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O,S-Diethyl dithiocarbonate

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Name

O,S-Diethyl dithiocarbonate

EINECS 210-813-4
CAS No. 623-79-0 Density 1.101 g/cm3
PSA 66.62000 LogP 2.06090
Solubility N/A Melting Point N/A
Formula C5H10OS2 Boiling Point 200 °C at 760 mmHg
Molecular Weight 150.266 Flash Point 74.8 °C
Transport Information N/A Appearance Yellow liquid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 623-79-0 (O,S-Diethyl dithiocarbonate) Hazard Symbols N/A
Synonyms

Carbonicacid, dithio-, O,S-diethyl ester (8CI);Xanthic acid, ethyl-, ethyl ester(6CI,7CI);Diethyl xanthate;Ethyl O-ethylxanthate;Ethyl S-ethylxanthate;NSC8847;O,S-Diethyl dithiocarbonate;

Article Data 38

O,S-Diethyl dithiocarbonate Synthetic route

64-67-5

diethyl sulfate

140-89-6

potassium ethyl xanthogenate

623-79-0

O,S-Diethyl dithiocarbonate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 1.5h; Ambient temperature;93%
140-89-6

potassium ethyl xanthogenate

75-03-6

ethyl iodide

623-79-0

O,S-Diethyl dithiocarbonate

Conditions
ConditionsYield
18-crown-6 ether In dichloromethane for 1h; Ambient temperature;82%
In ethanol for 2h; Heating;55%
With ethanol
2905-52-4

bis(ethoxythiocarbonyl) sulfide

623-79-0

O,S-Diethyl dithiocarbonate

Conditions
ConditionsYield
In toluene Heating; Irradiation;69%
Zersetzen;
In toluene for 0.0833333h; Heating; Irradiation; Yield given;
3278-35-1

S-(ethoxycarbonyl) O-ethyl dithiocarbonate

623-79-0

O,S-Diethyl dithiocarbonate

Conditions
ConditionsYield
In n-heptane for 2.5h; Heating; Irradiation;59%
Heating; Irradiation;59%
In toluene Heating; Irradiation;
140-89-6

potassium ethyl xanthogenate

cyclooctatetraene dibromide

A

623-79-0

O,S-Diethyl dithiocarbonate

B

(4Z,6Z,8Z)-(3aS,9aR)-3a,9a-Dihydro-cycloocta[1,3]dithiol-2-one

Dithiocarbonic acid S-((7R,8R)-8-ethoxythiocarbonylsulfanyl-bicyclo[4.2.0]octa-2,4-dien-7-yl) ester O-ethyl ester

Dithiocarbonic acid S-((1S,2S,7S,8R)-8-ethoxythiocarbonylsulfanyl-bicyclo[5.1.0]octa-3,5-dien-2-yl) ester O-ethyl ester

Conditions
ConditionsYield
In acetone for 22h; Ambient temperature; Yield given. Further byproducts given;A 11%
B n/a
C 30%
D 12%
In acetone for 22h; Ambient temperature; Further byproducts given;A 11%
B n/a
C 30%
D 12%
140-89-6

potassium ethyl xanthogenate

cyclooctatetraene dibromide

A

623-79-0

O,S-Diethyl dithiocarbonate

Dithiocarbonic acid S-((1R,2R,7R,8S)-8-bromo-bicyclo[5.1.0]octa-3,5-dien-2-yl) ester O-ethyl ester

Dithiocarbonic acid S-((7R,8R)-8-ethoxythiocarbonylsulfanyl-bicyclo[4.2.0]octa-2,4-dien-7-yl) ester O-ethyl ester

Dithiocarbonic acid S-((1S,2S,7S,8R)-8-ethoxythiocarbonylsulfanyl-bicyclo[5.1.0]octa-3,5-dien-2-yl) ester O-ethyl ester

Conditions
ConditionsYield
In acetone for 22h; Ambient temperature; Further byproducts given;A 11%
B 1.6%
C 30%
D 12%
140-89-6

potassium ethyl xanthogenate

A

623-79-0

O,S-Diethyl dithiocarbonate

Dithiocarbonic acid S-((1R,2R,7R,8S)-8-bromo-bicyclo[5.1.0]octa-3,5-dien-2-yl) ester O-ethyl ester

Dithiocarbonic acid S-((7R,8R)-8-ethoxythiocarbonylsulfanyl-bicyclo[4.2.0]octa-2,4-dien-7-yl) ester O-ethyl ester

Dithiocarbonic acid S-((1S,2S,7S,8R)-8-ethoxythiocarbonylsulfanyl-bicyclo[5.1.0]octa-3,5-dien-2-yl) ester O-ethyl ester

Conditions
ConditionsYield
With 7,8-Dibromobicyclo<4.2.0>octa-2,4-diene In N,N-dimethyl-formamide for 18h; Ambient temperature; Further byproducts given;A 29%
B n/a
C 25%
D 10%
74-96-4

ethyl bromide

140-89-6

potassium ethyl xanthogenate

623-79-0

O,S-Diethyl dithiocarbonate

Conditions
ConditionsYield
With ethanol
In ethanol
In acetone Heating;
With ethanol for 4h; Esterification; Heating;
In ethanol for 4h; Heating;
75-00-3

chloroethane

140-89-6

potassium ethyl xanthogenate

623-79-0

O,S-Diethyl dithiocarbonate

Conditions
ConditionsYield
With ethanol
502-55-6

bis-ethoxythiocarbonyldisulfane

A

75-15-0

carbon disulfide

B

623-79-0

O,S-Diethyl dithiocarbonate

C

762-03-8

thiocarbonic acid O,O'-diethyl ester

D

15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
bei der Destillation; Produkt 5:Schwefel;

O,S-Diethyl dithiocarbonate Specification

The O,S-Diethyl dithiocarbonate, with the CAS registry number 623-79-0 and EINECS registry number 210-813-4, has the IUPAC name of O-ethyl ethylsulfanylmethanethioate. And the molecular formula of the chemical is C5H10OS2.

The characteristics of this chemical are as followings: (1)ACD/LogP: 2.60; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.6; (4)ACD/LogD (pH 7.4): 2.6; (5)ACD/BCF (pH 5.5): 55.62; (6)ACD/BCF (pH 7.4): 55.62; (7)ACD/KOC (pH 5.5): 617.78; (8)ACD/KOC (pH 7.4): 617.78; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 66.62 Å2; (13)Index of Refraction: 1.531; (14)Molar Refractivity: 42.24 cm3; (15)Molar Volume: 136.3 cm3; (16)Polarizability: 16.74×10-24cm3; (17)Surface Tension: 42.3 dyne/cm; (18)Density: 1.101 g/cm3; (19)Flash Point: 74.8 °C; (20)Enthalpy of Vaporization: 41.84 kJ/mol; (21)Boiling Point: 200 °C at 760 mmHg; (22)Vapour Pressure: 0.469 mmHg at 25°C.    

Preparation of O,S-Diethyl dithiocarbonate: This chemical can be prepared by 1,2,m-trithio-dicarbonic acid O,O'-diethyl ester. The reaction will need reagent toluene. The reaction time is 5 minutes with heating.

Uses of O,S-Diethyl dithiocarbonate: It can be used to produce dithiocarbonic acid S,S'-diethyl ester. This reaction will need reagent Aliquat 336. The reaction time is 1 hour with temperature of 100°C, and the yield is about 85%.   

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: S=C(OCC)SCC
(2)InChI: InChI=1/C5H10OS2/c1-3-6-5(7)8-4-2/h3-4H2,1-2H3
(3)InChIKey: JGZZEAPGGFAOAY-UHFFFAOYAU

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