97-56-3

Usage

Uses

Used in the Oil and Fat Industry:
O-AMINOAZOTOLUENE is used as a coloring agent for oils, fats, and waxes. It provides a stable and heat-resistant color, making it suitable for coloring paraffin.
Used in the Manufacturing Industry:
O-AMINOAZOTOLUENE is used as a chemical intermediate in the production of dyes and pigments, such as C.I. 11160.
Used in the Chemical Industry:
O-AMINOAZOTOLUENE is used in the ethanol process for yellow sheet crystallization. It also reacts with concentrated sulfuric acid to produce a brown color, which turns red-orange upon dilution. In concentrated nitric acid, it forms a red-brown solution, while in concentrated hydrochloric acid, it partially dissolves to form a brown solution. It is insoluble in 10% sulfuric acid and slightly soluble in 10% sodium hydroxide solution, resulting in a pale yellow color.
Properties and Applications:
O-AMINOAZOTOLUENE has a light fastness rating and is heat-resistant up to 150°C, with sublimation. It is indissolvable in water and has poor solubility in sodium carbonate (5%) and hydrochloric acid (5%).

Preparation

(a) will Sodium nitrite (1 Moore) to join O-Methylaniline (8.5 Moore) and hydrochloric acid (1 Moore), the temperature is maintained at 28 ℃ below, until diazotization finish. Add a small amount of hydrochloric acid (about 0.2 Moore), and heating (40 ℃, 3 hours), in order to separate, with Sodium hydroxide for mercerization, and distillation reservoir. In order to get the refined products, usable alcohol recrystallization; (b) O-Methylaniline?diazotization, and O-Methylaniline?base Methanesulfonic acid coupling, and then with Sodium hydroxide solution common boiling, hydrolysis off Methanesulfonic acid base.

Reactivity Profile

O-AMINOAZOTOLUENE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. O-AMINOAZOTOLUENE is sensitive to prolonged exposure to heat. O-AMINOAZOTOLUENE is incompatible with strong oxidizing agents.

Fire Hazard

Flash point data for O-AMINOAZOTOLUENE are not available. O-AMINOAZOTOLUENE is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion. Moderately toxic by subcutaneous route. An experimental teratogen. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO,. See also AROMATIC AMINES.

Potential Exposure

An azo compound used in dyes, medicines; as a colorant in shoe polishes and other wax-based polishes.

Carcinogenicity

o-Aminoazotoluene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Standard

Light Fastness

Melting point

Stable

Purification Methods

Recrystallise the dye twice from EtOH, once from *benzene, then dry it in an Abderhalden drying apparatus. [Cilento J Am Chem Soc 74 968 1952, Sawicki J Org Chem 21 605 1956, Beilstein 16 H 334, 16 I 322, 16 II 178, 16 III 386, 16 IV 525.] CARCINOGENIC.

Incompatibilities

Dust may form explosive mixture in air. Azo compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This chemical is sensitive to prolonged exposure to heat. This chemical is incompatible with strong oxidizing agents.

InChI:InChI=1/C7H9N3/c1-6-4-2-3-5-7(6)9-10-8/h2-5H,1H3,(H2,8,9)

Upstream product

• 614-63-1 1,3-di-o-tolyltriazene 
• 95-53-4 o-toluidine 
• 7647-01-0 hydrogenchloride 
• 636-21-5 o-toluidine hydrochloride 

Downstream Products

• 63042-13-7 N-(2-methyl-4-o-tolylazo-phenyl)-succinamic acid 
• 588-23-8 4-acetamido-2',3-dimethylazobenzene 
• 83-63-6 Diacetylaminoazotoluen 
• 399-38-2 fluoro-acetic acid-(2-methyl-4-o-tolylazo-anilide) 
• 404-87-5 (2-methyl-4-o-tolylazo-phenyl)-carbamic acid-(2,2,2-trifluoro-ethyl ester) 
• 2002-40-6 bis-(2-methyl-4-o-tolylazo-phenyl)-diazene 
• 399-37-1 trifluoro-acetic acid-(2-methyl-4-o-tolylazo-anilide) 
• 102556-87-6 (2-methyl-4-o-tolylazo-anilinomethylene)-malonic acid diethyl ester 
• 114278-94-3 N,N-dimethyl-4-(2-methyl-4-o-tolylazo-phenylazo)-aniline 

Relevant academic research and scientific papers

Method of preparing solvent red 24

The invention discloses a method of preparing solvent red 24. The method comprises the steps of: feeding ortho-toluidine and methanol into a reactor, dropwise adding 30wt% of hydrochloric acid at 20-25 DEG C, cooling to 2-5 DEG C, dropwise adding 40wt% of sodium nitrite solution, performing thermal insulation for 3h, heating to a room temperature for thermal insulation for 2h, adding soft water, performing stirring and filtering, washing till a pH (potential of hydrogen) of filtrate is neutral, performing drying, feeding ortho-toluidine, the soft water and a single coupling material into the reactor, dropwise adding 30wt% of hydrochloric acid at 20-25 DEG C, cooling to 2-5 DEG C, dropwise adding 20wt% of sodium nitrite solution, performing thermal insulation for 4h, dropwise adding a mixedsolution of 2-naphthol and 5% alkaline liquor at 2-5 DEG C, performing thermal insulation for 2h, regulating the pH, performing thermal insulation for 5h, re-measuring the pH, performing filtering, and repeatedly cleaning and drying a filter cake. According to the method, reaction time is shortened; a reaction is relatively thorough; a product yield is increased by approximately 30%; almost no byproduct is generated; and a product is excellent in color light and strength.

Synthesis and properties of amphiphilic photoresponsive gelators for aromatic solvents

A sugar-based photoresponsive supergelator, N-glycosylazobenzene that shows selective gelation of aromatic solvents is described. The partial trans - cis isomerization of the azobenzene moiety allows photoinduced chopping of the entangled gel fibers to short fibers, resulting in controlled fiber length and gel - sol transition. The gelator is useful for the selective removal of toxic aromatic solvents from water.

Azo compounds reducing formation and toxicity of amyloid beta aggregation intermediates

The present invention relates to compounds suitable as modulators of protein misfolding and/or protein aggregation. The compounds are particularly suitable as inhibitors of amyloid aggregate formation and/or modulators of amyloid surface properties, and/or as activators of degradation or reduction of amyloid aggregates.

Azonium-ammonium tautomerism and inclusion complexation of 4-amino-2', 3-dimethylazobenzene

The spectral characteristics of 4-amino-2',3-dimethylazobenzene (GBC), 4-aminoazobenzene (AAB) and azobenzene (AB) have been studied in various solvents, varying hydrogen ion concentrations and in β-cyclodextrin (β-CD). The inclusion complexes of GBC, AAB and AB with β-CD have been analysed by UV-visible, fiuorometry, FT-IR,1H NMR, SEM and Cache-DFT methods. The solvent study shows that the azo form is present only in GBC and AAB molecules. No significant spectral difference is observed in GBC indicating that the presence of two methyl groups does not effectively change the spectral behaviour as compared to that of AAB. In acid solutions, unusual red shift is observed in the monocation suggesting that the azonium-ammonium tautomer is present in both molecules. The absorption maximum at ～500 nm, is due to the azonium cation while that at ～320 nm originates from the ammonium cation. In β-CD solutions, the increase in the fluorescence intensity and large bathochromic shift in S1 state indicates that both GBC and AAB form 2:2 inclusion complex, whereas AB forms 1:1 inclusion complex. Also, head-to-head dimer is formed in both the aminoazobenzene compounds.

Synthesis of deuterium-labeled azo dyes of the Sudan family

Carcinogenic amines are formed in vivo during the metabolism of Sudan azo dyes. The identification and assay of these polluting agents requires the availability of deuterated analogues. Accordingly, two series of derivatives labeled on the phenylazo and naphthol moieties were synthesized. The new compounds were obtained in satisfactory chemical yields and with an excellent degree of labeling. The structures were confirmed by 1H NMR spectroscopy and high-resolution mass spectrometry. Georg Thieme Verlag Stuttgart.

Water-soluble copper salts

An improved process for preparing water-soluble copper salts of carboxylic acids is described. More particularly, the improved process comprises the steps of (A) providing a mixture comprising (A-1) as a copper source, copper metal, a copper oxide or mixtures thereof, (A-2) at least one organic monocarboxylic acid containing about 10 to about 30 carbon atoms, (A-3) at least one alkanolamine compound characterized by the formula wherein R1 is a hydroxyalkyl group and R2 may be hydrogen or a hydroxyalkyl group, and (A-4) water, (B) treating the mixture with oxygen at a temperature up to about the reflux temperature of the mixture until the desired water-soluble copper salt is obtained, and (C) recovering the copper salt as an aqueous solution. The mixture (A) can be modified to include one or more dyes to produce colored solutions of the water-soluble metal salts. The water-soluble copper salts prepared in accordance with the method of the invention are useful in a variety of applications, particularly as a preservative for wood. The invention also relates to wood which has been treated with the water-soluble copper salts of the present invention.