Dinitroaniline

The dinitroanilines ( dinitroaminobenzenes ) are aromatic compounds ( aromatic amines ) with the general empirical formula C ₆ H ₅ N ₃ O ₄ . They are derived from both aniline and dinitrobenzene . The different arrangement of the substituents results in six constitutional isomers .

properties

Dinitroaniline
Surname	2,3-dinitroaniline	2,4-dinitroaniline	2,5-dinitroaniline	2,6-dinitroaniline	3,4-dinitroaniline	3,5-dinitroaniline
other names	2,3-dinitro-1-aminobenzene 2,3-Dinitrophenylamin 2,3-dinitroaniline	2,4-dinitro-1-aminobenzene 2,4-Dinitrophenylamin 2,4-dinitroaniline	2,5-dinitro-1-aminobenzene 2,5-Dinitrophenylamin 2,5-dinitroaniline	2,6-dinitro-1-amino-benzene , 2,6-Dinitrophenylamin 2,6-dinitroaniline	3,4-dinitro-1-aminobenzene 3,4-Dinitrophenylamin 3,4-dinitroaniline	3,5-dinitro-1-aminobenzene 3,5-Dinitrophenylamin 3,5-dinitroaniline
Structural formula
CAS number	602-03-9	97-02-9	619-18-1	606-22-4	610-41-3	618-87-1
	26471-56-7 (mixture of isomers)
PubChem	7321	69070	123081	12068	136407	12068
Molecular formula	C 6 H 5 N 3 O 4
Molar mass	183.12 g mol −1
Physical state	firmly
Brief description	colorless to yellowish, flammable powder
Melting point		187.8 ° C		136 ° C (decomposition)	154-158 ° C	160-162 ° C
density	1.646 g cm −3 (50 ° C)	1.61 g cm −3			1.736 g cm −3	1.601 g cm −3 (50 ° C)
solubility	soluble in water (1–2 g · l −1 at 20 ° C)
GHS labeling	no classification available	danger	no classification available	danger	danger	danger
H and P phrases	see above	300-310-330-373-411	see above	301-311-330-373	301-311-331-373	301-311-331-373
	see above	no EUH phrases	see above	no EUH phrases	no EUH phrases	no EUH phrases
	see above	260-264-273-280-284-301 + 310	see above	260-301 + 310-320-361-405-501	261-280-301 + 310-311	261-280-301 + 310-311

presentation

2,4-Dinitroaniline can be prepared by reacting 2,4-Dinitrochlorobenzene with ammonia or by acid hydrolysis of 2,4-Dinitroacetanilide .

use

Dinitroanilines are used as intermediates in the preparation of dyes and herbicides z (. As benfluralin , butralin , dinitramine , ethalfluralin , fluchloralin , isopropalin , nitralin , oryzalin , pendimethalin , prodiamine , profluralin and trifluralin for use on soybeans, cotton and rice, wherein the compounds inhibit the microtubulin system of plants).

safety instructions

Dinitroanilines are explosive and flammable when exposed to heat or friction.

Individual evidence

1. ↑ ^{a b c} Entry on 2,4-dinitroaniline in the GESTIS substance database of the IFA , accessed on November 7, 2016(JavaScript required) .
2. ↑ ^{a b} Entry on 2,6-Dinitroaniline in the GESTIS substance database of the IFA , accessed on November 7, 2016(JavaScript required) .
3. ↑ ^{a b c} data sheet 3,4-dinitroaniline from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
4. ↑ ^{a b} data sheet 3,5-dinitroaniline from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
5. ^ ^{A b} C. L. Yaws: Thermophysical properties of chemicals and hydrocarbons , 1st edition, p. 221, William Andrew Inc., New York, 2008 . ISBN 0-815-51596-0 , ( limited preview in Google Book Search).
6. ↑ Process for the production of nitroanilines .
7. ↑ Synergistic herbicidal mixtures comprising a sulphonyl urea derivative and a dinitroaniline .

Web links

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