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615-16-7

Basic Information
CAS No.: 615-16-7
Name: 2-Hydroxybenzimidazole
Article Data: 198
Molecular Structure:
Molecular Structure of 615-16-7 (2-Hydroxybenzimidazole)
Formula: C7H6N2O
Molecular Weight: 134.137
Synonyms: 2-Benzimidazolinone(6CI,7CI,8CI);1,3-Dihydro-2H-benzimidazol-2-one;1,3-Dihydro-2H-benzimidazole-2-one;1,3-Dihydrobenzimidazol-2-one;1H-Benzimidazol-2(3H)-one;2(3H)-Benzimidazolone;2(3H)-Oxobenzimidazole;2,3-Dihydro-2-oxo-1H-benzimidazole;2-Benzimidazolol;2-Benzimidazolone;N,N'-(1,2-Phenyleneurea);NSC 10383;NSC 178108;Urea,N,N'-(1,2-phenylene)-;o-Phenyleneurea;
EINECS: 210-412-4
Density: 1.252 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 123.5 °C at 760 mmHg
Flash Point: 42.6 °C
Solubility: insoluble in water
Appearance: off-white to pale brown crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-37/39
PSA: 48.91000
LogP: 1.26850
Synthetic route
95-54-5

1,2-diamino-benzene

530-62-1

1,1'-carbonyldiimidazole

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 18h;99%
at 20℃; for 22h;96%
In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;81%
5623-04-1

anthranilic hydroxamic acid

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
In formamide at 130℃; for 0.333333h;99%
at 150 - 170℃;
201230-82-2

carbon monoxide

95-54-5

1,2-diamino-benzene

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
With 1-Methylpyrrolidine; selenium In tetrahydrofuran at 100℃; under 22800.7 Torr; for 20h;99%
With carbon dioxide; oxygen; potassium iodide; palladium(II) iodide In 1,2-dimethoxyethane at 100℃; under 45600 Torr; for 2h;99%
With 1-Methylpyrrolidine; selenium; oxygen In tetrahydrofuran 1.) 31 kg/cm2, 100 degC, 20 h, 2.) 25 degC, 1 h;99%
1199-02-6

5-phenyl-3H-[1,3,4]oxadiazol-2-one

95-54-5

1,2-diamino-benzene

A

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

B

613-94-5

benzoic acid hydrazide

Conditions
ConditionsYield
In various solvent(s) at 150℃; for 5h;A 98%
B n/a
95-54-5

1,2-diamino-benzene

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
In N-methyl-acetamide; ethyl acetate98%
Multi-step reaction with 2 steps
1: benzene
2: 183 °C
View Scheme
Multi-step reaction with 2 steps
1: water
2: 150 °C
View Scheme
103-71-9

phenyl isocyanate

95-54-5

1,2-diamino-benzene

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent; Inert atmosphere; Schlenk technique; chemoselective reaction;96%
In N,N-dimethyl acetamide for 0.183333h; Irradiation;82%
124-38-9

carbon dioxide

95-54-5

1,2-diamino-benzene

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
In tetrahydrofuran; water at 20℃; under 7500.75 Torr; for 9h; UV-irradiation;96%
With Sn(IV)-doped DFNS supported CdSnO3 nanoparticles under 11251.1 Torr; for 1h; Kinetics; UV-irradiation;96%
With cesium fluoride In diethylene glycol dimethyl ether at 100℃; for 20h; Glovebox; Schlenk technique;95%
144167-52-2

1-(N-carbethoxyimidoyl)-2-benzimidazolone

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
at 200℃; high vacuum sublimation;95%
at 200℃; Product distribution; high vacuum sublimation; or with acid; other 1-(N-carbethoxyimidoyl)-2-benzimidazolones;95%
117576-29-1

(2‑aminophenyl)(1H‑benzo[d][1,2,3]triazol‑1‑yl)methanone

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
With trimethylsilylazide; triethylamine; aniline In toluene at 110℃; for 1h; Sealed tube;95%
95-54-5

1,2-diamino-benzene

615-16-7

1,3-dihydro-2H-benzimidazol-2-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 135 - 140℃; for 12h;94%
With sulfated polyborate at 120℃; for 1.5h;94%
With acetic acid In tetrahydrofuran; water at 100 - 135℃; for 5h; Inert atmosphere;93.7%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2-Oxobenzimidazole, with the CAS registry number 615-16-7 and EINECS registry number 210-412-4, has the systematic name of 1,3-dihydro-2H-benzimidazol-2-one. It is a kind of off-white to pale brown crystalline powder, and belongs to the following product categories: Benzimidazole; Pharmaceutical Intermediates; Benzimidazole Series; Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines; Imidazol & Benzimidazole; API intermediates; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. And the molecular formula of this chemical is C7H6N2O. What's more, it is usually used as a metabolite of the neuroleptic Droperidol.

The physical properties of 2-Oxobenzimidazole are as followings: (1)ACD/LogP: 1.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.12; (4)ACD/LogD (pH 7.4): 1.12; (5)ACD/BCF (pH 5.5): 4.18; (6)ACD/BCF (pH 7.4): 4.18; (7)ACD/KOC (pH 5.5): 96.89; (8)ACD/KOC (pH 7.4): 96.89; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 23.55 Å2; (13)Index of Refraction: 1.587; (14)Molar Refractivity: 36.03 cm3; (15)Molar Volume: 107 cm3; (16)Polarizability: 14.28×10-24cm3; (17)Surface Tension: 42.8 dyne/cm; (18)Density: 1.252 g/cm3; (19)Flash Point: 42.6 °C; (20)Enthalpy of Vaporization: 36.15 kJ/mol; (21)Boiling Point: 123.5 °C at 760 mmHg; (22)Vapour Pressure: 13.3 mmHg at 25°C.

Uses of 2-Oxobenzimidazole: It can react with acetyl chloride to produce 1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one. This reaction will need reagent (C2H5)3N. The reaction time is 5 hours with heating, and the yield is about 94%.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you should not breathe dust and then try to avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2Nc1ccccc1N2
(2)InChI: InChI=1/C7H6N2O/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10)
(3)InChIKey: SILNNFMWIMZVEQ-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 620mg/kg (620mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 42, 1958.

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