108-71-4

Basic information

• Product Name: toluene-3,5-diamine
• Synonyms: toluene-3,5-diamine;EINECS 203-609-1;1,3-diamino-5-methylbenzene;5-methyl-3-benzenediamine;toluene, 3,5-diamino-toluene;5-Methyl-1,3-benzenediamine;5-Methyl-m-phenylenediamine
• CAS NO: 108-71-4
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.1677
• EINECS: 203-609-1
• Mol File: 108-71-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 98.1°C
• Boiling Point: 217.6°C (rough estimate)
• Flash Point: 152.9 °C
• Appearance: /
• Density: 1.0343 (rough estimate)
• Vapor Pressure: 0.00306mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• CAS DataBase Reference: toluene-3,5-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: toluene-3,5-diamine(108-71-4)
• EPA Substance Registry System: toluene-3,5-diamine(108-71-4)

Safety Data

• Hazardous Substances Data: 108-71-4(Hazardous Substances Data)

Usage

General Description

Toluene-3,5-diamine is an organic compound that is used primarily as a component in the production of hair dyes and coloring products. It is also known by the chemical abbreviation TDA. Toluene-3,5-diamine is a type of aromatic amine, and can cause skin irritation and allergic reactions in some individuals. Exposure to this chemical should be limited and safety precautions should be taken when handling products containing toluene-3,5-diamine. Additionally, the production and use of toluene-3,5-diamine is regulated by various health and safety agencies to minimize potential risks to human health and the environment.

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

Upstream product

• 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 
• 614-71-1 2-ethoxytoluene 
• 1611-92-3 3,5-dibromotoluene 
• 49804-47-9 N-(4-methyl-2,6-dinitrophenyl)acetamide 
• 103-89-9 4-Methylacetanilide 
• 106-49-0 p-toluidine 
• 618-61-1 3-methyl-5-nitro-aniline 
• 99-99-0 1-methyl-4-nitrobenzene 
• 60546-37-4 4-methyl-2,6-dinitro-phenetole 

Downstream Products

• 14219-05-7 toluene-3,5-diisocyanate 
• 91-08-7 2,6-Toluene diisocyanate 
• 584-84-9 2,4-Toluene diisocyanate 
• 614-90-4 toluene-2,5-diisocyanate 
• 40553-77-3 2,8-Diamino-1,9-dimethylacridin 
• 14815-16-8 Di-trifluoracetyl-diaminotoluol-(3,5) 

Relevant articles and documents

Immobilized silver nanoparticles on silica gel as an efficient catalyst in nitroarene reduction

Nanoparticles have properties that can be fine-tuned by their size as well as shape. Hence, there is significant current interest in preparing nano-materials of small size dispersity and to arrange them in close-packed aggregates. This letter describes a way of synthesising silver nanoparticles and their protection to aggregate by silica gel. The combination of catalytic quantities of immobilized silver nanoparticles with reductive ability of NaBH4 efficiently reduces aromatic nitroarenes to the corresponding amines in aqueous medium. Noteworthy is that highly chemoselective reactions were achieved in the presence of other functional groups such as halogen and carboxylic acid groups. The silver particles immobilized on silica gel are stable in the presence of oxygen for several months.

DNA interaction of bromomethyl-substituted acridines

A series of acridines with bifunctional substituents was synthesized with the dual properties of DNA alkylation and intercalation. 4,5-Bis(bromomethyl)acridine (1) was previously reported to crosslink and intercalate with DNA. In this study, 1,8-bis(bromomethyl)acridine (2) and 2,7-bis(bromomethyl)acridine (3), monofunctional 2-(bromomethyl)-7-methylacridine (4) and 2,7-dimethylacridine (5) were synthesized, and their crosslinking and intercalative activities were investigated to assess the reactivity of bromomethyl acridines with DNA. Interstrand crosslinking activity was similar among the three bis(bromomethyl)acridines. The acridines exhibited intercalation activity for calf thymus DNA as follows: 3 > 4 > 2 = 1 5. Intracellular DNA-crosslinking and DNA-intercalating activities were evaluated using the Ames assay. 4 was mutagenic in Salmonella typhimurium TA100 and TA98, indicating that the bromomethyl group alkylated DNA bases. All three bis(bromomethyl)acridines were mutagenic in S. typhimurium TA92 and TA94, which can detect intracellular crosslinking DNA damage, whereas 5 was not mutagenic in these strains. The results showed that the bis(bromomethyl)acridines crosslinked DNA and intercalated between DNA bases, and 3 exhibited the highest crosslinking and intercalating activity.

Process for the production of the toluene diisocyanate

The invention relates to a process for the production of toluene diisocyanate, in which the crude toluenediamine obtained from the hydrogenation is purified and then phosgenated. The purification step reduces the total amount of cyclic ketones to less than 0.1 % by weight, based on 100% by weight of the toluenediamine.