Conditions | Yield |
---|---|
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 0.166667h; | 100% |
With tris paraperiodate In benzene for 0.5h; Heating; | 100% |
With dihydrogen peroxide In water | 100% |
potassium thioacyanate
p-nitrobenzyl <(R)-4-(2-benzothiazol-2-yldithio)-2-oxo-1-azetidinyl>isopropenylacetate
A
di(benzothiazol-2-yl)disulfide
B
(2S,3R)-3-Methyl-7-oxo-3-thiocyanatomethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
In dichloromethane; sulfuric acid; water for 12h; Ambient temperature; electrolysis procedure; | A 99% B 97% |
Conditions | Yield |
---|---|
With bromonitromethane In methanol | 98% |
With water; chlorine; ammonium chloride | |
With sulfuric acid; water; dihydrogen peroxide |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; ozone In methanol at 44℃; for 1.5h; Concentration; Temperature; Large scale; | 97.5% |
S-(benzo[d]thiazol-2-yl) benzenesulfonothioate
2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester
A
di(benzothiazol-2-yl)disulfide
4-phenylsulfonylthio-3-phenoxyacetamido-1-(1-benzyloxycarbonyl-2-methyl-2-propenyl)-2-azetidinone
Conditions | Yield |
---|---|
sodium benzenesulfonate In water; acetone for 3.5h; Ambient temperature; | A 96% B 91% |
2-(Benzothiazol-2-ylsulfanyl)-2-(3-methyl-but-2-enyl)-hexanedioic acid dimethyl ester
A
di(benzothiazol-2-yl)disulfide
B
2-(3-Methyl-but-2-enyl)-hexanedioic acid dimethyl ester
Conditions | Yield |
---|---|
In methanol; sulfuric acid Ambient temperature; Electrochemical reduction; | A 96% B 74% |
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In dichloromethane; acetone at 25℃; | 95% |
With dilauryl peroxide In 1,2-dichloro-ethane for 1h; Reflux; | 90% |
With potassium dichromate; acetic acid |
A
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 5h; | A n/a B 95% |
methanol
2-benzothiazol-2-ylsulfanyl-octanoic acid methyl ester
A
di(benzothiazol-2-yl)disulfide
B
2,2-Dimethoxy-octanoic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid; copper dichloride Ambient temperature; electrosynthesis; | A 58% B 94% |
With tetraethylammonium perchlorate; copper dichloride for 2.4h; Product distribution; Ambient temperature; electrosynthesis; further electrolytes, further α-sulfenylalkanoates; also without CuCl2; | A 80% B 83% |
N,N'-bis(phenylsulfonyl)sulfur diimide
A
di(benzothiazol-2-yl)disulfide
B
N,N'-bis(phenylsulfonyl)sulfoxylic diamide
Conditions | Yield |
---|---|
With 2-Mercaptobenzothiazole In benzene for 8h; Heating; | A 94% B 90% |
A
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 5h; | A n/a B 93% |
S-(benzo[d]thiazol-2-yl) benzenesulfonothioate
2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-methoxy-benzyl ester
A
di(benzothiazol-2-yl)disulfide
4-phenylsulfonylthio-3-phenylacetamido-1-(1-(p-methoxybenzyloxycarbonyl)-2-methyl-2-propenyl)-2-azetidinone
Conditions | Yield |
---|---|
sodium 2-mercaptobenzothiazole In water; acetone for 1.5h; Ambient temperature; | A n/a B 92% |
(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester
A
di(benzothiazol-2-yl)disulfide
B
2β-chloromethyl-2α-methylpenicillin-3α-carboxylic acid diphenylmethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 2h; | A n/a B 92% |
(R)-2-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-methoxy-benzyl ester
A
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 2h; | A n/a B 92% |
p-nitrobenzyl <(R)-4-(2-benzothiazol-2-yldithio)-2-oxo-1-azetidinyl>isopropenylacetate
A
di(benzothiazol-2-yl)disulfide
B
p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane at 0℃; for 2h; Product distribution; Mechanism; reactions of derivatives with HCl and HBr; | A n/a B 91% |
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 2h; | A n/a B 91% |
2-(2-benzothiazolyldithio)-3-bromo-α-(1-methylethylidene)-4-oxo-1-azetidineacetic acid β-nitrobenzyl ester
A
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 3h; | A n/a B 91% |
(R)-2-[(R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester
A
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 2h; | A n/a B 91% |
2-Mercaptobenzothiazole
A
di(benzothiazol-2-yl)disulfide
B
2-mercapto-6-nitrobenzothiazole
Conditions | Yield |
---|---|
In sulfuric acid | A 90% B n/a |
S-(benzo[d]thiazol-2-yl) benzenesulfonothioate
sodium benzenesulfonate
A
p-methoxybenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate
B
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
In acetone | A 90% B n/a |
Conditions | Yield |
---|---|
With copper(l) iodide; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 110℃; for 6h; Mechanism; Sealed tube; | 89% |
methanol
2-benzothiazol-2-ylsulfanyl-hexanedioic acid dimethyl ester
A
di(benzothiazol-2-yl)disulfide
B
2,2-Dimethoxy-hexanedioic acid dimethyl ester
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; copper dichloride Ambient temperature; electrosynthesis; | A 88% B 57% |
2-benzothiazol-2-ylsulfanyl-hexanedioic acid dimethyl ester
A
di(benzothiazol-2-yl)disulfide
B
2,2-Dimethoxy-hexanedioic acid dimethyl ester
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; copper dichloride In methanol Ambient temperature; electrosynthesis; | A 88% B 57% |
dimethyl 2-n-pentyl-(2-benzothiazolylthio)adipate
A
di(benzothiazol-2-yl)disulfide
B
2-Pentyl-hexanedioic acid dimethyl ester
C
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
In methanol; sulfuric acid Ambient temperature; Electrochemical reduction; | A 31% B 87% C 53% |
2-(Benzothiazol-2-ylsulfanyl)-2-(3-methyl-but-2-enyl)-octanoic acid methyl ester
A
di(benzothiazol-2-yl)disulfide
B
2-(3-Methyl-but-2-enyl)-octanoic acid methyl ester
C
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
In methanol; sulfuric acid Ambient temperature; Electrochemical reduction; | A 63% B 84% C 24% |
methanol
2-(Benzothiazol-2-ylsulfanyl)-4-methoxy-butyric acid methyl ester
A
di(benzothiazol-2-yl)disulfide
B
2,2,4-Trimethoxy-butyric acid methyl ester
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; copper dichloride Ambient temperature; electrosynthesis; | A 83% B 70% |
2-benzothiazol-2-ylsulfanyl-octanoic acid methyl ester
A
di(benzothiazol-2-yl)disulfide
B
2,2-Dimethoxy-octanoic acid methyl ester
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; copper dichloride In methanol for 2.4h; Ambient temperature; electrosynthesis; | A 80% B 83% |
2-(Benzothiazol-2-ylsulfanyl)-4-methoxy-butyric acid methyl ester
A
di(benzothiazol-2-yl)disulfide
B
2,2,4-Trimethoxy-butyric acid methyl ester
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; copper dichloride In methanol Ambient temperature; electrosynthesis; | A 83% B 70% |
2-thioxo-3H-1,3-benzothiazole
A
1,3-Benzothiazole
B
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With ozone In methanol; dichloromethane at 25℃; | A 11% B 83% |
With ozone In dichloromethane at 25℃; Product distribution; other 2-mercaptoheterazoles at different reaction conditions; | A 5% B 75% |
With dihydrogen peroxide; acetic acid at 25℃; for 0.0833333h; | A 35% B 43% |
dimethyl 2-(2-pentynyl)-2-(2-benzothiazolylthio)adipate
A
di(benzothiazol-2-yl)disulfide
B
2-Pent-2-ynyl-hexanedioic acid dimethyl ester
C
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
In methanol; sulfuric acid Ambient temperature; Electrochemical reduction; | A 50% B 82% C 22% |
2-benzothiazol-2-ylsulfanyl-2-(3-oxo-butyl)-octanoic acid methyl ester
A
di(benzothiazol-2-yl)disulfide
B
2-(3-Oxo-butyl)-octanoic acid methyl ester
C
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
In methanol; sulfuric acid Ambient temperature; Electrochemical reduction; | A 33% B 80% C 25% |
di(benzothiazol-2-yl)disulfide
(5-Amino-[1,2,4]thiadiazol-3-yl)-[(Z)-1-ethyl-propoxyimino]-acetic acid
(5-amino-[1,2,4]thiadiazol-3-yl)-(1-ethyl-propoxyimino)-thioacetic acid S-benzothiazol-2-yl ester
Conditions | Yield |
---|---|
With tributyl-amine; triethyl phosphite In acetonitrile at -10℃; | 100% |
di(benzothiazol-2-yl)disulfide
cyclohexylamine
N-(cyclohexyl)benzothiazole-2-sulfenamide
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene | 100% |
morpholine
di(benzothiazol-2-yl)disulfide
4-(benzothiazole-2-sulfenyl)-morpholine
Conditions | Yield |
---|---|
With sodium hydroxide In toluene | 99.5% |
With tetraethylammonium perchlorate In N,N-dimethyl-formamide for 16h; (electrolysis); |
di(benzothiazol-2-yl)disulfide
tert-butylamine
N-(tert-butyl)benzothiazole-2-sulfenamide
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 40 - 85℃; for 2.5h; Reagent/catalyst; Solvent; Large scale; | 99.5% |
Stage #1: di(benzothiazol-2-yl)disulfide In water at 20℃; for 0.5h; Reflux; Stage #2: tert-butylamine In water at 30 - 50℃; for 3h; Stage #3: With sodium hydroxide In water at 80 - 85℃; for 1h; Reagent/catalyst; | 98.5% |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 30℃; for 2h; Sealed tube; Electrochemical reaction; | 95% |
With oxygen In water at 60℃; under 2250.23 Torr; for 4h; Reagent/catalyst; | 76% |
With tetraethylammonium perchlorate In N,N-dimethyl-formamide at 15 - 22℃; for 8h; (electrolysis); |
di(benzothiazol-2-yl)disulfide
1-dodecylbromide
2-(dodecylthio)benzo[d]thiazole
Conditions | Yield |
---|---|
With RhCl(PPh3)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; under 760 Torr; for 24h; | 99% |
di(benzothiazol-2-yl)disulfide
(Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid
2-benzothiazolyl 2-(2-aminothiazol-4-yl)-2-<<1-(tert-butoxycarbonyl)-1-methylethoxy>imino>thioacetate
Conditions | Yield |
---|---|
With pyridine; N,N-dimethyl-aniline; triethyl phosphite In acetonitrile; benzene at 18 - 25℃; for 0.5h; Reagent/catalyst; Microwave irradiation; Green chemistry; | 98.5% |
di(benzothiazol-2-yl)disulfide
2-methylpropan-2-thiol
2-(tert-butyldisulfanyl)benzo[d]thiazole
Conditions | Yield |
---|---|
With palladium dichloride In dimethyl sulfoxide at 80℃; for 2h; Schlenk technique; Inert atmosphere; | 98% |
In chloroform for 6h; Ambient temperature; | 88% |
With methanol; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 4h; Electrochemical reaction; Inert atmosphere; | 65% |
di(benzothiazol-2-yl)disulfide
[3-(Benzothiazol-2-ylsulfanyl)-2-methyl-propyl]-trityl-amine
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran | 98% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h; | 97% |
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube; | 84% |
2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid
di(benzothiazol-2-yl)disulfide
2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-(methoxyimino)ethan-1-one
Conditions | Yield |
---|---|
With pyridine; triethylamine; triethyl phosphite In dichloromethane; acetonitrile at 16.5 - 23℃; for 2h; Temperature; Reagent/catalyst; | 97% |
Stage #1: 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid With N,N-dimethyl acetamide; triethylamine In dichloromethane; acetonitrile for 1.5h; Stage #2: di(benzothiazol-2-yl)disulfide With phosphonic Acid; triethyl phosphite In dichloromethane; acetonitrile at 31℃; for 2h; Reagent/catalyst; Temperature; | 92.74% |
morpholine
di(benzothiazol-2-yl)disulfide
4-(benzothiazole-2-sulfenyl)-morpholine
Conditions | Yield |
---|---|
In ethanol | 96.5% |
di(benzothiazol-2-yl)disulfide
(5-Amino-[1,2,4]thiadiazol-3-yl)-[(Z)-3,3-dimethyl-cyclobutoxyimino]-acetic acid
(5-amino-[1,2,4]thiadiazol-3-yl)-(3,3-dimethyl-cyclobutoxyimino)-thioacetic acid S-benzothiazol-2-yl ester
Conditions | Yield |
---|---|
With tributyl-amine; triethyl phosphite In acetonitrile at -10℃; | 96% |
tridec-1-ene-3-thiol
di(benzothiazol-2-yl)disulfide
2-(2-(tridec-1-en-3-yl)disulfanyl)benzo[d]thiazole
Conditions | Yield |
---|---|
In chloroform at 20℃; | 96% |
In chloroform | 96% |
di(benzothiazol-2-yl)disulfide
benzothiazolyl-2-sulfur trifluoride
Conditions | Yield |
---|---|
With potassium fluoride; chlorine In acetonitrile at 20℃; for 4h; | 95.5% |
With potassium fluoride; chlorine In acetonitrile at 20℃; |
Conditions | Yield |
---|---|
bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In dichloromethane at 80℃; for 3h; | 95% |
di(benzothiazol-2-yl)disulfide
4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzoic acid
PPIB-MBT
Conditions | Yield |
---|---|
With triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 2h; | 95% |
With triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 0.166667h; Microwave irradiation; | 95% |
Conditions | Yield |
---|---|
Stage #1: di(benzothiazol-2-yl)disulfide With triphenylphosphine In dichloromethane at 5℃; for 1h; Inert atmosphere; Stage #2: asaronic acid In dichloromethane at 5℃; for 1h; | 94.4% |
di(benzothiazol-2-yl)disulfide
2-hydroxy-2-phenylacetophenone
2-[(1,3-benzothiazol-2-yl)sulfanyl]-1,2-diphenylethanone
Conditions | Yield |
---|---|
With tributylphosphine In toluene for 8h; Heating; | 94% |
1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
Stage #1: di(benzothiazol-2-yl)disulfide With triphenylphosphine In dichloromethane at 20℃; for 1.5h; Stage #2: 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid In dichloromethane at 20℃; for 1h; | 94% |
Molecular Structure of 2,2'-Dithiobis(benzothiazole) (CAS NO.120-78-5):
IUPAC Name: 2-(1,3-benzothiazol-2-yldisulfanyl)-1,3-benzothiazole
Empirical Formula: C14H8N2S4
Molecular Weight: 332.4867
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 132.86Å2
Index of Refraction: 1.848
Molar Refractivity: 94.48 cm3
Molar Volume: 211.7 cm3
Surface Tension: 90.3 dyne/cm
Density: 1.57 g/cm3
Flash Point: 275.8 °C
Enthalpy of Vaporization: 77.79 kJ/mol
Boiling Point: 532.5 °C at 760 mmHg
Vapour Pressure: 6.97E-11 mmHg at 25°C
Water Solubility: <0.01 g/100 mL at 21 ºC
Merck: 3370
Melting point: 177-180 °C(lit.)
EINECS: 204-424-9
Product Categories: Rubber Chemicals; Industrial/Fine Chemicals; Xanthones; Organics; Carumonam; Cefixime; Spirapril; Building Blocks; Heterocyclic Building Blocks; Thiazoles
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 100mg/kg (100mg/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#02251, | |
mouse | LD50 | oral | 7gm/kg (7000mg/kg) | International Polymer Science and Technology. Vol. 3, Pg. 93, 1976. | |
rabbit | LD50 | skin | > 7940mg/kg (7940mg/kg) | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-1190-0987S, | |
rat | LD50 | intraperitoneal | 2600mg/kg (2600mg/kg) | International Polymer Science and Technology. Vol. 3, Pg. 93, 1976. | |
rat | LD50 | oral | > 12gm/kg (12000mg/kg) | National Technical Information Service. Vol. AD755-358, |
Reported in EPA TSCA Inventory.
Poison by intravenous and intraperitoneal routes. Slightly toxic by ingestion. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx. See also SULFIDES.
Hazard Codes: Xi,N
Risk Statements: 31-43-50/53
R31 :Contact with acids liberates toxic gas.
R43:May cause sensitization by skin contact.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 36/37-60-61
S36/37:Wear suitable protective clothing and gloves.
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
2,2'-Dithiobis(benzothiazole) , with CAS number of 120-78-5, can be called 1,2-Bis(2-benzothiazolyl)disulfide ; 2,2'-Benzothiazolyl disulfide ; 2,2'-Benzothiazyl disulfide ; 2,2'-Dibenzothiazole disulfide ; 2,2'-Dibenzothiazolyl disulfide ; 2,2'-Dithiobis ; 2-Benzothiazolyl disulfide ; 2-Mercaptobenzothiazole disulfide ; Bis(2-benzothiazolyl) disulfide ; Bis(benzothiazol-2-yl)disulfide ; Dibenzothiophene disulfide . It is a yellow amorphous powder. 2,2'-Dithiobis(benzothiazole) (CAS NO.120-78-5) is used as universal promoting agents like the natural rubber, synthetic rubber, reclaimed rubber. 2,2'-Dithiobis(benzothiazole) (CAS NO.120-78-5) is mainly used in the manufacture of tires, tire tube, rubber belt, rubber overshoes and general industrial products. High purity Benzothiazole disulfide (pharmaceutical grade) is the important manufacturing cephalosporin antiphlogistics pharmaceutical intermediates.
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