119-93-7 Usage
Description
2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available. 2-Tolidine can be produced by a benzidine rearrangement from a hydrazine derivative derived from 2-nitrotoluene.
Uses
Different sources of media describe the Uses of 119-93-7 differently. You can refer to the following data:
1. 2-Tolidine is a commercial aromatic amine used mainly for dye production. 2-Tolidine is an intermediate for the production of soluble azo dyes and insoluble pigments used particularly in the textile, leather and paper industries. 2-Tolidine was widely used as a reagent or indicator in analytical, clinical and forensic chemistry, such as in the analytical determination of gold, or determination of the chlorine level in swimming pool water.
2. o-Tolidine is used extensively in the manufacture of dyes. It is also used as a reagentfor the analysis of gold and free chlorine inwater.
3. Sensitive colorimetric reagent for gold and for free chlorine in water.
4. 3,3'-Dimethylbenzidine be used for preparation polyimide and epoxy resin material.
Chemical Properties
Different sources of media describe the Chemical Properties of 119-93-7 differently. You can refer to the following data:
1. LIGHT GREY-GREEN TO GREY POWDER
2. o-Tolidine is a white to reddish crystal or powder. Darkens on exposure to air. Often used in paste or wet cake form. Used as a basis for many dyes.
Preparation
1-Methyl-2-nitrobenzene?reduction for 3,3′-Dimethylbenzidine, and then b6-Amino-4-hydroxynaphthalene-2-sulfonic acid rearrangement of inversion.
General Description
White to reddish crystals or crystalline powder or a light tan powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
C.I. 37230 is sensitive to exposure to light. May be sensitive to prolonged exposure to air. A weak base that forms salts with hydrochloric acid or sulfuric acid. C.I. 37230 can be acetylated. Incompatible with strong agents .
Hazard
Eye, bladder and kidney irritant, bladder
cancer, and methemoglobinemia. Possible carcinogen.
Health Hazard
The information on toxicity and carcinogenicity of o-tolidine is very little. o-Tolidineoften contains other biphenylamine contaminants. Its structure and chemical propertiesare similar to those of benzidine. The toxicproperties are therefore expected to be similar to those of benzidine.o-Tolidine is absorbed into body throughthe skin, respiratory, and gastrointestinaltract. The acute oral and dermal toxicity wasmoderate in experimental animals. An oralLD50 value in rats is within the range of400 mg/kg.o-Tolidine produced bladder cancer in testspecies. Also, cancers in other tissues werenoted in some animals. ACGIH lists thissubstance as a suspected human carcinogen.
Fire Hazard
Flash point data for C.I. 37230 are not available; however, C.I. 37230 is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
tumorigenic data. Poison by intraperitoneal
route. Moderately toxic by ingestion.
Human mutation data reported. When
heated to decomposition it emits toxic
fumes of NOx.
Potential Exposure
Over 75% of o-tolidine is used as a dye and as an intermediate in the production of rubber products, dyestuffs, pigments and pesticides. Approximately 20% of o-tolidine is used in the production of polyurethane-based high-strength elastomers, coatings, and rigid plastics. o-Tolidine has also been used in small quantities in chlorine test kits by water companies and swimming pool owners. Used as a laboratory agent to detect blood.
Carcinogenicity
3,3′-Dimethylbenzidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification Methods
Dissolve the tolidine in *benzene by percolation through a column of activated alumina and crystallise it from *benzene/pet ether. [Beilstein 13 IV 410.]
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, strong reducing agents.
Waste Disposal
Dissolve in flammable solvent and spray into firebox of an incinera tor equipped with afterburner and scrubber. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
Check Digit Verification of cas no
The CAS Registry Mumber 119-93-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 119-93:
(5*1)+(4*1)+(3*9)+(2*9)+(1*3)=57
57 % 10 = 7
So 119-93-7 is a valid CAS Registry Number.
119-93-7Relevant articles and documents
ortho-Substituent effects on the in vitro and in vivo genotoxicity of benzidine derivatives
You,Brezzell,Das,Espadas-Torre,Hooberman,Sinsheimer
, p. 19 - 30 (1993)
Benzidine and its 3,3'-diamino, 3,3'-dimethyl, 3,3'-dimethoxy, 3,3'-difluoro, 3,3'-dichloro, 3,3'-dibromo, 3,3'-dicarbomethoxy and 3,3'-dinitro derivatives together with 2-nitrobenzidine and 3-nitrobenzidine were compared for their in vitro and in vivo genotoxicity. Relative mutagenicity was established with Salmonella strains TA98, TA98/1,8-DNP6 and TA100 with and without S9 activation. All the derivatives in the presence of S9 were more mutagenic than benzidine with 3,3'-dinitro- and 3-nitro-benzidine having the greatest mutagenicity. Mutagenicity in all 3 strains with S9 activation could be correlated to electron-withdrawing ability of substituent groups, as measured by the basicity of the amines. This correlation was explained on the basis that electron-withdrawing groups could favor the stability of the mutagenic intermediate N-hydroxylamine and also enhance the reactivityof the ultimate mutagenic species, the nitrenium ion. Mutagenicity was also correlated to the energy of the lowest unoccupied molecular orbitals (E(LUMO)). Hydrophibicity was found to have very limited effect on the relative mutagenicity of our benzidine derivatives. The in vivo endpoint was chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of benzidine and its derivatives. In contrast to the in vitro results, while all the amines were genotoxic in vivo, only the 3-nitro derivative had a significant increase in toxicity over benzidine.
Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds
-
Paragraph 0035; 0036; 0039; 0040, (2016/10/07)
The invention relates to a synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds. The method employs o-nitro alkyl (alkoxyl) benzene as an initial raw material, 2,2'-dialkyl(alkoxyl) hydrazobenzene is prepared through catalysis hydrogenation in an alkaline environment, hydrochloric acid acidifying rearrangement is carried out, 4,4'-diamino-3,3'-dialkyl(alkoxyl) biphenyl is prepared, finally, a diazotization reaction is carried out and 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds are prepared. The synthetic method is advantaged by cheap and easily available raw materials, mild reaction conditions, simple operation, high safety coefficient, high yield and low cost.
Electrochemical oxidation of o-anisidine, p-anisidine, diphenylamine and o-toluidine at platinum electrode
Sharma, Laxmi Kant,Kumar, Sanjeev,Singh,Siddiqui
experimental part, p. 1117 - 1123 (2011/05/05)
The oxidation of o-anisidine, p-anisidine, diphenylamine and o-toluidine was carried out at constant potential in non-aqueous system at platinum electrode. The electrolysis was carried out at controlled anodic potential in an electrochemical cell assembly containing reaction mixture, working as well as counter electrode and reference electrode. The oxidative products formed during the electrolysis of aromatic amines at platinum anode are discussed and reported here.
