Dinitroaniline

Last updated March 25, 2019

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.

A chemical compound is a chemical substance composed of many identical molecules composed of atoms from more than one element held together by chemical bonds. A chemical element bonded to an identical chemical element is not a chemical compound since only one element, not two different elements, is involved.

Aniline is an organic compound with the formula C₆H₅NH₂. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Its main use is in the manufacture of precursors to polyurethane and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.

Dinitrobenzenes are chemical compounds composed of a benzene ring and two nitro group (-NO₂) substituents. The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. Each isomer has the chemical formula C₆H₄N₂O₄ and a molar mass of about 168.11 g/mol. 1,3-Dinitrobenzene is the most common isomer and it is used in the manufacture of explosives.

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.

The chemical industry comprises the companies that produce industrial chemicals. Central to the modern world economy, it converts raw materials into more than 70,000 different products. The plastics industry contains some overlap, as most chemical companies produce plastic as well as other chemicals.

A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and may require a mordant to improve the fastness of the dye on the fiber.

Pesticides are substances that are meant to control pests, including weeds. The term pesticide includes all of the following: herbicide, insecticides nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, antimicrobial, fungicide and disinfectant (antimicrobial). The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects.

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]

The Dow Chemical Company, commonly referred to as Dow, is an American multinational chemical corporation headquartered in Midland, Michigan, United States, and the predecessor of the merged company DowDuPont. In 2017, prior to the merger, it was the second-largest chemical manufacturer in the world by revenue and the third-largest chemical company in the world by market capitalization. It ranked second in the world by chemical production in 2014.

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

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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
1 2 3 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
1 2 "3,5-Dinitroaniline". Sigma-Aldrich.
1 2 C. L. Yaws (2008). Thermophysical properties of chemicals and hydrocarbons (1st ed.). New York: William Andrew Inc. p. 221. ISBN 0-815-51596-0.

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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] 1 2 3 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[GESTIS_4-4] 1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[sigmaaldrich-5] 1 2 "3,5-Dinitroaniline". Sigma-Aldrich.

[Yaws-6] 1 2 C. L. Yaws (2008). Thermophysical properties of chemicals and hydrocarbons (1st ed.). New York: William Andrew Inc. p. 221. ISBN 0-815-51596-0.