328-74-5

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)aniline
• Synonyms: ,,,’,’,’-Hexafluoro-3,5-xylidine;,5-Bis-trifluoromethyl-phenylamine;,5-Xylidine, a,a,a,a',a',a'-hexafluoro-;,a,a,a',a',a'-Hexafluoro-3,5-xylidine;3,5-bis(trifluoromethyl)-anilin;3,5-bis(trifluoromethyl)-benzenamin;3,5-Bis(trifluoromethyl)benzenamine;5-Amino-α,α,α,αμ,αμ,αμ-hexafluoro-m-xylene, α,α,α,αμ,αμ,αμ-Hexafluoro-3,5-xylidine
• CAS NO: 328-74-5
• Molecular Formula: C₈H₅F₆N
• Molecular Weight: 229.12
• EINECS: 206-335-0
• Product Categories: Fluorobenzene;Anilines, Aromatic Amines and Nitro Compounds;Miscellaneous;Aniline series;Trifluoromethylbenzene serise
• Mol File: 328-74-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 168.2-169.2 °C
• Boiling Point: 85 °C15 mm Hg(lit.)
• Flash Point: 182 °F
• Appearance: Clear light yellow to yellow-brown/Liquid
• Density: 1.467 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.405mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 2.15±0.10(Predicted)
• Water Solubility: Not miscible in water.
• BRN: 654318
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)aniline(328-74-5)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)aniline(328-74-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 33-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36
• RIDADR: 2810
• WGK Germany: 3
• RTECS: ZE9800000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 328-74-5(Hazardous Substances Data)

Usage

Uses

3,5-Bis(trifluoromethyl)aniline was found to be a highly efficient monodentate transient directing group (MonoTDG) for the palladium-catalyzed direct dehydrogenative cross-coupling of benzaldehydes with arenes.

Synthesis

The synthesis of 3,5-Bis(trifluoromethyl)aniline is as follows is as follows：Put 259g (1mol) 3,5-Bis(trifluoromethyl)nitrobenzeneand 500g ethyl acetate into a 1L autoclave, add 5g palladium-carbon as a catalyst, raise the temperature to 60℃, then pass the hydrogen pressure to 2MPa, keep the temperature and react for 20 hours, then cooling, filtration, concentration, and distillation to obtain 3,5-Bis(trifluoromethyl)aniline with a purity of 98.5% and a yield of 87%.

InChI:InChI=1/C8H3F6NO2/c9-7(10,11)4-1-5(8(12,13)14)3-6(2-4)15(16)17/h1-3H

Upstream product

• 328-75-6 1-nitro-3,5-bis(trifluoromethyl)benzene 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 1122-58-3 dmap 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 
• 328-73-4 3,5-bis(trifluoromethyl)iodobenzene 
• 1246566-49-3 3,5-bis(trifluoromethyl)phenyl methanesulfonate 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 201230-82-2 carbon monoxide 
• 110-83-8 cyclohexene 

Downstream Products

• 16143-84-3 (3,5-bis(trifluoromethyl)methyl)acetanilide 
• 1683-20-1 isopropyl (3,5-bis(trifluoromethyl)phenyl)carbamate 
• 39886-33-4 5-methyl-oxazolidine-3-carboxylic acid (3,5-bis-trifluoromethyl-phenylcarbamoyl)-amide 
• 78872-47-6 3-[1-(3,5-Bis-trifluoromethyl-phenylamino)-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one 
• 78872-41-0 4-[1-(3,5-Bis-trifluoromethyl-phenylamino)-eth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 141539-83-5 sodium 1-(3,5-bistrifluoromethylphenylazo)-2-hydroxy-6-naphthalenesulfonate 
• 56661-31-5 4-bromo-N-3,5-bis(trifluoromethyl)phenylbenzamide 
• 819798-87-3 2-(3,5-bis-trifluoromethyl-phenylamino)-4,6-di-tert-butyl-phenol 
• 727741-42-6 N-(cyclohex-2-enyl)-3,5-bis(trifluoromethyl)benzenamine 
• 65141-19-7 (3,5-bis-trifluoromethylphenyl)carbamic acid phenyl ester 
• 642097-22-1 1,3-bis[3,5-bis(trifluoromethyl)phenyl]triazene 
• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 943722-81-4 C₁₇H₁₉F₆NO 
• 329015-65-8 N-[(3,5-bistrifluoromethyl)phenyl]-(S)-N^α-(tert-butoxycarbonyl)indoline-2-carboxamide 

Relevant articles and documents

Stereoselective Synthesis of Pyrroloquinolines by a Br?nsted Acid Catalyzed [4+2]-Heterocyclization of Indole-7-Carbaldehydes, Anilines and Electron-Rich Alkenes

The pyrrolo[3,2,1-ij]quinoline heterocyclic core is found in the structure of a variety of compounds with interesting applications and then, new efficient and flexible strategies to construct this skeleton are required. Here, a new diastereoselective tetrafluoroboric acid (HBF4)-catalyzed three-component coupling reaction of 1H-indole-7-carbaldehyde derivatives, anilines and electron-rich alkenes to give pyrrolo[3,2,1-ij]quinolines is described. The reaction involves an unusual [4+2]-heterocyclization between an in situ formed imine and an alkene. The new catalytic method, where water is the only by-product, is efficient, robust and flexible, and allows for multigram-scale synthesis.

Novel compound 1 - bromo -2 , 4, 6 -trifluoro -3, 5 -bis (trifluoromethyl) benzene and preparation method thereof (by machine translation)

The invention relates to the field of industrial organic synthesis, and particularly discloses a compound shown as a formula I, and the chemical formula is 1 - bromo -2 , 4, 6 -trifluoro -3, 5 -trifluoromethyl benzene and a preparation method thereof. The method comprises the steps of nitration, catalytic hydrogenation, chlorination, diazotization, fluoro and the like. The preparation method has the characteristics of easily available raw materials, simple process, controllable reaction conditions and the like, is suitable for industrial production and can be used as a key intermediate to prepare OLED materials. (by machine translation)

Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.