Dinitroaniline
Dinitroanilines are a class of chemical compounds with the chemical formula C6H5N3O4. They are derived from both aniline and dinitrobenzenes. There are six isomers: 2,3-dinitroaniline, 2,4-dinitroaniline, 2,5-dinitroaniline, 2,6-dinitroaniline, 3,4-dinitroaniline, and 3,5-dinitroaniline.
Dinitroanilines are intermediates in the preparation of various industrially important chemicals including dyes and pesticides. Herbicides which are derivatives of dinitroanilines include benfluralin, , , , , , , , , , oryzalin, pendimethalin, prodiamine, , and trifluralin.
2,4-Dinitroaniline can be prepared by reaction of 1-chloro-2,4-dinitrobenzene with ammonia or by acid hydrolysis of 2,4-dinitroacetanilide.[1]
Dinitroanilines are explosive and flammable with heat or friction.
Dinitroanilines were developed prior to 2015 by, among others, the Dow Chemical Company, who then sold their business to privately-held .[2]
Dinitroanilines | ||||||
Chemical name | 2,3-Dinitroaniline | 2,4-Dinitroaniline | 2,5-Dinitroaniline | 2,6-Dinitroaniline | 3,4-Dinitroaniline | 3,5-Dinitroaniline |
Alternate name | 2,3-Dinitro-1-aminobenzene 2,3-Dinitrophenylamine 2,3-Dinitraniline |
2,4-Dinitro-1-aminobenzene 2,4-Dinitrophenylamine 2,4-Dinitraniline |
2,5-Dinitro-1-aminobenzene 2,5-Dinitrophenylamine 2,5-Dinitraniline |
2,6-Dinitro-1-aminobenzene 2,6-Dinitrophenylamine 2,6-Dinitraniline |
3,4-Dinitro-1-aminobenzene 3,4-Dinitrophenylamine 3,4-Dinitraniline |
3,5-Dinitro-1-aminobenzene 3,5-Dinitrophenylamine 3,5-Dinitraniline |
Chemical structure | ||||||
CAS Number | 602-03-9 | 97-02-9 | 619-18-1 | 606-22-4 | 610-41-3 | 618-87-1 |
26471-56-7 (isomeric mixture) | ||||||
PubChem | CID 136400 from PubChem | CID 7321 from PubChem | CID 123081 from PubChem | CID 69070 from PubChem | CID 136407 from PubChem | CID 12068 from PubChem |
Chemical formula | C6H5N3O4 | |||||
Molar mass | 183.12 g/mol | |||||
Appearance | colorless to yellowish combustible powder | |||||
Melting point | 187.8 °C[3] | 136 °C (decomp.)[4] | 154–158 °C | 160–162 °C[5] | ||
Density | 1.646 g/cm (50 °C)[6] | 1.61 g/cm[3] | 1.736 g/cm | 1.601 g/cm (50 °C)[6] | ||
Solubility | soluble in water (1–2 g/L at 20 °C) | |||||
GHS hazard pictograms |
[3] | [4] | [5] | |||
H- and P-phrases | H300, H310, H330, H373, H411 | H302, H311, H332, H373 | H301, H311, H331, H373 | H301, H311, H331, H373 | ||
P260, P264, P273, P280, P284, P301+310 | P260, P301+310, P320, P361, P405, P501 | P261, P280, P301+310, P311 | P261, P280, P301+310, P311 | |||
R-phrases | R26/27/28 R33 R51/53 | R26/27/28 R33 R51/53 | R23/24/25 R33 | R23/24/25 R33 | ||
S-phrases | (S1/2) S28 S36/37 S45 S61 | S28 S36/37 S45 S61 | S28 S37 S45 | S28 S37 S45 |
References[]
- ^ WO 1991001292 Method for the Preparation of Nitroanilines
- ^ dowagro.com: "Gowan Company, L.L.C. Agrees to Acquire Global DNA Business from Dow AgroSciences LLC", 30 Nov 2015
- ^ Jump up to: a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Jump up to: a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Jump up to: a b "3,5-Dinitroaniline". Sigma-Aldrich.
- ^ Jump up to: a b C. L. Yaws (2008). Thermophysical properties of chemicals and hydrocarbons (1st ed.). New York: William Andrew Inc. p. 221. ISBN 978-0-815-51596-8.
- Anilines
- Nitrobenzenes