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5-Aminobenzimidazole

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5-Aminobenzimidazole Basic information

Product Name:
5-Aminobenzimidazole
Synonyms:
  • 1H-BENZIMIDAZOL-5-YLAMINE
  • 1H-BENZOIMIDAZOL-5-YLAMINE
  • 1H-BENZO[D]IMIDAZOL-6-AMINE
  • benzimidazol-5-ylamine
  • 1H-Benzimidazol-6-amine, 3H-Benzoimidazol-5-ylamine
  • 6-Amino-1H-benzimidazole
  • 1H-Benzimidazol-5-amine(9CI)
  • 1H-Benzimidazole-6-amine
CAS:
934-22-5
MF:
C7H7N3
MW:
133.15
EINECS:
213-279-0
Product Categories:
  • BENZIMIDAZOLE
  • Amines and Anilines
  • Heterocycles
Mol File:
934-22-5.mol
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5-Aminobenzimidazole Chemical Properties

Melting point:
163-168 °C
Boiling point:
222°C/3.5mmHg(lit.)
Density 
1.367
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
slightly sol. in Methanol
form 
powder to crystal
pka
14.47±0.30(Predicted)
color 
Light yellow to Brown
λmax
300nm(EtOH)(lit.)
InChI
InChI=1S/C7H7N3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,8H2,(H,9,10)
InChIKey
WFRXSXUDWCVSPI-UHFFFAOYSA-N
SMILES
C1NC2=CC(N)=CC=C2N=1
CAS DataBase Reference
934-22-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-36-22
Safety Statements 
26-36/37/39
WGK Germany 
3
RTECS 
DD5785000
HazardClass 
IRRITANT
HS Code 
2933998090
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5-Aminobenzimidazole Usage And Synthesis

Uses

5-Aminobenzimidazole is a useful research chemical. It inhibits gastric acid secretion in Shay-rats. Urinary metabolite of cambendazole.

Synthesis

94-52-0

934-22-5

The general procedure for the synthesis of 5-amino benzimidazole from 5-nitrobenzimidazole was as follows: 5-nitrobenzimidazole (10.0 g, 61.3 mmol) was dissolved in methanol (250 mL) and 10% Pd/C catalyst (0.40 g) was added. The hydrogenation reaction was carried out under atmospheric pressure hydrogen atmosphere for 20 hours. Upon completion of the reaction, the catalyst was removed by Celite filtration. The filtrate was concentrated under reduced pressure to give pure 5-aminobenzimidazole (yield not provided).

References

[1] Patent: WO2005/66156, 2005, A1. Location in patent: Page/Page column 33
[2] Patent: EP1437344, 2004, A1. Location in patent: Page 37
[3] Patent: WO2014/162039, 2014, A1. Location in patent: Page/Page column 40
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2362 - 2370
[5] Recueil des Travaux Chimiques des Pays-Bas, 1948, vol. 67, p. 45,48,51

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