Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium sulfide; N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Ambient temperature; | 95% |
sodium trithiocarbonate
1,2-diamino-benzene
A
1-methyl-2-pyridinethione
B
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With 2-chloro-1-methyl-pyridinium iodide In dimethyl sulfoxide at 40℃; for 1h; | A 95% B 85% |
Conditions | Yield |
---|---|
In water at 110℃; Green chemistry; | 93% |
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide for 0.0833333h; Irradiation; | 92% |
With pyridine |
Conditions | Yield |
---|---|
In ethanol for 3h; Cyclization; Heating; | 92% |
3-phenylimino-3H-benzimidazo<2,1-c><1,2,4>-dithiazole
aniline
A
2,3-dihydrobenzimidazol-2-thione
B
N,N',N''-triphenylguanidine
Conditions | Yield |
---|---|
at 90℃; for 1h; | A 91% B 87% |
5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide for 0.133333h; Irradiation; | 91% |
Conditions | Yield |
---|---|
Irradiation; microwave; | 90% |
In N,N-dimethyl acetamide for 0.0333333h; Irradiation; | 82% |
With PPA for 0.133333h; Irradiation; | 71% |
Conditions | Yield |
---|---|
In diethyl ether; water | A 87% B 83% |
potassium thioacyanate
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80℃; for 24h; Green chemistry; | 87% |
phenyl isothiocyanate
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
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
2-phenyl-2,3-dihydro-4H- [1,3]thiazino[3,2-a]benzimidazol-4-one
A
2,3-dihydrobenzimidazol-2-thione
B
(E)-N-benzylcinnamamide
Conditions | Yield |
---|---|
In ethanol for 1h; Heating; | A n/a B 83% |
3-(2-benzimidazolylthio)-1,4-dioxo-1,4-diphenyl-2-butene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol Heating; | 80% |
benzylamine
2-(4-methoxy-phenyl)-2,3-dihydro-1-thia-4a,9-diaza-fluoren-4-one
A
2,3-dihydrobenzimidazol-2-thione
B
(E)-3-(4-methoxyphenyl)-N-phenylmethyl-2-propenamide
Conditions | Yield |
---|---|
In ethanol for 1h; Heating; | A n/a B 76% |
1H-imidazole-1-carbodithioic acid methyl ester
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
In ethanol for 5h; Cyclization; Heating; | 74% |
1,2-diamino-benzene
sodium dimethyldithiocarbamate
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With aluminum (III) chloride In water; N,N-dimethyl-formamide at 120℃; for 0.5h; | 73% |
tert-butyl isothiocyanate
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 71% |
Conditions | Yield |
---|---|
at 180 - 190℃; for 1h; | 69% |
at 180 - 190℃; | 45% |
trifluoromethane sulfonyl chloride
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With triphenylphosphine; sodium iodide In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | 69% |
phenylene-1,2-diisothiocyanate
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With isopropylamine In acetonitrile for 0.2h; Ambient temperature; | 68% |
3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol for 3h; Heating; | 67% |
potassium ethyl xanthogenate
1,2-diamino-benzene
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
In ethanol; water at 80℃; Reflux; | 65% |
In ethanol; water | 60% |
With ethanol; water |
Conditions | Yield |
---|---|
With potassium sulfide at 140℃; for 24h; Sealed tube; Schlenk technique; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
In neat (no solvent) for 1h; Milling; Green chemistry; | 64% |
N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene
A
2,3-dihydrobenzimidazol-2-thione
B
N,N-diphenylthiourea
Conditions | Yield |
---|---|
for 0.116667h; Irradiation; microwave; | A 60% B 10% |
[1,3]thiazino[3,2-a]benzimidazol-4-one
benzylamine
B
2,3-dihydrobenzimidazol-2-thione
Conditions | Yield |
---|---|
at 184℃; for 1h; | A 58% B 30% |
Conditions | Yield |
---|---|
With sulfur; 2,2‐difluoro‐2‐(triphenylphosphonio)acetate at 80℃; for 0.0833333h; Inert atmosphere; Sealed tube; | 56% |
Conditions | Yield |
---|---|
With sulfur; potassium tert-butylate In 1,4-dioxane; 2-ethoxy-ethanol at 0℃; for 16h; | 53% |
Conditions | Yield |
---|---|
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
benzyl bromide
1-benzyl-2-(benzylthio)-1H-benzo-[d]-imidazole
Conditions | Yield |
---|---|
With sodium naphthalenide In tetrahydrofuran for 3h; Ambient temperature; | 100% |
2,3-dihydrobenzimidazol-2-thione
ethyl iodide
1-ethyl-2-(ethylthio)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With sodium naphthalenide In tetrahydrofuran for 5h; Ambient temperature; | 100% |
2,3-dihydrobenzimidazol-2-thione
1-iodo-propane
1-Propyl-2-propylsulfanyl-1H-benzoimidazole
Conditions | Yield |
---|---|
With sodium naphthalenide In tetrahydrofuran for 7h; Ambient temperature; | 100% |
2,3-dihydrobenzimidazol-2-thione
allyl bromide
1,2-diallyl sulfanyl-1H-benzoimidazole
Conditions | Yield |
---|---|
With sodium naphthalenide In tetrahydrofuran for 5h; Ambient temperature; | 100% |
2,3-dihydrobenzimidazol-2-thione
[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
Conditions | Yield |
---|---|
In 1,4-dioxane at 90℃; for 18h; Hantzsch type cyclization; | 100% |
2,3-dihydrobenzimidazol-2-thione
3-(4-nitrophenyl)oxirane-2,2-dicarbonitrile
2-(4-nitrophenyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
Conditions | Yield |
---|---|
In acetone for 48h; Ambient temperature; | 99% |
2,3-dihydrobenzimidazol-2-thione
formaldehyd
1,3-di(hydroxymethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione
Conditions | Yield |
---|---|
In ethanol; water for 0.166667h; hydroxymethylation; Heating; ultrasound irradiation; | 98% |
In ethanol for 0.5h; Alkylation; Heating; | 92% |
2,3-dihydrobenzimidazol-2-thione
3,5-di-tert-butyl-4-hydroxybenzyl acetate
Conditions | Yield |
---|---|
With formic acid In acetone at 20℃; for 48h; Temperature; | 98% |
2,3-dihydrobenzimidazol-2-thione
3,4-(methylenedioxy)-benzeneboronic acid
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate; sodium hydrogencarbonate In dimethyl sulfoxide at 100℃; Chan-Lam Coupling; chemoselective reaction; | 98% |
2,3-dihydrobenzimidazol-2-thione
methyl iodide
2-methylsulfanylbenzimidazole
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 97% |
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
4-Hydroxy-4-methyl-oct-2-ynenitrile
2-(2-Imino-2H-1-thia-4a,9-diaza-fluoren-4-yl)-hexan-2-ol
Conditions | Yield |
---|---|
With lithium hydroxide In 1,4-dioxane | 97% |
2,3-dihydrobenzimidazol-2-thione
methyl iodide
1-methyl-2-(methylthio)-1H-benzimidazole
Conditions | Yield |
---|---|
With sodium naphthalenide In tetrahydrofuran for 3h; Ambient temperature; | 97% |
2,3-dihydrobenzimidazol-2-thione
acetic anhydride
1-(2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone
Conditions | Yield |
---|---|
at 110 - 115℃; for 0.5h; | 97% |
for 3h; Reflux; | 94% |
2,3-dihydrobenzimidazol-2-thione
phenyl propargyl ketone
3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene
Conditions | Yield |
---|---|
In methanol for 3h; Heating; | 96% |
2,3-dihydrobenzimidazol-2-thione
3,5-di-tert-butyl-4-hydroxybenzyl acetate
1,3-bis(3,5-di(tert-butyl)-4-hydroxybenzyl)-1,3-dihydrobenzimidazole-2-thione
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 24h; Temperature; | 96% |
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 95% |
With hydrogenchloride for 2h; Heating; | 95% |
2,3-dihydrobenzimidazol-2-thione
allyl methyl carbonate
1-allyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 25℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide for 4h; Heating; | 95% |
2,3-dihydrobenzimidazol-2-thione
4-ethylphenylboronic acid
2-((4-ethylphenyl)thio)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
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
phenylboronic acid
2-(phenylsulfanyl)-1H-benzimidazole
Conditions | Yield |
---|---|
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
HgI2(benzo-1,3-imidazole-2-thione)
Conditions | Yield |
---|---|
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
ethyl bromide
2-(ethylsulfanyl)-1H-benzimidazole
Conditions | Yield |
---|---|
With sodium hydroxide In isopropyl alcohol at 40℃; for 1h; Cooling; | 94% |
2,3-dihydrobenzimidazol-2-thione
benzyl chloride
2-(benzylthio)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Reflux; | 93% |
Conditions | Yield |
---|---|
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
4-methylphenylboronic acid
2-[(4-methylphenyl)sulfanyl]-1H-benzimidazole
Conditions | Yield |
---|---|
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
3,4-dimethyl phenylboronic acid
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 30℃; Chan-Lam Coupling; chemoselective reaction; | 93% |
Reported in EPA TSCA Inventory.
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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