2,2'-Dithiobisbenzanilide supplier

Name
2,2'-Dithiobisbenzanilide
EINECS 205-201-9
CAS No. 135-57-9
Article Data16
CAS DataBase
Density 1.35 g/cm³
Solubility 48μg/L at 20℃
Melting Point 143-146 °C
Formula C₂₆H₂₀ N₂ O₂S₂
Boiling Point 489.8 °C at 760 mmHg
Molecular Weight 456.589
Flash Point 250 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Benzanilide,2',2'''-dithiobis- (6CI,7CI,8CI);2,2'-Dibenzamidodiphenyl disulfide;2,2'-Dibenzoylaminodiphenyl disulfide;2',2'''-Dithiodibenzanilide;Bis(2-benzamidophenyl) disulfide;Bis(2-benzoylaminophenyl)disulfide;Bis(o-benzamidophenyl) disulfide;Bisbenzamide;Di-o-benzamidophenyl disulfide;N,N'-(Dithiodi-2,1-phenylene)bis[benzamide];Noctizer SS;Peptazin BAFD;Peptisant 10;Pepton 22;Pepton 3S;Renazit 11;Vuchtazin RV/G-M;o,o'-Dibenzamidodiphenyl disulfide;o-(Benzoylamino)phenyl disulfide;
PSA 108.80000
LogP 7.13660

Synthetic route

: 1020-40-2
N-(2-mercaptophenyl)-benzamide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
With 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In ethanol; water at 40℃; for 0.233333h; Temperature;	98%

: 95-16-9
1,3-Benzothiazole

: 98-88-4
benzoyl chloride

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Stage #1: 1,3-Benzothiazole With sodium hydroxide at 70 - 80℃; for 2.5h; Large scale; Stage #2: With sodium hypochlorite In tetrachloromethane at 20 - 40℃; for 1h; Large scale; Stage #3: benzoyl chloride In trichlorofluoromethane at 40 - 60℃; for 0.5h; Large scale;	97.5%

: 98-88-4
benzoyl chloride

: 1141-88-4
2-Aminophenyl disulfide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Stage #1: benzoyl chloride; 2-Aminophenyl disulfide In chloroform; isopropyl alcohol for 10h; Reflux; Large scale; Stage #2: With triethylamine In chloroform; isopropyl alcohol at 20℃; for 5h; Large scale;	95.7%
With triethylamine In tetrahydrofuran at 20℃; Acylation;	90%
at 100℃;

: 1020-40-2
N-(2-mercaptophenyl)-benzamide

A: 883-93-2
2-Phenylbenzothiazole

B: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide; 1,2-dichloro-ethane Mechanism;	A 50% B 38%

: 102318-19-4
4'-Dimethylamino-2-benzamino-diphenylsulfid

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
With bromine

: 137-07-5
2-amino-benzenethiol

: 65-85-0
benzoic acid

A: 1020-40-2
N-(2-mercaptophenyl)-benzamide

B: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Stage #1: 2-amino-benzenethiol With 4-methoxytrityl resin chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Stage #2: benzoic acid With diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 3h; Stage #3: With triethylsilane; trifluoroacetic acid In dichloromethane Title compound not separated from byproducts;

...Expand

: 1155-00-6
bis(2-nitrophenyl)disulfide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate; alcohol 2: acetic acid ester View Scheme

: 88-73-3
2-Chloronitrobenzene

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Na2S2 2: hydrazine hydrate; alcohol 3: acetic acid ester View Scheme

: 98370-54-8
zinc 2-aminobenzenethiolate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: air; diluted ammonia 2: 100 °C View Scheme

: 62-53-3
aniline

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfur 2: alkali View Scheme

: copper(l) cyanide

: 98-88-4
benzoyl chloride

: 1141-88-4
2-Aminophenyl disulfide

A: 5005-14-1
N-(benzo[d]thiazol-2-yl)benzamide

B: 135-57-9
bis(2-benzoylaminophenyl) disulfide

Conditions

Conditions	Yield
With oxygen for 0.5h;

...Expand

: 60-80-0
antipyrine

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-(2-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;	99%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;	81%

: 616-47-7
1-methyl-1H-imidazole

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-(2-((1-methyl-1H-imidazol-2-yl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With iodine In dimethyl sulfoxide at 120℃; for 16h; Schlenk technique;	99%

: 4316-42-1
1-Butylimidazole

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-(2-((1-butyl-1H-imidazol-2-yl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With iodine In dimethyl sulfoxide at 120℃; for 16h; Schlenk technique;	99%

: 98-88-4
benzoyl chloride

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 1047-61-6
1-thiobenzoyloxy-2-(N-benzoylamino)benzene

Conditions

Conditions	Yield
Stage #1: bis(2-benzoylaminophenyl) disulfide With sodium tetrahydroborate In ethanol at 0 - 20℃; for 0.5h; Stage #2: benzoyl chloride With potassium carbonate In ethanol at 0 - 20℃; pH=9 - 10; Further stages.;	96%

: 120-72-9
indole

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 1448801-48-6
N-(2-((1H-indol-3-yl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 100℃; for 9h; Green chemistry;	96%

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 883-93-2
2-Phenylbenzothiazole

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide; 1,2-dichloro-ethane Mechanism;	92%
With phosphorus trichloride In toluene at 100℃; Reagent/catalyst; Inert atmosphere;	27%
With hydrogenchloride; tin
With sodium dithionite; acetone

: dicarbonyldinitrosyliron

: 603-35-0
triphenylphosphine

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: bis(triphenylphosphine)dinitrosyliron

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: bis(o-benzamidophenyl)disulfide; under N2; Fe(CO)2(NO)2 reacted with disulfide in THF; added to PPh3 at ambient temp.; stirred for 1 h; concd.; pptd. by addition of Et2O-hexane; filtered; solid dissolved in THF; crystd. by diffusion of hexane into THF soln. at -15°C; detd.by IR, UV-vis spectra;	92%

...Expand

: dicarbonyldinitrosyliron

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: [Fe(μ-SC6H4-o-NHC(O)Ph)(nitrosyl)2]2

Conditions

Conditions	Yield
In tetrahydrofuran Fe complex reacted with (SC6H4-o-NHCOPh)2 in THF at ambient temp.;	90%
In tetrahydrofuran under N2; THF soln. of Fe(CO)2(NO)2 added to THF soln. of disulfide at 0°C; stirred at ambient temp. overnight; filtered through Celite; pptd. by addition of hexane to filtrate;	90%

: dicarbonyldinitrosyliron

: 63995-75-5
sodium 3-(diphenylphosphanyl)benzenesulfonate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: [Fe(NO)2(diphenylphosphinobenzene-3-sulfonic acid sodium salt)2]

Conditions

Conditions	Yield
In tetrahydrofuran (N2); treatment of iron compd. with disulfide deriv. in THF, addn. to phosphine deriv. at room temp., stirring for 1 h; concg., addn. of diethyl ether, filtration, elem. anal.;	88%

...Expand

: N-(2-(pyridin-2-yl)propan-2-yl)benzamide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: C41H34N4O3S2

Conditions

Conditions	Yield
With benzoic acid; silver carbonate; nickel dichloride In 1,2-dichloro-ethane at 140℃; for 4h; Sealed tube;	88%

: 563-63-3
silver(I) acetate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 110-83-8
cyclohexene

: 2-((2-benzamidophenyl)thio)cyclohexyl acetate

Conditions

Conditions	Yield
With acetic acid In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube;	86%

...Expand

: 5-nitro-N-(2-(pyridin-2-yl)propan-2-yl)thiophene-2-carboxamide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 3-((2-benzamidophenyl)thio)-5-nitro-N-(2-(pyridin-2-yl)propan-2-yl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With copper diacetate; sodium carbonate In 1,4-dioxane at 130℃; for 12h;	85%

: methyllithium lithium bromide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N,N’-[methylenebis(sulfanediyl-2,1-phenylene)]dibenzamide

Conditions

Conditions	Yield
Stage #1: methyllithium lithium bromide; bis(2-benzoylaminophenyl) disulfide With chloro-trimethyl-silane; iodobromomethane In tetrahydrofuran; diethyl ether at -78℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether; water chemoselective reaction;	84%

: (Et4N)2(Fe4S4(SPh)4)

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: [(C2H5)4N]2[Fe4S4(2-(benzoylamino)benzenethiolate)4]

Conditions

Conditions	Yield
In acetonitrile Ar atmosphere, stirring (room temperature, overnight); concn. (reduced pressure), washing (Et2O), recrystn. (CH3CN/Et2O), drying (vacuum); elem. anal.;	81%

: 622-97-9
1-ethenyl-4-methylbenzene

: 563-63-3
silver(I) acetate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 2-((2-benzamidophenyl)thio)-1-(p-tolyl)ethyl acetate

Conditions

Conditions	Yield
With acetic acid In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; regioselective reaction;	80%

...Expand

: copper(l) cyanide

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 5005-14-1
N-(benzo[d]thiazol-2-yl)benzamide

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; oxygen In acetonitrile at 60℃; for 3h;	80%

: 35730-09-7
2,5-difluorobenzoyl chloride

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: C40H24F4N2O4S2

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; copper(l) cyanide In acetonitrile at 60℃;	80%

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 130-15-4
[1,4]naphthoquinone

: 2-[2-benzamido(phenylthio)]-1,4-naphthoquinone

Conditions

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; H3N*C2H6O6S2; tetrabutylammonium tetrafluoroborate; silver(I) acetate In dimethyl sulfoxide at 20℃; for 48h;	76%

: 874-14-6
1,3-dimethyluracil

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-{2-[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-thio]phenyl}benzamide

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; iodine In acetonitrile at 60℃; regioselective reaction;	76%
With dipotassium peroxodisulfate; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 60℃; regioselective reaction;	60%

: 13720-89-3
1-ethyl-1,4-dihydroquinolin-4-one

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-(2-((1-ethyl-4-oxo-1,4-dihydroquinolin-3-yl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; iodine In acetonitrile at 80℃; regioselective reaction;	76%

: 695-12-5
vinylcyclohexane

: 563-63-3
silver(I) acetate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 2-((2-benzamidophenyl)thio)-1-cyclohexylethyl acetate

Conditions

Conditions	Yield
With acetic acid In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; regioselective reaction;	75%

...Expand

: 536-74-3
phenylacetylene

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-(2-((phenylethynyl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With oxygen; potassium carbonate; copper(l) chloride In methanol; acetonitrile for 1.5h; Irradiation;	75%

: 77475-04-8
1-Ethyl-3-methyl-2-pyridone

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: N-(2-((1-ethyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)thio)phenyl)benzamide

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; lithium chloride In acetonitrile at 70℃; regioselective reaction;	68%

: 109-99-9
tetrahydrofuran

: 1162648-56-7
[Ni(tert-butylthiolato)(N-2-(mercaptoethyl)picolinamide(-2H))][NEt4]

: 7732-18-5
water

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: [Ni(o-benzoylaminobenzenethiolato)(N-2-(mercaptoethyl)picolinamide(-2H))][Et4N]*0.5H2O*0.5THF

Conditions

Conditions	Yield
In tetrahydrofuran; acetonitrile byproducts: (t-Bu)SS(t-Bu); (N2); using Schlenk techniques; mixing of (Et4N)(Ni(C5H4NCONCH2CH2S)(S(t-Bu))) and disulfide o-benzoylaminobenzene (0.5 mol-equiv.) in 1:1 MeCN/THF mixt. at room temp., stirring for 16 h; filtration, concn., stirring for 4 h in 1:1 THF/Et2O; elem. anal.;	67%

...Expand

: 824-79-3
sodium 4-methylbenzenesulfinate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: S-(2-(benzamido)phenyl) 4-toluenethiosulfonate

Conditions

Conditions	Yield
With iodine In dichloromethane at 20℃; for 24h; Inert atmosphere;	64.6%

: 616-47-7
1-methyl-1H-imidazole

: cadmium(II) nitrate tetrhydrate

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: #

Conditions

Conditions	Yield
With NaBH4 In tetrahydrofuran; ethanol addn. of NaBH4 to the disulfide in THF/EtOH, stirring (room temp., 1 h),addn. to ZnCl2 and 1-methylimidazole in THF, further stirring (1 h); evapn., addn. of toluene, stirring (ambient temp., overnight), filtration, removal of toluene (vac.), recrystn. (toluene/Et2O); elem. anal.;	63%

...Expand

: 616-47-7
1-methyl-1H-imidazole

: 135-57-9
bis(2-benzoylaminophenyl) disulfide

: 7646-85-7
zinc(II) chloride

: Zn(SC6H4NHCOC6H5)2(C4H6N2)2*0.5H2O

Conditions

Conditions	Yield
With NaBH4 In tetrahydrofuran; ethanol addn. of NaBH4 to the disulfide in THF/EtOH, stirring (room temp., 1 h),addn. to ZnCl2 and 1-methylimidazole in THF, further stirring (1 h); evapn., addn. of toluene, stirring (ambient temp., overnight), filtration, removal of toluene (vac.), recrystn. (MeCN); elem. anal.;	63%

...Expand

2,2'-Dithiobisbenzanilide Chemical Properties

The molecular formula of o-(BENZOYLAMINO)PHENYL DISULFIDE(135-57-9) is C₂₆H₂₀N₂O₂S₂ and its formula weight is 456.58 g/mol.Its product name is 2,2'-Dithiobisbenzanilide.EINECS is 205-201-9.The density of o-(BENZOYLAMINO)PHENYL DISULFIDE(135-57-9) is 1.35 g/cm³ and it has a melting point of 143-146°C .The boiling point is 489.8 °C at 760 mmHg.The refractive index is about 1.723 and molar refractivity is 133.7 cm³. Its flash point is 250 °C and the vapor pressenge is 9.67E-10 mmHg at 25°C.Surface tension is 69.2 dyne/cm and enthalpy of vaporization is 75.62 kJ/mol.
The chemical synonyms of o-(BENZOYLAMINO)PHENYL DISULFIDE(135-57-9) are O,O'-DIBENZAMIDODIPHENYL DISULFIDE;2,2’-dibenzoylaminodiphenyldisulfide;2’,2’’’-dithiobis-benzanilid;bis(o-benzamidophenyl)disulfide;bis-o-benzoylaminofenyl-disulfid;di-o-benzamidophenyldisulphide;n,n’-(dithiodi-2,1-phenylene)bis-benzamid and n,n’-(dithiodi-2,1-phenylene)bisbenzamide.The molecular structure of o-(BENZOYLAMINO)PHENYL DISULFIDE(135-57-9) is .

2,2'-Dithiobisbenzanilide Toxicity Data With Reference

eye-rbt 500 mg/24H MLD

85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague,Czechoslovakia, Avicenum.: 1986,1007.

It is combustible. Combustion produce the toxic fumes of nitrogen oxides and sulfur oxides.

2,2'-Dithiobisbenzanilide Consensus Reports

Reported in EPA TSCA Inventory.

2,2'-Dithiobisbenzanilide Safety Profile

An eye irritant. When heated to decomposition it emits toxic vapors of NO_x and SO_x.
Risk Statements is 36/37/38.
Safety Statements is 26-36/37/39.

2,2'-Dithiobisbenzanilide Specification

Its extinguishing agent is dry powder,foam, sand, carbon dioxide and water mist.

Product Name

2,2'-Dithiobisbenzanilide

Synthetic route

2,2'-Dithiobisbenzanilide Chemical Properties

2,2'-Dithiobisbenzanilide Toxicity Data With Reference

2,2'-Dithiobisbenzanilide Consensus Reports

2,2'-Dithiobisbenzanilide Safety Profile

2,2'-Dithiobisbenzanilide Specification

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