1,2-dibromo-4- (1,2-dibromoethyl) cyclohexane

Structural formula
	Structural formula without representation of the stereochemistry
General
Surname	1,2-dibromo-4- (1,2-dibromoethyl) cyclohexane
other names	Tetrabromethylcyclohexane (unspecific); DBE-DBCH; TBECH;
Molecular formula	C 8 H 12 Br 4
Brief description	White dust
External identifiers / databases
EC number	222-036-8
ECHA InfoCard	100.020.034
PubChem	18728
ChemSpider	17684
Wikidata	Q20054503
properties
Molar mass	427.797 g mol −1
Physical state	firmly
Melting point	70 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2-Dibromo-4- (1,2-dibromoethyl) cyclohexane ( DBE-DBCH or TBECH ) is a brominated organo - chemical compound that is used as a flame retardant .

properties

DBE-DBCH is a polybrominated derivative of ethylcyclohexane . Due to the substitution with four bromine atoms, DBE-DBCH has a significantly lower volatility .

Technical product and stereochemistry

Technical DBE-DBCH mainly consists of the racemates α-DBE-DBCH and β-DBE-DBCH in a ratio of approximately 1: 1.

Because DBE-DBCH contains four centers of chirality , there are theoretically four racemic diastereomers (= eight stereoisomers) of the chemical:

α-DBE-DBCH
β-DBE-DBCH
γ-DBE-DBCH
δ-DBE-DBCH.

The technical product consists mainly of the racemates α-DBE-DBCH and β-DBE-DBCH; this contains α-DBE-DBCH and β-DBE-DBCH in a ratio of approximately 1: 1.

use

In electronic waste an average concentration of 19 was in a 2011 study conducted ppm found, confirming the presence of DBE DBCH in electronic devices.

Effects

DBE-DBCH is an androgen agonist . No mutagenicity was found.

Individual evidence

↑ ^a ^b Entry on 1,2-dibromo-4- (1,2-dibromoethyl) cyclohexane in the Hazardous Substances Data Bank , accessed on June 7, 2015.
^ Jean-Claude Bradley, Jean-Claude Bradley, Andrew Lang, Antony Williams, Evan Curtin: ONS Open Melting Point Collection . In: Nature Precedings . August 11, 2011, doi : 10.1038 / npre.2011.6229.1 . See also Jean-Claude Bradley Open Melting Point Dataset. In: figshare. doi: 10.6084 / m9.figshare.1031637
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Åke Bergman , Andreas Rydén, Robin J. Law, Jacob de Boer, Adrian Covaci, Mehran Alaee, Linda Birnbaum, Myrto Petreas, Martin Rose, Shinichi Sakai, Nele Van den Eede, Ike van der Veen: A novel abbreviation standard for organobromine , organochlorine and organophosphorus flame retardants and some characteristics of the chemicals . In: Environment International . tape 49 , 2012, p. 57–82 , doi : 10.1016 / j.envint.2012.08.003 , PMC 3483428 (free full text).
↑ Shaogang Chu, Lewis T. Gauthier, Robert J. Letcher: Alpha and beta isomers of tetrabromoethylcyclohexane (TBECH) flame retardant: depletion and metabolite formation in vitro using a model rat microsomal assay . In: Environmental Science & Technology . tape 46 , no. 18 , 2012, p. 10263-10270 , doi : 10.1021 / es301546h , PMID 22909217 .
↑ Gilles Arsenault, Alan Lough, Chris Marvin, Alan McAlees, Robert McCrindle, Gordia MacInnis, Kerri Pleskach, Dave Potter, Nicole Riddell, E. d. Sverko, Sheryl Tittlemier, Gregg Tomy: Structure characterization and thermal stabilities of the isomers of the brominated flame retardant 1,2-dibromo-4- (1,2-dibromoethyl) cyclohexane. In: Chemosphere . 72, 2008, p. 1163, doi: 10.1016 / j.chemosphere.2008.03.044 .
^ Ruedi Taverna, Rolf Gloor, Urs Maier, Markus Zennegg, Renato Figi, Edy Birchler: Material flows in Swiss electronic waste . Metals, non-metals, flame retardants and polychlorinated biphenyls in small electrical and electronic devices . Federal Office for the Environment , Bern 2017. Environmental status No. 1717: 164 p.
↑ Sarah C. Marteinson, Robert J. Letcher, Kimberly J. Fernie: Exposure to the androgenic brominated flame retardant, 1,2-dibromo-4- (1,2-dibromoethyl) -cyclohexane (DBE-DBCH) age reproductive and aggressive behaviors in birds . In: Environmental Toxicology and Chemistry . 2015, p. 2395-2402 , doi : 10.1002 / etc.3078 .

[HSDB-1] Entry on 1,2-dibromo-4- (1,2-dibromoethyl) cyclohexane in the Hazardous Substances Data Bank , accessed on June 7, 2015.

[2] Jean-Claude Bradley, Jean-Claude Bradley, Andrew Lang, Antony Williams, Evan Curtin: ONS Open Melting Point Collection . In: Nature Precedings . August 11, 2011, doi : 10.1038 / npre.2011.6229.1 . See also Jean-Claude Bradley Open Melting Point Dataset. In: figshare. doi: 10.6084 / m9.figshare.1031637

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Åke Bergman , Andreas Rydén, Robin J. Law, Jacob de Boer, Adrian Covaci, Mehran Alaee, Linda Birnbaum, Myrto Petreas, Martin Rose, Shinichi Sakai, Nele Van den Eede, Ike van der Veen: A novel abbreviation standard for organobromine , organochlorine and organophosphorus flame retardants and some characteristics of the chemicals . In: Environment International . tape 49 , 2012, p. 57–82 , doi : 10.1016 / j.envint.2012.08.003 , PMC 3483428 (free full text).

[5] Shaogang Chu, Lewis T. Gauthier, Robert J. Letcher: Alpha and beta isomers of tetrabromoethylcyclohexane (TBECH) flame retardant: depletion and metabolite formation in vitro using a model rat microsomal assay . In: Environmental Science & Technology . tape 46 , no. 18 , 2012, p. 10263-10270 , doi : 10.1021 / es301546h , PMID 22909217 .

[6] Gilles Arsenault, Alan Lough, Chris Marvin, Alan McAlees, Robert McCrindle, Gordia MacInnis, Kerri Pleskach, Dave Potter, Nicole Riddell, E. d. Sverko, Sheryl Tittlemier, Gregg Tomy: Structure characterization and thermal stabilities of the isomers of the brominated flame retardant 1,2-dibromo-4- (1,2-dibromoethyl) cyclohexane. In: Chemosphere . 72, 2008, p. 1163, doi: 10.1016 / j.chemosphere.2008.03.044 .

[7] Ruedi Taverna, Rolf Gloor, Urs Maier, Markus Zennegg, Renato Figi, Edy Birchler: Material flows in Swiss electronic waste . Metals, non-metals, flame retardants and polychlorinated biphenyls in small electrical and electronic devices . Federal Office for the Environment , Bern 2017. Environmental status No. 1717: 164 p.

[8] Sarah C. Marteinson, Robert J. Letcher, Kimberly J. Fernie: Exposure to the androgenic brominated flame retardant, 1,2-dibromo-4- (1,2-dibromoethyl) -cyclohexane (DBE-DBCH) age reproductive and aggressive behaviors in birds . In: Environmental Toxicology and Chemistry . 2015, p. 2395-2402 , doi : 10.1002 / etc.3078 .