(2-AMINO-4-FLUORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

135.0 to 139.0 °C

Boiling point:

281.0±30.0 °C(Predicted)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

powder to crystal

pka

12.45±0.70(Predicted)

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2921.51.5000

(2-AMINO-4-FLUORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

N-(2-Amino-4-fluorophenyl)-1,1-dimethylethyl Ester Carbamic Acid is a reactant in the synthesis of Histone Deacetylase (HDAC) inhibitors in cancer lines.

Synthesis

General procedure for the synthesis of (2-amino-4-fluorophenyl)-carbamic acid-1,1-dimethylethyl ester from tert-butyl (4-fluoro-2-nitrophenyl)carbamate: To a solution of tetrahydrofuran (THF, 30 mL) of tert-butyl 4-fluoro-2-nitrophenylcarbamate (0.34 g) was added a pre-mixed aqueous solution of sodium bisulphite (2 g) and sodium bicarbonate (1 g) ( 50mL). To promote dissolution of the mixture, additional methanol (MeOH, 10 mL) was added, followed by stirring for 30 min at room temperature. Upon completion of the reaction, sodium chloride was added to saturate the solution. The reaction mixture was extracted with ethyl acetate (EtOAc, 2 x 30 mL). The organic phases were combined, dried over anhydrous sodium sulfate and filtered, and concentrated under reduced pressure to afford (2-amino-4-fluorophenyl)-carbamic acid-1,1-dimethylethyl ester (quantitative yield), and the product could be used in the subsequent reaction without further purification. The product was characterized by 1H-NMR (300 MHz, CDCl3): δ 7.5 (dd, 1H), 6.6 (dd, 1H), 6.5 (m, 1H), 6.4 (br s, 1H), 4.7 (br s, 2H), 1.5 (s, 9H) ppm; mass spectrometry analysis showed MH+ = 227 (minor peaks), 127 (-BOC fragment), 171 (-tBu fragment).

References

[1] Patent: US2008/85898, 2008, A1. Location in patent: Page/Page column 15
[2] Patent: US2008/119496, 2008, A1. Location in patent: Page/Page column 26
[3] Patent: WO2008/60301, 2008, A1. Location in patent: Page/Page column 63-64
[4] Patent: WO2009/48474, 2009, A1. Location in patent: Page/Page column 28
[5] Patent: CN107879975, 2018, A. Location in patent: Paragraph 0164; 0166

(2-AMINO-4-FLUORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER(579474-47-8)Related Product Information

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