB®-624 after Purge & Trap using "K" Trap, Fast GC Analysis

US EPA Method 8260 describes the analysis of volatile organic compounds in solid wastes and ground waters. This application illustrates the analysis of many compounds commonly analyzed by this method using purge and trap coupled to GC-MS.

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