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215082

Sigma-Aldrich

trans-1,4-Dichloro-2-butene

technical grade, 85%, remainder predominantly cis isomer

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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:
24852866
NACRES:
NA.22

grade

technical grade

Quality Level

100

vapor pressure

10 mmHg ( 20 °C)

Assay

85%

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 was used as starting reagent in the synthesis of trans-tetrahydrofuran (THF) ring building block. It was also employed in the chemical synthesis of swainsonine [(1S,2R,8R,8 αR)-trihydroxyindolizidine] and 9-alkylpurines.

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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Z M Wang et al.
Chirality, 12(7), 581-589 (2000-06-22)
A highly efficient synthetic method for the trans-tetrahydrofuran (THF) ring building block was established and the title compound was synthesized in 19 steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step.
A D Elbein et al.
Biochemistry, 26(9), 2502-2510 (1987-05-05)
The chemical synthesis of swainsonine [(1S,2R,8R,8 alpha R)-trihydroxyindolizidine] from trans-1,4-dichloro-2-butene was previously described [Adams, C. E., Walker, F. J., & Sharpless, K. B. (1985) J. Org. Chem. 50, 420-424]. A modification of that synthesis provided two other isomers, referred to
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
trans-1,4-dichlorobutene.
IARC monographs on the evaluation of carcinogenic risks to humans, 71 Pt 3, 1389-1391 (1999-09-07)
N A Hamill et al.
Environmental science & technology, 35(13), 2823-2827 (2001-07-17)
Gas-phase photocatalysis of 1,4-dichlorobut-2-enes and 3,4-dichlorobut-1-ene (DCB) has been studied using TiO2 and 3% WO3/TiO2 supported on SiO2. DCB was found to oxidize efficiently over these catalysts; however, only low rates of CO2 formation were observed. With these chlorinated hydrocarbons
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