402-14-2

Basic information

• Product Name: 3-Amino-4-nitrobenzitrifluoride
• Synonyms: 2-AMINO-1-NITRO-4-TRIFLUOROMETHYLBENZENE;2-NITRO-5-(TRIFLUOROMETHYL)ANILINE;3-AMINO-4-NITROBENZOTRIFLUORIDE;3-Amino-4-nitrobenzitrifluoride;3-amino-4-nitro(trifluoromethyl)benzene;2-Nitro-5-(trifluoromethyl)aniline ,98%;2-Nitro-5-(trifluoromethyl)aniline, 2-Amino-4-(trifluoromethyl)nitrobenzene;2-Nitro-5-trifluoroMethyl-phenylaMine
• CAS NO: 402-14-2
• Molecular Formula: C₇H₅F₃N₂O₂
• Molecular Weight: 206.12
• EINECS: -0
• Product Categories: Benzenes
• Mol File: 402-14-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 98-100°C
• Boiling Point: 290.5 °C at 760 mmHg
• Flash Point: 129.5 °C
• Appearance: /
• Density: 1.503 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO, Methanol
• PKA: -1.66±0.25(Predicted)
• BRN: 2732344
• CAS DataBase Reference: 3-Amino-4-nitrobenzitrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-nitrobenzitrifluoride(402-14-2)
• EPA Substance Registry System: 3-Amino-4-nitrobenzitrifluoride(402-14-2)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-22
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 402-14-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystalline powder

Uses

2-Nitro-5-(trifluoromethyl)aniline is a reagent in the synthesis of benzo[d]imidazole derivatives which has vasorelaxant activity and antihypertensive effects.

Upstream product

• 402-54-0 p-nitrobenzotrifluoride 
• 98-16-8 3-trifluoromethylaniline 
• 395-99-3 N-[2-nitro-5-(trifluoromethyl)phenyl]acetamide 
• 351-36-0 N-acetyl-3-trifluoromethylbenzenamine 

Downstream Products

• 294673-72-6 (2,4-dichloropyrimidin-5-yl)-N-[2-nitro-5-(trifluoromethyl)phenyl]carboxamide 
• 449-72-9 2,3-dimethyl-6-(trifluoromethyl)quinoxaline 
• 954239-03-3 tert-butyl (2-amino-5-(trifluoromethyl)phenyl)carbamate 
• 664997-23-3 5–trifluoromethyl–2–(1H–pyrrol–1–yl)aniline 
• 16499-52-8 2-nitro-5-(trifluoromethyl)benzonitrile 
• 1449379-17-2 4-[2-azido-5-(trifluoromethyl)phenyl]-2-methylbut-3-yn-2-yl acetate 
• 1449379-16-1 C₁₂H₁₀F₃N₃O 
• 163444-17-5 2-iodo-4-(trifluoromethyl)aniline 

Relevant articles and documents

Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H- benzimidazole bioisosteres

A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives with various 5- and 6-position bioisosteric substituents (-Cl, -F, -CF3, -CN), namely 1-7, were prepared using a short synthetic route. Each analogue was tested in vitro against the protozoa Giardia intestinalis and Trichomonas vaginalis in comparison with albendazole and metronidazole. Several analogues had IC50 values 1 μM against both species, which make them significantly more potent than either standard. Compound 4 [2,5(6)- bis(trifluoromethyl)-1H-benzimidazole], was 14 times more active than albendazole against T.:vaginalis. This compound (4) also showed moderate antimalarial activity against W2 and D6 strains of Plasmodium falciparum (5.98 and 6.12 μM, respectively). Studying further structure activity relationships through the use of bioisosteric substitution in these benzimidazolic derivatives should provide new leads against protozoal and possibly malarial diseases.

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.