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592-88-1

Basic Information
CAS No.: 592-88-1
Name: Diallyl sulfide
Article Data: 52
Molecular Structure:
Molecular Structure of 592-88-1 (Diallyl sulfide)
Formula: C6H10S
Molecular Weight: 114.211
Synonyms: Allylsulfide (6CI,7CI,8CI);Allyl monosulfide;Bis(2-propenyl) sulfide;Di(2-propenyl) sulfide;Diallyl monosulfide;Diallylthioether;NSC 20947;Oil garlic;Thioallyl ether;Allyl sulfide;
EINECS: 209-775-1
Density: 0.866 g/cm3
Melting Point: -83 °C
Boiling Point: 141.5 °C at 760 mmHg
Flash Point: 46.1 °C
Solubility: Soluble in alcohol, chloroform, ether, and carbon tetrachloride. Insoluble in water.
Appearance: clear colorless liquid
Hazard Symbols: IrritantXi
Risk Codes: 10-36/37/38
Safety: 26-36-37/39-23-16
Transport Information: UN 1993 3/PG 3
PSA: 25.30000
LogP: 2.09160
Synthetic route
14180-63-3

diallyl sulfoxide

592-88-1

diallyl sulphide

Conditions
ConditionsYield
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%
556-56-9

allyl iodid

592-88-1

diallyl sulphide

Conditions
ConditionsYield
With hexamethyldisilathiane at 150 - 160℃; for 7h;84%
With potassium sulfide
75-66-1

2-methylpropan-2-thiol

106-95-6

allyl bromide

A

37850-75-2

allyl tert-butyl sulfide

B

592-88-1

diallyl sulphide

Conditions
ConditionsYield
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
127699-25-6

Diallyl selenide

A

2179-57-9

diallyl disulphide

B

592-88-1

diallyl sulphide

Conditions
ConditionsYield
With hydrogen sulfide In dimethyl sulfoxide at 40℃; for 3h;A 11%
B 50.8%
1309645-82-6

bis[2-chloro-3-(trimethylsilyl)-propyl]sulfide

592-88-1

diallyl sulphide

Conditions
ConditionsYield
With potassium tert-butylate In methanol at 20℃; for 7h;47%
6329-40-4

Dithiocarbonic acid S-allyl ester O-benzyl ester

A

592-88-1

diallyl sulphide

B

538-74-9

dibenzyl sulfide

C

6937-97-9

allyl(benzyl)sulfide

Conditions
ConditionsYield
With 1,2-bis-(diphenylphosphino)ethane; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 65℃; for 7h;A n/a
B n/a
C 32%
22388-07-4

2-allylmercapto-1,3-benzothiazole

67-66-3

chloroform

A

95-16-9

1,3-Benzothiazole

B

2179-57-9

diallyl disulphide

C

592-88-1

diallyl sulphide

D

2-(1,1-dichloro-3-butenylthio)benzothiazole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation; Further byproducts given;A 24%
B 24%
C 15%
D n/a
22388-07-4

2-allylmercapto-1,3-benzothiazole

67-66-3

chloroform

A

95-16-9

1,3-Benzothiazole

B

2179-57-9

diallyl disulphide

C

592-88-1

diallyl sulphide

D

4271-09-4

2,2'-benzothiazolyl

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation; Further byproducts given;A 24%
B 24%
C 15%
D 2%
2179-57-9

diallyl disulphide

74-86-2

acetylene

A

592-88-1

diallyl sulphide

B

105278-48-6

Vinyl propen-1-yl sulfide

C

104324-36-9

(E)-allyl(prop-1-en-1-yl)sulfane

D

123351-73-5, 123351-76-8

1-vinylthio-3-(1-propenylthio)-1-propene

Conditions
ConditionsYield
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%
6704-15-0

β,β'-dihydroxydipropyl sulfide

592-88-1

diallyl sulphide

Conditions
ConditionsYield
With potassium hydroxide at 200℃;
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  • 592-88-1         C6H10S               Diallyl sulfide

  • Casno:

    592-88-1

    592-88-1 C6H10S Diallyl sulfide

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Chemistry

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 

Uses

 Allyl sulfide (CAS NO.592-88-1) is mianly used in the production of flavors.

Toxicity Data With Reference

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.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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: IrritantXi
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

Specification

  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- .