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4,4'-Dinitrodiphenyl disulfide is an organic compound that serves as a versatile reagent in various chemical reactions. It is characterized by its yellow or tan powder appearance and is known for its ability to participate in a range of electrophilic reactions.

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  • 100-32-3 Structure
  • Basic information

    1. Product Name: 4,4'-Dinitrodiphenyl disulfide
    2. Synonyms: P-NITROPHENYLDISULFIDE;P,P'-DINITRODIPHENYL DISULFIDE;4,4'-DINITRO DIPHENYL DISULFIDE;4-NITROPHENYL DISULFIDE;4-NITROPHENYL SULFIDE;BIS(P-NITROPHENYL) DISULFIDE;BIS(4-NITROPHENYL) DISULFIDE;DI(4-NITROPHENYL) DISULFIDE
    3. CAS NO:100-32-3
    4. Molecular Formula: C12H8N2O4S2
    5. Molecular Weight: 308.33
    6. EINECS: 202-840-5
    7. Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
    8. Mol File: 100-32-3.mol
  • Chemical Properties

    1. Melting Point: 181.0 to 186.0 °C
    2. Boiling Point: 478.783 °C at 760 mmHg
    3. Flash Point: 243.359 °C
    4. Appearance: yellow or tan powder
    5. Density: 1.5285 (rough estimate)
    6. Refractive Index: 1.6510 (estimate)
    7. Storage Temp.: Sealed in dry,Room Temperature
    8. Solubility: N/A
    9. Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
    10. CAS DataBase Reference: 4,4'-Dinitrodiphenyl disulfide(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4,4'-Dinitrodiphenyl disulfide(100-32-3)
    12. EPA Substance Registry System: 4,4'-Dinitrodiphenyl disulfide(100-32-3)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 20/21/22-40
    3. Safety Statements: 36
    4. WGK Germany: 3
    5. RTECS: JO1550000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 100-32-3(Hazardous Substances Data)

100-32-3 Usage

Uses

Used in Organic Synthesis:
4,4'-Dinitrodiphenyl disulfide is used as a reactant or reagent in several chemical processes for the synthesis of various organic compounds. Its applications include:
1. Electrophilic cyclization of 2-alkynylanisoles or alkynylanilines, where it aids in the formation of cyclic compounds with the help of its electrophilic properties.
2. Oxidative chlorination to sulfonyl chlorides, where it acts as a reagent to facilitate the conversion of substrates into sulfonyl chlorides through an oxidation process.
3. Arylation with triarylbismuthanes, in which it serves as a reagent to introduce aryl groups into the target molecule, enhancing its structural complexity and functionality.
4. Decarboxylative cross-coupling with dialkoxybenzoic acids, where it acts as a reactant to promote the formation of new carbon-carbon bonds, leading to the synthesis of complex organic molecules.
5. Disulfidation of alkenes, where it is used as a reagent to convert alkenes into their corresponding disulfide derivatives, which are important intermediates in the synthesis of various organic compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 100-32-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100-32:
(5*1)+(4*0)+(3*0)+(2*3)+(1*2)=13
13 % 10 = 3
So 100-32-3 is a valid CAS Registry Number.

100-32-3 Well-known Company Product Price

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  • Aldrich

  • (N21022)  4-Nitrophenyldisulfide  

  • 100-32-3

  • N21022-25G

  • 609.57CNY

  • Detail

100-32-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4'-Dinitrodiphenyl disulfide

1.2 Other means of identification

Product number -
Other names Bis(4-nitrophenyl) Disulfide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:100-32-3 SDS

100-32-3Synthetic route

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With air In dimethyl sulfoxide at 80℃;100%
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 0.0166667h;100%
CoCl2 In acetonitrile Ambient temperature;99%
(4-nitro-phenyl)-m-tolyl sulfone
77853-01-1

(4-nitro-phenyl)-m-tolyl sulfone

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

Toluene-3-thiosulfonic acid; compound with ammonia
77853-09-9

Toluene-3-thiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 43%
B 100%
C 40%
1-methoxy-4-((4-nitrophenyl)sulfonyl)benzene
22865-57-2

1-methoxy-4-((4-nitrophenyl)sulfonyl)benzene

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

4-Methoxy-benzenethiosulfonic acid; compound with ammonia
77853-03-3

4-Methoxy-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 56%
B 100%
C 32%
With sulfur; ammonia at 100℃; for 2h; Product distribution; titanium autoclave; various reactions temp. and amounts of S8;
para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With 1,10-Phenanthroline; potassium sulfide; iron oxide; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 0.5h; Inert atmosphere; Green chemistry;98%
With dmap; nickel(II) chloride hexahydrate; potassium thioacyanate; N,N-dimethyl-formamide at 140℃; for 15h;92%
With copper(l) iodide; hexachloroethane; sodium carbonate; thiourea In water at 120℃; for 13h;87%
4-nitrophenyl sulfone
1156-50-9

4-nitrophenyl sulfone

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

bis(4-nitrophenyl)sulfide
1223-31-0

bis(4-nitrophenyl)sulfide

C

4-Nitro-benzenethiosulfonic acid; compound with ammonia
74236-92-3

4-Nitro-benzenethiosulfonic acid; compound with ammonia

Conditions
ConditionsYield
With sulfur; ammonia at 40℃; for 2h; titanium autoclave;A 38%
B n/a
C 98%
4-nitrophenylthiolate
45797-13-5

4-nitrophenylthiolate

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With 2-bromo-2-nitro-1,3-propanediol In methanol for 48h; Irradiation;98%
With 2-bromo-2-nitro-1,3-propanediol In methanol Mechanism; Product distribution; Irradiation; other reagent and solvent;98%
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With 1,10-Phenanthroline; potassium sulfide; iron oxide; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 0.5h; Inert atmosphere; Green chemistry;97%
With sodium sulfide pentahydrate In N,N-dimethyl-formamide at 40 - 100℃; for 6h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;92.8%
With sodium disulfide In 1-methyl-pyrrolidin-2-one69%
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With ziconium(IV) oxychloride octahydrate; sodium iodide In water at 90℃; for 0.25h;95%
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 20h; chemoselective reaction;91%
With triphenylphosphine In tetrahydrofuran at 0℃;75%
C18H18N4O8S2
111680-13-8

C18H18N4O8S2

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)
58477-00-2

diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)

Conditions
ConditionsYield
With triphenylphosphine In benzene at 20℃; for 1h;A 95%
B n/a
C18H18N4O8S2
111680-13-8

C18H18N4O8S2

triphenylphosphine
603-35-0

triphenylphosphine

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)
58477-00-2

diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)

Conditions
ConditionsYield
In benzene at 20℃; for 1h;A 95%
B n/a
C14H13NO5S
77863-74-2

C14H13NO5S

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

3-Ethoxy-benzenethiosulfonic acid; compound with ammonia
77853-06-6

3-Ethoxy-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 47%
B 94%
C 40%
(p-Tol)3Bi=C(CO2Me){C(CO2Me)=NSO2Ph}

(p-Tol)3Bi=C(CO2Me){C(CO2Me)=NSO2Ph}

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

A

dimethyl 2-(N-(phenylsulfonyl))aminofumarate

dimethyl 2-(N-(phenylsulfonyl))aminofumarate

B

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

C

tri(p-tolyl)bismuth
5142-75-6

tri(p-tolyl)bismuth

Conditions
ConditionsYield
In dichloromethane Bi compd. added to CH2Cl2 soln. of 4-nitrobenzenethiol (molar ratio 1:2) at -78°C; warmed to room temp. with stirring; concd. under reduced pressure; recrystd. from CH2Cl2-hexane;A 92%
B 92%
C 94%
4-nitrophenylhydrazine hydrochloride
636-99-7

4-nitrophenylhydrazine hydrochloride

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With sulfur; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; N,N-dimethyl-formamide at 100℃; under 3750.38 Torr; for 18h; Sealed tube; Schlenk technique;94%
1,3-Dichloro-5-(4-nitro-benzenesulfonyl)-benzene
77853-02-2

1,3-Dichloro-5-(4-nitro-benzenesulfonyl)-benzene

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

3,5-Dichloro-benzenethiosulfonic acid; compound with ammonia
77853-10-2

3,5-Dichloro-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 42%
B 93%
C 40%
p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl chloride
5184-32-7

p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl chloride

triphenylphosphine
603-35-0

triphenylphosphine

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

C

N-p-tolylsulfonylphosphine imide
1058-14-6

N-p-tolylsulfonylphosphine imide

Conditions
ConditionsYield
Stage #1: p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl chloride; triphenylphosphine In benzene at 20℃; for 0.5h;
Stage #2: With water In benzene for 5h; Further stages.;
A 86%
B 93%
C 82%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With dmap; nickel(II) chloride hexahydrate; potassium thioacyanate; N,N-dimethyl-formamide at 140℃; for 15h;92%
With copper(l) iodide; hexachloroethane; sodium carbonate; thiourea In water at 120℃; for 11h;91%
With 1,10-Phenanthroline; copper(II) choride dihydrate; tetrabutyl ammonium fluoride; caesium carbonate; sulfur In water at 100℃; for 24h; Sealed tube;86%
4-nitrobenzenesulfenyl chloride
937-32-6

4-nitrobenzenesulfenyl chloride

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With triphenylphosphine In acetonitrile for 2h; Ambient temperature;90%
With triethylamine In acetonitrile Ambient temperature; overnight;75%
With cyclooctatetraene dianion bipotassium salt In tetrahydrofuran at -40℃; for 0.5h; Product distribution;
With cyclooctatetraene dianion bipotassium salt In tetrahydrofuran at -40℃; for 0.5h; Yield given;
Multi-step reaction with 2 steps
1: 70 percent / diethyl ether / 1 h / -50 - 20 °C
2: 85 percent / SeCl4 / 1,2-dimethoxy-ethane / 2 h / 0 °C
View Scheme
1-methoxy-3-(4-nitrobenzenesulfonyl)benzene
77863-75-3

1-methoxy-3-(4-nitrobenzenesulfonyl)benzene

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

3-Methoxy-benzenethiosulfonic acid; compound with ammonia
77853-08-8

3-Methoxy-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 55%
B 90%
C 33%
N-(benzenesulfonyl)-3-phenyloxaziridine
113548-13-3

N-(benzenesulfonyl)-3-phenyloxaziridine

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

N-benzylidenephenylsulfonamide
13909-34-7

N-benzylidenephenylsulfonamide

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
for 4.5h; Product distribution;A 90%
B 75%
C 30%
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

4,4'-dimethoxyphenyl disulfide
5335-87-5

4,4'-dimethoxyphenyl disulfide

C

1-(4-methoxyphenyl)-2-(4-nitrophenyl)disulfane
20168-74-5

1-(4-methoxyphenyl)-2-(4-nitrophenyl)disulfane

Conditions
ConditionsYield
Stage #1: 4-Methoxybenzenethiol; para-nitrobenzenethiol With dmap; water In ethanol at 20℃; for 0.0833333h;
Stage #2: With iodine In ethanol at 70℃; for 3h; Sealed tube;
A 2%
B 5%
C 90%
tris(4-nitrophenyl) trithioarsenite

tris(4-nitrophenyl) trithioarsenite

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With iodine In dichloromethane86%
p-nitro-N,N-bis(trimethylsilyl)benzenesulfenamide
135577-95-6

p-nitro-N,N-bis(trimethylsilyl)benzenesulfenamide

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

Se, N2

Se, N2

Conditions
ConditionsYield
With selenium tetrachloride In 1,2-dimethoxyethane at 0℃; for 2h;A 85%
B n/a
4-nitrobenzenesulfenyl chloride
937-32-6

4-nitrobenzenesulfenyl chloride

A

1-methylthio-4-nitro-benzene
701-57-5

1-methylthio-4-nitro-benzene

B

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

Conditions
ConditionsYield
With tetramethylstannane; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃; for 4h;A n/a
B 84%
thiophenol
108-98-5

thiophenol

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

4-nitrophenyl phenyl disulfide
20168-72-3

4-nitrophenyl phenyl disulfide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
Stage #1: thiophenol; para-nitrobenzenethiol With dmap; water In ethanol at 20℃; for 0.0833333h;
Stage #2: With iodine In ethanol at 70℃; for 3h; Sealed tube;
A 2%
B 80%
C 2%
(4-nitro-phenyl)-o-tolyl sulfone
42085-91-6

(4-nitro-phenyl)-o-tolyl sulfone

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

Toluene-2-thiosulfonic acid; compound with ammonia
77853-12-4

Toluene-2-thiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 1h; titanium autoclave;A 32%
B 79%
C 18%
p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl fluoride

p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl fluoride

triphenylphosphine
603-35-0

triphenylphosphine

A

C20H18N3O6S3(1-)*C24H19NO2PS(1+)

C20H18N3O6S3(1-)*C24H19NO2PS(1+)

B

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

C

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

D

N-p-tolylsulfonylphosphine imide
1058-14-6

N-p-tolylsulfonylphosphine imide

Conditions
ConditionsYield
In benzene at 20℃; for 4h;A 91.5 % Spectr.
B 79%
C 66%
D 4%
p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

A

4,4'-dichlorodiphenyl disulfide
1142-19-4

4,4'-dichlorodiphenyl disulfide

B

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

C

1-(4-chlorophenyl)-2-(4-nitrophenyl)disulfane
20168-75-6

1-(4-chlorophenyl)-2-(4-nitrophenyl)disulfane

Conditions
ConditionsYield
Stage #1: p-Chlorothiophenol; para-nitrobenzenethiol With dmap; water In ethanol at 20℃; for 0.0833333h;
Stage #2: With iodine In ethanol at 70℃; for 3h; Sealed tube;
A 5%
B 2%
C 79%
para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

benzyl alcohol
100-51-6

benzyl alcohol

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

1-(benzylsulphanyl)-4-Nitrobenzene
27691-43-6

1-(benzylsulphanyl)-4-Nitrobenzene

Conditions
ConditionsYield
at 180℃; Catalytic behavior; Inert atmosphere; Autoclave;A 17%
B 78%
3-methoxybenzenethiol
15570-12-4

3-methoxybenzenethiol

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

bis(3-methoxyphenyl)disulfide
59014-89-0

bis(3-methoxyphenyl)disulfide

C

1-(3-methoxyphenyl)-2-(4-nitrophenyl)disulfane

1-(3-methoxyphenyl)-2-(4-nitrophenyl)disulfane

Conditions
ConditionsYield
Stage #1: 3-methoxybenzenethiol; para-nitrobenzenethiol With dmap; water In ethanol at 20℃; for 0.0833333h;
Stage #2: With iodine In ethanol at 70℃; for 3h; Sealed tube;
A 2%
B 5%
C 78%
para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

1-dodecylthiol
112-55-0

1-dodecylthiol

A

didodecyl disulfide
2757-37-1

didodecyl disulfide

B

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

C

1-dodecyl-2-(4-nitrophenyl)disulfane

1-dodecyl-2-(4-nitrophenyl)disulfane

Conditions
ConditionsYield
Stage #1: para-nitrobenzenethiol; 1-dodecylthiol With dmap; water In ethanol at 20℃; for 0.0833333h;
Stage #2: With iodine In ethanol at 70℃; for 3h; Sealed tube;
A 5%
B 11%
C 78%
tris(3,4,5-trifluorophenyl)boroxine
223440-94-6

tris(3,4,5-trifluorophenyl)boroxine

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

(3,4,5-trifluorophenyl)-4-nitrophenylsulfide
1229514-26-4

(3,4,5-trifluorophenyl)-4-nitrophenylsulfide

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; oxygen In water; dimethyl sulfoxide at 90℃; under 757.576 Torr; for 6.5h;99%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

Conditions
ConditionsYield
With magnesium In methanol for 0.166667h; Ambient temperature;98%
With sodium tetrahydroborate In tetrahydrofuran; methanol at 50℃; for 1h;89%
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 0 - 35℃;85%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

4-nitrophenylsulphur trifluoride
1526-28-9

4-nitrophenylsulphur trifluoride

Conditions
ConditionsYield
With potassium fluoride; chlorine In acetonitrile at 20℃; for 4.5h;98%
With silver(II) fluoride In 1,1,2-Trichloro-1,2,2-trifluoroethane Heating;
With bis(fluoroxy)methane In acetonitrile at -20℃;
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

2-methyl-3-((4-nitrophenyl)thio)-1H-indole
1210054-39-9

2-methyl-3-((4-nitrophenyl)thio)-1H-indole

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2h; regioselective reaction;98%
With iron(III) trifluoride; iodine In acetonitrile at 80℃; for 36h; regioselective reaction;94%
With sodium tetrafluoroborate; potassium iodide In acetonitrile at 60℃; for 6h; Electrolysis;82%
With silver nitrate In ethanol; N,N-dimethyl-formamide at 70℃; for 8h; Sealed tube;63%
7,8-benzoquinoline
230-27-3

7,8-benzoquinoline

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

10-(4-nitrophenylsulfanyl)benzo[h]quinoline

10-(4-nitrophenylsulfanyl)benzo[h]quinoline

Conditions
ConditionsYield
With palladium diacetate; copper(ll) bromide In N,N-dimethyl-formamide at 140℃; for 24h; Sealed tube;98%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

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

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

5-nitro-3-((4-nitrophenyl)thio)-N-(2-(pyridin-2-yl)propan-2-yl)thiophene-2-carboxamide

5-nitro-3-((4-nitrophenyl)thio)-N-(2-(pyridin-2-yl)propan-2-yl)thiophene-2-carboxamide

Conditions
ConditionsYield
With copper diacetate; sodium carbonate In 1,4-dioxane at 130℃; for 12h;98%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

2-methyl-N-(perfluorophenyl)benzamide

2-methyl-N-(perfluorophenyl)benzamide

2-methyl-6-((4-nitrophenyl)thio)-N-(perfluorophenyl)benzamide

2-methyl-6-((4-nitrophenyl)thio)-N-(perfluorophenyl)benzamide

Conditions
ConditionsYield
With Boc-DL-Leu-OH; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide In dichloromethane at 90℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;98%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

methyl iodide
74-88-4

methyl iodide

1-methylthio-4-nitro-benzene
701-57-5

1-methylthio-4-nitro-benzene

Conditions
ConditionsYield
With water; rongalite; potassium carbonate In N,N-dimethyl-formamide for 0.166667h;97%
With disodium hydrogenphosphate; sodium dithionite In water; N,N-dimethyl-formamide at 20℃; for 0.2h;82%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

phenylboronic acid
98-80-6

phenylboronic acid

4-nitrophenyl phenyl sulfide
952-97-6

4-nitrophenyl phenyl sulfide

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper(l) iodide In water; dimethyl sulfoxide at 100℃; for 12h;97%
With [2,2]bipyridinyl; copper(l) iodide; air In dimethyl sulfoxide at 100℃; for 12h;97%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

tris(3-fluoro phenyl)boroxine
448-53-3

tris(3-fluoro phenyl)boroxine

(3-fluorophenyl)-4-nitrophenylsulfide
2249-00-5

(3-fluorophenyl)-4-nitrophenylsulfide

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; oxygen In water; dimethyl sulfoxide at 90℃; under 757.576 Torr; for 7h;97%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

4-nitrobenzenesulfenyl chloride
937-32-6

4-nitrobenzenesulfenyl chloride

Conditions
ConditionsYield
With chlorine In tetrachloromethane at 60℃; for 3h;96%
With chloroform; chlorine unter Ausschluss der Luftfeuchtigkeit;
With chlorine
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

p-nitrobenzenesulfonic acid
138-42-1

p-nitrobenzenesulfonic acid

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; acetonitrile at 20℃; for 1h;96%
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1.08333h; Micellar solution;93%
With nitric acid
With nitric acid
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

Conditions
ConditionsYield
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h;96%
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h;96%
With trichloroisocyanuric acid; tetrabutylammomium bromide; water In acetonitrile at 0 - 20℃; for 0.333333h;96%
N-chloroacetamide
598-49-2

N-chloroacetamide

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

N,N'-diacetyl-p-nitrobenzenesulfinamidine
88951-70-6

N,N'-diacetyl-p-nitrobenzenesulfinamidine

Conditions
ConditionsYield
With pyridine In benzene96%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

benzyl bromide
100-39-0

benzyl bromide

1-(benzylsulphanyl)-4-Nitrobenzene
27691-43-6

1-(benzylsulphanyl)-4-Nitrobenzene

Conditions
ConditionsYield
With water; rongalite; potassium carbonate In N,N-dimethyl-formamide for 0.25h;96%
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonium chloride In tetrahydrofuran; water for 0.2h; Heating;92%
With disodium hydrogenphosphate; sodium dithionite In water; N,N-dimethyl-formamide at 20℃; for 0.25h;73%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

1-dodecylbromide
143-15-7

1-dodecylbromide

p-nitrophenyl n-dodecyl thioether
73520-87-3

p-nitrophenyl n-dodecyl thioether

Conditions
ConditionsYield
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonium chloride In tetrahydrofuran; water for 3.3h; Heating;96%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

1-nitro-4-[(2-phenylethyl)sulfanyl]benzene
60091-82-9

1-nitro-4-[(2-phenylethyl)sulfanyl]benzene

Conditions
ConditionsYield
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonium chloride In tetrahydrofuran; water for 2.1h; Heating;96%
1-iodo-butane
542-69-8

1-iodo-butane

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

butyl(4-nitrophenyl)sulfane
27826-43-3

butyl(4-nitrophenyl)sulfane

Conditions
ConditionsYield
With water; rongalite; potassium carbonate In N,N-dimethyl-formamide for 0.25h;96%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

1-nitro-4-(4-nitrophenylmethylthio)benzene
42497-87-0

1-nitro-4-(4-nitrophenylmethylthio)benzene

Conditions
ConditionsYield
With water; rongalite; potassium carbonate In N,N-dimethyl-formamide for 0.166667h;96%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

2-phenylethynylaniline
13141-38-3

2-phenylethynylaniline

3-((4-nitrophenyl)thio)-2-phenyl-1H-indole
1213786-18-5

3-((4-nitrophenyl)thio)-2-phenyl-1H-indole

Conditions
ConditionsYield
With air; palladium dichloride In dimethyl sulfoxide at 80℃; for 24h;96%
With iodine In toluene at 110℃; for 8h; Schlenk technique;93%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

acetic anhydride
108-24-7

acetic anhydride

1-acetylsulfanyl-4-nitro-benzene
15119-62-7

1-acetylsulfanyl-4-nitro-benzene

Conditions
ConditionsYield
With rongalite; cesium fluoride In water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;96%
indole
120-72-9

indole

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

3-[(4-nitrophenyl)sulfanyl]-1H-indole
72496-80-1

3-[(4-nitrophenyl)sulfanyl]-1H-indole

Conditions
ConditionsYield
With iron(III) trifluoride; iodine In acetonitrile at 80℃; for 36h; regioselective reaction;96%
With iodine; dimethyl sulfoxide In carbonic acid dimethyl ester at 40℃; for 10h;92%
Stage #1: di(p-nitrophenyl) disulfide With tetrabutylammomium bromide; triethylamine In dichloromethane for 1h; Cooling with ice; Green chemistry;
Stage #2: indole In dichloromethane at 70℃; for 3.5h; Green chemistry;
85%
di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

S-(4-nitrophenyl) 4-methylbenzothioate
39248-99-2

S-(4-nitrophenyl) 4-methylbenzothioate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium carbonate In water at 100℃; for 2h;96%

100-32-3Relevant articles and documents

Oxidation of thiols using K2S2O8 in ionic liquid

Hajipour, Abdol R.,Mostafavi, Majid,Ruoho, Arnold E.

, p. 1920 - 1923 (2009)

A green, straightforward, and novel method for oxidation of thiols to the corresponding disulfides is reported using K2S2O8 in the ionic liquid 1-butyl-3-methylimidazolium bromide [(bmim)Br] at 65-70C. The corresponding disulfides were obtained in excellent yield and short reaction time.

REDUCTION OF HALONITROBENZENES TO HALOANILINES BY HYDROGEN SULFIDE

Rybakova, I. A.,Shekhtman, R. I.,Prilezhaeva, E. N.,Litvinov, V. P.,Shakhovskoi, G. P.

, p. 1901 - 1903 (1991)

A selective method has been developed for the preparation of haloanilines by the reduction of the corresponding halonitrobenzenes using hydrogen sulfide in the presence of tetraalkylammonium hydroxide.

Selective synthesis of organic sulfides or disulfides by solvent exchange from aryl halides and KSCN catalyzed by NiCl2·6H2O

Abbasi, Mohammad,Nowrouzi, Najmeh,Latifi, Hadis

, p. 112 - 117 (2016)

A method for selective synthesis of symmetric sulfides or disulfides from the reaction of aryl halides with KSCN by solvent exchange is introduced. Aryl halides were selectively converted to the symmetric disulfides or sulfides in high yields when they are treated with KSCN in the presence of NiCl2·6H2O and DMAP at 140?°C in DMF or poly ethylene glycol (PEG-200) respectively.

Facile solvent-free oxidation of thiols mediated by mineral supports

Sainte-Marie, Laurent,Guibe-Jampel, Eryka,Therisod, Michel

, p. 9661 - 9662 (1998)

Oxidation of thiols dispersed without solvent on a weakly basic mineral support was easily performed by heating in air.

On the reaction of triaryl trithioarsenites, (ArS)3As, with iodine

Markaki, Maria D.,Ioannou, Panayiotis V.

, p. 921 - 929 (2006)

Iodine in dry nonprotic solvents oxidizes triaryl trithioarsenites, (ArS)3 As, to As(III) iodide, AsI3, and disulfides, ArSSAr. The reaction most likely involves arylsulfenyl iodide, ArSI, as an intermediate. With triphenyl and tris(

Alumina: An Efficient and Reusable Catalyst for the Oxidative Coupling of Thiols with DMSO

Hirano, Masao,Yakabe, Sigetaka,Monobe, Hiroyuki,Morimoto, Takashi

, p. 472 - 473 (1998)

An inexpensive combination of common laboratory reagents, dimethyl sulfoxide (DMSO) and Chromatographic neutral alumina, gives an efficient, selective, and high-yielding oxidation of aromatic, aliphatic and alicyclic thiols to the corresponding disulfides in excellent yields under relatively mild conditions.

Ligand-free copper-catalysed direct synthesis of diaryl sulfides and diaryl disulfides in wet poly(ethylene glycol)

Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis

, (2017)

An improved protocol has been developed for the one-pot CuI-catalysed preparation of symmetric diaryl sulfides from their available aryl halides in the presence of thiourea as sulfur transfer agent and in the absence of both ligand and organic solvent. This catalytic system was also used for the high-yielding preparation of diaryl disulfides in the presence of C2Cl6 as oxidant.

A facile, high-yielding method for the conversion of halides to mercaptans

Bieniarz,Cornwell

, p. 939 - 942 (1993)

An efficient, high-yield, one-pot preparation of alkyl and activated aryl mercaptans is presented. The method relies on sodium thiophosphate displacement of the halide, followed by mild hydrolysis of the intermediate phosphorothioate.

Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds

Al-Khalil,Bowman,Gaitonde,Marley,Richardson

, p. 1557 - 1565 (2001)

α-Nitrothiocyanates R2C(SCN)NO2 have been prepared by oxidative addition of thiocyanate anion to nitronate anions and undergo SRN1 substitution reactions by loss of thiocyanate with nitronate anions, phenylsulfinate, azide and p-nitro- and p-chloro-benzenethiolates in dipolar aprotic solvents. 2-Nitro-2-thiocyanatopropane and other 2-substituted-2-nitropropanes [Me2C(X)NO2 with X = I, Br, Cl, NO2, PhSO2] react with thiolates by SRN1 reactions and/or redox reactions to give disulfides by a polar abstraction or chain SET (SET2) mechanisms. The products are dependent on the nucleophilicity of the thiolates, the polarisability of the α-substituent, the solvent and the presence of light catalysis, radical traps or strong electron acceptors. 2-Substituted-2-nitropropanes [Me2C(X)NO2 with X = N3, NO2, CN, p-NO2-C6H4-N=N] undergo SRN1 substitutions with thiolates by loss of nitrite. 2-Substituted-2-nitropropanes Me2C(X)NO2 and thiolates only yield disulfides in methanol due to solvation of the nitro groups.

Synthesis and 13C NMR spectra of N-substituted para-quinone imines: II. N-arylthio- and N-arylsulfonyl-l,4-benzoquinone imines with enhanced electron-withdrawing character of the quinoid ring

Pirozhenko,Avdeenko,Yusina,Konovalova

, p. 1142 - 1148 (2002)

Introduction of chlorine substituents into quinone imine fragment results in virtually the same variations in the chemical shifts of the quinoid ring carbons both in N-arylthio and N-arylsulfonyl-1,4-benzoquinone imines as compared to the unsubstituted analogs. In both classes of chloro-substituted compounds the effect of substituents in the benzene ring on the character and the range of chemical shifts variations for the carbon signals from the quinoid ring also turned out to be identical. Any differences observed may be due to the change in the geometry of the molecules, in particular, to the increase in the bond angle C=N-S.

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