Conditions | Yield |
---|---|
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
A
Dimethyldisulphide
B
benzyl chloride
Conditions | Yield |
---|---|
With copper(l) chloride; copper dichloride In acetonitrile for 96h; Ambient temperature; | A 100% B 60% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
methyl iodide
A
Dimethyldisulphide
B
tertamethylammonium iodide
Conditions | Yield |
---|---|
In chloroform Product distribution; Ambient temperature; var. amino thioethers, var. electrophiles; | A 96% B 96% |
Conditions | Yield |
---|---|
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h; | A n/a B 95% |
methanol
methylthiol
A
carbon disulfide
B
Dimethyldisulphide
C
dimethyltrisulfane
Conditions | Yield |
---|---|
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
A
2,3-dimethylindole
B
Dimethyldisulphide
Conditions | Yield |
---|---|
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
S-methyl decanethioate
A
S-(2-methoxy)ethyl decanethioate
B
Dimethyldisulphide
Conditions | Yield |
---|---|
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h; | A 93% B n/a |
S-methyl decanethioate
di-tert-butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate
A
S-[2-(t-butoxycarbonyl)amino]ethyl decanethioate
B
Dimethyldisulphide
Conditions | Yield |
---|---|
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h; | A 92% B n/a |
dicarbonyl(cyclopentadienyl)iron(II) chloride
lithium methylsulfinyl carbanion
A
cyclopentadienyl iron(II) dicarbonyl dimer
B
methylthiol
C
Dimethyldisulphide
D
1,2-bis(methylthio)ethane
Conditions | Yield |
---|---|
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% |
sodium thiomethoxide
A
Dimethyldisulphide
B
methyl 2-nitrophenyl sulfide
Conditions | Yield |
---|---|
In methanol at -15℃; methylthiodeazoniation; dimerization; | A n/a B 91% C n/a |
sodium thiomethoxide
A
Dimethyldisulphide
B
methyl 2,4-dinitriophenyl sulfide
Conditions | Yield |
---|---|
In methanol at -15℃; methylthiodediazoniation; dimerization; | A n/a B 89% C n/a |
bis(cyclopentadienyl)titanium dichloride
lithium methylsulfinyl carbanion
B
methylthiol
C
Dimethyldisulphide
Conditions | Yield |
---|---|
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% |
sodium thiomethoxide
A
Dimethyldisulphide
B
1-methoxy-2-(methylsulfanyl)benzene
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation; | A n/a B 88% C n/a |
sodium thiomethoxide
A
Dimethyldisulphide
B
1-methylthio-4-nitro-benzene
Conditions | Yield |
---|---|
In methanol at -15℃; methylthiodeazoniation; dimerization; | A n/a B 88% C n/a |
2,4-dithiapentane
3<(t-Butyl) dimethyl silyloxy>-1-bromobutan
((Z)-5-Bromo-pent-1-enyl)-trimethyl-silane
A
Dimethyldisulphide
B
(Z)-9-(tert-Butyl-dimethyl-silanyloxy)-6,6-bis-methylsulfanyl-1-trimethylsilanyl-dec-1-ene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran | A n/a B 87% |
tert-butylethylene
S-methyl methanethiosulfinate
trifluoroacetic anhydride
A
methanethiosulfonic acid S-methyl ester
B
Dimethyldisulphide
C
methyl 3,3-dimethyl-1-trifluoroacetoxy-2-butyl sulfide
Conditions | Yield |
---|---|
In tetrachloromethane 1) -20 deg C, 2) up to rt; | A 12% B 17% C 87% |
sodium thiomethoxide
A
Dimethyldisulphide
B
1-methoxy-4-methylsulfanyl-benzene
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; methylthiodediazoniation; dimerization; | A n/a B 87% C n/a |
sodium thiomethoxide
A
Dimethyldisulphide
B
4-methylphenyl methylsulfide
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation; | A n/a B 86% C n/a |
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation; | A n/a B 86% C n/a |
sodium thiomethoxide
A
Dimethyldisulphide
B
4-chlorophenyl methyl sulfide
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; methylthiodediazoniation; dimerization; | A n/a B 86% C n/a |
Conditions | Yield |
---|---|
In methanol at 20 - 25℃; methylthiodediazoniation; dimerization; | A n/a B 86% C n/a |
sodium thiomethoxide
A
Dimethyldisulphide
B
1-methoxy-3-methylsulfanyl-benzene
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; Dimerization; methylthiodediazoniation; | A n/a B 85% C n/a |
Conditions | Yield |
---|---|
In methanol at 0 - 5℃; methylthiodeazoniation; dimerization; | A n/a B 85% C n/a |
ethylthioacetic acid methyl ester
A
N-[N-[N-{(1,1-dimethylethoxy)carbonyl}-L-γ-glutamyl]-3-(butyloylsulfuryl)-L-alanine] dimethyl ester
B
Dimethyldisulphide
Conditions | Yield |
---|---|
[RhCl(PPh3)] In 1,2-dichloro-benzene at 150℃; for 1.5h; | A 85% B n/a |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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
Dimethyldisulphide
4,5-Dibromo-1-methyl-2-(methylthio)imidazole
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In benzene at 35 - 45℃; for 8h; Irradiation; | 100% |
Dimethyldisulphide
1,2-dimethyl-5-trimethylstannylimidazole
1,2-dimethyl-5-methylthioimidazole
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane 1.) -100 deg C, 1 h, 2.) room temperature, 1.5 h; | 100% |
Dimethyldisulphide
4-bromo-1-ethoxymethyl-5-methylthio-2-phenylthioimidazole
1-ethoxymethyl-4,5-bis(methylthio)-2-phenylthioimidazole
Conditions | Yield |
---|---|
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
naphtho<1,8-bc:4,5-b'c'>dithiophene
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In benzene-d6 | 100% |
Conditions | Yield |
---|---|
With copper(l) chloride; copper dichloride In acetonitrile for 96h; Ambient temperature; | A 100% B 60% |
Dimethyldisulphide
8-Phenyl-tetrahydro-8λ5-[1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole
Conditions | Yield |
---|---|
In benzene for 2h; Irradiation; var. time; | 100% |
In benzene at 20℃; Irradiation; relative rate constants, inhibition by α-methyl styrene; |
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; | 100% |
Conditions | Yield |
---|---|
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
(1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide
(3-methylsulfanyl-1-phenyl-1-propen-1-yl)pentamethyl phosphoric triamide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water | 100% |
Dimethyldisulphide
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
(4-bromo-2,6-dimethylphenoxy)triisopropylsilane
2,6-dimethyl-4-methylsulfanylphenoxytriisopropylsilane
Conditions | Yield |
---|---|
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
Dimethyldisulphide
2-bromo-5-(methylthio)thiophene
Conditions | Yield |
---|---|
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
2-methoxyanthracene
3-methylthio-2-methoxyanthracene
Conditions | Yield |
---|---|
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
2-methoxy-6-phenylnaphthalene
2-methoxy-3-methylthio-6-phenylnaphthalene
Conditions | Yield |
---|---|
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
6-n-decyl-3-methylthio-2-methoxynaphthalene
Conditions | Yield |
---|---|
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)
Dimethyldisulphide
Ru(meso-tetrakis(2,4,6-trimethylphenyl)porphyrin)(MeSSMe)2
Conditions | Yield |
---|---|
In benzene at 20℃; for 24h; | 100% |
In benzene-d6 identified by NMR; |
Dimethyldisulphide
2,6-dimethoxyanthracene
2,6-dimethoxy-3,7-bis(methylthio)anthracene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
Stage #1: 1-methoxypyrene With n-butyllithium Inert atmosphere; Schlenk technique; Stage #2: Dimethyldisulphide Inert atmosphere; Schlenk technique; | 100% |
Dimethyldisulphide
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
4-(tert-butyldimethylsilyloxy)-1-butyne
tert-Butyl-dimethyl-(4-methylsulfanyl-but-3-ynyloxy)-silane
Conditions | Yield |
---|---|
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
but-3-ynyloxy-triisopropyl-silane
Conditions | Yield |
---|---|
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
Dimethyldisulphide
Conditions | Yield |
---|---|
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% |
The IUPAC name of Dimethyl disulfide is (methyldisulfanyl)methane. With the CAS registry number 624-92-0, it is also named as Methyl disulfide. The product's category is Sulfide Flavor. Besides, it is colourless to yellow liquid with a very unpleasant smell, which should be stored in sealed containers in a cool, dry place away from oxidizing agents and reducing agents. It is stable, but incompatible with strong bases, strong oxidizing agents, strong reducing agents. In addition, its molecular formula is C2H6S2 and molecular weight is 94.19.
The other characteristics of this product can be summarized as: (1)EINECS: 210-871-0; (2)ACD/LogP: 1.77; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.77; (5)ACD/LogD (pH 7.4): 1.77; (6)ACD/BCF (pH 5.5): 13.04; (7)ACD/BCF (pH 7.4): 13.04; (8)ACD/KOC (pH 5.5): 218.72; (9)ACD/KOC (pH 7.4): 218.72; (10)#H bond acceptors: 0; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.522; (14)Molar Refractivity: 27.3 cm3; (15)Molar Volume: 89.4 cm3; (16)Surface Tension: 32.1 dyne/cm; (17)Density: 1.052 g/cm3; (18)Flash Point: 24.4 °C; (19)Melting Point: -85 °C; (20)Water Solubility: <0.1 g/100 mL at 20 °C; (21)Enthalpy of Vaporization: 33.78 kJ/mol; (22)Boiling Point: 109.7 °C at 760 mmHg; (23)Vapour Pressure: 28.7 mmHg at 25 °C.
Preparation of Dimethyl disulfide: this chemical can be prepared by the reaction of Dimethyl sulfate with Disodium disulfide.
Na2S+S→Na2S2
Na2S2+(CH3)2SO4→CH3SSCH3+Na2SO4
Uses of Dimethyl disulfide: this chemical is used as an intermediate of solvent and pesticide. It is also used as additive of fuel and lubricant. Additionally, it can be used as cooking inhibitor in ethylene furnace and refining equipment. The product can be used in the preparation of food flavors. Similarly, it can react with Diethyldisulfane to get Ethyl-methyl-disulfane.
This reaction needs NO, air and CD3CN at temperature of 20 °C for 1 hour. The yield is 49 %.
When you are using this chemical, please be cautious about it as the following: it is highly Flammable. Please keep away from sources of ignition. It is also harmful and very toxic by inhalation and if swallowed. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Moreover, you should wear suitable protective clothing, gloves and eye/face protection. After contact with skin, wash immediately with plenty of soap-suds. And in case of insufficient ventilation, wear suitable respiratory equipment. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). Additionally, it is toxic to aquatic organisms that may cause long-term adverse effects in the aquatic environment. Please avoid release to the environment. Refer to special instructions safety data sheet. This material and its container must be disposed of as hazardous waste.
People can use the following data to convert to the molecule structure.
(1)SMILES: S(SC)C
(2)InChI: InChI=1/C2H6S2/c1-3-4-2/h1-2H3
(3)InChIKey: WQOXQRCZOLPYPM-UHFFFAOYAV
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LD50 | unreported | 138mg/kg (138mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 16(6), Pg. 46, 1972. | |
mouse | LC50 | inhalation | 12300ug/m3/2H (12.3mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 16(6), Pg. 46, 1972. | |
rat | LC50 | inhalation | 15850ug/m3/2H (15.85mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 16(6), Pg. 46, 1972. |
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