User:Smokefoot/sandbox4

Smokefoot/sandbox4
	<img alt="Skeletal formula of cis-1,2-dichloroethene" src="//up.wiki.x.io/wikipedia/commons/thumb/2/2d/Cis-1%2C2-dichloroethene.png/144px-Cis-1%2C2-dichloroethene.png" decoding="async" width="144" height="110" class="mw-file-element" data-file-width="708" data-file-height="541">
	<img alt="Ball-and-stick model of cis-1,2-dichloroethene" src="//up.wiki.x.io/wikipedia/commons/thumb/d/d1/Cis-1%2C2-dichloroethene-3D-balls.png/144px-Cis-1%2C2-dichloroethene-3D-balls.png" decoding="async" width="144" height="120" class="mw-file-element" data-file-width="1100" data-file-height="916">
Names
	Other names cis-1,2-Dichloroethene
Identifiers
CAS Number	156-59-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18882 <img alt="check" src="//up.wiki.x.io/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" data-file-width="600" data-file-height="600"> ;
ChemSpider	558928 <img alt="check" src="//up.wiki.x.io/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" data-file-width="600" data-file-height="600"> ;
KEGG	C06792 <img alt="check" src="//up.wiki.x.io/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" data-file-width="600" data-file-height="600"> ;
PubChem CID	643833;
	InChI InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1- Key: KFUSEUYYWQURPO-UPHRSURJSA-N;
	SMILES C(=C\Cl)\Cl;
Properties
Chemical formula	C2H2Cl2
Molar mass	96.95 g/mol
Appearance	colorless liquid
Odor	sweet
Density	1.28 g/cm3
Melting point	−81.47 °C
Boiling point	60.2 °C
Magnetic susceptibility (χ)	−51.0·10−6 cm3/mol (cis);
Dipole moment	1.9 D
Hazards
Flash point	2–4 °C; 36–39 °F; 275–277 K
Explosive limits	5.6–12.8%
	Lethal dose or concentration (LD, LC):
LCLo (lowest published)	16,000 ppm (rat, 6 hr, cis-isomer)ref name=Ullmann/>
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (790 mg/m3)
REL (Recommended)	TWA 200 ppm (790 mg/m3)
IDLH (Immediate danger)	1000 ppm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Smokefoot/sandbox4
Names
	Other names trans-1,2-Dichloroethylene; 1,2-DCE; sym-Dichloroethylene
Identifiers
CAS Number	156-60-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18882 ;
ChemSpider	553742 ;
PubChem CID	643833;
	InChI InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1+ Key: KFUSEUYYWQURPO-OWOJBTEDSA-N;
	SMILES C(=C/Cl)\Cl;
Properties
Chemical formula	C2H2Cl2
Molar mass	96.95 g/mol
Appearance	colorless liquid
Odor	sweet
Density	1.26 g/cm3
Melting point	−49.44 °C
Boiling point	48.5 °C
Magnetic susceptibility (χ)	−48.9·10−6 cm3/mol (trans);
Dipole moment	0 D
Hazards
Flash point	2–4 °C; 36–39 °F; 275–277 K
Explosive limits	5.6–12.8%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	770 mg/kg (oral, rat); 1275 mg/kg (oral, rat)
LC50 (median concentration)	21,273 ppm (mouse, 6 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (790 mg/m3)
REL (Recommended)	TWA 200 ppm (790 mg/m3)
IDLH (Immediate danger)	1000 ppm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tracking categories (test):

SizeSet

trans-1,2-Dichloroethene is an organochloride with the molecular formula C₂H₂Cl₂. It is a geometric isomer of cis-1,2-dichloroethene. The two are often used as a mixture. Both have modest solubility in water, are colorless liquids, and have sweet odors. The trans compound is mainly used as a specialized degreaser.^[2] In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.^[4]

Production and reactions

Industrially both isomers of 1,2-dichloroethene arise as byproducts of the production of vinyl chloride, which is produced on a vast scale. Unlike vinyl chloride, neither isomer of 1,2-dichloroethene polymerizes.^[2]

trans-DCE is used for cleaning of electronics and other speciallized cleaning applications.^[5]

trans-1,2-Dichloroethene participates in cycloaddition reactions.^[6]

Safety

The isomers of 1,2-dichloroethene compounds have "moderate oral toxicity to rats".^[2]

References

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c ^d E.-L. Dreher; T. R. Torkelson; K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01. ISBN 978-3527306732.
^ ^a ^b "1,2-Dichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Pitzer, Kenneth S.; Hollenberg, J. L. (1954). "cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.^–1 and the Thermodynamic Properties". J. Am. Chem. Soc. 76 (6): 1493–1496. doi:10.1021/ja01635a010.
^ "Chlorinated Solvents and Feed Stock - Axiall". Archived from the original on 2016-04-08. Retrieved 2016-03-23.
^ Wang, Xiao Min; Hou, Xuelong; Zhou, Zhongyuan; Mak, Thomas C. W.; Wong, Henry N. C. (1993). "Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: Synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,JKL]tetraphenylene". The Journal of Organic Chemistry. 58 (26): 7498–7506. doi:10.1021/jo00078a031.

External links

International Chemical Safety Card 0436
NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).

Category:Chloroalkenes Category:Halogenated solvents

Tracking categories (test):

SizeSet

cis-1,2-Dichloroethene is an organochloride with the molecular formula C₂H₂Cl₂. It is a geometric isomer of trans-1,2-dichloroethene. The two are often used as a mixture. Both have low solubility in water, are colorless liquids, and have sweet odors. The trans compound finds some applications as a specialized degreaser,^[1] whereas the cis compound is a specialized reagent in organic synthesis.

Production

Industrially both isomers of 1,2-dichloroethene arise as byproducts of the production of vinyl chloride, which is produced on a vast scale. Unlike vinyl chloride, neither isomer of 1,2-dichloroethene polymerizes.^[1]

E-Z relative stability

In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.^[3]

Safety

The isomers of 1,2-dichloroethene compounds have "moderate oral toxicity to rats".^[1]

References

^ ^a ^b ^c ^d E.-L. Dreher; T. R. Torkelson; K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01. ISBN 978-3527306732.
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
^ Pitzer, Kenneth S.; Hollenberg, J. L. (1954). "cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.^–1 and the Thermodynamic Properties". J. Am. Chem. Soc. 76 (6): 1493–1496. doi:10.1021/ja01635a010.

External links

International Chemical Safety Card 0436
NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).

Category:Chloroalkenes Category:Halogenated solvents

[NIOSH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-2] E.-L. Dreher; T. R. Torkelson; K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01. ISBN 978-3527306732.

[IDLH-3] "1,2-Dichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[4] Pitzer, Kenneth S.; Hollenberg, J. L. (1954). "cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.^–1 and the Thermodynamic Properties". J. Am. Chem. Soc. 76 (6): 1493–1496. doi:10.1021/ja01635a010.

[5] "Chlorinated Solvents and Feed Stock - Axiall". Archived from the original on 2016-04-08. Retrieved 2016-03-23.

[6] Wang, Xiao Min; Hou, Xuelong; Zhou, Zhongyuan; Mak, Thomas C. W.; Wong, Henry N. C. (1993). "Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: Synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,JKL]tetraphenylene". The Journal of Organic Chemistry. 58 (26): 7498–7506. doi:10.1021/jo00078a031.

[Ullmann-7] E.-L. Dreher; T. R. Torkelson; K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01. ISBN 978-3527306732.

[NIOSH-8] NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).

[9] Pitzer, Kenneth S.; Hollenberg, J. L. (1954). "cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.^–1 and the Thermodynamic Properties". J. Am. Chem. Soc. 76 (6): 1493–1496. doi:10.1021/ja01635a010.

[1]

[2]

[3]

[4]

[5]

[6]

[1]

[2]

[3]

User:Smokefoot/sandbox4

Contents

Production and reactions

Safety

See also

References

External links

Production

E-Z relative stability

Safety

See also

References

External links

Names


Other names trans-1,2-Dichloroethylene 1,2-DCE sym-Dichloroethylene
Identifiers
CAS Number	156-60-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18882^Y
ChemSpider	553742^Y
PubChem CID	643833
InChI InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1+ Key: KFUSEUYYWQURPO-OWOJBTEDSA-N
SMILES C(=C/Cl)\Cl
Properties
Chemical formula	C₂H₂Cl₂
Molar mass	96.95 g/mol
Appearance	colorless liquid^[1]
Odor	sweet^[2]
Density	1.26 g/cm³
Melting point	−49.44 °C
Boiling point	48.5 °C
Magnetic susceptibility (χ)	−48.9·10⁻⁶ cm³/mol (trans)
Dipole moment	0 D
Hazards
Flash point	2–4 °C; 36–39 °F; 275–277 K
Explosive limits	5.6–12.8%^[1]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	770 mg/kg (oral, rat) 1275 mg/kg (oral, rat)^[3]
LC₅₀ (median concentration)	21,273 ppm (mouse, 6 hr)^[3]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (790 mg/m³)^[1]
REL (Recommended)	TWA 200 ppm (790 mg/m³)^[1]
IDLH (Immediate danger)	1000 ppm^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references