4-nitrobiphenyl

Structural formula
General
Surname	4-nitrobiphenyl
other names	1-nitro-4-phenylbenzene p -nitrobiphenyl
Molecular formula	C 12 H 9 NO 2
Brief description	White to yellowish crystal needles, sweetish odor
External identifiers / databases
CAS number 92-93-3 EC number 202-204-7 ECHA InfoCard 100.002.005 PubChem 7114 ChemSpider 21109008 DrugBank DB12300 Wikidata Q30899078
properties
Molar mass	199.21 g mol −1
Physical state	firmly
density	1.328 g cm −3
Melting point	114-115 ° C
boiling point	340 ° C
solubility	practically insoluble in water
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 350-411 P: 201-280-308 + 313
Toxicological data	2230 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-Nitrobiphenyl is an aromatic nitro compound with a biphenyl basic structure.

presentation

The production of 4-nitrobiphenyl 2 was first described by Gustav Schultz in 1874 . The compound is obtained by nitration of biphenyl 1 , whereby Hans Huebner was able to show that 2-nitrobiphenyl 3 is formed as a by-product :

Synthesis of 4-nitrobiphenyl by nitration of biphenyl

Alternatively, 4-nitrobiphenyl can be obtained via a palladium- catalyzed Negishi reaction . First, bromobenzene 1 is reacted with lithium in diethyl ether to form phenyllithium 2 . Reaction of phenyllithium with a solution of zinc chloride in THF gives phenylzinc chloride 3 . This is reacted with 4-nitroiodobenzene 4 and a Pd catalyst, prepared by reaction of bis (triphenylphosphine) palladium chloride Pd (PPh ₃ ) ₂ Cl ₂ with diisobutylaluminum hydride to 4-nitrobiphenyl 5 implemented:

Synthesis of 4-nitrobiphenyl from bromobenzene and 4-nitroiodobenzene

use

By reduction of the nitro compound obtained 4-aminobiphenyl , as an intermediate in the synthesis of dyes or rubber - antioxidants was used.

properties

In animal experiments, among other things, 4-aminobiphenyl was detected as a metabolite of 4-nitrobiphenyl. It was also in vitro rapid reduction of 4-nitrobiphenyl for 4-aminobiphenyl found in the presence of rat liver enzymes. 4-aminobiphenyl has been shown to be carcinogenic in humans , so that a carcinogenic effect of 4-nitrobiphenyl is also suspected in humans. 4-Nitrobiphenyl is listed in the REACH Regulation (EC) No. 1907/2006 Annex XVII and may therefore not be placed on the market or used either as a substance or in mixtures in concentrations of> 0.1% by weight.

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on 4-nitrobiphenyl in the GESTIS substance database of the IFA , accessed on October 31, 2019(JavaScript required) .
2. ↑ Entry on 4-nitrobiphenyl in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on October 31, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
3. ↑ Gustav Schultz: About Diphenyl . In: Justus Liebig's Annals of Chemistry . tape 174 , no. 2 , 1874, p. 201 , doi : 10.1002 / jlac.18741740206 .
4. ^ H. Hübner: Mittheilungen from the Göttingen University Laboratory . In: Reports of the German Chemical Society . tape 8 , no. 1 , January 1875, p. 870 , doi : 10.1002 / cber.187500801286 .
5. ↑ Ivica Cepanec: Synthesis of Biaryls . Elsevier, Amsterdam, San Diego, Oxford, London 2004, ISBN 978-0-08-044412-3 , pp. 127 ( limited preview in Google Book search).
6. ^ German statutory accident insurance (ed.): Aromatic amines. A working aid in the determination of occupational diseases . 4th edition. Berlin 2018, ISBN 978-3-86423-225-1 , pp. 74 ( limited preview in Google Book search).
7. ↑ 4-aminobiphenyl. (PDF) In: IARC Monographs on the Identification of Carcinogenic Hazards to Humans. International Agency for Research on Cancer, accessed November 1, 2019 . 
8. ↑ Annex XVII of the REACH regulation. Federal Institute for Occupational Safety and Health, accessed on November 1, 2019 (as of January 7, 2019).