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Amadis Chemical offer CAS#624-92-0;CAT#A833808
Cas No: 624-92-0
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Dimethyl disulfide
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Methyl disulfide 624-92-0
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Dimethyl Disulfide
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Methyl disulfide
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624-92-0 Usage

Fire extinguishing agent

Dry powder, dry sand, carbon dioxide fire extinguishing agent, foam, 1211 fire extinguishing agent.

Chemical Properties

Light yellow transparent liquid, malodorous, insoluble in water, Soluble in ethanol, ethyl ether and acetic acid.

storage

Store in a cool, well-ventilated warehouse, separated with oxidant, acid.

Production method

Dimethyl disulfide can be prepared by the reaction between imethyl sulfate and sodium sulfide. under stirring, sulfur powder  was added into sodium sulfide solution. The above reaction system was heated  Up to 80-90℃, after reaction for 1 h, cooled to about 30 ℃. Dimethyl sulfate was dropped into the reaction system and the reaction was continued for 2h. Then, distillation, stratification, Separating waste alkali liquor, then through distillation and final products are prepared.
In industry,dimethyl sulfate method is adopted to synthesize dimethyl disulfide. Na2S+S→Na2S2Na2S2+(CH3)2SO4→CH3SSCH3+Na2SO4
Solid sodium sulfide and water are dropped into the reaction kettle , heated , temperature is controlled in the range of  the of 50 ~60 ℃, dissolving sodium sulfide, adding equimolar sulfur, remaining the temperature for 1h, cooling to 45℃, dripping dimethyl sulfate into the reaction kettle, remaining the temperature for 1h, then through distillation dimethyl sulfate can be prepared.
It also can be prepared by the reaction between Magnesium methyl iodide and disulfur dichloride.
It can be prepared by the reaction between sodium disulfide and Methyl sodium sulfate.
It can be prepared by heating Methyl sodium thiosulfate which is the reaction product of methyl bromide and sodium thiosulfate.

Quantity restrictions

FEMA(mg/kg):
bakery product 16.9;Frozen dairy products 4.8;Meat products 2.2;soft sweets 9.4;Jelly and pudding 8.3;

Usage

In China:
  • Methyl disulfide is used as a solvent and pesticide intermediates, fuel and lubricating oil additives and Coking inhibitor for ethylene cracking furnace and oil refining equipment etc. It is the principal raw material for methylsufonyl chloride and methanesulfonic acid products. It is used in the synthesis of 4-Methylthio-M-Cresol which is the intermediate of Fenthion and fenamithion. It is  also  used in the synthesis of  p-Methyl Thiophenol which is the intermediate of sulprofos. It is also used as a purifying agent for solvents and  catalysts. It is allowed to be used as a Food Flavoring by GB 2760—1996. Dimethyl disulfide reacted with methylphenol to prouduce 2-methyl-4-hydroxy thioanisole , which condensed  with O, O-Dimethyl sulfide phosphorus oxychloride to produce Fenthion. Fenthion is a highly efficient organophosphorus pesticide with low toxicity and it has a good control effect on rice borers, soybean budworm and gadfly larvae. It Also can be used as a veterinary medicine to exterminate Gadfly maggots and cattle ticks.
International uses:
  • DMDS is used as a food additive in onion, garlic, cheese, meats, soups, savory flavors, and fruit flavors.
  • In agricural application, prior to planting, DMDS can be either injected beneath the soil surface with specialized
  • application equipment or applied to the soil surface through a drip irrigation line. Regardless of
  • the application method, the treated area must be covered with a plastic tarp to retain the
  • fumigant in the soil to improve efficacy and mitigate odor concerns.
  • DMDS can also be used for oil refining and petrochemical industries.
  • Petrochemical plants use DMDS dimethyl disulfide) for hydrocracking catalysts sulfiding in refineries.
  • DMDS (dimethyl disulfide) is the most common compound used for hydrocracking catalysts sulfiding in refineries.
  • DMDS (dimethyl disulfide) in petrochemical is injected continously at low rate in ethylene crackers. It prevents coke formation and mitigates CO formation.
  • DMDS is used in the preparation of 4-(methylthio)phenol which is used in the production of various pesticides. DMDS and chlorine are reacted with borontriflouride phenolate to produce 4-(methylthio)phenol. Thiophene and DMDS are blended with combustible hydrocarbon fuel gas to impart a gassy odor to the fuel gas. DMDS is used as a sulfiding reagent to control catalyst activity.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Purification Methods

Pass it through neutral alumina before use. [Trost Chem Rev 78 363 1978, Beilstein 1 IV 1281.]

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Chemical Properties

colourless to yellow liquid with a very unpleasant smell

General Description

A colorless oily liquid with a garlic-like odor. Denser than water and slightly soluble in water. Flash point 40°F. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

Reactivity Profile

DMDS is a reducing agent. A dangerous fire hazard when exposed to oxidizing materials. Emits toxic fumes of oxides of sulfur when heated to decomposition or on contact with acids [Sax, 9th ed., 1996, p. 1320].

Toxicity

GRAS(FEMA)

Definition

ChEBI: An organic disulfide that is methane in which one of the hydrogens has been replaced by a methyldisulfanyl group.

Flammability hazard characteristics

Flammable in case of fire, high temperature and oxidant, decomposing out toxic sulfur oxide gas in case of acid or high heat.
InChI:InChI=1/C2H6S2/c1-3-4-2/h1-2H3

624-92-0SDS

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 dimethyl disulfide

1.2 Other means of identification

Product number -
Other names Methyldisulfide

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:624-92-0 SDS

624-92-0Synthetic route

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
With trimethylsilyl iodide In 1,2-dichloro-ethane for 16h; Heating;100%
With sulfuric acid; sulfur dioxide; potassium iodide In water at 80℃; for 1h;92.9%
With tungsten(VI) chloride; sodium iodide In acetonitrile for 12h; Ambient temperature;90%
S-methyl O-benzyl dithiocarbonate
28925-45-3

S-methyl O-benzyl dithiocarbonate

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

benzyl chloride
100-44-7

benzyl chloride

Conditions
ConditionsYield
With copper(l) chloride; copper dichloride In acetonitrile for 96h; Ambient temperature;A 100%
B 60%
9-methylsulfinyl-10-(methylthio)anthracene

9-methylsulfinyl-10-(methylthio)anthracene

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
Stage #1: 9-methylsulfinyl-10-(methylthio)anthracene With air; sulfuric acid In dichloromethane at 20℃; for 0.0833333h; Rearrangement;
Stage #2: With water; sodium hydrogencarbonate Hydrolysis;
A n/a
B 100%
methylthiol
74-93-1

methylthiol

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
Stage #1: methylthiol With sodium hydroxide at 51℃;
Stage #2: With oxygen at 55℃; under 4500.45 Torr; Temperature; Pressure; Reagent/catalyst;
97.6%
With Cu,Na-X zeolite; oxygen at 189.9℃; Product distribution; Mechanism; other catalysts; other temp.;
With air at 170 - 270℃;
N,N-dimethylmethane sulfenamide
33696-21-8

N,N-dimethylmethane sulfenamide

methyl iodide
74-88-4

methyl iodide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

tertamethylammonium iodide
75-58-1

tertamethylammonium iodide

Conditions
ConditionsYield
In chloroform Product distribution; Ambient temperature; var. amino thioethers, var. electrophiles;A 96%
B 96%
dibutyl disulfide
629-45-8

dibutyl disulfide

S-methyl decanethioate
1680-29-1

S-methyl decanethioate

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

S-butyl decanethioate

S-butyl decanethioate

Conditions
ConditionsYield
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h;A n/a
B 95%
methanol
67-56-1

methanol

methylthiol
74-93-1

methylthiol

A

carbon disulfide
75-15-0

carbon disulfide

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

C

dimethyltrisulfane
3658-80-8

dimethyltrisulfane

Conditions
ConditionsYield
Stage #1: methanol; methylthiol With hydrogen sulfide; aluminum oxide with 14percent by weight of potassium tungstate at 400℃;
Stage #2: With sulfur; N-cyclohexyl-cyclohexanamine
A n/a
B 94.9%
C n/a
2,3-dimethyl-3-methylsulfanyl-3H-indole
53475-19-7

2,3-dimethyl-3-methylsulfanyl-3H-indole

A

2,3-dimethylindole
91-55-4

2,3-dimethylindole

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
With mercaptoacetic acid In dichloromethane for 0.5h; Heating;A 93%
B n/a
With mercaptoacetic acid In dichloromethane for 0.5h; Mechanism; Heating;
bis(2-methoxyethyl) disulfide
69177-66-8

bis(2-methoxyethyl) disulfide

S-methyl decanethioate
1680-29-1

S-methyl decanethioate

A

S-(2-methoxy)ethyl decanethioate
1020261-42-0

S-(2-methoxy)ethyl decanethioate

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h;A 93%
B n/a
S-methyl decanethioate
1680-29-1

S-methyl decanethioate

di-tert-butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate
67385-10-8

di-tert-butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate

A

S-[2-(t-butoxycarbonyl)amino]ethyl decanethioate
1020261-43-1

S-[2-(t-butoxycarbonyl)amino]ethyl decanethioate

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h;A 92%
B n/a
dicarbonyl(cyclopentadienyl)iron(II) chloride
12107-04-9

dicarbonyl(cyclopentadienyl)iron(II) chloride

lithium methylsulfinyl carbanion
10543-35-8

lithium methylsulfinyl carbanion

A

cyclopentadienyl iron(II) dicarbonyl dimer
38117-54-3

cyclopentadienyl iron(II) dicarbonyl dimer

B

methylthiol
74-93-1

methylthiol

C

Dimethyldisulphide
624-92-0

Dimethyldisulphide

D

1,2-bis(methylthio)ethane
6628-18-8

1,2-bis(methylthio)ethane

E

lithium chloride

lithium chloride

Conditions
ConditionsYield
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp.; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;A 55%
B n/a
C 21%
D 8%
E 92%
2-nitrobenzenediazonium o-benzenedisulfonamide

2-nitrobenzenediazonium o-benzenedisulfonamide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

methyl 2-nitrophenyl sulfide
3058-47-7

methyl 2-nitrophenyl sulfide

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at -15℃; methylthiodeazoniation; dimerization;A n/a
B 91%
C n/a
2,4-dinitrobenzenediazonium o-benzenedisulfonimide

2,4-dinitrobenzenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

methyl 2,4-dinitriophenyl sulfide
2363-23-7

methyl 2,4-dinitriophenyl sulfide

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at -15℃; methylthiodediazoniation; dimerization;A n/a
B 89%
C n/a
bis(cyclopentadienyl)titanium dichloride
1271-19-8

bis(cyclopentadienyl)titanium dichloride

lithium methylsulfinyl carbanion
10543-35-8

lithium methylsulfinyl carbanion

A

Cp2Ti(SMe)2

Cp2Ti(SMe)2

B

methylthiol
74-93-1

methylthiol

C

Dimethyldisulphide
624-92-0

Dimethyldisulphide

D

titanium(IV) oxide

titanium(IV) oxide

E

lithium chloride

lithium chloride

Conditions
ConditionsYield
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp.; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;A 31%
B n/a
C 9%
D 43%
E 89%
2-methoxybenzenediazonium o-benzenedisulfonamide

2-methoxybenzenediazonium o-benzenedisulfonamide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

1-methoxy-2-(methylsulfanyl)benzene
2388-73-0

1-methoxy-2-(methylsulfanyl)benzene

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation;A n/a
B 88%
C n/a
4-nitrobenzenediazonium o-benzenedisulfonimide

4-nitrobenzenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

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

1-methylthio-4-nitro-benzene

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at -15℃; methylthiodeazoniation; dimerization;A n/a
B 88%
C n/a
2,4-dithiapentane
1618-26-4

2,4-dithiapentane

3<(t-Butyl) dimethyl silyloxy>-1-bromobutan
65566-22-5

3<(t-Butyl) dimethyl silyloxy>-1-bromobutan

((Z)-5-Bromo-pent-1-enyl)-trimethyl-silane
139929-52-5

((Z)-5-Bromo-pent-1-enyl)-trimethyl-silane

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

(Z)-9-(tert-Butyl-dimethyl-silanyloxy)-6,6-bis-methylsulfanyl-1-trimethylsilanyl-dec-1-ene
79538-96-8

(Z)-9-(tert-Butyl-dimethyl-silanyloxy)-6,6-bis-methylsulfanyl-1-trimethylsilanyl-dec-1-ene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuranA n/a
B 87%
tert-butylethylene
558-37-2

tert-butylethylene

S-methyl methanethiosulfinate
13882-12-7

S-methyl methanethiosulfinate

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

methanethiosulfonic acid S-methyl ester
2949-92-0

methanethiosulfonic acid S-methyl ester

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

C

methyl 3,3-dimethyl-1-trifluoroacetoxy-2-butyl sulfide
73682-79-8

methyl 3,3-dimethyl-1-trifluoroacetoxy-2-butyl sulfide

Conditions
ConditionsYield
In tetrachloromethane 1) -20 deg C, 2) up to rt;A 12%
B 17%
C 87%
4-methoxybenzenediazonium o-benzenedisulfonimide

4-methoxybenzenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

1-methoxy-4-methylsulfanyl-benzene
1879-16-9

1-methoxy-4-methylsulfanyl-benzene

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; methylthiodediazoniation; dimerization;A n/a
B 87%
C n/a
4-toluenediazonium o-benzenedisulfonimide

4-toluenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation;A n/a
B 86%
C n/a
C6H4S2O4N(1-)*N2C6H5CH2(1+)

C6H4S2O4N(1-)*N2C6H5CH2(1+)

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

methyl o-tolyl sulfide
14092-00-3

methyl o-tolyl sulfide

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation;A n/a
B 86%
C n/a
4-(chloro)benzenediazonium benzo[d][1,3,2]dithiazol-2-ide-1,1,3,3-tetraoxide

4-(chloro)benzenediazonium benzo[d][1,3,2]dithiazol-2-ide-1,1,3,3-tetraoxide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

4-chlorophenyl methyl sulfide
123-09-1

4-chlorophenyl methyl sulfide

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; methylthiodediazoniation; dimerization;A n/a
B 86%
C n/a
4-hydroxybenzenediazonium o-benzenedisulfonimide

4-hydroxybenzenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

4-hydroxythioanisole
1073-72-9

4-hydroxythioanisole

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 20 - 25℃; methylthiodediazoniation; dimerization;A n/a
B 86%
C n/a
3-methoxybenzenediazonium o-benzenedisulfonimide

3-methoxybenzenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

1-methoxy-3-methylsulfanyl-benzene
2388-74-1

1-methoxy-3-methylsulfanyl-benzene

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation;A n/a
B 85%
C n/a
4-Bromobenzenediazonium o-benzenedisulfonimide

4-Bromobenzenediazonium o-benzenedisulfonimide

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

Dimethyldisulphide
624-92-0

Dimethyldisulphide

B

(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

C

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

Conditions
ConditionsYield
In methanol at 0 - 5℃; methylthiodeazoniation; dimerization;A n/a
B 85%
C n/a
N-Boc-glutathione disulfide tetramethyl ester

N-Boc-glutathione disulfide tetramethyl ester

ethylthioacetic acid methyl ester
2432-51-1

ethylthioacetic acid methyl ester

A

N-[N-[N-{(1,1-dimethylethoxy)carbonyl}-L-γ-glutamyl]-3-(butyloylsulfuryl)-L-alanine] dimethyl ester
1020261-44-2

N-[N-[N-{(1,1-dimethylethoxy)carbonyl}-L-γ-glutamyl]-3-(butyloylsulfuryl)-L-alanine] dimethyl ester

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h;A 85%
B n/a
methyl iodide
74-88-4

methyl iodide

A

dimethylsulfide
75-18-3

dimethylsulfide

B

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Conditions
ConditionsYield
With potassium hydroxide; sulfur; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 6.1%
B 84.3%
With sodium hydroxide; sulfur; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 10%
B 82%
With sodium hydroxide; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 14.0 % Chromat.
B 62.0 % Chromat.
With potassium hydroxide; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 6.1 % Chromat.
B 84.3 % Chromat.
Dimethyldisulphide
624-92-0

Dimethyldisulphide

methylsulphinyl chloride
676-85-7

methylsulphinyl chloride

Conditions
ConditionsYield
With sulfuryl dichloride; acetic acid at -20 - 20℃; for 2.5h;100%
With sulfuryl dichloride; acetic acid at -20 - 35℃; for 6.3h;97%
With sulfuryl dichloride; acetic acid at -20 - 35℃; for 6h;97%
N-methyl-2,4,5-tribromoimidazole
1003-91-4

N-methyl-2,4,5-tribromoimidazole

Dimethyldisulphide
624-92-0

Dimethyldisulphide

4,5-Dibromo-1-methyl-2-(methylthio)imidazole
145083-26-7

4,5-Dibromo-1-methyl-2-(methylthio)imidazole

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) r.t., 12 h;100%
With n-butyllithium 1) THF, -78 deg C, 5 min; Yield given. Multistep reaction;
Dimethyldisulphide
624-92-0

Dimethyldisulphide

Ph2CCHHgBr
67341-86-0

Ph2CCHHgBr

methyl 2,2-diphenylethenyl sulfide
15096-10-3

methyl 2,2-diphenylethenyl sulfide

Conditions
ConditionsYield
In benzene at 35 - 45℃; for 8h; Irradiation;100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

1,2-dimethyl-5-trimethylstannylimidazole
86051-74-3

1,2-dimethyl-5-trimethylstannylimidazole

1,2-dimethyl-5-methylthioimidazole
86051-77-6

1,2-dimethyl-5-methylthioimidazole

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) -100 deg C, 1 h, 2.) room temperature, 1.5 h;100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

4-bromo-1-ethoxymethyl-5-methylthio-2-phenylthioimidazole
81356-73-2

4-bromo-1-ethoxymethyl-5-methylthio-2-phenylthioimidazole

1-ethoxymethyl-4,5-bis(methylthio)-2-phenylthioimidazole
81356-72-1

1-ethoxymethyl-4,5-bis(methylthio)-2-phenylthioimidazole

Conditions
ConditionsYield
With n-butyllithium In diethyl ether; hexane 1.) -70 deg C, 1 h, 2.) room temperature;100%
With n-butyllithium In diethyl ether at -70℃;100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

naphtho<1,8-bc:4,5-b'c'>dithiophene
41879-78-1

naphtho<1,8-bc:4,5-b'c'>dithiophene

2,5-bis(methylthio)naphtho[1,8-bc:4,5-b'c']dithiophene

2,5-bis(methylthio)naphtho[1,8-bc:4,5-b'c']dithiophene

Conditions
ConditionsYield
Stage #1: naphtho<1,8-bc:4,5-b'c'>dithiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -30℃; for 1.5h;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -30℃; for 1.5h;
100%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) THF, -30 deg C, 1.5 h, 2.) THF, -30 deg C, 1.5 h; Yield given. Multistep reaction;
Dimethyldisulphide
624-92-0

Dimethyldisulphide

2,3-methano-2,4-didehydroadamantane

2,3-methano-2,4-didehydroadamantane

Conditions
ConditionsYield
In benzene-d6100%

A

B

benzyl chloride
100-44-7

benzyl chloride

Conditions
ConditionsYield
With copper(l) chloride; copper dichloride In acetonitrile for 96h; Ambient temperature;A 100%
B 60%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

8-Phenyl-tetrahydro-8λ5-[1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole
57680-64-5

8-Phenyl-tetrahydro-8λ5-[1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole

6a-Methylsulfanyl-6a-phenyl-tetrahydro-1,6-dioxa-3a-aza-6aλ5-phospha-pentalene

6a-Methylsulfanyl-6a-phenyl-tetrahydro-1,6-dioxa-3a-aza-6aλ5-phospha-pentalene

Conditions
ConditionsYield
In benzene for 2h; Irradiation; var. time;100%
In benzene at 20℃; Irradiation; relative rate constants, inhibition by α-methyl styrene;
2-lithio-1,3-dithiane
36049-90-8

2-lithio-1,3-dithiane

Dimethyldisulphide
624-92-0

Dimethyldisulphide

2-(methylthio)-1,3-dithiane
14758-37-3

2-(methylthio)-1,3-dithiane

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃;100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

methyl thiotosylate
4973-66-4

methyl thiotosylate

Conditions
ConditionsYield
With iodine In dichloromethane at 20℃; for 1h;100%
With iodine at 30℃; for 2h;90%
With copper(l) iodide; 1,10-Phenanthroline; ammonium tetrafluoroborate In N,N-dimethyl acetamide; water at 30℃; for 36h;79%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

(1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide
560095-49-0

(1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide

(3-methylsulfanyl-1-phenyl-1-propen-1-yl)pentamethyl phosphoric triamide
560095-81-0

(3-methylsulfanyl-1-phenyl-1-propen-1-yl)pentamethyl phosphoric triamide

Conditions
ConditionsYield
Stage #1: (1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.166667h;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -50 - 20℃;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

di-isopropyl ether
108-20-3

di-isopropyl ether

sodium hydrogensulfite

sodium hydrogensulfite

4-amino-4'-chlorodiphenyl ether
101-79-1

4-amino-4'-chlorodiphenyl ether

4-chloro-4'-thiomethyldiphenylether

4-chloro-4'-thiomethyldiphenylether

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

1,1'-bis[N-[(2S)-2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]-N-(E)-[phenylmethylideneamino]]ferrocene

1,1'-bis[N-[(2S)-2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]-N-(E)-[phenylmethylideneamino]]ferrocene

[1,1'-bis[N-[(2S)-2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]-N-[(E)phenylmethylideneamino]]]-[(Sp)-2-methylsulfanyl]ferrocene

[1,1'-bis[N-[(2S)-2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]-N-[(E)phenylmethylideneamino]]]-[(Sp)-2-methylsulfanyl]ferrocene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane Fe-complex in THF was cooled to -78°C, nBuLi in hexane was added,stirred for 9 h at -78°C under Ar, ligand was added dropwise, wa rmed to room temp. overnight, cooled to 0°C, quenched with aq. NH4Cl; washed with brine, dried over MgSO4, concd. under reduced pressure, column chromy. on silica gel with pentane-Et2O; elem. anal.;100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

tricarbonyl((3a,7a-trans)-octahydro-3-(t-butyl)-2-(η(6)-phenyl)benzoxazole)chromium(0)

tricarbonyl((3a,7a-trans)-octahydro-3-(t-butyl)-2-(η(6)-phenyl)benzoxazole)chromium(0)

tricarbony(l(3a,7a-trans)-octahydro-3-(t-butyl)-2-(η(6)-2'-methylthiophenyl)benzoxazole)chromium(0)

tricarbony(l(3a,7a-trans)-octahydro-3-(t-butyl)-2-(η(6)-2'-methylthiophenyl)benzoxazole)chromium(0)

Conditions
ConditionsYield
With BuLi In tetrahydrofuran N2-atmosphere, absence of light; addn. of slight excess of BuLi (in hexanes) to Cr-complex soln. (in THF) at -78°C, stirring (-78°C, 2.5 h), addn. of excess Me2S2, stirring (-78°C, 3.5 h), warming to room temp. over 45 min; evapn. (reduced pressure), dissoln. in Et2O, filtration (Celite), evapn., recrystn. (hexanes/Et2O); elem. anal.;100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

(4-bromo-2,6-dimethylphenoxy)triisopropylsilane
852950-12-0

(4-bromo-2,6-dimethylphenoxy)triisopropylsilane

2,6-dimethyl-4-methylsulfanylphenoxytriisopropylsilane
852950-13-1

2,6-dimethyl-4-methylsulfanylphenoxytriisopropylsilane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;100%
Stage #1: (4-bromo-2,6-dimethylphenoxy)triisopropylsilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
100%
2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

Dimethyldisulphide
624-92-0

Dimethyldisulphide

2-bromo-5-(methylthio)thiophene
86369-96-2

2-bromo-5-(methylthio)thiophene

Conditions
ConditionsYield
Stage #1: 2,5-dibromothiophen With n-butyllithium In hexanes; diethyl ether at -78 - -65℃;
Stage #2: Dimethyldisulphide In hexanes; diethyl ether at 0 - 20℃;
100%
Stage #1: 2,5-dibromothiophen With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In diethyl ether; hexane at 20℃; for 8h; Inert atmosphere;
98%
Stage #1: 2,5-dibromothiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - -30℃;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78 - 0℃;
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 12h; Inert atmosphere;
Dimethyldisulphide
624-92-0

Dimethyldisulphide

2-methoxyanthracene
42298-28-2

2-methoxyanthracene

3-methylthio-2-methoxyanthracene
1309600-92-7

3-methylthio-2-methoxyanthracene

Conditions
ConditionsYield
Stage #1: 2-methoxyanthracene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at 0 - 20℃; for 7h; Inert atmosphere;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

2-methoxy-6-phenylnaphthalene
59115-43-4

2-methoxy-6-phenylnaphthalene

2-methoxy-3-methylthio-6-phenylnaphthalene
1310197-78-4

2-methoxy-3-methylthio-6-phenylnaphthalene

Conditions
ConditionsYield
Stage #1: 2-methoxy-6-phenylnaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Inert atmosphere;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

6-n-decyl-2-methoxynaphthalene

6-n-decyl-2-methoxynaphthalene

6-n-decyl-3-methylthio-2-methoxynaphthalene
1310197-76-2

6-n-decyl-3-methylthio-2-methoxynaphthalene

Conditions
ConditionsYield
Stage #1: 6-n-decyl-2-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Inert atmosphere;
100%
Stage #1: 6-n-decyl-2-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78 - 20℃; for 18h;
100%
bis(acetonitrile)(5,10,15,20-tetramesitylporphyrinato)ruthenium(II)
97877-74-2

bis(acetonitrile)(5,10,15,20-tetramesitylporphyrinato)ruthenium(II)

Dimethyldisulphide
624-92-0

Dimethyldisulphide

Ru(meso-tetrakis(2,4,6-trimethylphenyl)porphyrin)(MeSSMe)2
1357363-89-3

Ru(meso-tetrakis(2,4,6-trimethylphenyl)porphyrin)(MeSSMe)2

Conditions
ConditionsYield
In benzene at 20℃; for 24h;100%
In benzene-d6 identified by NMR;
Dimethyldisulphide
624-92-0

Dimethyldisulphide

2,6-dimethoxyanthracene
36319-03-6

2,6-dimethoxyanthracene

2,6-dimethoxy-3,7-bis(methylthio)anthracene
1397972-18-7

2,6-dimethoxy-3,7-bis(methylthio)anthracene

Conditions
ConditionsYield
Stage #1: 2,6-dimethoxyanthracene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at 0 - 20℃; for 9h; Inert atmosphere;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

1-methoxypyrene
34246-96-3

1-methoxypyrene

1-methoxy-2-methylthiopyrene
1527009-83-1

1-methoxy-2-methylthiopyrene

Conditions
ConditionsYield
Stage #1: 1-methoxypyrene With n-butyllithium Inert atmosphere; Schlenk technique;
Stage #2: Dimethyldisulphide Inert atmosphere; Schlenk technique;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

2-(4-(methoxymethoxy)phenyl)-5,5-dimethyl-1,3-dioxane

2-(4-(methoxymethoxy)phenyl)-5,5-dimethyl-1,3-dioxane

2-(4-(methoxymethoxy)-3-(methylthio)phenyl)-5,5-dimethyl-1,3-dioxane

2-(4-(methoxymethoxy)-3-(methylthio)phenyl)-5,5-dimethyl-1,3-dioxane

Conditions
ConditionsYield
Stage #1: 2-(4-(methoxymethoxy)phenyl)-5,5-dimethyl-1,3-dioxane With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 0.333333h;
Stage #2: Dimethyldisulphide In tetrahydrofuran at -78 - 20℃; for 3h;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

1,3-dibromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)benzene

1,3-dibromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)benzene

(3-bromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)sulfane

(3-bromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)sulfane

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

4-(tert-butyldimethylsilyloxy)-1-butyne
78592-82-2

4-(tert-butyldimethylsilyloxy)-1-butyne

tert-Butyl-dimethyl-(4-methylsulfanyl-but-3-ynyloxy)-silane
125657-48-9

tert-Butyl-dimethyl-(4-methylsulfanyl-but-3-ynyloxy)-silane

Conditions
ConditionsYield
Stage #1: 4-(tert-butyldimethylsilyloxy)-1-butyne With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at 20℃; for 3h; Inert atmosphere;
100%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

but-3-ynyloxy-triisopropyl-silane
153495-48-8

but-3-ynyloxy-triisopropyl-silane

triisopropyl((4-(methylthio)but-3-yn-1-yl)oxy)silane

triisopropyl((4-(methylthio)but-3-yn-1-yl)oxy)silane

Conditions
ConditionsYield
Stage #1: but-3-ynyloxy-triisopropyl-silane With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at 20℃; for 3h; Inert atmosphere;
100%
2-bromo-4-fluoro-1-(methoxymethoxy)benzene
474711-11-0

2-bromo-4-fluoro-1-(methoxymethoxy)benzene

Dimethyldisulphide
624-92-0

Dimethyldisulphide

4-fluoro-1-(methoxymethoxy)-2-(methylsulfanyl)benzene

4-fluoro-1-(methoxymethoxy)-2-(methylsulfanyl)benzene

Conditions
ConditionsYield
Stage #1: 2-bromo-4-fluoro-1-(methoxymethoxy)benzene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 1h; Inert atmosphere;
Stage #2: Dimethyldisulphide In diethyl ether; pentane at 20℃; for 1h; Inert atmosphere;
100%

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