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882-33-7 Usage

Chemical Description

Diphenyl disulfide is a compound with two phenyl groups attached to a sulfur atom.

Description

Diphenyl disulfide is a colorless crystalline material with the formula (C6H5S)2 and often abbreviated Ph2S2. It is most commonly utilized as a reagent for integration of a phenylthio functionality into molecules. The phenylthio group in the compound has a useful function due to the numerous of reaction that it can facilitate in organic chemistry. Phenysulfides, for instance, undergo oxidative elimination, producing alkenes under relatively mild, normal conditions. Also phenyl sulfides can serve as a source of carbon-centered radicals in radical reactions. Diphenyl disulfide is usually synthesized by the oxidation of thiophenol: 2 PhSH + I2 → Ph2S2 + 2 HI

Reactions and Uses

With Alkenes Ph2S2 adds cleanly to many dienes and alkenes upon catalysis by BF3.OMe2. The trifluoroacetoxysulfenylation of unsaturated esters, nitriles, amides, and carboxylic acids is possible with Ph2S2. As a Source of Thiiyl Radicals In the presence of radical initiators, upon thermolysis or photolysis, thiiyl radicals can be generated from PhSSPh. Therefore, the radicals generated add reversibly to alkynes and alkenes generating vinyl and alkyl radicals respectively (1). Reduction Ph2S2 undergoes reduction, which is a characteristic of disulfides. Hydride reagents such as super hydride and sodium borohydride can be used as reductants. Ph2S2 + 2 M → 2 MSPh (M = Li, Na, K)

Occurrence

Naturally occurring phytoalexin-like substan

Uses

Diphenyl disulfide is one of the most popular organic disulfides used in organic synthesis. It is used as a reagent for the α-phenylsulfenylation of carbonyl compounds. It participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism. It is the hydrolysis product of dyfonate.

Preparation

By heating and passing a stream of air over an ammoniacal solution of thiophenol.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 1770, 1987 DOI: 10.1248/cpb.35.1770Tetrahedron Letters, 25, p. 703, 1984 DOI: 10.1016/S0040-4039(01)80004-6

Purification Methods

Crystallise the disulfide from MeOH. [Alberti et al. J Am Chem Soc 108 3024 1986]. Also crystallise it repeatedly from hot Et2O, then dry it in a vacuum at 30o over P2O5, fuse it under N2 and re-dry it; the whole procedure being repeated, with a final drying under a vacuum for 24hours. Alternatively, recrystallise it from hexane/EtOH solution. [Burkey & Griller J Am Chem Soc 107 246 1985, Beilstein 6 H 323, 6 IV 1560.]

Check Digit Verification of cas no

The CAS Registry Mumber 882-33-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,8 and 2 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 882-33:
(5*8)+(4*8)+(3*2)+(2*3)+(1*3)=87
87 % 10 = 7
So 882-33-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H

882-33-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A12586)  Diphenyl disulfide, 98%   

  • 882-33-7

  • 50g

  • 224.0CNY

  • Detail
  • Alfa Aesar

  • (A12586)  Diphenyl disulfide, 98%   

  • 882-33-7

  • 250g

  • 833.0CNY

  • Detail
  • USP

  • (1457957)  Nelfinavir Related Compound E  United States Pharmacopeia (USP) Reference Standard

  • 882-33-7

  • 1457957-50MG

  • 14,500.98CNY

  • Detail
  • Aldrich

  • (169021)  Phenyldisulfide  99%

  • 882-33-7

  • 169021-10G

  • 258.57CNY

  • Detail
  • Aldrich

  • (169021)  Phenyldisulfide  99%

  • 882-33-7

  • 169021-50G

  • 400.14CNY

  • Detail
  • Aldrich

  • (169021)  Phenyldisulfide  99%

  • 882-33-7

  • 169021-250G

  • 1,341.52CNY

  • Detail

882-33-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenyl Disulfide

1.2 Other means of identification

Product number -
Other names Disulfide, diphenyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:882-33-7 SDS

882-33-7Synthetic route

S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With ethyl phosphinate In ethanol other reagent;100%
With ethyl phosphinate In ethanol Product distribution; other reagent;100%
With tungsten(VI) chloride; sodium iodide In acetonitrile for 1.5h; Ambient temperature;98%
thiophenol
108-98-5

thiophenol

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With pyridine chromium peroxide for 0.1h; Product distribution; effect of various chromium(VI) based oxidants;100%
With bis(tetra-n-butylammonium) tetrakis(benzenethiolato-μ3-sulfidoiron); oxygen In acetonitrile at 0℃; for 0.166667h; other iron-sulfur complex or other iron compounds as the catalyst in reaction oxidation;100%
With barium ferrate(VI) In benzene for 0.25h; Product distribution; Heating;100%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;100%
With tungsten(VI) chloride; sodium iodide In acetonitrile for 16h; Ambient temperature;97%
With Silphos; iodine In acetonitrile for 10h; Heating;96%
benzenesulfinyl-benzoyloxy-methane
41065-20-7

benzenesulfinyl-benzoyloxy-methane

A

formaldehyd
50-00-0

formaldehyd

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With potassium hydroxide In methanolA 100%
B 61%
thiophenol
108-98-5

thiophenol

A

bis(benzenethio)tellurium(II)
75264-81-2

bis(benzenethio)tellurium(II)

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With (2,2,4,4-tetrafluoropropoxy)tellurane In diethyl ether at -50 - -40℃; for 0.166667h;A 100%
B n/a
Perbenzoic acid
93-59-4

Perbenzoic acid

bis-benzenesulfenyl-amine
24364-84-9

bis-benzenesulfenyl-amine

A

benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

B

biphenyl
92-52-4

biphenyl

C

benzoic acid
65-85-0

benzoic acid

D

diphenyldisulfane
882-33-7

diphenyldisulfane

E

N2, tar

N2, tar

Conditions
ConditionsYield
In benzene Kinetics; Product distribution; Mechanism; isotopic effect, effect of benzoic acid and styrene on the reaction;A 1.4%
B 0.2%
C 100%
D 50%
E n/a
pentamethylcyclopentadienyl-ruthenium(III) chloride

pentamethylcyclopentadienyl-ruthenium(III) chloride

allyl phenyl thioether
5296-64-0

allyl phenyl thioether

A

π-allyl(dichloro)(pentamethylcyclopentadienyl)ruthenium (IV)

π-allyl(dichloro)(pentamethylcyclopentadienyl)ruthenium (IV)

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With ethanol In dichloromethane CH2Cl2 soln. of reagents was stirred at 0°C for 1 h under N2; concd., chromd. on silica gel with hexane-ethyl acetate;A 100%
B n/a
pentamethylcyclopentadienyl-ruthenium(III) chloride

pentamethylcyclopentadienyl-ruthenium(III) chloride

(2-methylallyl)(phenyl)sulfane
702-00-1

(2-methylallyl)(phenyl)sulfane

A

(η5-C5Me5)RuCl2(η3-CH2CMeCH2)

(η5-C5Me5)RuCl2(η3-CH2CMeCH2)

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In dichloromethane CH2Cl2, 0°C, 1 h;A 100%
B n/a
thiophenol
108-98-5

thiophenol

[(trifluoroacetyl)imino]tris-(2-methylphenyl)-λ(5)-bismuthane
233257-02-8

[(trifluoroacetyl)imino]tris-(2-methylphenyl)-λ(5)-bismuthane

A

tri-o-tolylbismuth
10050-08-5

tri-o-tolylbismuth

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In benzene room temp., 3 h;A 100%
B 80%
N-benzylidene-S-phenylthiohydroxylamine
52777-99-8

N-benzylidene-S-phenylthiohydroxylamine

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With oxygen; copper(II) bis(trifluoromethanesulfonate) In toluene at 80℃; for 3h;100%
Benzoyl bromide
618-32-6

Benzoyl bromide

thallium thiophenoxide
57340-80-4

thallium thiophenoxide

A

phenyl thiobenzoate
884-09-3

phenyl thiobenzoate

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In diethyl ether for 0.5h;A 99%
B 1%
p-(1-methyl-1-nitropropyl)nitrobenzene
110637-93-9, 58324-83-7

p-(1-methyl-1-nitropropyl)nitrobenzene

sodium thiophenolate
930-69-8

sodium thiophenolate

A

2-(p-nitrophenyl)-2-butyl phenyl sulfide
110637-97-3

2-(p-nitrophenyl)-2-butyl phenyl sulfide

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In dimethyl sulfoxide for 0.75h;A 99%
B 99%
thallium thiophenoxide
57340-80-4

thallium thiophenoxide

benzoyl chloride
98-88-4

benzoyl chloride

A

phenyl thiobenzoate
884-09-3

phenyl thiobenzoate

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In diethyl ether for 1h;A 99%
B 1%
diphenyl-N-(p-toluenesulfonyl)selenimide
52867-19-3

diphenyl-N-(p-toluenesulfonyl)selenimide

thiophenol
108-98-5

thiophenol

A

diphenylselenide
1132-39-4

diphenylselenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In chloroform for 0.25h; Product distribution; Ambient temperature;A 96%
B 99%
C 97%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

thiophenol
108-98-5

thiophenol

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In chloroform for 0.166667h; Product distribution; Ambient temperature;A 98%
B 99%
C 97%
triphenyl bismuth (2+); dichloride
507233-69-4, 594-30-9, 28719-54-2

triphenyl bismuth (2+); dichloride

thiophenol
108-98-5

thiophenol

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 60℃; for 18h;99%
thallium thiophenoxide
57340-80-4

thallium thiophenoxide

acetyl chloride
75-36-5

acetyl chloride

A

S-phenyl thioacetate
934-87-2

S-phenyl thioacetate

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In diethyl ether for 0.5h;A 99%
B 1%
tetra-n-butylammonium difluorotriphenylstannate

tetra-n-butylammonium difluorotriphenylstannate

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With sulfur In N,N-dimethyl-formamide at 130℃; for 5.5h; Substitution;99%
(C6H5)4SbSC6H5*0.06CHCl3

(C6H5)4SbSC6H5*0.06CHCl3

A

biphenyl
92-52-4

biphenyl

B

diphenyl sulfide
139-66-2

diphenyl sulfide

C

triphenylantimony
603-36-1

triphenylantimony

D

diphenyldisulfane
882-33-7

diphenyldisulfane

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. of Sb compd. in a sealed tube on heating to 140°C for 3 h; not isolated, detected by GLC and TLC;A 21%
B 69%
C 99%
D 30%
E 6%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

S-phenyl tert-butylcarbamothioate
56741-04-9

S-phenyl tert-butylcarbamothioate

A

N-(tert-butyl)phenanthrene-9-carboxamide
1579273-93-0

N-(tert-butyl)phenanthrene-9-carboxamide

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
Stage #1: 9-bromophenanthrene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: S-phenyl tert-butylcarbamothioate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h;
A 76%
B 99%
1-Bromo-2,4,6-triisopropylbenzene
21524-34-5

1-Bromo-2,4,6-triisopropylbenzene

S-phenyl (1-adamantyl)thiocarbamate

S-phenyl (1-adamantyl)thiocarbamate

A

N-(1-adamantyl)-2,4,6-triisopropylbenzamide

N-(1-adamantyl)-2,4,6-triisopropylbenzamide

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: S-phenyl (1-adamantyl)thiocarbamate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h; Schlenk technique;
A 98%
B 99%
1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

S-phenyl (1-adamantyl)thiocarbamate

S-phenyl (1-adamantyl)thiocarbamate

A

N-(1-adamantyl)-4-(tert-butyl)benzamide
331434-35-6

N-(1-adamantyl)-4-(tert-butyl)benzamide

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
Stage #1: 1-bromo-4-tert-butylbenzene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: S-phenyl (1-adamantyl)thiocarbamate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h; Schlenk technique;
A 86%
B 99%
sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With iodine; triphenylphosphine In water at 100℃; Green chemistry;98%
With tungsten(VI) chloride; sodium iodide In acetonitrile for 12h; Ambient temperature;95%
With Silphos; iodine In acetonitrile for 12h; Heating;95%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

thallium thiophenoxide
57340-80-4

thallium thiophenoxide

A

phenylthiotrimethylsilane
4551-15-9

phenylthiotrimethylsilane

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In diethyl ether for 18h;A 98%
B 2%
bromobenzene
108-86-1

bromobenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; basolite C300 In water; N,N-dimethyl-formamide at 130℃; for 6h; Green chemistry;98%
With sulfur; potassium hydroxide In water at 130℃; for 7.5h; Green chemistry;95%
With copper(l) iodide; hexachloroethane; sodium carbonate; thiourea In water at 120℃; for 15h;93%
2-[(1-phenylmethyl)sulfinyl]pyridine
87577-90-0

2-[(1-phenylmethyl)sulfinyl]pyridine

phenylmagnesium bromide

phenylmagnesium bromide

A

2-Benzylpyridine
101-82-6

2-Benzylpyridine

B

S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

C

S-phenyl benzenethiosulfinate
1208-20-4, 6930-77-4, 133670-27-6

S-phenyl benzenethiosulfinate

D

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In tetrahydrofuran Product distribution; Mechanism; Ambient temperature; investigation of reaction with various Grignard reagents and n-BuLi;A 98%
B 3%
C 60%
D 16%
In tetrahydrofuran Ambient temperature;A 98%
B 3%
C 60%
D 16%
2-[(1-phenylmethyl)sulfinyl]pyridine
87577-90-0

2-[(1-phenylmethyl)sulfinyl]pyridine

A

2-Benzylpyridine
101-82-6

2-Benzylpyridine

B

S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

C

S-phenyl benzenethiosulfinate
1208-20-4, 6930-77-4, 133670-27-6

S-phenyl benzenethiosulfinate

D

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With phenylmagnesium bromide In tetrahydrofuran Ambient temperature;A 98%
B 3%
C 60%
D 16%
With phenylmagnesium bromide In tetrahydrofuran Ambient temperature;A 98%
B 3%
C 60%
D 16%
Acetyl bromide
506-96-7

Acetyl bromide

thallium thiophenoxide
57340-80-4

thallium thiophenoxide

A

S-phenyl thioacetate
934-87-2

S-phenyl thioacetate

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In diethyl ether for 1h;A 98%
B 1%
α-naphthol
90-15-3

α-naphthol

4'-nitrobenzenesulfenanilide
64168-52-1

4'-nitrobenzenesulfenanilide

A

2-phenylthio-1-naphthol
68143-73-7

2-phenylthio-1-naphthol

B

4-(phenylthio)naphthalen-1-ol
19133-53-0

4-(phenylthio)naphthalen-1-ol

C

4-nitro-aniline
100-01-6

4-nitro-aniline

D

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given;A 42%
B 33%
C 98%
D 14%
α-naphthol
90-15-3

α-naphthol

4'-nitrobenzenesulfenanilide
64168-52-1

4'-nitrobenzenesulfenanilide

A

2-phenylthio-1-naphthol
68143-73-7

2-phenylthio-1-naphthol

B

4-(phenylthio)naphthalen-1-ol
19133-53-0

4-(phenylthio)naphthalen-1-ol

C

4-nitro-aniline
100-01-6

4-nitro-aniline

D

2,4-bis(phenylthio)naphthalen-1-ol
103929-98-2

2,4-bis(phenylthio)naphthalen-1-ol

E

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.166667h; Product distribution; Mechanism; 1.5 eqiv. TFA;A 42%
B 33%
C 98%
D 10%
E 14%
diphenyldisulfane
882-33-7

diphenyldisulfane

thiophenol
108-98-5

thiophenol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; methanol for 2h; Heating;100%
With sodium tetrahydroborate In tetrahydrofuran; methanol for 2h; Heating; solvent effect (t-BuOH, DME, 1,4-dioxane, EtOH);100%
With sodium diethylpiperidinohydroaluminate In tetrahydrofuran at 0℃; for 3h;98%
diphenyldisulfane
882-33-7

diphenyldisulfane

benzenesulfenyl chloride
931-59-9

benzenesulfenyl chloride

Conditions
ConditionsYield
With chlorine In dichloromethane at 0℃; for 0.333333h;100%
With (Dichloroiodo)benzene In dichloromethane at 20℃; for 0.333333h;95%
With chlorine In tetrachloromethane at -78℃;93%
diphenyldisulfane
882-33-7

diphenyldisulfane

benzenesulphinyl chloride
4972-29-6

benzenesulphinyl chloride

Conditions
ConditionsYield
With sulfuryl dichloride; acetic acid at -40℃; for 3h;100%
With sulfuryl dichloride; acetic acid at -20 - 35℃; for 5.3h;85%
With sulfuryl dichloride; acetic acid at -20 - 35℃; for 6h;85%
methoxybenzene
100-66-3

methoxybenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

1-methoxy-4-(phenylsulfanyl)benzene
5633-57-8

1-methoxy-4-(phenylsulfanyl)benzene

Conditions
ConditionsYield
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Heating;100%
With dipotassium peroxodisulfate In trifluoroacetic acid at 20℃; for 16h;89%
Stage #1: diphenyldisulfane With thionyl chloride In 1,2-dichloro-ethane at 5 - 30℃; for 4h;
Stage #2: With aluminum (III) chloride In 1,2-dichloro-ethane at 5 - 10℃; for 1h;
Stage #3: methoxybenzene In 1,2-dichloro-ethane for 4h;
88.5%
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Product distribution; Heating; effect of Lewis acid and silver salt;
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

diphenyldisulfane
882-33-7

diphenyldisulfane

2,4-dinitro-1-phenylsulfanyl-benzene
2486-09-1

2,4-dinitro-1-phenylsulfanyl-benzene

Conditions
ConditionsYield
With borax; N-Acetylcysteine In methanol; water for 1h; Ambient temperature;100%
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonim bromide In tetrahydrofuran; water for 4h; Product distribution; Heating;95%
With sodium hydroxide; cetyltrimethylammonim bromide; Aminoiminomethanesulfinic acid In tetrahydrofuran for 4h; Heating;95%
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonim bromide In tetrahydrofuran; water for 4h; Heating;95%
With aluminium trichloride; zinc In water; N,N-dimethyl-formamide at 65℃; for 6h;95%
iodobenzene
591-50-4

iodobenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
at 230 - 270℃; for 8h; Mechanism; other aryl iodides;100%
at 230 - 270℃; for 8h;100%
With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;97%
2,2-dimethyl-propanol-1
75-84-3

2,2-dimethyl-propanol-1

diphenyldisulfane
882-33-7

diphenyldisulfane

neopentyl phenyl sulphide
7210-80-2

neopentyl phenyl sulphide

Conditions
ConditionsYield
With tributylphosphine In tetrahydrofuran at 62℃; under 7500600 Torr; for 3h; other pressures and times; var. prim. and sec. alcohols;100%
With tributylphosphine In tetrahydrofuran at 62℃; under 7500600 Torr; for 3h;100%
2-methylmethoxybenzene
578-58-5

2-methylmethoxybenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

1-methoxy-2-methyl-4-(phenylsulfanyl)benzene
107777-12-8

1-methoxy-2-methyl-4-(phenylsulfanyl)benzene

Conditions
ConditionsYield
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Heating;100%
methyl (R)-3-hydroxy-2-methylpropionate
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

diphenyldisulfane
882-33-7

diphenyldisulfane

(S)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester
121783-48-0

(S)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester

Conditions
ConditionsYield
With tributylphosphine In acetonitrile for 4.5h; Ambient temperature;100%
With tributylphosphine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;95%
tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

diphenyldisulfane
882-33-7

diphenyldisulfane

phenylthioethylene
1822-73-7

phenylthioethylene

Conditions
ConditionsYield
In benzene at 35 - 45℃; for 4h; Irradiation;100%
<(E)-3,3-dimethyl-1-butenyl>mercuric chloride
36525-02-7, 79178-05-5

<(E)-3,3-dimethyl-1-butenyl>mercuric chloride

diphenyldisulfane
882-33-7

diphenyldisulfane

E-3,3-Dimethylbut-1-en-1-yl-phenylsulfid
53847-74-8

E-3,3-Dimethylbut-1-en-1-yl-phenylsulfid

Conditions
ConditionsYield
In benzene at 35 - 45℃; for 6h; Irradiation;100%
2-[1,3]Dioxolan-2-ylmethyl-3,3-dimethyl-butan-1-ol
138814-74-1

2-[1,3]Dioxolan-2-ylmethyl-3,3-dimethyl-butan-1-ol

diphenyldisulfane
882-33-7

diphenyldisulfane

2-(3,3-Dimethyl-2-phenylsulfanylmethyl-butyl)-[1,3]dioxolane
138814-75-2

2-(3,3-Dimethyl-2-phenylsulfanylmethyl-butyl)-[1,3]dioxolane

Conditions
ConditionsYield
With pyridine; tributylphosphine at 25℃;100%
5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione
87817-91-2

5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

diphenyldisulfane
882-33-7

diphenyldisulfane

5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione
87817-96-7

5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -70℃;100%
2-(2-(but-3-yn-1-yl)-1,3-dioxolan-2-yl)ethan-1-ol
91798-92-4

2-(2-(but-3-yn-1-yl)-1,3-dioxolan-2-yl)ethan-1-ol

diphenyldisulfane
882-33-7

diphenyldisulfane

2-(3-butynyl)-2-<2-(phenylthio)ethyl>-1,3-dioxolane
91798-93-5

2-(3-butynyl)-2-<2-(phenylthio)ethyl>-1,3-dioxolane

Conditions
ConditionsYield
With tributylphosphine In benzene for 0.5h;100%
diphenyldisulfane
882-33-7

diphenyldisulfane

1-ethoxymethyl-5-lithio-2-phenylthioimidazole
67319-06-6

1-ethoxymethyl-5-lithio-2-phenylthioimidazole

1-ethoxymethyl-2,5-bis(phenylthio)imidazole
86051-84-5

1-ethoxymethyl-2,5-bis(phenylthio)imidazole

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -70℃;100%
With n-butyllithium In tetrahydrofuran at -78℃;100%
diphenyldisulfane
882-33-7

diphenyldisulfane

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

1,2:3,4-di-O-isopropylidene-6-S-phenyl-6-thio-α-D-galactopyranoside
104495-07-0

1,2:3,4-di-O-isopropylidene-6-S-phenyl-6-thio-α-D-galactopyranoside

Conditions
ConditionsYield
With tributylphosphine In tetrahydrofuran at 62℃; under 10000 Torr; for 5h;100%
With tributylphosphine In pyridine at 20℃; for 24h;96%
With pyridine; tributylphosphine for 20h; Ambient temperature;95%
With tributylphosphine In pyridine for 12h; Ambient temperature;86%
diphenyldisulfane
882-33-7

diphenyldisulfane

(E)-5-[(2R,3R)-3-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-methyl-oxiranyl]-2-methyl-pent-2-en-1-ol
176043-45-1

(E)-5-[(2R,3R)-3-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-methyl-oxiranyl]-2-methyl-pent-2-en-1-ol

(2R,3R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((E)-4-methyl-5-phenylsulfanyl-pent-3-enyl)-oxirane
176043-46-2

(2R,3R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((E)-4-methyl-5-phenylsulfanyl-pent-3-enyl)-oxirane

Conditions
ConditionsYield
With tributylphosphine In dichloromethane for 0.5h; Ambient temperature;100%
diphenyldisulfane
882-33-7

diphenyldisulfane

(Z)-6-(1-Methylcyclohexa-2,5-dienyl)hex-5-en-1-ol
181576-34-1

(Z)-6-(1-Methylcyclohexa-2,5-dienyl)hex-5-en-1-ol

3-Methyl-3-[(Z)-6-(phenylsulfenyl)hex-1-enyl]cyclohexa-1,4-diene
252869-48-0

3-Methyl-3-[(Z)-6-(phenylsulfenyl)hex-1-enyl]cyclohexa-1,4-diene

Conditions
ConditionsYield
With pyridine; tributylphosphine100%
With tributylphosphine In pyridine at 20℃; for 7h; Substitution;100%
3-hydroxy-(2S)-methylpropionate
80657-57-4

3-hydroxy-(2S)-methylpropionate

diphenyldisulfane
882-33-7

diphenyldisulfane

(R)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester
165457-66-9

(R)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester

Conditions
ConditionsYield
With tributylphosphine In tetrahydrofuran at 20℃; for 24h;100%
With tributylphosphine In tetrahydrofuran for 24h; Ambient temperature;99%
With tributylphosphine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;85%
With tributylphosphine In N,N-dimethyl-formamide at 0 - 25℃; for 5h; Yield given;
diphenyldisulfane
882-33-7

diphenyldisulfane

(1S,2R,3R)-1-acetoxymethyl-2-hydroxymethyl-3-phenylcyclopropane
248256-35-1

(1S,2R,3R)-1-acetoxymethyl-2-hydroxymethyl-3-phenylcyclopropane

Acetic acid (1S,2S,3R)-2-phenyl-3-phenylsulfanylmethyl-cyclopropylmethyl ester
392656-02-9

Acetic acid (1S,2S,3R)-2-phenyl-3-phenylsulfanylmethyl-cyclopropylmethyl ester

Conditions
ConditionsYield
With tributylphosphine In pyridine at 20℃; for 1h;100%
With tributylphosphine In pyridine at 20℃; Substitution;
diphenyldisulfane
882-33-7

diphenyldisulfane

(+/-)-(2S,3R)-2,3-epoxy-1-(phenylthio)nonane

(+/-)-(2S,3R)-2,3-epoxy-1-(phenylthio)nonane

Conditions
ConditionsYield
With tributylphosphine In pyridine at 0℃;100%
diphenyldisulfane
882-33-7

diphenyldisulfane

(2S)-2-vinyl-3-phenyl-1-propanol
392655-66-2

(2S)-2-vinyl-3-phenyl-1-propanol

(3S)-3-phenylthiomethyl-4-phenyl-1-butene

(3S)-3-phenylthiomethyl-4-phenyl-1-butene

Conditions
ConditionsYield
With tributylphosphine In pyridine at 20℃; for 1h;100%
diphenyldisulfane
882-33-7

diphenyldisulfane

(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol

[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane
474248-58-3

[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Conditions
ConditionsYield
With tributylphosphine In pyridine at 20℃; for 24h;100%
cyclopentadecanone oxime
34341-05-4

cyclopentadecanone oxime

diphenyldisulfane
882-33-7

diphenyldisulfane

N-(phenylsulfenyl)cyclopentadecanimine

N-(phenylsulfenyl)cyclopentadecanimine

Conditions
ConditionsYield
With tributylphosphine In tetrahydrofuran at 20℃;100%

882-33-7Relevant articles and documents

Cycloaddition Reactions of Highly Stabilized Isoquinolinium Methylides to Nonactivated Olefins and Electron-Rich Olefins

Tsuge, Otohiko,Kanemasa, Shuji,Sakamoto, Kazushige,Takenaka, Shigeori

, p. 2513 - 2524 (1988)

Highly stabilized isoquinolinium methylides bearing two electron-withdrawing substituents at the ylide carbon undergo cycloadditions with aryl-substituted olefins (acenaphthylene,(E)- and (Z)-stilbenes, indene, and stirene), alkyl-substituted olefins (norbornene, (Z)-3-hexene-1,6-dinitrile, 1-hexene, 2-propen-1-ol, and 3-(trimethylsilyloxy)propene), and electron-rich olefins (vinylene carbonate, butyl vinyl ether, and phenyl vinyl sulfide).These cycloadditions proceed in an exclusively regioselective and mostly stereoselective manner.

Structure-activity relationships of phenyl- and benzoylpyrroles

Laatsch,Renneberg,Hanefeld,Kellner,Pudleiner,Hamprecht,Kraemer,Anke

, p. 537 - 546 (1995)

Antitumor, antimicrobial, and phytotoxic activities of the marine antibiotic pentabromopseudilin (la) and related phenyl-, benzyl- and benzoyl pyrroles were compared. All activities depended strongly on the substituent pattern, with the natural compound 1a being the most active one. As judged from model reactions, a covalent bond of nucleophiles to the pyrrole system may be involved in the inhibition of macromolecular syntheses.

-

Takebayashi et al.

, p. 376,377, 378 (1966)

-

Metal- and solvent-free, iodine-catalyzed cyclocondensation and C[sbnd]H bond sulphenylation: A facile access to C-4 sulfenylated pyrazoles via a domino multicomponent reaction

Sun, Pengfei,Yang, Daoshan,Wei, Wei,Sun, Xuejun,Zhang, Wenhui,Zhang, Hui,Wang, Yu,Wang, Hua

, p. 2022 - 2029 (2017)

We describe herein a green and efficient MCRs protocol to synthesize C-4 sulfenylated pyrazoles by iodine-catalyzed cyclocondensation and direct C[sbnd]H bond sulphenylation reactions. Through this protocol, two new C[sbnd]N bonds and one C[sbnd]S bond ar

Schumann, H.,Albrecht, I.,Gallagher, M.,Hahn, E.,Janiak, C.,et al.

, p. 2307 - 2316 (1988)

Stereoselective access to trisubstituted fluorinated alkenyl thioethers

Fabre, Indira,Poisson, Thomas,Pannecoucke, Xavier,Gillaizeau, Isabelle,Ciofini, Ilaria,Grimaud, Laurence

, p. 1921 - 1927 (2017)

We report the first copper-catalyzed olefinic ethoxy carbonyl difluoromethylation of alkenyl thioethers via direct C-H bond functionalization using BrCF2COOEt. The developed methodology allows the preparation of trisubstituted olefins with a controlled stereochemistry. A mechanistic study is reported and a radical mechanism is revealed.

Mixed-chalcogenide diplatinum complexes; an investigation of ligand exchange processes using ESI mass spectrometry

Fortney-Zirker, Ryland G.,Henderson, William,Tiekink, Edward R.T.

, p. 83 - 96 (2017)

Routes to mixed-chalcogen diplatinum complexes have been explored using Electrospray Ionisation Mass Spectrometry (ESI-MS) as a powerful technique to probe reaction solutions on the microscale. Exchange reactions of binuclear platinum(II) complexes [Ptsu

The phenyl thiyl radical as initiator in vinyl polymerizations. Investigations into the initiation step by the aminoxyl trapping technique

Busfield, W. Ken,Heiland, Kirstin,Jenkins, Ian D.

, p. 1109 - 1112 (1995)

The reactions of phenyl thiyl radicals with styrene, methyl methacrylate, methacrylonitrile, and vinylacetate in the presence of an aminoxyl radical scavenger have been studied. Two main products were formed: diphenyl disulfide, and the expected product formed by addition of the thiyl radical to the double bond of the monomer followed by trapping by the aminoxyl radical. The relative reactivity of the monomers towards addition of phenyl thiyl radicals at 60°C was: VA:MAN:MMA:STY = 1:50:100:500.

Chemical Evolution: A Model System That Selects and Amplifies a Receptor for the Tripeptide (D)Pro(L)Val(D)Val

Hioki, Hideaki,Clark Still

, p. 904 - 905 (1998)

-

-

Baig,Owen

, p. 1400 (1967)

-

The enzymic oxidation of thiols.

Bocks

, p. 9C-11C (1966)

-

Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias

supporting information, p. 20543 - 20550 (2021/08/12)

Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.

Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst

Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming

supporting information, p. 6059 - 6064 (2021/08/23)

Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.

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