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324515

Sigma-Aldrich

trans-1,4-Dichloro-2-butene

98%

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About This Item

Linear Formula:
ClCH2CH=CHCH2Cl
CAS Number:
110-57-6
Molecular Weight:
125.00
Beilstein:
1719693
EC Number:
203-779-7
MDL number:
MFCD00000988
UNSPSC Code:
12352100
PubChem Substance ID:
24859448
NACRES:
NA.22

vapor pressure

10 mmHg ( 20 °C)

Assay

98%

form

liquid

refractive index

n20/D 1.488 (lit.)

bp

74-76 °C/40 mmHg (lit.)

mp

1-3 °C (lit.)

density

1.183 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-OWOJBTEDSA-N

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Application

trans-1,4-Dichloro-2-butene may be used for the alkylation of adenine to 9-alkylpurines. It can react with diethyl malonate to form vinylcyclopropane derivative. It can also undergo asymmetric allylic alkylation with Grignard reagents in the presence of copper thiophene carboxylate catalyst.

Other Notes

85%, remainder predominantly cis isomer

Signal Word

Danger

Hazard Statements

H226,H301,H312,H314,H330

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

127.4 °F - closed cup

Flash Point(C)

53 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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High Diversity on Simple Substrates: 1, 4?Dihalo?2?butenes and Other Difunctionalized Allylic Halides for Copper?Catalyzed SN2? Reactions.
Falciola C A, et al.
Chemistry?A European Journal, 14(34), 10615-10627 (2008)
Improved selectivity in the preparation of some 1, 1-difunctionalized 3-cyclopentenes. High yield synthesis of 3-cyclopentenecarboxylic acid.
Depres JP and Greene AE.
The Journal of Organic Chemistry, 49(5), 928-931 (1984)
S Phadtare et al.
Journal of medicinal chemistry, 30(2), 437-440 (1987-02-01)
Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led in 90-95% regioselectivity to 9-alkylpurines 6a and 6b. The title compounds 2a and 2b were obtained by
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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