1,2-dibromoethene

Structural formula
General
Surname	1,2-dibromoethene
other names	Acetylenedibromide
Molecular formula	C 2 H 2 Br 2
Brief description	light brown liquid
External identifiers / databases
EC number	208-747-6
ECHA InfoCard	100.007.953
PubChem	10897
ChemSpider	10435
Wikidata	Q161467
properties
Molar mass	185.84 g mol −1
Physical state	liquid
density	2.25–2.27 g cm −3 (mixture)
boiling point	107-110 ° C
Vapor pressure	4.2 k Pa (25 ° C)
Refractive index	1.5428 ( cis , 20 ° C); 1.5505 ( trans , 18 ° C);
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-315-319-335
	P: 261-301 + 310-305 + 351 + 338
Toxicological data	117 mg kg −1 ( LD 50 , rat , oral , mixture)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,2-Dibromoethene is a chemical compound that occurs in two isomeric forms (cis-1,2-Dibromoethene and trans-1,2-Dibromoethene).

Extraction and presentation

1,2-Dibromoethene can be obtained by an addition reaction of ethyne with bromine .

{\ displaystyle \ mathrm {C_ {2} H_ {2} + Br_ {2} \ longrightarrow C_ {2} H_ {2} Br_ {2}}}

properties

Physical Properties

Due to its high density, 1,2-dibromoethene is included in the group of heavy liquids .

Chemical properties

1,2-dibromoethene reacts with bromine further to 1,1,2,2-tetrabromoethane (C ₂ H ₂ Br ₄ ), what does that mean in the production of 1,2-dibromoethene with a high bromine concentration always 1,1,2, 2-tetrabromoethane is produced as a by-product.

{\ displaystyle \ mathrm {C_ {2} H_ {2} Br_ {2} + Br_ {2} \ longrightarrow C_ {2} H_ {2} Br_ {4}}}

use

1,2-Dibromoethene is used as an intermediate in the synthesis of chemical compounds (e.g. enediynes ).

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet 1,2-dibromoethene from Sigma-Aldrich , accessed on March 15, 2011 ( PDF ).
↑ ^a ^b Data sheet 1,2-Dibromoethylene (PDF) from Fisher Scientific , accessed on February 13, 2014.
↑ CSIRO Land and Water: Petroleum and Solvent Vapors: Quantifying their Behavior, Assessment and Exposure ( Memento of March 21, 2015 in the Internet Archive ) (PDF; 1.6 MB), July 2004, accessed on June 10, 2013.
↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-144.
^ Andreas von Usedom: Organic chemistry, biochemistry, chemical industry . Mentor, 2003, ISBN 978-3-580-64134-4 , pp. 21 ( limited preview in Google Book search).
↑ Krishna's Advanced Organic Chemistry; Volume 1 . ISBN 81-8283-078-8 , pp. 499 ( limited preview in Google Book search).
↑ Janet Wisniewski Grissom, Gamini U. Gunawardena, Detlef Klingberg, Dahai Huang: The chemistry of enediynes, enyne allenes and related compounds. In: Tetrahedron. 52, 1996, p. 6453, doi: 10.1016 / 0040-4020 (96) 00016-6 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet 1,2-dibromoethene from Sigma-Aldrich , accessed on March 15, 2011 ( PDF ).

[fisher_science-2] Data sheet 1,2-Dibromoethylene (PDF) from Fisher Scientific , accessed on February 13, 2014.

[3] CSIRO Land and Water: Petroleum and Solvent Vapors: Quantifying their Behavior, Assessment and Exposure ( Memento of March 21, 2015 in the Internet Archive ) (PDF; 1.6 MB), July 2004, accessed on June 10, 2013.

[CRC90_3_144-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-144.

[Andreas_von_Usedom-5] Andreas von Usedom: Organic chemistry, biochemistry, chemical industry . Mentor, 2003, ISBN 978-3-580-64134-4 , pp. 21 ( limited preview in Google Book search).

[6] Krishna's Advanced Organic Chemistry; Volume 1 . ISBN 81-8283-078-8 , pp. 499 ( limited preview in Google Book search).

[DOI10.1016/0040-4020(96)00016-6-7] Janet Wisniewski Grissom, Gamini U. Gunawardena, Detlef Klingberg, Dahai Huang: The chemistry of enediynes, enyne allenes and related compounds. In: Tetrahedron. 52, 1996, p. 6453, doi: 10.1016 / 0040-4020 (96) 00016-6 .