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D62209

Sigma-Aldrich

trans-1,2-Dichloroethylene

98%

Synonym(s):

trans-1,2-Dichloroethene, trans-Acetylene dichloride

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About This Item

Linear Formula:
ClCH=CHCl
CAS Number:
156-60-5
Molecular Weight:
96.94
Beilstein:
1420761
EC Number:
205-860-2
MDL number:
MFCD00062942
UNSPSC Code:
12352100
PubChem Substance ID:
24894012
NACRES:
NA.22

vapor pressure

5.16 psi ( 20 °C)

Assay

98%

form

liquid

expl. lim.

12.8 %

refractive index

n20/D 1.446 (lit.)

bp

48 °C (lit.)

mp

−50 °C (lit.)

density

1.257 g/mL at 25 °C (lit.)

SMILES string

Cl\C=C\Cl

InChI

1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1+

InChI key

KFUSEUYYWQURPO-OWOJBTEDSA-N

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General description

trans-1,2-Dichloroethylene is an organic solvent used in freon cleaning agents.

Application

trans-1,2-Dichloroethylene can be involved in the synthesis of:
  • (E)-Chloroenynes by reacting with 1-alkyne and piperidine in the presence of PdCl2(PPh3)2 catalyst in ethyl ether as a solvent.
  • (E)-3-trimethylsilyl-1-chloro-1-propene by reacting with trimethylsilylmethylmagnesium chloride (TMSCH2MgCl) in the presence of Co(II) or Co(III) acetylacetonate.
  • trans-1,2-Bis(tri-n-butylstannyl)ethylene which is an important reagent for the synthesis of myriad of natural products.
  • trans-1-Chloroalkenes by reacting with Grignard reagents in the presence of tetrakis(triphenylphosphine)nickel as catalyst.

accessory

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H332,H412

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

42.8 °F - closed cup

Flash Point(C)

6.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Suzuki Coupling Reactions of (E)-and (Z)-Chloroenynes with Boronic Acids: Versatile Access to Functionalized 1, 3-Enynes
Tikad A, et al.
European Journal of Organic Chemistry, 2010(4), 725-731 (2010)
Cobalt-catalyzed mono-coupling of R3SiCH2MgCl with 1, 2-dihalogenoethylene: a general route to γ-substituted (E)-allylsilanes.
Kamachi T, et al.
Tetrahedron Letters, 45(24), 4677-4679 (2004)
Preparation of trans-1, 2-bis(tributylstannyl) ethylene.
Corey EJ and Wollenberg RH
The Journal of Organic Chemistry, 40(25), 3788-3789 (1975)
A convenient preparation of trans(or cis)-1-chloroalkenes from trans(or cis)-1, 2-dichloroethylene: A new synthesis of the sex pheromone of lobesia botrana.
Ratovelomanana V and Linstrumelle G
Tetrahedron Letters, 22(4), 315-318 (1981)
Florian Schevenels et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(13), 4335-4343 (2013-01-22)
Highly functionalised benzofurans have been prepared from ortho-hydroxyphenones and 1,1-dichloroethylene. The key intermediate, a chloromethylene furan, smoothly rearranged into the corresponding benzofuran carbaldehyde under acidic conditions. Some mechanistic investigations have been performed and several biologically active benzofurans have been synthesised.
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