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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

42.8 °F - closed cup

flash_point_c

6.0 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9516
MKCH7824
MKBH9850V
MKBG0757V
STBB8854V

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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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