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, butralin, chlornidine, dinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, 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 Gowan Company.[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
CAS Number	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
H- and P-phrases		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
Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
"3,5-Dinitroaniline". Sigma-Aldrich.
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.

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[1] WO 1991001292 Method for the Preparation of Nitroanilines

[2] wagro.com: "Gowan Company, L.L.C. Agrees to Acquire Global DNA Business from Dow AgroSciences LLC", 30 Nov 2015

[GESTIS_2-3] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[GESTIS_4-4] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[sigmaaldrich-5] "3,5-Dinitroaniline". Sigma-Aldrich.

[Yaws-6] 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.