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CAS NO:95-53-4
EC NO:202-429-0
o-Toluidine (ortho-toluidine) is an organic compound with the chemical formula CH3C6H4NH2.
o-Toluidine is the most important of the three isomeric toluidines.
o-Toluidine is a colorless liquid although commercial samples are often yellowish.
o-Toluidine is a precursor to the herbicides metolachlor and acetochlor.
Synthesis and reactions
o-Toluidine is produced industrially by nitration of toluene to give a mixture of nitrotoluenes, favoring the ortho isomer. This mixture is separated by distillation. 2-Nitrotoluene is hydrogenated to give o-toluidine.
The conversion of o-toluidine to the diazonium salt gives access to the 2-bromo, 2-cyano-, and 2-chlorotoluene derivatives. N-acetylation is also demonstrated.
Prilocaine, an amino amide-type local anesthetic, yields o-toluidine when metabolized by carboxylesterase enzymes. Large prilocaine doses can cause methemoglobinemia due to oxidation of hemoglobin by o-toluidine.
Properties:
Chemical formula: C7H9N
Molar mass: 107.156 g·mol−1
Appearance: Colorless liquid
Odor: Aromatic, aniline-like odor
Density: 1.004 g/cm3
Melting point: −23.68 °C (−10.62 °F; 249.47 K)
Boiling point: 200 to 202 °C (392 to 396 °F; 473 to 475 K)
Solubility in water: 0.19 g/100 ml at 20 °C
Vapor pressure: 0.307531 mmHg (25 °C)
Refractive index (nD): 1.56987
Viscosity: 4.4335 (20 °C)
o-Toluidine is a synthetic, light sensitive, light yellow liquid that is slightly soluble in water and miscible with carbon tetrachloride, diethyl ether and ethanol. The hydrochloride is a synthetic, light sensitive, white crystalline powder that is soluble in dimethylsulfoxide and ethanol.
o-Toluidine and o-toluidine hydrochloride are used primarily as intermediates in the manufacture of dyes and pigments. When heated to decomposition, o-toluidine emits toxic fumes of nitrogen oxides while the hydrochloride also produces hydrochloric acid. Four studies of workers exposed to o-toluidine reported an excess of bladder cancers.
o-Toluidine and o-toluidine hydrochloride are reasonably anticipated to be human carcinogens.
O-toluidine appears as a clear colorless or light yellow liquid. May become reddish brown on exposure to air and light. Flash point 185°F. Has about the same density as water and is very slightly soluble in water. Vapors are heavier than air. Confirmed carcinogen.
O-toluidine is an aminotoluene in which the amino substituent is ortho to the methyl group.
O-toluidine has a role as a carcinogenic agent.
The principal commercial use of o-toluidine is in the manufacture of dyes.
O-toluidine is also used in the manufacture of rubber vulcanization accelerators, hypnotic and anesthetic pharmaceuticals, and pesticides.
An intermediate used in the organic synthesis of dyes, pharmaceuticals, and other chemicals
o-Toluidine and o-toluidine hydrochloride are used primarily as intermediates in the manufacture of more than 90 dyes and pigments. They are used in acid-fast dyestuffs, azo pigment dyes, triarylmethane dyes, sulfur dyes, and indigo compounds.
o-Toluidine is also used as an intermediate for synthetic rubber and rubber vulcanizing chemicals, pharmaceuticals, and pesticides. Other minor uses of o-toluidine and its hydrochloride salt are as an intermediate in organic synthesis and as an ingredient in a clinical laboratory reagent for glucose analysis.
Industry Uses:
-Intermediates
Consumer Uses:
-Chemical intermediate
o-Toluidine is a synthetic chemical that is a light yellow liquid at ambient temperature.
o-Toluidine is used primarily in the manufacture of dyestuffs, although it is also used in the production of rubber, chemicals and pesticides and as a curing agent for epoxy resin systems.
o-Toluidine undergoes chemically oxidative polymerization with aniline in the presence of ammonium persulfate as an oxidant in HCl medium.
o-Toluidine was used in determination of glucose in biological materials.
o-Toluidine was used as precursor in the synthesis of poly(o-toluidine) and copper nanoparticle composite material.
Physicochemical Information:
Boiling point: 200 °C (1013 hPa)
Density: 0.998 g/cm3 (20 °C)
Explosion limit: 1.5 - 7.5 %(V)
Flash point: 85 °C
Ignition temperature: 480 °C
Melting Point: -28 °C
pH value: 7.4 (H₂O, 20 °C) Aqueous solution
Vapor pressure: 0.35 hPa (25 °C)
Solubility: 15 g/l
o-Toluidine (CH3C6H4NH2) is a colorless to pale-yellow liquid.
o-Toluidine is a toxic substance harmful to the eyes, skin, and when swallowed or inhaled.
o-Toluidine is used in many industries.
o-Toluidine is used in some hair dyes, weed and pest killers, rubber, and in some laboratory processes.
O-toluidine, also known as 2-aminotoluene or 1-amino-2-methylbenzene, is a member of the class of compounds known as aminotoluenes. Aminotoluenes are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.
O-toluidine is soluble (in water) and a strong basic compound (based on its pKa).
O-toluidine can be found in tea, which makes O-toluidine a potential biomarker for the consumption of this food product.
O-toluidine is formally rated as a carcinogenic (IARC 1) potentially toxic compound.
Use
Production of dyes, vulcanization accelerator, organic synthesis; photographic dye; reagent in clinical assay for glucose and hemoglobin; component of tobacco smoke
ortho-Toluidine (o-toluidine) is a high-production-volume chemical used in the manufacture of rubber chemicals, herbicide intermediates, dye intermediates, and some drugs like the local anesthetic prilocaine.
Description
Light yellow liquid, becomes reddish-brown on exposure to air and light, aromatic aniline-like odor.
Uses
Printing textiles blue-black, making various colors fast to acids.
Formula: C7H9N / C6H4CH3NH2
Molecular mass: 107.2
Boiling point: 200°C
Melting point: -16°C (beta-form)
Melting point: -24.4°C (alpha-form)
Relative density (water = 1): 1.00
Solubility in water, g/100ml at 20°C: 1.62 (poor)
Vapour pressure, Pa at 25°C: 34.5
Relative vapour density (air = 1): 3.7
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.00
Flash point: 85°C c.c.
Auto-ignition temperature: 480°C
Explosive limits, vol% in air: 1.5-7.5
Octanol/water partition coefficient as log Pow: 1.43
o-Toluidine is used in the production of dyes, as a presumptive test for blood in forensic science. And it is also used in determination of glucose in biological materials, as a precursor in the synthesis of poly(o-toluidine) and copper nanoparticle composite material.
Chemical Properties
O-Toluidine is a light yellow to reddish brown liquid. On exposure to light and atmospheric air, the compound quickly turns a dark color. The compound has extensive use in a large number of industries around the world. For instance, as an intermediate in the manufacture of azo and indigo dyes, pigments, sulfur dyes, pesticides, pharmaceutical products, rubber and vulcanizing chemicals, and similar products.
A clear colorless or light yellow liquid. May become reddish brown on exposure to air and light. Flash point 185°F. Has about the same density as water and is very slightly soluble in water. Vapors are heavier than air. Confirmed carcinogen.
o-Toluidine is used in the manufacture ofvarious dyes, in printing textiles blue-blackand as an intermediate in rubber chemicals,pesticides, and pharmaceuticals.
o-Toluidine was used in determination of glucose in biological materials.
o-Toluidine was used as precursor in the synthesis of poly(o-toluidine) and copper nanoparticle composite material.
A carcinogenic and toxic aromatic amine contained in hair dye, henna and dyed hair samples.
o-Toluidine, is a methemoglobin-inducing chemical and a human carcinogen. Commercial production of o-toluidine was first reported in the United States in 1922.
o-Toluidine and its hydrochloride salt are used primarily as intermediates in the manufacture of dyes and pigments for printing textiles, in color photography, and as biologic stains. In addition, o-toluidine is used as an intermediate for rubber vulcanizing chemicals, pharmaceuticals, and pesticides. Other minor uses include intermediate for organic synthesis and clinical laboratory reagent for glucose analysis.
ChEBI: An aminotoluene in which the amino substituent is ortho to the methyl group.
The production of O-toluidine is based on the catalytic hydrogenation of O-nitrotoluene or the amination of toluene with methylhydroxylamine in the presence of aluminum trichloride (Windholz 1983).
o-Toluidine is available as a technical grade with a minimum of 99.5% purity containing m-toluidine (0.4% maximum) and/or ptoluidine (0.1% maximum) as impurities (Anon. 1978). The stabilized technical grade may also contain less than 0.5% of unidentified stabilizing agents to prevent darkening.
O-toluidine is a clear colorless or light yellow liquid, may become reddish brown on exposure to air and light, and white precipitate at the presence of formaldehyde.
o-Toluidine is slightly soluble in water, soluble in dilute acid, alcohol and ether.
o-Toluidines vapor can form explosive mixture with air. The maximum allowable concentration in air is 5ppm.
O-toluidine is flammable when exposed to heat or flame.
o-Toluidine will, when heated, emit toxic gases toxic similar to that of aniline. Once it enters human body, it will cause the formation of hemoglobin, resulting in the occurrence of neurological disorders and cyanosis.
o-Toluidine has about the same density as water and is very slightly soluble in water. Vapors are heavier than air. Confirmed carcinogen.
The chemical properties of the toluidines are quite similar to those of aniline and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic.
o-Toluidine is used or applied in different circumstances.
o-Toluidine is used the most for dye, especially for coloring hair. The other usages of o-toluidine are specific determination of glucose in blood and the most recent one, the separation of toxic metal ions, which is still in the research phase.
o-Toluidine has been used as a dye precursor since the 19th century, when synthetic dye was produced.In the years that followed, the aromatic amine functioned as a precursor of many dyes and pigments for consumer goods. But when the carcinogenicity of o-toluidine for animals was recognized, and that it potentiality could be carcinogenic for humans, the production of o-toluidine and its use in dye manufacturing has been largely banned in the Western world and in many parts of the East. But there are still a few dyes that are based on this compound. The most known compounds are petroleum products and yellow organic pigments.
o-Toluidine is also an essential compound in the production of 4-chloro-o-toluidine and 4-amino-2′,3-dimethylazobenzene, which are also dyes.
About o-Toluidine
Helpful information
o-Toluidine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
o-Toluidine is used by professional workers (widespread uses), at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which o-Toluidine is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which o-Toluidine is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
o-Toluidine is used in the following products: laboratory chemicals.
o-Toluidine is used in the following areas: scientific research and development.
Other release to the environment of o-Toluidine is likely to occur from: indoor use as reactive substance.
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which o-Toluidine is most likely to be released to the environment.
Uses at industrial sites
o-Toluidine is used in the following products: laboratory chemicals.
o-Toluidine has an industrial use resulting in manufacture of another substance (use of intermediates).
o-Toluidine is used in the following areas: scientific research and development.
o-Toluidine is used for the manufacture of: chemicals.
Release to the environment of o-Toluidine can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and manufacturing of the substance.
Manufacture
Release to the environment of o-Toluidine can occur from industrial use: manufacturing of the substance.
Physical and Chemical Properties
Light yellow flammable liquid that turns red-brown when exposed to air and sunlight.
Use
For dyes, pesticides, pharmaceuticals and organic synthesis intermediates
The manufacture of jujube red base GBC, red base G, red base RL, phenol ASD, acid peach 3B, basic fuchsin and basic peach T and other intermediates, also for pesticides (such as chloramidine) and saccharin and other intermediates.
o-Toluidine is also a raw material for the preparation of mineral dressing agent toluene arsenic acid.
IUPAC names:
2-amino-1-methylbenzene
2-aminotoluene
2-methylaniline
2-Methylbenzolamin
o-Toluidine
o-toluidine
o-Toluidine
o-toluidine
SYNONYMS:
o-Toluidine [ACD/IUPAC Name] [Wiki]
1885-29-6 [RN]
202-429-0 [EINECS]
217-549-9 [EINECS]
2-Aminotoluene
2-Methylaniline
5RXH2B211R
95-53-4 [RN]
B635MZ0ZLU
Benzenamine, 2-methyl- [ACD/Index Name]
o-Toluidin [German] [ACD/IUPAC Name]
o-Toluidine [French] [ACD/IUPAC Name]
o-Toluidyna [Polish]
toluidine [Wiki]
XU2975000
(2-methylphenyl)amine
151985-13-6 [RN]
162607-18-3 [RN]
194423-47-7 [RN]
1-AMINO-2-METHYLBENZENE
1-amino-2-methylbeznene
1-Methyl-2-aminobenzene
2-(4-Piperidinyl)acetamide [ACD/IUPAC Name]
2-(4-piperidyl)acetamide
2-(Methyl-d3)-aniline
2,4-Dideuterio-6-methylaniline
1-amino-2-methylbenzene
1-Methyl-2-aminobenzene
2-AMINO-1-METHYLBENZENE
2-AMINOTOLUENE
2-AMINOTOLUENE, O-TOLUIDINE
2-METHYLANILINE
2-Toluidine
AKOS BBS-00004267
ORTHO-TOLUIDINE
O-TOLUIDINE
O-TOLUIDINE REAGENT
2-Methyl-1-aminobenzene
2-methyl-anilin
2-methylbenzamine
2-methyl-benzenamin
2-Methylbenzenamine
2-methyl-Benzenamine
2-methylphenylamine
Aniline, 2-methyl-
