O-Tolidine

O-Tolidine Basic information
Product Name:O-Tolidine
Synonyms:3,3'-Dimethyl-[1,1'-biphenyl]-4,4'-Diamine(O-Tolidine);1’-biphenyl)-4,4’-diamine,3,3’-dimethyl-(;1’-Biphenyl)-4,4’-diamine,3,3’-dimethyl-(1;1’-biphenyl)-4,4’-diamine-3,3’-dimethyl-(;1’-biphenyl]-4,4’-diamine,3,3’-dimethyl-[;2-Tolidin;2-Tolidina;3,3’-dimethyl-4,4’-biphenyldiamine
CAS:119-93-7
MF:C14H16N2
MW:212.29
EINECS:204-358-0
Product Categories:Organics;Intermediates of Dyes and Pigments;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines
Mol File:119-93-7.mol
O-Tolidine Structure
O-Tolidine Chemical Properties
Melting point 128-131 °C(lit.)
Boiling point 300.5 °C
density 0.9678 (rough estimate)
refractive index n20/D 1.341
Fp 244 °C
storage temp. -20°C
solubility 2% HCl: 10 mg/mL, clear
form powder (may contain lumps)
pka4.59±0.10(Predicted)
Colour Index 37230
color light brown
Water Solubility Slightly soluble in water.
Merck 14,9514
BRN 2210640
Exposure limitsTLV-TWA none; carcinogenicity: A2 — Suspected Human Carcinogen (ACGIH), Animal Limited Evidence (IARC).
InChIKeyNUIURNJTPRWVAP-UHFFFAOYSA-N
IARC2B (Vol. 1, Sup 7) 1987
NIST Chemistry Reference[1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethyl-(119-93-7)
EPA Substance Registry System3,3'-Dimethylbenzidine (119-93-7)
Safety Information
Hazard Codes T,N,F
Risk Statements 45-68-51/53-22-11
Safety Statements 53-45-61-16
RIDADR UN 3082 9/PG 3
WGK Germany 3
RTECS DD1225000
8
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29215900
Hazardous Substances Data119-93-7(Hazardous Substances Data)
Toxicitydog,LDLo,oral,600mg/kg (600mg/kg),Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 58, Pg. 167, 1907.
MSDS Information
ProviderLanguage
C.I. 37230 English
SigmaAldrich English
ACROS English
ALFA English
O-Tolidine Usage And Synthesis
Description2-Tolidine, also known as orthotolidine or 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.
Chemical Propertieso-Tolidine is a white to reddish crystal or powder and has an aniline-like odor. It is soluble in alcohol, ether, and dilute acid, but only slightly soluble in water. It has a tendency to darken when exposed to air and is commonly utilized in paste or wet cake form. This compound serves as a fundamental component for the production of numerous dyes.
Useso-Tolidine is used extensively in the manufacture of dyes, especially in the production of soluble azo dyes and insoluble pigments for the textile, leather, and paper sectors. Additionally, It is also used as a sensitive colorimetric reagent for the analysis of gold and free chlorine in water.
Uses3,3'-Dimethylbenzidine be used for preparation polyimide and epoxy resin material.
PreparationThere are two commonly used methods for producing o-Tolidine. The first method involves reducing ortho-nitrotoluene to 1,2-diorthotolylhydrazine, which is then rearranged with acid. The second method involves reducing o-nitrotoluene using zinc dust and caustic soda, then converting the resulting hydrazotoluene to o-Tolidine by boiling it with hydrochloric acid. Once either of these methods is completed, o-Tolidine can be extracted and purified through techniques such as solvent extraction and recrystallization.
DefinitionChEBI: 3,3'-Dimethylbenzidine is a member of biphenyls.
General Description3,3'-dimethylbenzidine appears as white to reddish crystals or crystalline powder or a light tan powder. (NTP, 1992)
Air & Water ReactionsInsoluble in water.
Reactivity ProfileC.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 .
HazardEye, bladder and kidney irritant, bladder cancer, and methemoglobinemia. Possible carcinogen.
Health HazardThe 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 HazardFlash point data for C.I. 37230 are not available; however, C.I. 37230 is probably combustible.
Safety ProfileConfirmed 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 ExposureOver 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.
Carcinogenicity3,3′-Dimethylbenzidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
ShippingUN2811 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 MethodsDissolve the tolidine in *benzene by percolation through a column of activated alumina and crystallise it from *benzene/pet ether. [Beilstein 13 IV 410.]
IncompatibilitiesIncompatible 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 DisposalDissolve 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.
ACID RED 114 N,N'-(3,3'-Dimethyl-4,4'-biphenyldiyl)bis(3-oxobutanamide) DIANIL BLUE 2R Direct Blue 53 O-TOLUIDINE DISULFONIC ACID TIMTEC-BB SBB003162 3,3'-Dimethyl-4,4'-biphenylene diisocyanate 4,4'-DIAMINOBIPHENYL-3,3'-DICARBOXYLIC ACID ROSAZURIN B DIRECT FAST RED 3B 3,3'-DIMETHYLNAPHTHIDINE 3,3'-Dimethylbenzidine dihydrochloride 4,4'-DIMETHYLBIPHENYL Tetramethylbenzidine CI 23790 Direct Blue 14 3,3'-Dimethylbiphenyl 2,2'-Dimethyl-1,1'-biphenyl-4,4'-diamine dihydrochloride

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