2-AMINO-5-FLUOROBENZAMIDE Chemical Properties

Melting point:

143-148℃

Boiling point:

259.3±25.0 °C(Predicted)

Density 

1.344±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

15.23±0.50(Predicted)

form 

Crystalline

color 

Off-white

InChI

InChI=1S/C7H7FN2O/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H2,10,11)

InChIKey

RHJMYIPLYKQZJM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

63069-49-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2924297099

2-AMINO-5-FLUOROBENZAMIDE Usage And Synthesis

Uses

2-Amino-5-fluoro-benzamide?is a useful reagent to prepare various quinazolinones including the enantioselective synthesis of fluoro-dihydroquinazolones and -benzooxazinones.

Synthesis

General procedure for the synthesis of 2-amino-5-fluorobenzamide from 2-amino-5-fluorobenzoic acid: A solution of 2-amino-5-fluorobenzoic acid (3 g, 19.34 mmol) in tetrahydrofuran (64.5 mL) was added to a round-bottomed flask, and a toluene solution of 20% phosgene (11.2 mL, 21.3 mmol) was slowly added dropwise. The reaction mixture was stirred at room temperature for 18 h. The mixture was subsequently cooled to 0 °C and concentrated ammonium hydroxide solution (27.9 mL, 193 mmol) was carefully added. The mixture was gradually warmed to room temperature and stirring was continued for 1 hour. After completion of the reaction, the organic phase was diluted with ethyl acetate, washed sequentially with aqueous dipotassium hydrogen phosphate and saturated brine, dried over anhydrous sodium sulfate and concentrated to give the white solid product 2-amino-5-fluorobenzamide (2.46 g, 82% yield). Mass spectral data: M(C7H7FN2O) = 154.14, (M + H - NH3)+ = 138.

References

[1] Patent: US2008/182852, 2008, A1. Location in patent: Page/Page column 28
[2] Molecules, 2017, vol. 22, # 2,
[3] Patent: WO2018/125961, 2018, A1. Location in patent: Page/Page column 77
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 23, p. 4479 - 4487
[5] Patent: US6479499, 2002, B1

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