diallyl sulfoxide
diallyl sulphide
Conditions | Yield |
---|---|
With trifluoromethylsulfonic anhydride; potassium iodide In acetonitrile at 20℃; for 0.0833333h; | 95% |
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; potassium iodide for 0.0333333h; Neat (no solvent); chemoselective reaction; | 93% |
With iodine; sodium hydrogensulfite In chloroform at 50℃; for 3h; Temperature; | 90% |
With Silphos; iodine In acetonitrile for 0.25h; Heating; | 89% |
With sodium iodide at 20℃; for 1h; Green chemistry; | 87% |
Conditions | Yield |
---|---|
With hexamethyldisilathiane at 150 - 160℃; for 7h; | 84% |
With potassium sulfide |
2-methylpropan-2-thiol
allyl bromide
A
allyl tert-butyl sulfide
B
diallyl sulphide
Conditions | Yield |
---|---|
With sodium methylate In methanol 0 deg C, 1 h; 25 deg C, overnight; Yields of byproduct given. Title compound not separated from byproducts; | A 66% B n/a |
Conditions | Yield |
---|---|
With hydrogen sulfide In dimethyl sulfoxide at 40℃; for 3h; | A 11% B 50.8% |
bis[2-chloro-3-(trimethylsilyl)-propyl]sulfide
diallyl sulphide
Conditions | Yield |
---|---|
With potassium tert-butylate In methanol at 20℃; for 7h; | 47% |
Dithiocarbonic acid S-allyl ester O-benzyl ester
A
diallyl sulphide
B
dibenzyl sulfide
C
allyl(benzyl)sulfide
Conditions | Yield |
---|---|
With 1,2-bis-(diphenylphosphino)ethane; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 65℃; for 7h; | A n/a B n/a C 32% |
2-allylmercapto-1,3-benzothiazole
chloroform
A
1,3-Benzothiazole
B
diallyl disulphide
C
diallyl sulphide
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation; Further byproducts given; | A 24% B 24% C 15% D n/a |
2-allylmercapto-1,3-benzothiazole
chloroform
A
1,3-Benzothiazole
B
diallyl disulphide
C
diallyl sulphide
D
2,2'-benzothiazolyl
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation; Further byproducts given; | A 24% B 24% C 15% D 2% |
diallyl disulphide
acetylene
A
diallyl sulphide
B
Vinyl propen-1-yl sulfide
C
(E)-allyl(prop-1-en-1-yl)sulfane
D
1-vinylthio-3-(1-propenylthio)-1-propene
Conditions | Yield |
---|---|
With potassium hydroxide; hydroquinone In water; dimethyl sulfoxide at 40 - 45℃; under 9880 - 15200 Torr; for 4h; Further byproducts given; | A 0.7% B 17.8% C 1.4% D 19.6% |
Conditions | Yield |
---|---|
With potassium hydroxide at 200℃; |
Conditions | Yield |
---|---|
at 117℃; Disproportionierung im geschlossenen Gefaess; |
3,3'-thiodipropanol
diallyl sulphide
Conditions | Yield |
---|---|
With potassium hydroxide at 200℃; |
Conditions | Yield |
---|---|
With sodium sulfide; ethanol | |
With potassium hydrosulfide | |
With polyglycol; sodium sulfide In water at 70 - 80℃; for 2h; | 99 % Chromat. |
With bis(tributyltin)sulfide In chloroform at 110℃; for 12h; | 98 % Chromat. |
Conditions | Yield |
---|---|
With potassium hydrosulfide | |
With potassium sulphide; ethanol; water at 50℃; zuletzt bei Siedetemperatur; | |
With sodium sulfide; tetrabutylammomium bromide In water at 70 - 80℃; for 2h; | 89 % Chromat. |
Conditions | Yield |
---|---|
With potassium sulfide at 120℃; |
diallyl disulphide
A
3-vinyl-4H-<1,2>-dithiin
B
diallyl sulphide
C
diallyl trisulfide
D
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 50℃; for 168h; Further byproducts given; | A 0.7 % Chromat. B 3 % Chromat. C 9.7 % Chromat. D 0.47 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
D
5-methyl-4,7-dithiadeca-1,9-diene
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.45 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
D
2‐ethenyl‐4H‐1,3‐dithiine
Conditions | Yield |
---|---|
at 50℃; for 168h; Further byproducts given; | A 3 % Chromat. B 9.7 % Chromat. C 0.47 % Chromat. D 0.3 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.68 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.42 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.86 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Yield given. Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D n/a |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Yield given. Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D n/a |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 2.3 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.2 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.7 % Chromat. |
diallyl disulphide
A
diallyl sulphide
B
diallyl trisulfide
C
diallyl tetrasulfide
Conditions | Yield |
---|---|
at 80℃; for 240h; Further byproducts given; | A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.25 % Chromat. |
Conditions | Yield |
---|---|
With 1,1,3,3-tetramethyl-2-thiourea; sodium hydride 1) DMF, room temp., 1 h; 2) DMF, hexane, room temp., 10 min.; Yield given. Multistep reaction; |
diallyl disulphide
acetylene
A
(E,E)-bis-(1-propenyl) sulfide
B
diallyl sulphide
C
Vinyl propen-1-yl sulfide
D
1,2-bis(1-propylenylthio)ethene
E
1-vinylthio-3-allylthio-1-propene
F
1-vinylthio-3-(1-propenylthio)-1-propene
Conditions | Yield |
---|---|
With potassium hydroxide; hydroquinone In dimethyl sulfoxide at 40℃; under 6840 - 13680 Torr; for 4h; Product distribution; other temperatures, times, amount of potassium hydroxide, inhibitors and the conc. of water in DMSO; |
diallyl sulphide
diallyl sulfoxide
Conditions | Yield |
---|---|
With Mn(III) Schiff-base; dihydrogen peroxide In water; acetic acid at 20℃; for 0.0666667h; | 100% |
With 2-hydroperoxyhexafluoro-2-propanol In dichloromethane at -78℃; for 2h; | 98% |
With dihydrogen peroxide; Amberlyst 15 In methanol at 20℃; for 0.5h; | 98% |
diallyl sulphide
diallyl sulfone
Conditions | Yield |
---|---|
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In methanol; water at 40℃; | 100% |
With 1H-imidazole; tetra-n-butylammonium hydrogen monopersulfate In dichloromethane at 25℃; for 0.0333333h; chemoselective reaction; | 100% |
With tert.-butylhydroperoxide; [Mo2(O)4{[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 0.416667h; Reflux; | 100% |
N-chloro-succinimide
diallyl sulphide
2-propenyl 3-chloro-1-propenyl sulfide
Conditions | Yield |
---|---|
In tetrachloromethane at 4℃; for 10h; | 100% |
Conditions | Yield |
---|---|
With tungsten In octane; chlorobenzene at 80℃; for 1h; | A 100% B n/a |
With chloroaryloxide neopentylidene complex of tungsten (1) | A 90% B n/a |
(2,6-Ph2C6H3O)2W(Cl)=CHC(CH3)3*OEt2 In chlorobenzene at 80℃; for 3h; | A 88% B n/a |
diallyl sulphide
2-propenyl 3-chloro-1-propenyl sulfide
Conditions | Yield |
---|---|
With N-chloro-succinimide In tetrachloromethane at 0℃; | 100% |
diallyl sulphide
2,2-difluoroethyl triflate
Conditions | Yield |
---|---|
In neat (no solvent) at 60℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
diallyl sulphide
trifluoromethanesulfonic acid 2-fluoroethyl ester
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 15h; Inert atmosphere; Sealed tube; | 99% |
Conditions | Yield |
---|---|
at 60℃; for 15h; Inert atmosphere; | 99% |
diallyl sulphide
pyridazine-4,5-dicarbonitrile
Conditions | Yield |
---|---|
In chloroform at 110℃; Diels-Alder reaction; | 97% |
diallyl sulphide
Conditions | Yield |
---|---|
In methanol N2-atmosphere; evapn., extg. (CH2Cl2), filtering, pptn. on ether addn. (0°C), filtering, washing (ether), drying (vac.); | 97% |
Conditions | Yield |
---|---|
at 60℃; for 15h; Inert atmosphere; | 96% |
diallyl sulphide
Conditions | Yield |
---|---|
In methanol N2-atmosphere; refluxing (18 h); evapn., extg. (CH2Cl2), filtering, pptn. on ether addn. (0°C), filtering, washing (ether), drying (vac.); elem. anal.; | 94% |
tetrafluoroboric acid diethyl ether
diallyl sulphide
Conditions | Yield |
---|---|
In chlorobenzene cooling (-45°C), stirring; dissolving (acetone), filtration (celite), rinsing (acetone), concentration, evaporation, stirring (ether), filtration, drying (vac.); elem. anal.; | 93% |
diallyl sulphide
3,5-bis(chloromethyl)-1,4-thiaselenane
Conditions | Yield |
---|---|
With selenium(II) chloride In acetonitrile at 0℃; for 2h; Solvent; regioselective reaction; | 93% |
diallyl sulphide
2-(3-oxo-3-phenyl-prop-1-ynyl)-cyclohex-1-enecarbaldehyde
Conditions | Yield |
---|---|
dirhodium tetraacetate In 1,2-dichloro-ethane at 80℃; for 72h; | 92% |
diallyl sulphide
trifluoromethanesulfonic acid 2-fluoroethyl ester
Conditions | Yield |
---|---|
In neat (no solvent) at 60℃; for 15h; Inert atmosphere; Sealed tube; | 92% |
diallyl sulphide
3,5-bis(bromomethyl)-1,4-thiaselenane
Conditions | Yield |
---|---|
With selenium dibromide In acetonitrile at 0℃; for 2h; Solvent; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; [Mo2(O)4{[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 0.0833333h; Reflux; | A 90% B 10% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol for 2h; Ambient temperature; | A 81% B 2% |
With 1H-imidazole; (TMPP)MnOAc; tetrabutylammonium periodite In dichloromethane at 20℃; for 4h; Reagent/catalyst; | A 17.3% B 26.6% |
diallyl sulphide
(2-formyl-cyclohex-1-enyl)-propynoic acid methyl ester
Conditions | Yield |
---|---|
dirhodium tetraacetate In dichloromethane for 120h; Heating; | A n/a B 90% |
diallyl sulphide
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
hexa-1,5-dien-3-yl(phenyl)sulfane
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 70℃; for 18h; Solvent; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 90% |
ethyl 2-phenyldiazoacetate
diallyl sulphide
ethyl 2-phenyl-2-(allylthio)-4-pentenoate
Conditions | Yield |
---|---|
With Rh2[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 | 89% |
With silver trifluoromethanesulfonate In dichloromethane at 35℃; for 21h; Doyle-Kirmse reaction; Inert atmosphere; chemoselective reaction; | 84% |
diethyl (1-diazo-2,2,2-trifluoroethyl)phosphonate
diallyl sulphide
diethyl [1-(allylthio)-1-(trifluoromethyl)but-3-en-1-yl]phosphonate
Conditions | Yield |
---|---|
With bis(1,1,1-trifluoroacetylacetonato)copper(II) In toluene at 100℃; Inert atmosphere; | 89% |
diallyl sulphide
diazoethane
Conditions | Yield |
---|---|
rhodium(II) acetate at 25℃; for 0.333333h; | A 11% B 87% |
(η5-cyclopentadienyl)Re(NO)(P(C6H5)3)(CF3SO3)
diallyl sulphide
Conditions | Yield |
---|---|
In chlorobenzene 48 h; volatiles removal (vac.), dissolving (acetone), filtration, washing (ether and pentane), drying; elem. anal.; | 86% |
In not given elem. anal., (1)H-, (13)C-, (31)P-NMR; | 79-86 |
diallyl sulphide
monochloroborane dimethyl sulfide complex
5-chloro-1-thia-5-boracyclooctane
Conditions | Yield |
---|---|
In pentane to a mixt. of diallyl sulfide in pentane (dry ice-acetone bath) is added dropwise a chloroborane-dimethyl sulfide complex to the vigorously-stirred soln. over a period of 2 h (-20°C), mixt. is warmed to room temp. and stirred (2 h); solvent is removed, residue is heated to 150°C and then distd. under reduced pressure, elem. anal.; | 84.8% |
diallyl sulphide
methyl 2-diazo-2-(dimethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
dirhodium tetraacetate In dichloromethane Heating; | 84% |
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide; 4,4'-dicyano-4,4'-azo-di-valeric acid In water at 80℃; for 4h; | 84% |
Conditions | Yield |
---|---|
In chloroform-d1 Ar atmosphere, addn. of butadiyne to soln. of Ru complex, 30 min, addn. of S(C3H5)2, 30 min; removement of solvent (vacuum), concn. of mother liquor, recrystn. (CH2Cl2/Et2O); elem. anal.; | 84% |
Molecular Structure of Allyl sulfide (CAS NO.592-88-1):
IUPAC Name: 3-Prop-2-enylsulfanylprop-1-ene
Molecular Formula: C6H10S
Molecular Weight: 114.20
EINECS: 209-775-1
FEMA: 2042
storage temp.: 2-8 °C
Melting Point: -83 °C
Index of Refraction: 1.478
Molar Refractivity: 37.29 cm3
Molar Volume: 131.7 cm3
Surface Tension: 26.7 dyne/cm
Density: 0.866 g/cm3
Flash Point: 46.1 °C
Enthalpy of Vaporization: 36.31 kJ/mol
Boiling Point: 141.5 °C at 760 mmHg
Vapour Pressure: 7.3 mmHg at 25 °C
Water Solubility: 621 mg/L at 25 °C
Product Categories: sulfide Flavor
Appearance: clear colorless liquid
Canonical SMILES: C=CCSCC=C
InChI: InChI=1S/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2
InChIKey: UBJVUCKUDDKUJF-UHFFFAOYSA-N
Classification Code: Anticarcinogenic agents; Antineoplastic agents; Antioxidants; Mutation data; Protective Agents
Allyl sulfide (CAS NO.592-88-1) is mianly used in the production of flavors.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Chemical Toxicology. Vol. 26, Pg. 299, 1988. | |
rabbit | LDLo | intravenous | 330mg/kg (330mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Biochemical Journal. Vol. 4, Pg. 107, 1909. |
rat | LD50 | oral | 2980mg/kg (2980mg/kg) | Food and Chemical Toxicology. Vol. 26, Pg. 299, 1988. |
Reported in EPA TSCA Inventory.
Poison by intravenous route. Moderately toxic by ingestion. An irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits toxic SOx. Explosive reaction with N-bromosuccinimide.
Safety Information of Allyl sulfide (CAS NO.592-88-1):
Hazard Codes: Xi
Risk Statements: 10-36/37/38
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39-23-16
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
S16:Keep away from sources of ignition.
S23:Do not breathe vapour.
RIDADR: UN 1993 3/PG 3
WGK Germany: 2
RTECS: BC4900000
HazardClass: 3
PackingGroup: III
Allyl sulfide (CAS NO.592-88-1), its Synonyms are 2-Propenyl sulphide ; 3,3-Thiobis(1-propene) ; Allyl monosulfide ; Diallyl monosulfide ; Diallyl sulfide ; Diallyl thioether ; Oil garlic ; Thioallyl ether ; 1-Propene, 3,3'-thiobis- .
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