• Name

  2-Phenylbenzimidazole

• EINECS 211-939-2
• CAS No. 716-79-0
• Article Data721
• CAS DataBase
• Density 1.211 g/cm³
• Solubility Slightly soluble in water.
• Melting Point 293-296 °C(lit.)
• Formula C₁₃H₁₀N₂
• Boiling Point 395.4 °C at 760 mmHg
• Molecular Weight 194.236
• Flash Point 210 °C
• Transport Information
• Appearance white to beige-grey powder and/or chunks
• Safety 26-39
• Risk Codes 22-37/38-41
• Molecular Structure
• Hazard Symbols Xn
• Synonyms Benzimidazole,2-phenyl- (6CI,8CI);2-Phenyl-1H-benzimidazole;G 570;Gainex;NSC 251956;Phenizidole;Phenzidol;Phenzidole;
• PSA 28.68000
• LogP 3.22990

Synthetic route

721-47-1

2'-Aminobenzanilid

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With 2,6-lutidine hydrochloride; bis(triphenylphosphine)palladium(II)-chloride In N,N-dimethyl acetamide at 140℃; under 4912.9 Torr; for 1h;	100%
With sodium dihydrogenphosphate In water at 120℃; for 16h; Sealed tube;	95%
With Amberlyst-15 In water at 90℃; for 0.5h; Irradiation;	92%

620-40-6

tribenzylamine

95-54-5

1,2-diamino-benzene

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With 5%-palladium/activated carbon In water; toluene at 110℃; for 20h; Inert atmosphere;	100%

88-74-4

2-nitro-aniline

100-51-6

benzyl alcohol

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With palladium with copper supported on alumina In water at 179.84℃; under 26252.6 Torr; for 12h; Autoclave;	100%
With JRC-TIO-7-supported iridium catalyst In 1,3,5-trimethyl-benzene at 80℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 160℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;	97%

434-45-7

1,1,1-trifluoroacetophenone

615-28-1

o-phenylenediamine dihydrochloride

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
In N,N-dimethyl acetamide at 120 - 130℃; for 24h;	99.6%

100-52-7

benzaldehyde

95-54-5

1,2-diamino-benzene

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With [3-(1-methylimidazolium-3-yl)propane-1-sulfonate]3PW12O40; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 40℃; for 10h;	99%
With graphene sulfonic acid In 1,4-dioxane at 20℃; for 2h; Reagent/catalyst;	99%
With ISO-PECH polyamine catalyst In methanol at 20℃; for 0.0666667h; Catalytic behavior; Solvent; Green chemistry;	99%

95-54-5

1,2-diamino-benzene

100-51-6

benzyl alcohol

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With C19H35Cl2CoN2P; sodium triethylborohydride In toluene at 150℃; for 24h; Molecular sieve; Schlenk technique;	99%
With sodium t-butanolate In water at 75℃; for 8h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	96%
In 1,3,5-trimethyl-benzene at 120℃; for 18h; Temperature; Inert atmosphere; Schlenk technique;	96%

93-97-0

benzoic acid anhydride

95-54-5

1,2-diamino-benzene

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; water at 445℃; under 225023 Torr; for 0.00277778h; Temperature; Pressure; Supercritical conditions;	97%
With potassium fluoride on basic alumina; magnesium sulfate In acetonitrile at 20℃; for 1h;	90%
With o-benzenedisulfonimide In neat (no solvent) at 50℃; for 6h; Green chemistry;	87%
With water In 1-methyl-pyrrolidin-2-one at 445℃; under 262526 Torr; for 0.000627778h; Catalytic behavior; Pressure; Flow reactor; Green chemistry;	98 %Chromat.

965-50-4

N-(4-methoxyphenyl)-3-oxo-3-phenylpropanamide

95-54-5

1,2-diamino-benzene

A

104-94-9

4-methoxy-aniline

B

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide In neat (no solvent) at 120℃; for 1.5h;	A 92% B 97%

...Expand

95-54-5

1,2-diamino-benzene

88-99-3

benzene-1,2-dicarboxylic acid

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
at 250℃; under 187519 Torr; for 3h; Temperature; Autoclave; Inert atmosphere;	97%
Multi-step reaction with 2 steps 1: 3 h / 200 °C / 187519 Torr / Autoclave; Inert atmosphere 2: water / 3 h / 375 °C / 187519 Torr / Autoclave; Inert atmosphere View Scheme

717-57-7

N-benzylidene-o-phenylenediamine

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With copper(ll) bromide In toluene at 100℃; for 24h; Mechanism;	96%
With 8-quinolinol; oxygen; caesium carbonate; nickel dichloride for 0.216667h; Microwave irradiation;	93%
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	83%

2700-22-3

Benzylidenemalononitrile

A

1867-37-4

Benzylmalononitrile

B

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With benzaldehyde; 1,2-diamino-benzene In ethanol for 6h; Ambient temperature;	A 96% B n/a
With benzaldehyde; 1,2-diamino-benzene In ethanol for 6h; Product distribution; Ambient temperature; other aldehydes;

591-50-4

iodobenzene

201230-82-2

carbon monoxide

95-54-5

1,2-diamino-benzene

A

744-38-7

1,2-dibenzamidobenzene

B

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(triphenylphosphine)palladium(II)-chloride In N,N-dimethyl acetamide at 145℃; under 4912.9 Torr; for 2.5h;	A 96% B n/a
With 2,6-dimethylpyridine; bis(triphenylphosphine)palladium(II)-chloride In N,N-dimethyl acetamide at 145℃; under 4912.9 Torr; for 19h;	A 2% B 75%

...Expand

1527-91-9

N-phenylbenzamidine

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With 2C28H17N3O7(2-)*2Cu(2+)*6C3H7NO; benzoic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 24h; Reagent/catalyst;	96%
With phenyliodine(III) diacetate; caesium carbonate In 2,2,2-trifluoroethanol at 0℃; for 0.5h; Solvent; Reagent/catalyst; Time;	95%
With peracetic acid; iodobenzene at 50℃; for 1.5h;	95%

14717-15-8

N-(benzylidene)-2-nitroaniline

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With triphenylphosphine for 0.0833333h; Cadogan reaction; Microwave irradiation;	96%
With 3,4,7,8-Tetramethyl-o-phenanthrolin; palladium diacetate; molybdenum hexacarbonyl In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; Sealed tube;	62%

106987-24-0

N-(2-nitrophenyl)benzenecarboximidamide

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate; acetic acid at 20 - 80℃; Inert atmosphere;	96%

95-54-5

1,2-diamino-benzene

1663-61-2

triethoxymethylbenzene

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With ammonium chloride In water Inert atmosphere; Reflux; Green chemistry;	96%
With o-benzenedisulfonimide In neat (no solvent) at 20 - 25℃; for 3h; Green chemistry;	92%

5822-13-9

N-benzyl-1,2-phenylenediamine

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In N,N-dimethyl-formamide at 110℃; for 5h; Reagent/catalyst; Solvent; Temperature; Time;	96%
With iron(III) chloride hexahydrate In N,N-dimethyl-formamide at 100℃; for 24h;	79%
With triethylamine; copper(I) bromide In N,N-dimethyl-formamide at 20 - 100℃; Reagent/catalyst; chemoselective reaction;	67%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; dimethyl sulfoxide at 100℃; for 2h; Sealed tube;	60%
With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 14h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time;

95-54-5

1,2-diamino-benzene

65-85-0

benzoic acid

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
Stage #1: benzoic acid In dichloromethane at 0℃; for 0.25h; Stage #2: 1,2-diamino-benzene With pyridine In dichloromethane at 20℃; for 6h; Further stages.;	95%
In neat (no solvent) for 1h; Milling; Green chemistry;	95%
With diphosphorus tetraiodide In acetonitrile at 80℃; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Sealed tube; Inert atmosphere;	95%

728-90-5

N-(2-nitrophenyl)benzanilide

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 10% palladium on activated carbon In acetic acid at 120℃; for 15h; Inert atmosphere;	95%
With triphenylphosphine In N,N-dimethyl-formamide; 1,2-dichloro-benzene at 250℃; under 750.075 Torr; for 0.5h; Inert atmosphere; Microwave irradiation;	76%
With hydrogenchloride; tin

4857-06-1

2-chloro-1H-benzoimidazole

98-80-6

phenylboronic acid

716-79-0

2-phenyl-1H-benzoimidazole

Conditions

Conditions	Yield
With potassium tert-butylate; ClPd[N,N(2,6-iPr2C6H3)2-imidazol-2-yl]cinnamyl In isopropyl alcohol at 20℃; for 15h; Suzuki-Miyaura cross-coupling reaction;	95%
With N-heterocyclic carbene-palladacycle; sodium t-butanolate In isopropyl alcohol at 20℃; for 1h; Suzuki-Miyaura cross-coupling;	94%
With potassium carbonate In ethanol; water at 50℃; for 5h; Suzuki-Miyaura coupling reaction; Inert atmosphere;	92%

716-79-0

2-phenyl-1H-benzoimidazole

26663-57-0

2-cyclohexyl-4,5,6,7-tetrahydrobenzimidazole

Conditions

Conditions	Yield
With hydrogen; Rh on carbon In hydrogenchloride at 120℃; under 73550.8 Torr;	100%
With acetic acid; platinum at 80℃; Hydrogenation;

716-79-0

2-phenyl-1H-benzoimidazole

74-88-4

methyl iodide

2622-63-1

1-methyl-2-phenylbenzimidazole

Conditions

Conditions	Yield
Stage #1: 2-phenyl-1H-benzoimidazole With potassium tert-butylate In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	100%
Stage #1: 2-phenyl-1H-benzoimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;	89%
Stage #1: 2-phenyl-1H-benzoimidazole With potassium hydroxide In dimethyl sulfoxide at 30℃; for 0.75h; Stage #2: methyl iodide In dimethyl sulfoxide at 30℃; for 0.75h;	85%

716-79-0

2-phenyl-1H-benzoimidazole

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

C27H37N2(1+)*C13H9N2(1-)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.25h; Equilibrium constant; Inert atmosphere; Glovebox; Schlenk technique;	100%

616-38-6

carbonic acid dimethyl ester

716-79-0

2-phenyl-1H-benzoimidazole

2622-63-1

1-methyl-2-phenylbenzimidazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 6h; Product distribution; Further Variations:; Temperatures; Solvents; Pressures; reaction times; microwave irradiation;	98%
With 18-crown-6 ether; potassium carbonate at 100℃; for 10h;	70%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane

682-30-4

Diethyl vinylphosphonate

716-79-0

2-phenyl-1H-benzoimidazole

1251832-49-1

O,O-diethyl 2-(2-phenyl-1H-benzimidazol-1-yl)ethylphosphonate

Conditions

Conditions	Yield
Stage #1: 2-phenyl-1H-benzoimidazole With potassium hydroxide; sodium hydroxide In 1-methyl-pyrrolidin-2-one; methanol at 60℃; for 5h; Inert atmosphere; Stage #2: Diethyl vinylphosphonate In 1-methyl-pyrrolidin-2-one; methanol for 10h; Inert atmosphere;	97%

716-79-0

2-phenyl-1H-benzoimidazole

17341-93-4

2,2,2-Trichloroethyl chloroformate

C16H11Cl3N2O2

Conditions

Conditions	Yield
In tetrahydrofuran for 2h; Inert atmosphere;	97%

2009-97-4

ethyl 2-diazo-3-oxobutanoate

716-79-0

2-phenyl-1H-benzoimidazole

ethyl 6-hydroxy-6-methyl-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-5-carboxylate

Conditions

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate In 2,2,2-trifluoroethanol at 20℃; for 16h; Schlenk technique; Inert atmosphere;	97%

2-PHENYLBENZIMIDAZOLE Chemical Properties

2-PHENYLBENZIMIDAZOLE Uses

2-PHENYLBENZIMIDAZOLE Toxicity Data With Reference

2-PHENYLBENZIMIDAZOLE Consensus Reports

2-PHENYLBENZIMIDAZOLE Safety Profile

2-PHENYLBENZIMIDAZOLE Specification