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2,2'-Dithiobis(benzothiazole)

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2,2'-Dithiobis(benzothiazole)

EINECS 204-424-9
CAS No. 120-78-5 Density 1.57 g/cm3
PSA 132.86000 LogP 5.70540
Solubility <0.01 g/100 mL at 21 °C in water Melting Point 177-180 °C(lit.)
Formula C14H8N2S4 Boiling Point 532.5 °C at 760 mmHg
Molecular Weight 332.495 Flash Point 275.8 °C
Transport Information UN 3077 9/PG 3 Appearance yellow amorphous powder
Safety 36/37-60-61 Risk Codes 31-43-50/53
Molecular Structure Molecular Structure of 120-78-5 (2,2'-Dithiobis(benzothiazole)) Hazard Symbols IrritantXi,DangerousN
Synonyms

Vulcanization accelerator DM (MBTS);2,2'-Benzothiazolyl disulfide;2-Benzothiazyldisulfide;2-Mercaptobenzothiazole disulfide;AcceleratorDM;Altax;Benzothiazolyl disulfide;Benzothiazyldisulfide;Bis(2-benzothiazolyl) disulfide;Bis(benzothiazol-2-yl)disulfide;2,2'-Dithiobis(benzothiazole);1,2-Bis(2-benzothiazolyl)disulfide;

Article Data 95

2,2'-Dithiobis(benzothiazole) Synthetic route

149-30-4

2-Mercaptobenzothiazole

120-78-5

di(benzothiazol-2-yl)disulfide

Conditions
ConditionsYield
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 water100%
333-20-0

potassium thioacyanate

71355-12-9, 95835-16-8

p-nitrobenzyl <(R)-4-(2-benzothiazol-2-yldithio)-2-oxo-1-azetidinyl>isopropenylacetate

A

120-78-5

di(benzothiazol-2-yl)disulfide

B

112110-51-7

(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
ConditionsYield
In dichloromethane; sulfuric acid; water for 12h; Ambient temperature; electrolysis procedure;A 99%
B 97%
2492-26-4

sodium 2-mercaptobenzothiazole

120-78-5

di(benzothiazol-2-yl)disulfide

Conditions
ConditionsYield
With bromonitromethane In methanol98%
With water; chlorine; ammonium chloride
With sulfuric acid; water; dihydrogen peroxide
80756-85-0

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

120-78-5

di(benzothiazol-2-yl)disulfide

Conditions
ConditionsYield
With tetrabutylammomium bromide; ozone In methanol at 44℃; for 1.5h; Concentration; Temperature; Large scale;97.5%
41475-98-3

S-(benzo[d]thiazol-2-yl) benzenesulfonothioate

57562-33-1, 68128-75-6

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

120-78-5

di(benzothiazol-2-yl)disulfide

91939-45-6, 106138-52-7

4-phenylsulfonylthio-3-phenoxyacetamido-1-(1-benzyloxycarbonyl-2-methyl-2-propenyl)-2-azetidinone

Conditions
ConditionsYield
sodium benzenesulfonate In water; acetone for 3.5h; Ambient temperature;A 96%
B 91%
72844-42-9

2-(Benzothiazol-2-ylsulfanyl)-2-(3-methyl-but-2-enyl)-hexanedioic acid dimethyl ester

A

120-78-5

di(benzothiazol-2-yl)disulfide

B

72844-50-9

2-(3-Methyl-but-2-enyl)-hexanedioic acid dimethyl ester

Conditions
ConditionsYield
In methanol; sulfuric acid Ambient temperature; Electrochemical reduction;A 96%
B 74%
149-30-4

2-thioxo-3H-1,3-benzothiazole

120-78-5

di(benzothiazol-2-yl)disulfide

Conditions
ConditionsYield
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

(R)-2-[2-(Benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

A

120-78-5

di(benzothiazol-2-yl)disulfide

B

benzhydryl 6,6-dibromo-2β-chloromethyl-2α-methylpenam-3α-carboxylate

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In dichloromethane; water at 0℃; for 5h;A n/a
B 95%
67-56-1

methanol

70203-06-4

2-benzothiazol-2-ylsulfanyl-octanoic acid methyl ester

A

120-78-5

di(benzothiazol-2-yl)disulfide

B

74391-99-4

2,2-Dimethoxy-octanoic acid methyl ester

Conditions
ConditionsYield
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%
667-20-9

N,N'-bis(phenylsulfonyl)sulfur diimide

A

120-78-5

di(benzothiazol-2-yl)disulfide

B

81955-02-4

N,N'-bis(phenylsulfonyl)sulfoxylic diamide

Conditions
ConditionsYield
With 2-Mercaptobenzothiazole In benzene for 8h; Heating;A 94%
B 90%

2,2'-Dithiobis(benzothiazole) Chemical Properties

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

2,2'-Dithiobis(benzothiazole) Toxicity Data With Reference

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,

2,2'-Dithiobis(benzothiazole) Consensus Reports

Reported in EPA TSCA Inventory.

2,2'-Dithiobis(benzothiazole) Safety Profile

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: IrritantXi,DangerousN
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) Specification

 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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