2-AMINO-4-TRIFLUOROMETHYL-BENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

65-68 °C(Solv: ethanol (64-17-5); water (7732-18-5))

Boiling point:

267.5±40.0 °C(Predicted)

Density 

1.343±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

1.06±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H8F3NO2/c1-15-8(14)6-3-2-5(4-7(6)13)9(10,11)12/h2-4H,13H2,1H3

InChIKey

DZICUHOFOOPVFM-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2922498590

2-AMINO-4-TRIFLUOROMETHYL-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

2-Amino-4-trifluoromethylbenzoic Acid Methyl Ester is an intermediate used to prepare quinazolinedione sulfonamides as competitive AMPA receptor antagonists. It is also used in the synthesis of (arylamino)pyrimidobenzazepinones and pyrimidobenzazepinethiones as inhibitors of polo-like kinase 1 and potential antitumor agents.

Synthesis

Step 2; Preparation of methyl 2-amino-4-trifluoromethylbenzoate; Methyl 2-nitro-4-(trifluoromethyl)benzoate (106 g, 425 mmol) was dissolved in ethanol. To a slurry of 10% palladium carbon (11.0 g) in ethyl acetate (200 mL) was added ethyl acetate (2.2 L), and the suspension was stirred for 3 h at room temperature and 60 °C under a hydrogen atmosphere. Upon completion of the reaction, the suspension was filtered through a Celite pad and the pad was washed with additional ethyl acetate. The filtrate was concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using isohexane/ethyl acetate (9:1) as eluent to afford methyl 2-amino-4-trifluoromethylbenzoate as a white crystalline solid (84 g, 95% yield).

References

[1] Patent: WO2006/2342, 2006, A1. Location in patent: Page/Page column 55-56
[2] Patent: US2004/102636, 2004, A1
[3] Patent: US2008/269265, 2008, A1. Location in patent: Page/Page column 10
[4] Patent: EP1449834, 2004, A2. Location in patent: Page 16
[5] Patent: EP1042305, 2005, B1. Location in patent: Page/Page column 21

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