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D62004

Sigma-Aldrich

cis-1,2-Dichloroethylene

97%

Synonym(s):

cis-1,2-DCE, cis-Acetylene dichloride

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About This Item

Linear Formula:
ClCH=CHCl
CAS Number:
156-59-2
Molecular Weight:
96.94
Beilstein:
1071208
EC Number:
205-859-7
MDL number:
MFCD00000925
UNSPSC Code:
12352100
PubChem Substance ID:
24894011
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.449 (lit.)

bp

60 °C (lit.)

mp

−80 °C (lit.)

density

1.284 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-UPHRSURJSA-N

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Application

cis-1,2-Dichloroethylene (cis-1,2-DCE) is generally used in the preparation of various enediynes for Bergman cyclization. Applications include the synthesis of:
  • 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines to prepare corresponding substituted carbazoles.
  • (Z)-1-aryl-3-henen-1,5-diynes to obtain the corresponding aryl substituted benzotriazoles.


It is used as a linker to synthesize boron-dipyrromethene (BODIPY)-based photosensitizer for photodynamic therapy (PDT). cis-1,2-DCE can also be used as a precursor to synthesize intermediates of sporolide B.

accessory

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 2 - Skin Irrit. 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1,1-Dichloroethylene (stabilised with hydroquinone monomethyl ether) for synthesis

Sigma-Aldrich

8.03209

1,1-Dichloroethylene

Total synthesis of sporolide B.
Nicolaou, et al.
Angewandte Chemie (International Edition in English), 48(19), 3449-3453 (2009)
Toward singlet oxygen delivery at a measured rate: a self-reporting photosensitizer.
Erbas-Cakmak S and Akkaya EU
Organic Letters, 16(11), 2946-2949 (2014)
Sara Kleindienst et al.
Systematic and applied microbiology, 40(3), 150-159 (2017-03-16)
Taxonomic assignments of anaerobic dichloromethane (DCM)-degrading bacteria remain poorly constrained but are important for understanding the microbial diversity of organisms contributing to DCM turnover in environmental systems. We describe the taxonomic classification of a novel DCM degrader in consortium RM
Reaction of (Z)-1-Aryl-3-hexen-1, 5-diynes with Sodium Azide: Synthesis of 1-Aryl-1 H-benzotriazoles.
Chen Z-Y and Wu M-J
Organic Letters, 7(3), 475-477 (2005)
Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization.
Jones GB, et al.
The Journal of Organic Chemistry, 67(16), 5727-5732 (2002)
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