106877-31-0

Basic information

• Product Name: 3-methyl-4-trifluoromethylaniline
• Synonyms: 3-methyl-4-trifluoromethylaniline;4-Trifluoromethyl-3-toluidine;3-Methyl-4-trifluoromethyl-phenylamine
• CAS NO: 106877-31-0
• Molecular Formula: C₈H₈F₃N
• Molecular Weight: 175.1510296
• Mol File: 106877-31-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methyl-4-trifluoromethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-4-trifluoromethylaniline(106877-31-0)
• EPA Substance Registry System: 3-methyl-4-trifluoromethylaniline(106877-31-0)

Safety Data

• Hazardous Substances Data: 106877-31-0(Hazardous Substances Data)

Usage

General Description

3-methyl-4-trifluoromethylaniline is an organic compound with a chemical formula C9H9F3N. It is a derivative of aniline, containing a methyl group and a trifluoromethyl group attached to the fourth carbon of the aromatic ring. 3-methyl-4-trifluoromethylaniline is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. It is also utilized as a building block in organic chemistry and serves as a versatile starting material for the production of various functionalized aromatic compounds. 3-methyl-4-trifluoromethylaniline is a yellowish to brownish crystalline solid with a characteristic odor, and it is classified as a hazardous chemical due to its potential health and environmental risks.

Upstream product

• 99-52-5 2-methyl-4-nitro-benzenamine 
• 5326-38-5 2-iodo-5-nitrotoluene 
• 1960-52-7 2-methyl-4-nitro-1-(trifluoromethyl)benzene 
• 75-63-8 Bromotrifluoromethane 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 179637-55-9 2-Cyano-N-(3-methyl-4-trifluoromethyl-phenyl)-acetamide 
• 929910-74-7 3-methyl-5-nitro-3H-imidazole-4-carboxylic acid (3-methyl-4-trifluoromethyl-phenyl)-amide 
• 1445983-45-8 5-(3-((1-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)cyclopropylamino)methyl)-4-(trifluoromethyl)phenyl)-N-methyl-N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)pentanamide 
• 1445985-73-8 5-(3-((1-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)cyclopropylamino)methyl)-4-(trifluoromethyl)phenyl)pentanoic acid 
• 1445985-72-7 methyl 5-(3-((1-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)cyclopropylamino)methyl)-4-(trifluoromethyl)phenyl)pentanoate 
• 1445985-71-6 methyl 5-(3-((1-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)cyclopropylamino)methyl)-4-(trifluoromethyl)phenyl)pent-4-ynoate 
• 1445983-30-1 (4-cyclopropyl-3,4-dihydroquinoxalin-1(2H)-yl)(1-(5-iodo-2-(trifluoromethyl)benzylamino)cyclopropyl)methanone 
• 1261682-47-6 2-(bromomethyl)-4-iodo-1-(trifluoromethyl)benzene 
• 930599-57-8 4-iodo-2-methyl-1-(trifluoromethyl)benzene 
• 147076-36-6 (1-(3-methyl-4-trifluoromethylphenyl-carbomyl)-2-cyclopropyl-2-oxo-propionitrile) 
• 195723-99-0 4-trifluoromethyl-3-toluidine hydroxyacetate 

Relevant articles and documents

Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series

Acylaminobenzothiazole hits were identified as potential inhibitors of Trypanosoma cruzi replication, a parasite responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure-activity relationship, allowing optimization of antiparasite activity, physicochemical parameters, and ADME properties. We identified compound 50 as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079 μM) and an enhanced metabolic stability (human clearance = 0.41 mL/min/g) and opportunity for the oral route of administration. After tolerability assessment, 50 demonstrated a promising in vivo efficacy.

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Synthesis, structure-activity relationships, and pharmacokinetic properties of dihydroorotate dehydrogenase inhibitors: 2-cyano-3-cyclopropyl- 3-hydroxy. N-[3'-methyl-4'-(trifluoromethyl)phenyl]propenamide and related compounds

The active metabolite (2) of the novel immunosuppressive agent leflunomide (1) has been shown to inhibit the enzyme dihydroorotate dehydrogenase (DHODH). This enzyme catalyzes the fourth step in de novo pyrimidine biosynthesis. A series of analogues of the active metabolite 2 have been synthesized. Their in vivo biological activity determined in rat and mouse delayed type hypersensitivity has been found to correlate well with their in vitro DHODH potency. The most promising compound (3) has shown activity in rat and mouse collagen (II)-induced arthritis models (ED50 = 2 and 31 mg/kg, respectively) and has shown a shorter half-life in man when compared with leflunomide. Clinical studies in rheumatoid arthritis are in progress.

Reactions of Trifluoromethyl Bromide and Related Halides: Part 10. Perfluoroalkylation of Aromatic Compounds induced by Sulphur Dioxide Radical Anion Precursors

Perfluoroalkylation of electron-rich aromatic compounds with trifluoromethyl bromide, or long-chain perfluoroalkyl iodides, was performed in the presence of sodium dithionite or zinc-sulphur dioxide.This alkylation occurred at the ortho and para positions relative to the amino or hydroxy substitutent.Pyrroles were perfluoroalkylated regioselectively at the 2-position.This alkylation was interpreted as a radical aromatic substitution; the formation of the perfluoroalkyl radical can be induced by a single-electron transfer from sulphur dioxide radical anion to the perfluoroalkyl halide.

Process for perfluoroalkylation of aromatic derivatives

A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.