2-Hydroxybenzimidazole supplier

Name
2-Hydroxybenzimidazole
EINECS 210-412-4
CAS No. 615-16-7
Article Data198
CAS DataBase
Density 1.252 g/cm³
Solubility insoluble in water
Melting Point >300 °C(lit.)
Formula C₇H₆N₂O
Boiling Point 123.5 °C at 760 mmHg
Molecular Weight 134.137
Flash Point 42.6 °C
Transport Information
Appearance off-white to pale brown crystalline powder
Safety 22-24/25-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N-methyl-acetamide; ethyl acetate	98%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trimethylsilylazide; triethylamine; aniline In toluene at 110℃; for 1h; Sealed tube;	95%

: 95-54-5
1,2-diamino-benzene

: 57-13-6
urea

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
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%

: 1711-61-1
5-(4-chlorophenyl)-3H-[1,3,4]oxadiazol-2-one

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N,N-dimethyl acetamide for 0.133333h; Irradiation;	93%

: 201230-82-2
carbon monoxide

: 88-74-4
2-nitro-aniline

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In toluene at 150℃; under 22800 Torr; for 4h;	92%
With tin(IV) chloride; triethylamine; bis(triphenylphosphine)platinum(II) dichloride In 1,4-dioxane at 140℃; for 4h;	56%

: 28144-70-9
anthranilic acid amide

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With iodosylbenzene In dichloromethane at 20℃; for 2h; Hofmann rearrangement;	92%
With potassium hydroxide; [bis(acetoxy)iodo]benzene In methanol at 0℃; for 1h;	82%

: 622-58-2
p-Tolylisocyanate

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;	92%

: 5097-82-5
5-phenyl-1H-tetrazolone

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 16h; Irradiation;	90%

: 120811-68-9
1-benzoyl-4-(o-aminophenyl)semicarbazide

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In various solvent(s) at 150℃; for 5h;	90%

: 1202680-24-7
phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In toluene for 11h; Solvent; Reflux; Green chemistry;	90%

: 83-01-2
diphenylcarbamic chloride

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N,N-dimethyl acetamide for 0.0666667h; Irradiation;	89%

: 74124-79-1
di(succinimido) carbonate

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In acetonitrile for 8h; Ambient temperature;	88%

: 95-54-5
1,2-diamino-benzene

: 616-38-6
carbonic acid dimethyl ester

A: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

B: 3097-21-0
1,3-dimethyl-1,3-dihydrobenzimidazol-2-one

C: 4760-34-3
N-methyl-1,2-phenylenediamine

Conditions

Conditions	Yield
With lead(II) nitrate at 169.85℃; for 0.5h;	A 88% B n/a C n/a

...Expand

: 32276-00-9
S,S"-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate

: 95-54-5
1,2-diamino-benzene

A: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

B: 86-93-1
1-Phenyl-1H-tetrazole-5-thiol

Conditions

Conditions	Yield
In acetonitrile for 12h;	A 87% B n/a

...Expand

: 34840-26-1
1,3-dicarbethoxy-S-methylisothiourea

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Heating;	85%

: 34840-23-8
1,3-Dicarbomethoxy-S-methylisothiourea

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Heating;	85%

: 917-61-3
sodium isocyanate

: 95-54-5
1,2-diamino-benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N,N-dimethyl acetamide for 0.0666667h; Irradiation;	81%

: 118-92-3
anthranilic acid

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With sodium azide; ammonium chloride; trichlorophosphate; N,N-dimethyl-formamide at 0 - 20℃; Curtius rearrangement;	80%
With polymer-supported diphenylphosphoryl azide; triethylamine In benzene for 24h; Heating;	75%

: 95-54-5
1,2-diamino-benzene

: 623-49-4
ethyl cyanoformate

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With lithium bromide In 1,4-dioxane at 100 - 105℃; for 1h;	78%

: (2-oxo-2,3-dihydro-1H-benz[d]imidazol-1-yl)(phenyl)methyl acetate

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 70℃; for 1h;	76%

: 16807-48-0
3‐acetyl‐2‐hydroxy‐6‐methyl‐4H‐pyran‐4‐one

: 95-54-5
1,2-diamino-benzene

A: 615-15-6
2-Methyl-1H-benzimidazole

B: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

C: 111008-23-2
4-(2-oxopropylidene)-1,2,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Conditions

Conditions	Yield
In xylene Heating; 1:1 molar ratio;	A n/a B n/a C 75%

...Expand

: 124-38-9
carbon dioxide

: 13435-10-4
1,2-bis(trimethylsilylamino)benzene

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With pyridine; C14H34Cl2InNO2Si2 In toluene at 110℃; under 2280.15 Torr; for 12h;	73%

: 95-54-5
1,2-diamino-benzene

: 5852-49-3
5-phenyl-1,3,4-oxathiazol-2-one

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	72.5%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 85694-84-4, 86100-43-8
benzimidazolin-2-one disodium salt

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 0.5h;	100%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 616-38-6
carbonic acid dimethyl ester

: 3097-21-0
1,3-dimethyl-1,3-dihydrobenzimidazol-2-one

Conditions

Conditions	Yield
With lead(II) nitrate at 199.85℃; for 20h;	100%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 108-12-3
isopentanoyl chloride

: 93202-27-8
5-isovalerylbenzimidazolin-2-one

Conditions

Conditions	Yield
With aluminium trichloride In 1,1,2,2-tetrachloroethylene at 90 - 100℃; for 1h;	98%
With carbon disulfide; aluminium trichloride

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 79-04-9
chloroacetyl chloride

: 93202-41-6
5-(2-chloroethanoyl)-1,3-dihydrobenzimidazol-2-one

Conditions

Conditions	Yield
With aluminium trichloride In 1,1,2,2-tetrachloroethylene at 90 - 100℃; for 1h;	98%
With aluminum (III) chloride In 1,1,2,2-tetrachloroethane at 100℃; for 1h; Cooling with ice;	93%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 24424-99-5
di-tert-butyl dicarbonate

: 161468-58-2
2,3-Dihydro-2-oxo-1H-benzimidazole-1,3-(2H)-dicarboxylic acid bis(1,1-dimethylethyl ester)

Conditions

Conditions	Yield
With dmap In tetrahydrofuran for 1h; Heating;	98%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 2033-29-6
5,6-dichloro-1,3-dihydrobenzoimidazol-2-one

Conditions

Conditions	Yield
With sulfuryl dichloride In acetic acid Ambient temperature;	98%
With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	97%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 122-04-3
4-nitro-benzoyl chloride

: 1240613-76-6
1-(4-nitrobenzoyl)-1,3-dihydrobenzimidazol-2-one

Conditions

Conditions	Yield
With pyridine at 0 - 80℃; for 4.25h;	98%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 7623-09-8
2-chloropropionyl chloride

: 5-(2-chloropropanoyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 5 - 25℃; for 19h; Friedel-Crafts Alkylation; Inert atmosphere; regioselective reaction;	98%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 108-24-7
acetic anhydride

: 2735-73-1
1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
for 6h; Heating;	97%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 4857-06-1
2-chloro-1H-benzoimidazole

Conditions

Conditions	Yield
With trichlorophosphate; phenol at 103 - 107℃; for 12h;	97%
With trichlorophosphate at 100℃; for 15h;	91%
With trichlorophosphate In neat (no solvent)	80%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 15354-69-5
5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose

: 869104-29-0
1,3-N,N'-bis-(6-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-6-yl)benzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide; toluene at 100℃; for 2h;	97%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 105-39-5
chloroacetic acid ethyl ester

: 83330-80-7
diethyl 2,2'-(2-oxo-1H-benzimidazole-1,3[2H]-diyl)diacetate

Conditions

Conditions	Yield
With sodium hydride In neat (no solvent) for 0.333333h; Milling; Green chemistry;	97%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 79-30-1
isobutyryl chloride

: 93202-43-8
5-isobutyrylbenzimidazolin-2-one

Conditions

Conditions	Yield
With aluminium trichloride In 1,1,2,2-tetrachloroethylene at 90 - 100℃; for 1h;	96%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 161468-58-2
2,3-Dihydro-2-oxo-1H-benzimidazole-1,3-(2H)-dicarboxylic acid bis(1,1-dimethylethyl ester)

: 161468-45-7
2,3-Dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	96%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 74-96-4
ethyl bromide

: 6648-01-7
1,3-diethyl-1,3-dihydro-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutyl-ammonium chloride In benzene at 60℃; for 5h;	95%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 79-03-8
propionyl chloride

: 93202-42-7
5-propionylbenzimidazolin-2-one

Conditions

Conditions	Yield
With aluminium trichloride In 1,1,2,2-tetrachloroethylene at 90 - 100℃; for 1h;	95%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 74-88-4
methyl iodide

: 3097-21-0
1,3-dimethyl-1,3-dihydrobenzimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutyl-ammonium chloride In benzene at 60℃; for 5h;	95%
Stage #1: 1,3-dihydro-2H-benzimidazol-2-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h;	83%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	79%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 1609-47-8
diethyl dicarbonate

: 161468-57-1
2-oxo-benzoimidazole-1,3-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With dmap In tetrahydrofuran for 0.5h;	95%

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 75-36-5
acetyl chloride

: 2735-73-1
1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With triethylamine for 5h; Heating;	94%
With pyridine

: 615-16-7
1,3-dihydro-2H-benzimidazol-2-one

: 7325-39-5
ethyl pyridine-2-yl carbonate

: 41120-23-4
ethyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 0.5h; Heating;	94%
With potassium carbonate In acetonitrile for 2h; Reflux; Inert atmosphere;	87%

2-Hydroxybenzimidazole Consensus Reports

Reported in EPA TSCA Inventory.

2-Hydroxybenzimidazole 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.

Product Name

2-Hydroxybenzimidazole

Synthetic route

2-Hydroxybenzimidazole Consensus Reports

2-Hydroxybenzimidazole Specification

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