Diethyl thiodicarbonate

Base Information

• Chemical Name: Diethyl thiodicarbonate
• CAS No.: 2905-52-4
• Molecular Formula: C6H10 O2 S3
• Molecular Weight: 210.342
• European Community (EC) Number: 220-808-9
• UNII: SU8BGG88DU
• DSSTox Substance ID: DTXSID20183288
• Nikkaji Number: J306.832C
• Wikidata: Q83054029
• Mol file: 2905-52-4.mol

Synonyms:Diethyl thiodicarbonate;2905-52-4;Bis(ethoxythiocarbonyl)sulfide;BIS-(ETHOXYTHIOCARBONYL)SULFIDE;EINECS 220-808-9;Thiodicarbonic acid (((HO)C(S))2-S), diethyl ester;Thiodicarbonic acid ([(HO)C(S)]2-S), diethyl ester;SU8BGG88DU;O-ethyl ethoxycarbothioylsulfanylmethanethioate;bis(ethoxythiocarbonyl)sulfur;Bis(ethoxythiocarbonyl) sulfide;bis(ethoxythiocarbonyl) sulphide;SCHEMBL3588443;C,C'-Diethyl dicarbonodithioate;C6H10O2S3;DTXSID20183288;Bis[ethoxy(thiocarbonyl)] sulfide;Ethyl carbonodithioate anhydrosulfide;C6-H10-O2-S3;Xanthic acid, ethyl-, anhydrosulfide;Dicarbonodithioic acid, C,C'-diethyl ester;Bis-(thioformic acid O-ethyl ester)-sulfide;FT-0716707;Thiodicarbonic acid ([(HO)C(S)]2S), diethyl ester;Carbonic acid, dithio-, anhydrosulfide, O,O-diethyl ester

Chemical Property of Diethyl thiodicarbonate

Chemical Property:

• Melting Point: 52-53oC
• Boiling Point: 247.9°Cat760mmHg
• Flash Point: 103.7°C
• PSA: 107.94000
• Density: 1.28g/cm³
• LogP: 2.36240
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 209.98429308
• Heavy Atom Count: 11
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

BIS(ETHOXYTHIOCARBONYL)SULFIDE 98.00% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=S)SC(=S)OCC

Technology Process of Diethyl thiodicarbonate

There total 21 articles about Diethyl thiodicarbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Chlor(thioameisensaeure)-O-ethylester (2812-73-9) → bis(ethoxythiocarbonyl) sulfide (2905-52-4)

Guidance literature:

With sodium sulfide; cetyltributylphosphonium bromide; In dichloromethane; at 0 ℃; for 1.25h;

Reference yield: 91.0%

potassium ethyl xanthogenate (140-89-6) → bis(ethoxythiocarbonyl) sulfide (2905-52-4)

Guidance literature:

With 2-chloro-4,5-dihydroimidazole hemisulfate; In methanol; for 0.5h; Ambient temperature;

DOI:10.1039/P19920000047

Reference yield: 65.0%

potassium ethyl xanthogenate (140-89-6) + tetracyano-1,4-dithiine (2448-55-7) → bis(ethoxythiocarbonyl) sulfide (2905-52-4) + dipotassium bis(2-mercapto-1,2-dicyanovinyl)sulfide (5927-79-7)

Guidance literature:

In acetone; for 0.5h; Ambient temperature;

DOI:10.1021/jo01313a019

upstream raw materials:

phosgene

potassium ethyl xanthogenate

bromocyane

ethanol

Downstream raw materials:

S-(ethoxycarbonyl) O-ethyl dithiocarbonate

ethylxanthogenate

O,S-Diethyl dithiocarbonate

O,S-di-(2,2,2-trimethylethyl) dithiocarbonate

Refernces

• 1、 Saczewski, Franciszek,Gdaniec, Maria. "2-Chloro-4,5-dihydroimidazole. Part VII. Reactions with Carbon Disulfide and Potassium O-Alkyl Dithiocarbonates. Synthesis and Transformations of 2,3,7,8-tetrahydro-5H-diimidazothiadiazine-5-thione". . p. 47 - 50. Retrieved 2007/10/02.
• 2、 Palominos, Mario A.,Santos, Jose G.,Valderrama, Jaime A.,Vega, Juan C.. "Pyrothiocarbonates. Part 2. Reaction of S-Ethoxycarbonyl O-Ethyl Dithiocarbonate with some Potassium O-Alkylthiocarbonates". . p. 2641 - 2643. Retrieved 2007/10/02.