95-70-5

Basic information

• Product Name: 2,5-Diaminotoluene
• Synonyms: 2,5-DIAMINO TOLUENE FREE;2-Methyl-1,4-phenylene diamine;1-METHYL-2,5-DIAMINOBENZENE;DIAMINOTOLUENES;4-TOLUYLENEDIAMINE;1,4-DIAMINO-2-METHYLBENZENESULFATE;TOLUENE-2,5-DIAMINE(ANDITSSALTS);2-methyl-p-phenylenediamine 2,5-toluenediamine
• CAS NO: 95-70-5
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• EINECS: 202-442-1
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 95-70-5.mol
• Article Data: 35

Chemical Properties

• Melting Point: 64°C
• Boiling Point: 273°C
• Flash Point: 140.6 °C
• Appearance: purple crystal
• Density: 1.0343 (rough estimate)
• Vapor Pressure: 0.00565mmHg at 25°C
• Refractive Index: 1.5103 (estimate)
• Solubility: Soluble in water
• PKA: 5.98±0.10(Predicted)
• Water Solubility: 500g/L at 20℃
• CAS DataBase Reference: 2,5-Diaminotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diaminotoluene(95-70-5)
• EPA Substance Registry System: 2,5-Diaminotoluene(95-70-5)

Safety Data

• Hazard Codes: T,N
• Statements: 20/21-25-43-51/53
• Safety Statements: 24-37-45-61
• RIDADR: 2811
• RTECS: XS9700000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 95-70-5(Hazardous Substances Data)

Usage

Description

p-Toluylenediamine is a hair dye associated with contact dermatitis in hairdressers. Cross reactivity is observed with PPD.

Chemical Properties

Colorless plates. Soluble in water, ethanol, ether, and hot benzene 2,5-Toluenediamine is used in hair and fur dyes.

Uses

2,5-Toluenediamine is used primarily in hair dye formulations as one of the major oxidation dye precursors. It is also used in the synthesis of saframine, a family of dyes used as biological stain, and may be present in indelible ink, antifreeze, and nail polish. As may be expected from its use in hair dye formulations, hairdressers and barbers may be exposed to 2,5-TDA. Workers in the dye manufacturing industry may also be exposed.

Definition

ChEBI: A diamine in which the two amino groups are substituted into toluene at the 2- and 5-positions.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 6182, 1980 DOI: 10.1021/ja00539a054

Flammability and Explosibility

Nonflammable

Contact allergens

Toluene-2,5-diamine is a permanent hair dye involved in contact dermatitis in hairdressers and consumers. It does not cross-react with PPD, but cosensitization is frequent.

Safety Profile

Poison by ingestion and subcutaneous routes. A skin irritant. Mutation data reported. Questionable carcinogen. Has a toxic action upon the liver and can cause fatty degeneration of that organ. Its total effect upon the body seems to take place three chfferent ways. It is toxic to the central nervous system, producing jaundice by action on the liver and spleen, and anemia by destruction of the red blood cells. This action is quite similar to that of aniline, although by no means identical with it. Its high boiling point and the fact that the material is solid at room temperature make it somewhat less hazardous than aniline, particularly at ordinary working temperatures. The literature contains a reference to a permanent injury to an eye due to the use of this material as an eyelash dye. It is considered to be an irritating dye material. When heated to decomposition it emits toxic fumes of NOx. See also other toluene diamine entries and AROMATIC AMINES.

Carcinogenicity

The possible carcinogenicity of 2,5-TDA (as sulfate salt [6369-59-1]) was tested by the National Cancer Institute in a dietary feeding study. Groups of 50 male and female F344 rats (600 or 2000 ppm) and B6C3F1 mice (600 or 1000 ppm) were given diets containing 2,5-TDA for 78 weeks and then observed for an additional period of 28–31 weeks for rats and 16–19 weeks for mice. The only statistically significant increased incidence was in lung tumors in high-dose female mice, but the evidence was not convincing enough to be attributed to 2,5-TDA. Overall, the compound was considered noncarcinogenic.

InChI:InChI=1/C7H10N2.ClH/c1-5-4-6(8)2-3-7(5)9;/h2-4H,8-9H2,1H3;1H

Upstream product

• 7647-01-0 hydrogenchloride 
• 3398-09-2 3-methyl-4-m-tolylazo-aniline 
• 3963-79-9 3-methyl-4-p-tolylazo-aniline 
• 64-19-7 acetic acid 
• 16714-19-5 1-azido-2-methyl-4-nitrobenzene 
• 121-14-2 2,4-dinitrotoluene 
• 618-85-9 3,5-dinitrotoluene 
• 606-20-2 2,6-dinitrotoluene 
• 602-01-7 1-methyl-2,3-dinitrobenzene 
• 610-39-9 3,4-Dinitrotoluene 
• 619-15-8 2,5-dinitrotoluene 
• 202865-85-8 1-bromo-4-iodo-2-methylbenzene 
• 97-56-3 o-aminoazotoluene 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 69950-77-2 C₁₇H₃₀N₄O₆P₂S₂ 
• 72255-63-1 6-(4-Amino-3-methyl-phenylamino)-1H-pyrimidine-2,4-dione 
• 126314-32-7 2-methylbenzene-1,4-di-4'-morpholine 
• 91-08-7 2,6-Toluene diisocyanate 
• 14219-05-7 toluene-3,5-diisocyanate 
• 584-84-9 2,4-Toluene diisocyanate 
• 614-90-4 toluene-2,5-diisocyanate 
• 226947-06-4 Mo(S₂CN(CH₂CH₃)2)2Cl₂(NC₆H₃(CH₃)NH₂) 
• 40015-81-4 2-methyl-1,4-cyclohexanediamine 
• 64-18-6 formic acid 
• 64-19-7 acetic acid 
• 121711-46-4 C₁₃H₁₈N₂S₄ 
• 19972-70-4 N,N'-(2,5-Tolylene)bis(methyldithiocarbamate) 

Relevant articles and documents

Novel environment-friendly production process for preparing amine product and H - acid through silane chemical reduction of several nitro compounds

The invention relates to the field of new materials for fine chemicals, and relates to a reduction reaction of a series of nitro compounds, in particular to m-nitroaniline. Several particular important amine compounds such as m-phenylenediamine, 5 - amino o-cresol, 2 - methyl p-phenylenediamine, 1/2 - naphthylamine, H - acid amine and 2, 4, 6 - trimethyl-M-phenylenediamine are prepared from the corresponding mono-or double-nitro compound precursors with a new environmental protection production process technology of and acids derived from the novel process technology. H.

A capping agent dissolution method for the synthesis of metal nanosponges and their catalytic activity towards nitroarene reduction under mild conditions

We report a general strategy for the synthesis of metal nanosponges (M = Ag, Au, Pt, Pd, and Cu) using a capping agent dissolution method where addition of water to the M@BNHx nanocomposite affords the metal nanosponges. The B-H bond of the BNHx polymer gets hydrolysed upon addition of water and produces hydrogen gas bubbles which act as dynamic templates leading to the formation of nanosponges. The rate of B-H bond hydrolysis has a direct impact on the final nanostructure of the materials. The metal nanosponges were characterized using powder XRD, electron microscopy, XPS, and BET surface area analyzer techniques. The porous structure of these nanosponges offers a large number of accessible surface sites for catalytic reactions. The catalytic activity of these metal nanosponges has been demonstrated for the reduction of 4-nitrophenol where palladium exhibits the highest catalytic activity (k = 0.314 min?1). The catalytic activity of palladium nanosponge was verified for the tandem dehydrogenation of ammonia borane and the hydrogenation of nitroarenes to arylamines in methanol at room temperature. The reduction of various substituted nitroarenes was proven to be functional group tolerant except for a few halogenated nitroarenes (X = Br and I) and >99% conversion was noted within 30-60 min with high turnover frequencies (TOF) at low catalyst loading (0.1 mol%). The catalyst could be easily separated out from the reaction mixture via centrifugation and was recyclable over several cycles, retaining its porous structure.

Unique Chemoselective Hydrogenation using a Palladium Catalyst Immobilized on Ceramic

A heterogeneous palladium catalyst supported on a ceramic (5 % Pd/ceramic) was developed. The catalyst exhibited a specific chemoselectivity for hydrogenation that has never been achieved by other palladium-catalyzed methods. Either aliphatic or aromatic N-Cbz groups could be deprotected to the corresponding free-amines, while the hydrogenolysis of benzyl esters and ethers did not proceed. Furthermore, aryl chlorides and epoxides were tolerant under the Pd/ceramic-catalyzed hydrogenation conditions. 5 % Pd/ceramic could be reused without any loss of catalyst activity, as no palladium leaching was detected in the reaction media.