N-methyl-4-(trifluoromethyl)aniline

Base Information

• Chemical Name: N-methyl-4-(trifluoromethyl)aniline
• CAS No.: 22864-65-9
• Molecular Formula: C8H8F3N
• Molecular Weight: 175.153
• Hs Code.: 2921430090
• European Community (EC) Number: 626-543-9
• DSSTox Substance ID: DTXSID30568183
• Nikkaji Number: J1.052.980H
• Mol file: 22864-65-9.mol

Synonyms:N-methyl-4-(trifluoromethyl)aniline;22864-65-9;4-(Trifluoromethyl)-N-methylaniline;4-Trifluoromethyl-N-methylaniline;MFCD07369717;4-TRIFLUOROMETHYL-N-METHYLANILINE 97;N-Methyl-4-trifluoromethylaniline;BENZENAMINE, N-METHYL-4-(TRIFLUOROMETHYL)-;N-METHYL-N-[4-(TRIFLUOROMETHYL)PHENYL]AMINE;N-methyl-4-(trifluoromethyl)-aniline;METHYL-(4-TRIFLUOROMETHYL-PHENYL)-AMINE;SCHEMBL130264;N-Methyl-p-trifluoromethylaniline;DTXSID30568183;ZPZMEUPGKHBKPZ-UHFFFAOYSA-N;CS-M1968;N-methyl-p-(trifluoromethyl)aniline;AKOS000256655;FS-2364;AC-28570;AM808201;SY052871;4-(Trifluoromethyl)-N-methylaniline, 97%;M2774;EN300-1265877;J-014883;F8883-1311

Chemical Property of N-methyl-4-(trifluoromethyl)aniline

Chemical Property:

• Vapor Pressure: 0.474mmHg at 25°C
• Refractive Index: n20/D 1.4888(lit.)
• Boiling Point: 193.041 °C at 760 mmHg
• PKA: 2.58±0.12(Predicted)
• Flash Point: 70.549 °C
• PSA: 12.03000
• Density: 1.23 g/cm³
• LogP: 2.82010
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 175.06088375
• Heavy Atom Count: 12
• Complexity: 136

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(Trifluoromethyl)-N-methylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=CC=C(C=C1)C(F)(F)F
• Uses: 4-(Trifluoromethyl)-N-methylaniline is used in the synthesis of Tasquinimod (T007820), an orally active antiangiogenic agent which may inhibit HDAC4 signalling. This affects cancer cell survival thus making this compound and anti-cancer agent.

Technology Process of N-methyl-4-(trifluoromethyl)aniline

There total 30 articles about N-methyl-4-(trifluoromethyl)aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-trifluoromethylphenylamine (455-14-1) → N-methyl-4-(trifluoromethyl)aniline (22864-65-9)

Guidance literature:

formaldehyd; 4-trifluoromethylphenylamine; With sodium methylate; In methanol; at 50 ℃; for 5h; Inert atmosphere;

With methanol; sodium tetrahydroborate; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.202003364

Reference yield: 99.0%

N-methyl-N-(4-(trifluoromethyl)phenyl)formamide → N-methyl-4-(trifluoromethyl)aniline (22864-65-9)

Guidance literature:

With C₁₈H₃₇ClMoNO₂P₂; hydrogen; sodium triethylborohydride; In tetrahydrofuran; toluene; at 100 ℃; for 24h; under 37503.8 Torr; Autoclave; Glovebox;

DOI:10.1039/c9sc03453f

Reference yield: 96.0%

N-methyl-N-(4-(trifluoromethyl)phenyl)acetamide → N-methyl-4-(trifluoromethyl)aniline (22864-65-9) + N-ethyl-N-methyl-4-(trifluoromethyl)aniline

Guidance literature:

With triethyl borane; Triethoxysilane; sodium hydroxide; In hexane; at 80 ℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;

upstream raw materials:

4-trifluoromethylphenylamine

trimethyl orthoformate

1-(azidomethyl)-4-(trifluoromethyl)benzene

N,N-dimethyl-4-(trifluoromethyl)aniline

Downstream raw materials:

ethyl N-methyl-N-4-trifluoromethylphenylcarbamate

1,2-dihydro-4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-3-quinolinecarboxamide

(Z)-2-Cyano-3-hydroxy-N-methyl-3,N-bis-(4-trifluoromethyl-phenyl)-acrylamide

N-methyl-N-(4-trifluoromethyl-phenyl)-1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxamide

Refernces

• 1、 Sarki, Naina,Goyal, Vishakha,Tyagi, Nitin Kumar,Puttaswamy,Narani, Anand,Ray, Anjan,Natte, Kishore. "Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol". . p. 1722 - 1729. Retrieved 2021/04/19.
• 2、 Hornink, Milene Macedo,Lopes, Alice Uva,Andrade, Leandro Helgueira. "Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals". supporting information. p. 296 - 308. Retrieved 2020/11/09.