1H-Benzimidazole-2-methanol

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CAS:4856-97-7
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1H-Benzimidazole-2-methanol Basic information
Product Name:1H-Benzimidazole-2-methanol
Synonyms:BENZIMIDAZOLE-2-METHANOL;IFLAB-BB F0266-0027;1H-BENZIMIDAZOL-2-YLMETHANOL;(1H-BENZOIMIDAZOL-2-YL)-METHANOL;1H-BENZIMIDAZOLE-2-METHANOL;2-(HYDROXYMETHYL)-1H-BENZIMIDAZOLE;1H-BENZIMIDAZOLE-2-METHANOL 97%;2-HYDROXYMETHYLBENZIMIDAZOLE
CAS:4856-97-7
MF:C8H8N2O
MW:148.16
EINECS:225-451-2
Product Categories:Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Heterocycles series;Imidazol&Benzimidazole;Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Benzimidazole Series;BENZIMIDAZOLE;Alcohols and Derivatives;Heterocycles
Mol File:4856-97-7.mol
1H-Benzimidazole-2-methanol Structure
1H-Benzimidazole-2-methanol Chemical Properties
Melting point 171-175 °C (lit.)
Boiling point 268.75°C (rough estimate)
density 1.1828 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility soluble in Methanol
form Crystalline Powder
pka11.57±0.10(Predicted)
color Off-white to light brown
InChIInChI=1S/C8H8N2O/c11-5-8-9-6-3-1-2-4-7(6)10-8/h1-4,11H,5H2,(H,9,10)
InChIKeyIAJLTMBBAVVMQO-UHFFFAOYSA-N
SMILESC1(CO)NC2=CC=CC=C2N=1
CAS DataBase Reference4856-97-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36-36/37
WGK Germany 3
HazardClass IRRITANT
HS Code 29339900
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
1H-Benzimidazole-2-methanol English
SigmaAldrich English
ACROS English
1H-Benzimidazole-2-methanol Usage And Synthesis
Chemical PropertiesOff-white to light brown crystalline powder
Uses2-Benzimidazolemethanol was used in the preparation of 2-(chloromethyl)-1-(methylsulfonyl)benzimidazole via methanesulfonylation. It was also used in the synthesis of 1H-benzimidazol-2-ylmethyl diethyl phosphate.
Synthesis
Glycolic acid

79-14-1

o-Phenylenediamine

95-54-5

1H-Benzimidazole-2-methanol

4856-97-7

The compound was prepared based on known methods with some modifications [19,20]. O-phenylenediamine (27 g, 0.25 mol) was dissolved in 500 mL of 4 M HCl, mixed with a solution of ethanoic acid (34.2 g, 0.45 mol) in 250 mL of 4 M HCl, stirred and heated under reflux conditions for 2 hours. Upon completion of the reaction, the reaction mixture was slowly cooled to room temperature and subsequently alkalized to pH neutral with aqueous sodium hydroxide. The precipitated solid was separated by filtration, dried and purified by recrystallization using hot water (Scheme 1). Product I was obtained: white to light brown powder, melting point 171-174 °C, yield 89.1%.

References[1] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[2] Bulletin of the Chemical Society of Ethiopia, 2014, vol. 28, # 3, p. 451 - 456
[3] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2209 - 2220
[4] Patent: CN106905241, 2017, A. Location in patent: Paragraph 0127-0129
[5] Patent: CN107118249, 2017, A. Location in patent: Paragraph 0117; 0118; 0119
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