Tris (2,3-dibromopropyl) phosphate

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Tris (2,3-dibromopropyl) phosphate
other names	TDPP; Tris (2,3-dibromo-1-propanol) phosphate; Phosphoric acid (tri-bromopropyl) ester; Phosphoric acid tris-2,3-dibromopropyl ester;
Molecular formula	C 9 H 15 Br 6 O 4 P
Brief description	colorless to yellowish odorless liquid
External identifiers / databases
EC number	204-799-9
ECHA InfoCard	100.004.364
PubChem	31356
Wikidata	Q2443865
properties
Molar mass	697.93 g mol −1
Physical state	liquid
density	2.27 g cm −3
Melting point	5.5 ° C
boiling point	390 ° C
Vapor pressure	0.03 Pa (25 ° C)
solubility	practically insoluble in water; miscible with carbon tetrachloride , chloroform and methylene chloride ; hydrolyzed in acids and bases;
Refractive index	1.5772 (20 ° C)
safety instructions
H and P phrases	H: 302-315-350-400
	P: 201-273-308 + 313
Toxicological data	810 mg kg −1 ( LD 50 , rat , oral ) ; > 8000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

Tris (2,3-dibromopropyl) phosphate is a chemical compound that is used as a flame retardant in plastics and textiles. Its use in children's items was banned in the USA in 1977.

Extraction and presentation

Tris (2,3-dibromopropyl) phosphate can be obtained by a two-step process. Here, bromine to allyl alcohol , and the resulting 2,3-dibromopropanol with phosphorus oxychloride implemented.

properties

Tris (2,3-dibromopropyl) phosphate is a flammable, hardly inflammable, viscous, colorless to yellowish odorless liquid that is practically insoluble in water.

safety instructions

The substance is mutagenic and classified as a group 2A carcinogen according to the International Agency for Research on Cancer (IARC) . It also falls under the scope of the Rotterdam Convention . In the USA, the sale of children's clothing containing tris (2,3-dibromopropyl) phosphate has been banned since 1977.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on tris (2,3-dibromopropyl) phosphate in the GESTIS substance database of the IFA , accessed on September 29, 2017(JavaScript required) .

↑ ^a ^b IARC monograph

↑ ^a ^b ^c ^d Entry on Tris (2,3-dibromopropyl) phosphate in the Hazardous Substances Data Bank , accessed on September 29, 2017.

↑ Nat. Toxicology Program (NTP) (NIH): Report on Carcinogens (12th Ed.) . DIANE Publishing, 2011, ISBN 1-4379-8736-2 , pp. 428 ( limited preview in Google Book search).

↑ M. Prival, E. McCoy, B Gutter, H. Rosendranz: Tris (2,3-dibromopropyl) phosphate: Mutagenicity of a widely used flame retardant . In: Science . 195, No. 4273, 1977, pp. 76-78. doi : 10.1126 / science.318761 . PMID 318761 .

^ Agents Classified by the IARC Monographs

↑ CPSC Bans TRIS-Treated Children's Garments ( Memento of the original from March 20, 2012 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , Consumer Product Safety Commission @1@ 2

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on tris (2,3-dibromopropyl) phosphate in the GESTIS substance database of the IFA , accessed on September 29, 2017(JavaScript required) .

[iarc-2] IARC monograph

[HSDB-3] Entry on Tris (2,3-dibromopropyl) phosphate in the Hazardous Substances Data Bank , accessed on September 29, 2017.

[Nat._Toxicology_Program_(NTP)_(NIH)-4] Nat. Toxicology Program (NTP) (NIH): Report on Carcinogens (12th Ed.) . DIANE Publishing, 2011, ISBN 1-4379-8736-2 , pp. 428 ( limited preview in Google Book search).

[5] M. Prival, E. McCoy, B Gutter, H. Rosendranz: Tris (2,3-dibromopropyl) phosphate: Mutagenicity of a widely used flame retardant . In: Science . 195, No. 4273, 1977, pp. 76-78. doi : 10.1126 / science.318761 . PMID 318761 .

[6] Agents Classified by the IARC Monographs