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, and mostly derived from trifluralin. Dinitroaniline herbicides include benfluralin, butralin, chlornidine, dinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, nitrofor, oryzalin, pendimethalin, prodiamine, profluralin, and trifluralin. Trifluralin and pendimethalin are the most widely commercially used.
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. Since they are made from readily obtainable raw materials, during World War I Germany used them as Ersatz high explosives.
Dinitroanilines were developed prior to 2015 by, among others, the Dow Chemical Company, who then sold their business to privately-held Gowan Company. [2]
Dinitroanalines may have medically useful anti-microbial properties, some research has been done on trifluralin and derivatives.
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 | ![]() ![]() ![]() ![]() | ![]() ![]() ![]() | ![]() ![]() ![]() | ![]() ![]() ![]() | ||
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+P310 | P260, P301+P310, P320, P361, P405, P501 | P261, P280, P301+P310, P311 | P261, P280, P301+P310, P311 |
2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.
Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols. Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
Pendimethalin is an herbicide of the dinitroaniline class used premergently and postemergently to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is a K1-group according to the Herbicide Resistance Action Committee (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals, corn, soybeans, rice, potato, legumes, fruits, vegetables, and nuts, plus lawns and ornamental plants.
Mecoprop is a common general use herbicide found in many household weed killers and "weed-and-feed" type lawn fertilizers. It is primarily used to control broadleaf weeds. It is often used in combination with other chemically related herbicides such as 2,4-D, dicamba, and MCPA, which mimic the plant hormone IAA (auxin) and kill most broadleaf weeds by causing uncontrolled growth.
The Institute for Occupational Safety and Health of the German Social Accident Insurance is a German institute located in Sankt Augustin near Bonn and is a main department of the German Social Accident Insurance. Belonging to the Statutory Accident Insurance means that IFA is a non-profit institution.
Trifluralin is a common pre-emergent selective herbicide, a dinitroaniline. With about 14 million pounds (6,400 t) used in the United States in 2001, and 3–7 million pounds (1,400–3,200 t) in 2012, it is one of the most widely used herbicides. Trifluralin is also used in Australia, and New Zealand. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.
The monohalomethanes are organic compounds in which a hydrogen atom in methane is replaced by a halogen. They belong to the haloalkanes or to the subgroup of halomethanes.
2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.
Benfluralin is an herbicide of the dinitroaniline class. The mechanism of action of benfluralin involves pre-emergent inhibition of mitosis, root and shoot development, same as trifluralin, from which benfluralin was developed in 1963.
Dinoterb is a chemical compound previously used as a contact herbicide. It is an uncoupler, affecting respiration in mitochondria and photosynthesis in chloroplasts. It is banned for use in the European Union and use was suspended in the United States in 1986.
Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.
Fluroxypyr is an herbicide in the class of synthetic auxins. It is used to control broadleaf weeds and woody brush. It is formulated as the 1-methylheptyl ester (fluroxypyr-MHE).
Dinitrobenzenes are nitrobenzenes 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.
Bifenox is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis.
2,4-Dinitroaniline is a chemical compound with a formula of C6H5N3O4. It is used as an explosive and as a reagent to detect and characterize aldehydes and ketones.
2-Ethylhexyl acrylate is a colorless liquid acrylate used in the making of paints, plastics and adhesives. It has an odor that has been variously described as pleasant or acrid and musty.
GESTIS Substance Database is a freely accessible online information system on chemical compounds. It is maintained by the Institut für Arbeitsschutz der Deutschen Gesetzlichen Unfallversicherung. Information on occupational medicine and first aid is compiled by Henning Heberer and his team.
1,3,5-Triethylbenzene is a chemical compound of the group of aromatic hydrocarbons.
Nitralin is a selective pre-emergent dinitroaniline herbicide that is closely related to trifluralin, and released two years later in 1966. Today it is largely obsolete. It was used in the USA and Australia to control annual grasses and broad-leaved weeds, and was applied on vines, crops and turf.