5-Amino-1,3-dihydro-2H-benzimidazol-2-one Chemical Properties

Melting point:

>300 °C

Boiling point:

201.4±19.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

vapor pressure 

0.001Pa at 20℃

storage temp. 

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

form 

Powder

pka

11.80±0.30(Predicted)

color 

White to Amber to Dark purple

InChI

InChI=1S/C7H7N3O/c8-4-1-2-5-6(3-4)10-7(11)9-5/h1-3H,8H2,(H2,9,10,11)

InChIKey

BCXSVFBDMPSKPT-UHFFFAOYSA-N

SMILES

C1(=O)NC2=CC=C(N)C=C2N1

LogP

-0.33 at 23℃ and pH6.5-7.5

CAS DataBase Reference

95-23-8(CAS DataBase Reference)

EPA Substance Registry System

2H-Benzimidazol-2-one, 5-amino-1,3-dihydro- (95-23-8)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:5-Amino-1,3-dihydro-2H-benzimidazol-2-one

5-Amino-1,3-dihydro-2H-benzimidazol-2-one Usage And Synthesis

Chemical Properties

Crystalline powder

Uses

5-Amino-2-hydroxybenzimidazole is an important reagent in the discovery of potent and selective non-nucleotide small molecule inhibitors of CD73

Synthesis

Step: 21b Synthesis of 5-amino-1,3-dihydrobenzimidazol-2-one. Pd/C catalyst (140 mg) was added to a mixed solution of methanol and ethyl acetate containing 5-nitro-1,3-dihydrobenzimidazol-2-one (1.4 g, 7.8 mmol) and the hydrogenation reaction was carried out for 6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, the unfolding agent was a chloroform solution of 10% methanol). After completion of the reaction, the reaction mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated to give the target product 5-amino-1,3-dihydrobenzimidazol-2-one (1 g, 86% yield).

References

[1] Patent: WO2012/59932, 2012, A1. Location in patent: Page/Page column 161-162
[2] Patent: WO2009/42907, 2009, A1. Location in patent: Page/Page column 78-79
[3] Journal of the American Chemical Society, 1958, vol. 80, p. 1662
[4] Patent: WO2012/115479, 2012, A2. Location in patent: Page/Page column 23
[5] Patent: CN104151251, 2017, B. Location in patent: Paragraph 0024

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