Trichloroanilines

In chemistry, the trichloroanilines form a group of aromatic compounds that are derived from both aniline and chlorobenzene . The structure consists of a benzene ring with an attached amino group  (–NH ₂ ) and three chlorine  (–Cl) as substituents . Their different arrangement results in six constitutional isomers with the empirical formula C ₆ H ₄ Cl ₃ N. All substances are sparingly soluble in water and toxic.

Trichloroanilines
Surname	2,3,4-trichloroaniline	2,3,5-trichloroaniline	2,3,6-trichloroaniline	2,4,5-trichloroaniline	2,4,6-trichloroaniline	3,4,5-trichloroaniline
other names	1-amino-2,3,4-trichlorobenzene, 2,3,4-trichlorophenylamine	1-amino-2,3,5-trichlorobenzene, 2,3,5-trichlorophenylamine	1-amino-2,3,6-trichlorobenzene, 2,3,6-trichlorophenylamine	1-amino-2,4,5-trichlorobenzene, 2,4,5-trichlorophenylamine	1-amino-2,4,6-trichlorobenzene, 2,4,6-trichlorophenylamine	1-amino-3,4,5-trichlorobenzene, 3,4,5-trichlorophenylamine
Structural formula
CAS number	634-67-3	18487-39-3	88963-39-7	636-30-6	634-93-5	634-91-3
PubChem	12464	87676	184908	12487	12471	12469
Molecular formula	C 6 H 4 Cl 3 N
Molar mass	196.46 g mol −1
Physical state	firmly
Brief description	crystalline solids
Melting point	65-67 ° C	-		93-94 ° C	73-75 ° C	97 ° C
boiling point	292 ° C	-	-	270 ° C	262 ° C	-
solubility	practically insoluble in water
GHS labeling	danger		no classification available	danger
H and P phrases	301-311-331-373-410		see above	301-311-331-373-410
	no EUH phrases		see above	no EUH phrases
	no P-phrases		see above	261-273-280 301 + 310-311-501

use

Trichloroanilines are used as intermediate products in the production of other chemical compounds (e.g. 2,4,5-trichloroaniline for pigments and azo dyes ).

Tetra- and pentachloroanilines

Tetrachloroanilines (C ₆ H ₃ Cl ₄ N) have four chlorine atoms on the benzene ring. They are produced by further chlorinating trichloroanilines (e.g. 2,3,4,6-tetrachloroaniline by chlorinating 2,4,5-trichloroaniline). There are three different isomers.

Pentachloroaniline is also known (C ₆ H ₂ Cl ₅ N, M = 265.35 g mol ⁻¹ ).

Individual evidence

1. ↑ ^{a b c d} Entry for CAS no. 634-67-3 in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
2. ↑ ^{a b c} Entry for CAS no. 18487-39-3 in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
3. ↑ ^{a b c d} Entry for CAS no. 636-30-6 in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
4. ↑ ^{a b c d} Entry for CAS no. 634-93-5 in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
5. ↑ ^{a b c} Entry for CAS no. 634-91-3 in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
6. ↑ 2,4,5-Trichloroaniline BUA Summary (English). ( Memento of the original from May 21, 2003 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 591 kB). 
7. ↑ TU Darmstadt: Chemistry for Schoolchildren: Synthetic Organic Dyes (PDF; 625 kB) ( Memento from March 19, 2013 in the Internet Archive ), accessed on April 21, 2013.
8. ↑ M. Mullin, G. Sawka, L. Safe, S. McCrindle, S. Safe: Synthesis of the Octa- and nonachlorobiphenyl isomers and congeners and their quantitation in commercial polychlorinated biphenyls and identification in human breast milk , in: J Anal Toxicol , 1981 , 5 (3) , pp. 138-142; PMID 6790872 .
9. ↑ External identifiers or database links for pentachloroaniline : CAS number: 527-20-8, EC number: 208-410-3, ECHA InfoCard: 100.007.647 , PubChem : 10693 , ChemSpider : 10243 , Wikidata : Q27291304 .