| Identification | More | [Name]
3'-Trifluoromethylisobutyranilide | [CAS]
1939-27-1 | [Synonyms]
2-METHYL-N-(3-TRIFLUOROMETHYLPHENYL) PROPANAMIDE
3'-TRIFLUOROMETHYL-ISO-BUTYRANILIDE
TIMTEC-BB SBB008101
2-methyl-n-(alpha,alpha,alpha-trifluoro-m-tolyl)propionamide
2-methyl-N-[3-(trifluoromethyl)phenyl]propionamide
3-(Isobutyryladmino)-1-(trifluoro-methyl)benzene
Ethanone, 1-(2-hydroxy-4,5-dimethylphenyl)- | [EINECS(EC#)]
406-740-4 | [Molecular Formula]
C11H12F3NO | [MDL Number]
MFCD00043455 | [Molecular Weight]
231.21 | [MOL File]
1939-27-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
100-101 °C | [Boiling point ]
313.5±42.0 °C(Predicted) | [density ]
1.220±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
14.33±0.70(Predicted) | [color ]
Off-White to Pale Orange | [CAS DataBase Reference]
1939-27-1(CAS DataBase Reference) | [NIST Chemistry Reference]
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| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . |
| Hazard Information | Back Directory | [Uses]
2-Methyl-N-[3-(trifluoromethyl)phenyl]propanamide is used as a reagent to synthesize Flutamide (F598850), an oral nonsteroidal antiandrogen that is hepatotoxic and commonly used to treat patients with prostate cancer. | [Synthesis]
GENERAL METHOD: A mixture of cobalt(II) oxalate dihydrate (Sigma-Aldrich, 0.294 mmol), Cs2CO3 (2.94 mmol), isobutyramide (1.47 mmol), DMEDA (0.588 mmol), distilled water (0.3 mL), and 3-iodobenzotrifluoride (2.205 mmol) was added to a reaction vial containing a polytetrafluoroethylene sealed screw cap in an 8.0 mL reaction flask. The reaction mixture was stirred in a closed system at 120°C to 130°C for 24 hours. The non-homogeneous mixture was then cooled to room temperature and diluted with CH2Cl2. The combined organic extracts were dried with anhydrous Na2SO4, filtered and the solvent removed under reduced pressure. The crude product was loaded onto a silica gel column using a minimal amount of CH2Cl2 and purified by column chromatography to afford N-(3-(trifluoromethyl)phenyl)isobutyramide. The structure and purity of the product were confirmed by 1H NMR and 13C NMR spectral analysis. | [References]
[1] Synlett, 2015, vol. 26, # 12, p. 1697 - 1701 |
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