Tris (2,3-dibromopropyl) isocyanurate

Structural formula
	Stereoisomene mixture ; simplified structural formula without stereochemistry
General
Surname	Tris (2,3-dibromopropyl) isocyanurate
other names	1,3,5-tris (2,3-dibromopropyl) -1,3,5-triazinane-2,4,6-trione; TDBP-TAZTO;
Molecular formula	C 12 H 15 Br 6 N 3 O 3
Brief description	White dust
External identifiers / databases
EC number	257-913-4
ECHA InfoCard	100.052.631
PubChem	103634
ChemSpider	93567
Wikidata	Q57985217
properties
Molar mass	728.69 g mol −1
Physical state	firmly
Melting point	110 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tris (2,3-dibromopropyl) isocyanurate ( TDBP-TAZTO ) is a chemical compound that has a central six-membered isocyanuric acid and three 2,3-dibromopropyl substituents and is used as a flame retardant .

Manufacturing

Tris (2,3-dibromopropyl) isocyanurate is obtained by bromination of triallyl isocyanurate , whereby a stereoisomer mixture in the ratio 1: 3: 3: 1 [( R , R , R ), ( R , R , S ), ( R , S , S ), ( S , S , S )] is created.

use

Tris (2,3-dibromopropyl) isocyanurate is used as an additive flame retardant. In 2015, 5,000–6,000 tons of it were imported or manufactured in Japan.

Environmental relevance

The chemical has been found in water, soil, sediments , worms, and fish and has been shown to have biomagnification potential .

Individual evidence

↑ ^a ^b ^c Data sheet Tris (2,3-dibromopropyl) isocyanurate 97% from Sigma-Aldrich , accessed on October 28, 2018 ( PDF ).
↑ Entry on 1,3,5-Tris (2,3-dibromopropyl) -1,3,5-triazinane-2,4,6-trione in the ChemSpider database of the Royal Society of Chemistry , accessed on October 28, 2018 .
↑ 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).
↑ External identifiers or database links for triallyl isocyanurate : CAS number: 1025-15-6, EC number: 213-834-7, ECHA InfoCard: 100.012.577 , GESTIS substance database : 493859 , PubChem : 13931 , ChemSpider : 13329 , Wikidata : Q27286126 .
↑ Patent CN103694186B : A tri (2,3-dibromopropyl) isocyanurate production process. Inventor: KONG QINGCHI; GAO JIANGUO; LI RUYI; LI DONGDONG; CUI MIN; KONG QINGCHI; GAO JIANGUO; LI RUYI; LI DONGDONG; CUI MIN. ‌
↑ Ethel Eljarrat, Damià Barceló: Brominated Flame Retardants . Springer Science & Business Media, 2011, ISBN 978-3-642-19268-5 ( limited preview in Google book search).
↑ Japan Chemicals Collaborative Knowledge Database (J-CHECK). Retrieved October 24, 2018 .
↑ Ting Ruan, Yawei Wang, Chang Wang, Pu Wang, Jianjie Fu: Identification and Evaluation of a Novel Heterocyclic Brominated Flame Retardant Tris (2,3-dibromopropyl) Isocyanurate in Environmental Matrices near a Manufacturing Plant in Southern China . In: Environmental Science & Technology . tape 43 , no. 9 , May 2009, p. 3080-3086 , doi : 10.1021 / es803397x .

[Sigma-1] Data sheet Tris (2,3-dibromopropyl) isocyanurate 97% from Sigma-Aldrich , accessed on October 28, 2018 ( PDF ).

[2] Entry on 1,3,5-Tris (2,3-dibromopropyl) -1,3,5-triazinane-2,4,6-trione in the ChemSpider database of the Royal Society of Chemistry , accessed on October 28, 2018 .

[3] 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).

[4] External identifiers or database links for triallyl isocyanurate : CAS number: 1025-15-6, EC number: 213-834-7, ECHA InfoCard: 100.012.577 , GESTIS substance database : 493859 , PubChem : 13931 , ChemSpider : 13329 , Wikidata : Q27286126 .

[5] Patent CN103694186B : A tri (2,3-dibromopropyl) isocyanurate production process. Inventor: KONG QINGCHI; GAO JIANGUO; LI RUYI; LI DONGDONG; CUI MIN; KONG QINGCHI; GAO JIANGUO; LI RUYI; LI DONGDONG; CUI MIN. ‌

[6] Ethel Eljarrat, Damià Barceló: Brominated Flame Retardants . Springer Science & Business Media, 2011, ISBN 978-3-642-19268-5 ( limited preview in Google book search).

[7] Japan Chemicals Collaborative Knowledge Database (J-CHECK). Retrieved October 24, 2018 .

[8] Ting Ruan, Yawei Wang, Chang Wang, Pu Wang, Jianjie Fu: Identification and Evaluation of a Novel Heterocyclic Brominated Flame Retardant Tris (2,3-dibromopropyl) Isocyanurate in Environmental Matrices near a Manufacturing Plant in Southern China . In: Environmental Science & Technology . tape 43 , no. 9 , May 2009, p. 3080-3086 , doi : 10.1021 / es803397x .