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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

D62004-BULK:
D62004-10G:4548173194509
D62004-1G:4548173194516
D62004-50G:4548173292571
D62004-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7830
MKCK1803
MKBX5945V
MKBV2831V
MKBQ2835V

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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)
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)
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)
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
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Global Trade Item Number

SKUGTIN
D62004-1G4061837084942
D62004-10G4061833587416
D62004-50G4061837077494

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