2-amino-alpha,alpha,alpha-trifluoro-p-creso Chemical Properties

Melting point:

121-122 °C(Solv: benzene (71-43-2))

Boiling point:

234.5±40.0 °C(Predicted)

Density 

1.432±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Solid

pka

8.36±0.18(Predicted)

InChI

InChI=1S/C7H6F3NO/c8-7(9,10)4-1-2-6(12)5(11)3-4/h1-3,12H,11H2

InChIKey

BHTKIYIEMXRHGL-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(C(F)(F)F)C=C1N

Safety Information

HS Code 

2908190090

2-amino-alpha,alpha,alpha-trifluoro-p-creso Usage And Synthesis

Uses

2-Amino-4-(trifluoromethyl)phenol is used in the studies on the structure activity relationship of benzoxazolone carboxamides as potent acid ceramidase inhibitors.

Synthesis

The general procedure for the synthesis of 2-amino-4-trifluoromethylphenol from 2-nitro-4-trifluoromethylphenol was as follows: 2-nitro-4-trifluoromethylphenol (340 μL, 2.41 mmol) was dissolved in methanol (50 mL), and catalytically hydrogenated at room temperature and atmospheric pressure using a 10% Pd/C catalyst cartridge through an H-Cube hydrogenation reactor. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure to give 2-amino-4-trifluoromethylphenol (438 mg, 100% yield) as a light brown solid. Mass spectrum (chemical ionization, m/z): [M+H]+ 178, [M-H]- 176; 1H NMR (CDCl3): δ 6.96 (d, J=2.0 Hz, 1H), 6.89-6.94 (m, 1H), 6.74 (d, J=8.2 Hz, 1H), 4.10 (br s, 2H).

References

[1] Patent: WO2009/37293, 2009, A1. Location in patent: Page/Page column 52
[2] Patent: WO2009/37294, 2009, A1. Location in patent: Page/Page column 93
[3] Patent: US2014/142114, 2014, A1. Location in patent: Paragraph 0859; 0860
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2009, vol. 184, # 3, p. 651 - 659
[5] Patent: WO2005/85202, 2005, A1. Location in patent: Page/Page column 53-54

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