4-aminobiphenyl

Structural formula
General
Surname	4-aminobiphenyl
other names	4-aminodiphenyl; p -phenylaniline; Biphenyl-4-ylamine; p -aminobiphenyl; p -aminodiphenyl; 4-biphenylamine; Xenylamine;
Molecular formula	C 12 H 11 N
Brief description	colorless, flammable solid with a floral odor
External identifiers / databases
EC number	202-177-1
ECHA InfoCard	100.001.980
PubChem	7102
Wikidata	Q229922
properties
Molar mass	169.23 g mol −1
Physical state	firmly
density	1.16 g cm −3
Melting point	52-54 ° C
boiling point	302 ° C
Vapor pressure	5.79 × 10 -4 mmHg (25 ° C)
solubility	practically insoluble in water; soluble in alcohol, ether and chloroform;
safety instructions
H and P phrases	H: 302-350
	P: 201-308 + 313
Authorization procedure under REACH	particularly worrying : carcinogenic ( CMR )
Toxicological data	500 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-aminobiphenyl is a chemical compound from the group of amino compounds , more precisely a derivative of biphenyl . It is a colorless, flammable solid with a flowery odor, which turns purple on contact with air due to oxidation .

Representation and occurrence

4-aminobiphenyl is by reduction of 4-nitrobiphenyl accessible.

The compound is formed during the reductive cleavage of azo dyes that contain 4-aminodiphenyl as a diazo component and occurs as an impurity of diphenylamine . 4-aminodiphenyl was detected in cigarette smoke, with a concentration that was 30 times higher than that of mainstream smoke in sidestream smoke (“ passive smoke ”).

use

4-aminobiphenyl was previously used as a gum antioxidant and as an intermediate in the manufacture of azo dyes. But after the development of bladder cancer on contact with the substance had already been established in the 1950s to 1970s, production was discontinued.

According to the Consumer Goods Ordinance (BedGgstV), azo dyes that release more than 30 mg of 4-aminobiphenyl in one kilogram of finished product through reductive cleavage may not be used for textiles or leather products that may come into direct contact with human skin for a long time.

proof

4-aminobiphenyl can be detected by thin layer chromatography after absorption in sulfuric acid and conversion into the free base .

toxicology

4-aminobiphenyl is a very potent bladder carcinogen and is therefore classified as a carcinogen. As sulfinamide, which is an intermediate product of metabolism, it binds covalently to cysteine residues in hemoglobin. It also forms DNA adducts in the body , which has been immunologically proven by bladder biopsy of smokers.

Web links

Detection of carcinogenic aromatic amines in the urine of non-smokers

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 4-aminobiphenyl in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c ^d 13th Report on Carcinogens (RoC): 4-Aminobiphenyl ( Memento from November 29, 2014 in the Internet Archive ), accessed on November 18, 2014.
↑ Entry on biphenyl-4-ylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.
↑ Barry Leonard; Eighth Annual Report on Carcinogens: 1998 Summary.
^ ^A ^b G. Eisenbrand, M. Metzler: Toxikologie für Chemiker, Georg Thieme Verlag Stuttgart ISBN 3-13-127001-2 , page 158
↑ Ordinance on subject matter. Appendix 1 (to §3). In: Laws on the Internet. Federal Ministry of Justice and Consumer Protection, accessed on November 1, 2019 .
↑ DGUV Information 213-502 Info - Procedure for the determination of 4-aminodiphenyl (previously: BGI 505-2) .
^ M. Maclure, MS Bryant, PL Skipper, SR Tannenbaum: Decline of the hemoglobin adduct of 4-aminobiphenyl during withdrawal from smoking. In: Cancer Research . Volume 50, Number 1, January 1990, pp. 181-184, PMID 2293553 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 4-aminobiphenyl in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[nioehs-2] 13th Report on Carcinogens (RoC): 4-Aminobiphenyl ( Memento from November 29, 2014 in the Internet Archive ), accessed on November 18, 2014.

[CLP_100.001.980-3] Entry on biphenyl-4-ylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[SVHC-4] Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.

[5] Barry Leonard; Eighth Annual Report on Carcinogens: 1998 Summary.

[Eisenbrand-6] A ^b G. Eisenbrand, M. Metzler: Toxikologie für Chemiker, Georg Thieme Verlag Stuttgart ISBN 3-13-127001-2 , page 158

[7] Ordinance on subject matter. Appendix 1 (to §3). In: Laws on the Internet. Federal Ministry of Justice and Consumer Protection, accessed on November 1, 2019 .

[8] DGUV Information 213-502 Info - Procedure for the determination of 4-aminodiphenyl (previously: BGI 505-2) .

[9] M. Maclure, MS Bryant, PL Skipper, SR Tannenbaum: Decline of the hemoglobin adduct of 4-aminobiphenyl during withdrawal from smoking. In: Cancer Research . Volume 50, Number 1, January 1990, pp. 181-184, PMID 2293553 .