Product Name

  • Name

    2-Mercaptobenzimidazole

  • EINECS 209-502-6
  • CAS No. 583-39-1
  • Article Data71
  • CAS DataBase
  • Density 1.39 g/cm3
  • Solubility <0.1 g/100 mL at 23.5 °C in water
  • Melting Point 300-304 °C(lit.)
  • Formula C7H6N2S
  • Boiling Point 270.6 °C at 760 mmHg
  • Molecular Weight 150.204
  • Flash Point 117.5 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance White to yellow crystals or cream colored powder
  • Safety 26-36-24/25
  • Risk Codes 20/21/22-36/37/38-22
  • Molecular Structure Molecular Structure of 583-39-1 (2-Mercaptobenzimidazole)
  • Hazard Symbols HarmfulXn
  • Synonyms 2-Benzimidazolinethione;Antiegene MB;Usaf ek-6540;NCI-C56268;2-Thiol benzimidazole;Vulkanox MB;Merkaptobenzimidazol;Sumilizer MB;Antigen MB;Usaf xf-21;1,3-dihydrobenzoimidazole-2-thione;AOMB;2-Benzimidazolethiol;Anitiegene MB;ASM MB;Rubber aging inhibitor MB;2,3-Dimethyl-4-nitropyridine-N-oxide;2-Mercapto benzimidazoie;MB;2-Mercapto benzimdazole;
  • PSA 67.48000
  • LogP 1.85160

Synthetic route

carbon disulfide
75-15-0

carbon disulfide

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;95%
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In neat (no solvent) at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst;93%
With Cyclohexyl isocyanide In ethanol at 20℃; for 3h;92%
tetrachloromethane
56-23-5

tetrachloromethane

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With sodium sulfide; N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Ambient temperature;95%
sodium trithiocarbonate
534-18-9

sodium trithiocarbonate

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

1,2-diamino-benzene

A

1-methyl-2-pyridinethione
2044-27-1

1-methyl-2-pyridinethione

B

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide In dimethyl sulfoxide at 40℃; for 1h;A 95%
B 85%
Thiram
137-26-8

Thiram

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In water at 110℃; Green chemistry;93%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In N,N-dimethyl acetamide for 0.0833333h; Irradiation;92%
With pyridine
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

3-methyl-1-(methyldithiocarbonyl)imidazolium iodide

3-methyl-1-(methyldithiocarbonyl)imidazolium iodide

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In ethanol for 3h; Cyclization; Heating;92%
3-phenylimino-3H-benzimidazo<2,1-c><1,2,4>-dithiazole
72885-89-3

3-phenylimino-3H-benzimidazo<2,1-c><1,2,4>-dithiazole

aniline
62-53-3

aniline

A

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

B

N,N',N''-triphenylguanidine
101-01-9

N,N',N''-triphenylguanidine

Conditions
ConditionsYield
at 90℃; for 1h;A 91%
B 87%
5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione
23766-28-1

5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In N,N-dimethyl acetamide for 0.133333h; Irradiation;91%
thiourea
17356-08-0

thiourea

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
Irradiation; microwave;90%
In N,N-dimethyl acetamide for 0.0333333h; Irradiation;82%
With PPA for 0.133333h; Irradiation;71%
Triphenylphosphonio-thiobenzimidazolat

Triphenylphosphonio-thiobenzimidazolat

A

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

B

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
In diethyl ether; waterA 87%
B 83%
potassium thioacyanate
333-20-0

potassium thioacyanate

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 24h; Green chemistry;87%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With acetic acid In N,N-dimethyl acetamide for 0.183333h; Irradiation;86%
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;86%
benzylamine
100-46-9

benzylamine

2-phenyl-2,3-dihydro-4H- [1,3]thiazino[3,2-a]benzimidazol-4-one
326007-50-5

2-phenyl-2,3-dihydro-4H- [1,3]thiazino[3,2-a]benzimidazol-4-one

A

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

B

(E)-N-benzylcinnamamide
57152-94-0, 104047-17-8, 5100-00-5

(E)-N-benzylcinnamamide

Conditions
ConditionsYield
In ethanol for 1h; Heating;A n/a
B 83%
3-(2-benzimidazolylthio)-1,4-dioxo-1,4-diphenyl-2-butene
103742-59-2

3-(2-benzimidazolylthio)-1,4-dioxo-1,4-diphenyl-2-butene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With hydrazine hydrate In methanol Heating;80%
benzylamine
100-46-9

benzylamine

2-(4-methoxy-phenyl)-2,3-dihydro-1-thia-4a,9-diaza-fluoren-4-one
326881-96-3

2-(4-methoxy-phenyl)-2,3-dihydro-1-thia-4a,9-diaza-fluoren-4-one

A

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

B

(E)-3-(4-methoxyphenyl)-N-phenylmethyl-2-propenamide
612095-65-5

(E)-3-(4-methoxyphenyl)-N-phenylmethyl-2-propenamide

Conditions
ConditionsYield
In ethanol for 1h; Heating;A n/a
B 76%
1H-imidazole-1-carbodithioic acid methyl ester
74734-11-5

1H-imidazole-1-carbodithioic acid methyl ester

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In ethanol for 5h; Cyclization; Heating;74%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

sodium dimethyldithiocarbamate
128-04-1

sodium dimethyldithiocarbamate

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With aluminum (III) chloride In water; N,N-dimethyl-formamide at 120℃; for 0.5h;73%
tert-butyl isothiocyanate
590-42-1

tert-butyl isothiocyanate

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;71%
thiosemicarbazide
79-19-6

thiosemicarbazide

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
at 180 - 190℃; for 1h;69%
at 180 - 190℃;45%
trifluoromethane sulfonyl chloride
421-83-0

trifluoromethane sulfonyl chloride

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With triphenylphosphine; sodium iodide In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;69%
phenylene-1,2-diisothiocyanate
71105-17-4

phenylene-1,2-diisothiocyanate

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With isopropylamine In acetonitrile for 0.2h; Ambient temperature;68%
3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene
103742-55-8

3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 3h; Heating;67%
potassium ethyl xanthogenate
140-89-6

potassium ethyl xanthogenate

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In ethanol; water at 80℃; Reflux;65%
In ethanol; water60%
With ethanol; water
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With potassium sulfide at 140℃; for 24h; Sealed tube; Schlenk technique; Inert atmosphere;65%
ammonium thiocyanate

ammonium thiocyanate

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
In neat (no solvent) for 1h; Milling; Green chemistry;64%
N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene
50521-79-4

N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene

A

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

B

N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

Conditions
ConditionsYield
for 0.116667h; Irradiation; microwave;A 60%
B 10%
[1,3]thiazino[3,2-a]benzimidazol-4-one
19950-81-3

[1,3]thiazino[3,2-a]benzimidazol-4-one

benzylamine
100-46-9

benzylamine

A

1,3-di(N-benzylcarbamoylethyl)-2,3-dihydro-1H-benz[d]imidazole-2-thione

1,3-di(N-benzylcarbamoylethyl)-2,3-dihydro-1H-benz[d]imidazole-2-thione

B

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
at 184℃; for 1h;A 58%
B 30%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With sulfur; 2,2‐difluoro‐2‐(triphenylphosphonio)acetate at 80℃; for 0.0833333h; Inert atmosphere; Sealed tube;56%
chloroform
67-66-3

chloroform

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

1,2-diamino-benzene

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With sulfur; potassium tert-butylate In 1,4-dioxane; 2-ethoxy-ethanol at 0℃; for 16h;53%
1-aminobenzimidazole
6299-92-9

1-aminobenzimidazole

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

Conditions
ConditionsYield
With sulfur a) from 165 to 170 deg C, 15 min, b) from 295 to 300 deg C, 1 h;50%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-2-(benzylthio)-1H-benzo-[d]-imidazole
87216-52-2

1-benzyl-2-(benzylthio)-1H-benzo-[d]-imidazole

Conditions
ConditionsYield
With sodium naphthalenide In tetrahydrofuran for 3h; Ambient temperature;100%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

ethyl iodide
75-03-6

ethyl iodide

1-ethyl-2-(ethylthio)-1H-benzo[d]imidazole
124530-66-1

1-ethyl-2-(ethylthio)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With sodium naphthalenide In tetrahydrofuran for 5h; Ambient temperature;100%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

1-iodo-propane
107-08-4

1-iodo-propane

1-Propyl-2-propylsulfanyl-1H-benzoimidazole
124530-67-2

1-Propyl-2-propylsulfanyl-1H-benzoimidazole

Conditions
ConditionsYield
With sodium naphthalenide In tetrahydrofuran for 7h; Ambient temperature;100%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

allyl bromide
106-95-6

allyl bromide

1,2-diallyl sulfanyl-1H-benzoimidazole
124530-69-4

1,2-diallyl sulfanyl-1H-benzoimidazole

Conditions
ConditionsYield
With sodium naphthalenide In tetrahydrofuran for 5h; Ambient temperature;100%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

[1-bromo-1-(1,1,2,2-tetrafluoroethoxy)methyl]phenylketone
1369761-90-9

[1-bromo-1-(1,1,2,2-tetrafluoroethoxy)methyl]phenylketone

3-phenyl-2-(1,1,2,2-tetrafluoroethoxy)-2,3-dihydrobenzo[4,5]imidazo[2,1-b]thiazol-3-ol
1369762-01-5

3-phenyl-2-(1,1,2,2-tetrafluoroethoxy)-2,3-dihydrobenzo[4,5]imidazo[2,1-b]thiazol-3-ol

Conditions
ConditionsYield
In 1,4-dioxane at 90℃; for 18h; Hantzsch type cyclization;100%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

3-(4-nitrophenyl)oxirane-2,2-dicarbonitrile
34559-52-9

3-(4-nitrophenyl)oxirane-2,2-dicarbonitrile

2-(4-nitrophenyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
80815-13-0

2-(4-nitrophenyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one

Conditions
ConditionsYield
In acetone for 48h; Ambient temperature;99%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

formaldehyd
50-00-0

formaldehyd

1,3-di(hydroxymethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione
6028-35-9

1,3-di(hydroxymethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione

Conditions
ConditionsYield
In ethanol; water for 0.166667h; hydroxymethylation; Heating; ultrasound irradiation;98%
In ethanol for 0.5h; Alkylation; Heating;92%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

3,5-di-tert-butyl-4-hydroxybenzyl acetate
14387-17-8

3,5-di-tert-butyl-4-hydroxybenzyl acetate

2-[(3,5-di(tert-butyl)-4-hydroxybenzyl)sulfanyl]-1H-benzimidazole

2-[(3,5-di(tert-butyl)-4-hydroxybenzyl)sulfanyl]-1H-benzimidazole

Conditions
ConditionsYield
With formic acid In acetone at 20℃; for 48h; Temperature;98%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

1-(benzo[d][1,3]dioxol-5-yl)-1H-benzo[d]imidazole

1-(benzo[d][1,3]dioxol-5-yl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With copper(II) acetate monohydrate; sodium hydrogencarbonate In dimethyl sulfoxide at 100℃; Chan-Lam Coupling; chemoselective reaction;98%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

methyl iodide
74-88-4

methyl iodide

2-methylsulfanylbenzimidazole
7152-24-1

2-methylsulfanylbenzimidazole

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran97%
With ethanol
With sodium hydroxide
With SeH(1-) 1.) methanol, reflux, 2) ethanol, room temp., overnight;
With potassium carbonate In acetonitrile at 20℃; for 16h;
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

4-Hydroxy-4-methyl-oct-2-ynenitrile
108940-34-7

4-Hydroxy-4-methyl-oct-2-ynenitrile

2-(2-Imino-2H-1-thia-4a,9-diaza-fluoren-4-yl)-hexan-2-ol
108940-35-8

2-(2-Imino-2H-1-thia-4a,9-diaza-fluoren-4-yl)-hexan-2-ol

Conditions
ConditionsYield
With lithium hydroxide In 1,4-dioxane97%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

methyl iodide
74-88-4

methyl iodide

1-methyl-2-(methylthio)-1H-benzimidazole
4344-61-0

1-methyl-2-(methylthio)-1H-benzimidazole

Conditions
ConditionsYield
With sodium naphthalenide In tetrahydrofuran for 3h; Ambient temperature;97%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

acetic anhydride
108-24-7

acetic anhydride

1-(2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone
21541-32-2

1-(2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone

Conditions
ConditionsYield
at 110 - 115℃; for 0.5h;97%
for 3h; Reflux;94%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

phenyl propargyl ketone
3623-15-2

phenyl propargyl ketone

3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene
103742-55-8

3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene

Conditions
ConditionsYield
In methanol for 3h; Heating;96%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

3,5-di-tert-butyl-4-hydroxybenzyl acetate
14387-17-8

3,5-di-tert-butyl-4-hydroxybenzyl acetate

1,3-bis(3,5-di(tert-butyl)-4-hydroxybenzyl)-1,3-dihydrobenzimidazole-2-thione
54114-47-5

1,3-bis(3,5-di(tert-butyl)-4-hydroxybenzyl)-1,3-dihydrobenzimidazole-2-thione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 24h; Temperature;96%
methanol
67-56-1

methanol

2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

2-methylsulfanylbenzimidazole
7152-24-1

2-methylsulfanylbenzimidazole

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;95%
With hydrogenchloride for 2h; Heating;95%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

allyl methyl carbonate
35466-83-2

allyl methyl carbonate

1-allyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione
87216-53-3

1-allyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 25℃; for 3h;95%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

phenylacetylene
536-74-3

phenylacetylene

(Z)-2-(2-phenylethenylthio)-1H-benzimidazole

(Z)-2-(2-phenylethenylthio)-1H-benzimidazole

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide for 4h; Heating;95%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

4-ethylphenylboronic acid
63139-21-9

4-ethylphenylboronic acid

2-((4-ethylphenyl)thio)-1H-benzo[d]imidazole
5315-67-3

2-((4-ethylphenyl)thio)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In water; N,N-dimethyl-formamide at 80℃; Chan-Lam Coupling; chemoselective reaction;95%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

phenylboronic acid
98-80-6

phenylboronic acid

2-(phenylsulfanyl)-1H-benzimidazole
2360-29-4

2-(phenylsulfanyl)-1H-benzimidazole

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In water; N,N-dimethyl-formamide at 80℃; Solvent; Chan-Lam Coupling; chemoselective reaction;95%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

mercury(II) iodide

mercury(II) iodide

HgI2(benzo-1,3-imidazole-2-thione)
405063-60-7

HgI2(benzo-1,3-imidazole-2-thione)

Conditions
ConditionsYield
In methanol soln. of stoich. amt. of org. compd. added dropwise to soln. of Hg compd.; after few d filtered, washed with cold MeOH, dried in air, elem. anal.;94%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

ethyl bromide
74-96-4

ethyl bromide

2-(ethylsulfanyl)-1H-benzimidazole
14610-11-8

2-(ethylsulfanyl)-1H-benzimidazole

Conditions
ConditionsYield
With sodium hydroxide In isopropyl alcohol at 40℃; for 1h; Cooling;94%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

benzyl chloride
100-44-7

benzyl chloride

2-(benzylthio)-1H-benzo[d]imidazole
51290-77-8

2-(benzylthio)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Reflux;93%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

benzoimidazole
51-17-2

benzoimidazole

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid at 25℃; for 0.0166667h;93%
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 0.0833333h;84%
With sodium hydrogencarbonate In dimethyl sulfoxide at 100℃; for 20h;30%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-[(4-methylphenyl)sulfanyl]-1H-benzimidazole
4946-28-5

2-[(4-methylphenyl)sulfanyl]-1H-benzimidazole

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In water; N,N-dimethyl-formamide at 80℃; Chan-Lam Coupling; chemoselective reaction;93%
2,3-dihydrobenzimidazol-2-thione
583-39-1

2,3-dihydrobenzimidazol-2-thione

3,4-dimethyl phenylboronic acid
55499-43-9

3,4-dimethyl phenylboronic acid

1-(3,4-dimethylphenyl)-2-((3,4-dimethylphenyl)thio)-1H-benzo[d]imidazole

1-(3,4-dimethylphenyl)-2-((3,4-dimethylphenyl)thio)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 30℃; Chan-Lam Coupling; chemoselective reaction;93%

2-Mercaptobenzimidazole Consensus Reports

Reported in EPA TSCA Inventory.

2-Mercaptobenzimidazole Specification

The 2-Mercaptobenzimidazole is an organic compound with the formula C7H6N2S. The IUPAC name of this chemical is 1,3-dihydrobenzimidazole-2-thione. With the CAS registry number 583-39-1, it is also named as 1H-Benzimidazol-2-thiol. The product's categories are Rubber Chemicals; Benzimidazole; Industrial/Fine Chemicals; PharmaceuticaL Intermediates; Organics; Imidazole; Imidazoles; Intermediates of Rabeprazole. Besides, it is a white to yellow crystals or cream colored powder, which should be stored in a cold and dry place. This chemical is used as antioxidants and used for polyethylene. It is a new anti-leprosy drugs in medicine. And it is also used for copper plating brightener.

Physical properties about 2-Mercaptobenzimidazole are: (1)ACD/LogP: 1.66; (2)ACD/LogD (pH 5.5): 0.04; (3)ACD/LogD (pH 7.4): 0.03; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.91; (7)ACD/KOC (pH 7.4): 1.9; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)Polar Surface Area: 38.57 Å2; (11)Index of Refraction: 1.744; (12)Molar Refractivity: 43.74 cm3; (13)Molar Volume: 107.9 cm3; (14)Polarizability: 17.34×10-24cm3; (15)Surface Tension: 72.9 dyne/cm; (16)Density: 1.39 g/cm3; (17)Flash Point: 117.5 °C; (18)Enthalpy of Vaporization: 50.88 kJ/mol; (19)Boiling Point: 270.6 °C at 760 mmHg; (20)Vapour Pressure: 0.00677 mmHg at 25°C.

Preparation: this chemical can be prepared by O-phenylenediamine and  carbon disulfide. Chemical reaction equation is as follows:



When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: S=C2Nc1ccccc1N2
(2)InChI: InChI=1/C7H6N2S/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10)
(3)InChIKey: YHMYGUUIMTVXNW-UHFFFAOYAG
(4)Std. InChI: InChI=1S/C7H6N2S/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10)
(5)Std. InChIKey: YHMYGUUIMTVXNW-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04376,
mouse LD50 oral 750mg/kg (750mg/kg)   Farmatsevtichnii Zhurnal Vol. 17(1), Pg. 36, 1962.
rat LD intraperitoneal > 50mg/kg (50mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Toxicological Sciences. Vol. 24, Pg. 399, 1999.
rat LD50 oral 300mg/kg (300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: COMA
Journal of Toxicological Sciences. Vol. 23, Pg. 53, 1998.

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