3278-35-1

Basic information

• Product Name: diethyl thiodicarbonate
• Synonyms: Thiodicarbonic acid ((HO)C(O)SC(S)(OH)), OC,OC'-diethyl ester; AI3-19742; Ethyl xanthogen ethyl formate; NSC 403191; Xanthic acid, ethyl-, anhydrosulfide with O-ethyl thiocarbonate; Xanthic acid, ethyl-, anhydrosulfide with O-ethyl thiolcarbonate; Carbonic acid, dithio-, anhydrosulfide with O-ethyl thiocarbonate, O-ethyl ester (8CI); Diethyl thiodicarbonate ((OH)C(O)SC(S)(OH)); Thiodicarbonic acid ((HO)C(O)SC(S)(OH)), diethyl ester; Thiodicarbonic acid, diethyl ester; O,O-diethyl dithiodicarbonate
• CAS NO: 3278-35-1
• Molecular Formula: C₆H₁₀O₃S₂
• Molecular Weight: 194.2718
• EINECS: 221-911-1
• Mol File: 3278-35-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 236°C at 760 mmHg
• Flash Point: 96.5°C
• Density: 1.242g/cm³
• Vapor Pressure: 0.0487mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: diethyl thiodicarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl thiodicarbonate(3278-35-1)
• EPA Substance Registry System: diethyl thiodicarbonate(3278-35-1)

Safety Data

• Hazardous Substances Data: 3278-35-1(Hazardous Substances Data)

Usage

General Description

Diethyl thiodicarbonate is a chemical compound with the molecular formula C5H10O2S. It is a colorless to pale yellow liquid that is commonly used as a reagent in organic synthesis. Diethyl thiodicarbonate is known for its ability to selectively introduce the thiol functional group into organic molecules through a nucleophilic substitution reaction. diethyl thiodicarbonate is also used in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. Due to its reactivity and potential hazards, diethyl thiodicarbonate should be handled and stored with appropriate safety precautions.

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 541-41-3 chloroformic acid ethyl ester 
• 2905-52-4 bis(ethoxythiocarbonyl) sulfide 
• 44414-28-0 O-ethyl thiocarbonate ion 
• 36955-31-4 bis(ethoxycarbonyl) sulphide 
• 28563-38-4 ethylxanthogenate 
• 35832-93-0 ethoxy(potassiosulfanyl)methanethione 
• 2812-73-9 Chlor(thioameisensaeure)-O-ethylester 
• 7732-18-5 water 
• 140-90-9 sodium O-ethyl dithiocarbonate 

Downstream Products

• 6628-16-6 carbethoxythiosemicarbazide 
• 3111-89-5 O-ethyl-N-phenylthiocarbamate 
• 1020-77-5 3-(4-nitro-phenyl)-thiocarbazic acid O-ethyl ester 
• 5470-26-8 ethyl pyrrolidine-1-carboxylate 
• 56525-82-7 1-pyrrolidinecarbothioic acid O-ethyl ester 
• 28563-38-4 ethylxanthogenate 
• 44414-28-0 O-ethyl thiocarbonate ion 
• 54287-92-2 N-(4-pyridyl) ethyl carbamate 
• 2905-52-4 bis(ethoxythiocarbonyl) sulfide 
• 36955-31-4 bis(ethoxycarbonyl) sulphide 
• 4092-75-5 bis(butoxythiocarbonyl) sulphide 
• 65573-07-1 S-(ethoxycarbonyl) O-butyldithiocarbonate 
• 82524-67-2 S-ethoxythiocarbonyl O-butyl dithiocarbonate 
• 623-54-1 O-ethyl S-methyl dithiocarbonate 

Relevant articles and documents

Preparation method of xanthate compound

The invention discloses a preparation method of an xanthate compound. The method is characterized in that an xanthate and a chloride react at 0-60 DEG C in the presence of a phase transfer catalyst toprepare the xanthate compound with high purity and high yield. Compared with the existing method, the process for preparing xanthate compounds by phase transfer catalysis without solvent (self-solvent) is simple, the product purity is good, the yield is high, and the method is economic and environment-friendly and is suitable for industrial production.

PYROTHIOCARBONATES III. SYNTHESIS OF S-(ALKOXYCARBONYL) O-ALKYLDITHIOCARBONATES

An efficient and general preparation of S-(alkoxycarbonyl)-O-alkyldithiocarbonates is described.The method is based on the reaction of potassium O-alkylmonothiocarbonates with O-alkylchlorothiocarbonates in acetone-water (9:1) at 0 deg C.The yields are 91-100percent.

A General Strategy for Elaboration of the Dithiocarbonyl Functionality, -(C=O)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disulfane and Related Derivatives of Thiocarbonic Acids

A variety of sulfenyl chlorides have been reacted with a variety of alkoxythiocarbonyl compounds to give adducts which then lose (spontaneously, or upon thermolysis, or in the presence of Lewis acid catalyst) the alkyl chloride to provide an assortment of dithiocarbonyl compounds in good to excellent yields.The preparations of bis(chlorocarbonyl)disulfane (1), ((trichloromethyl)dithio)carbonyl chloride (2), ((alkoxycarbonyl)dithio)carbonyl chlorides (3 and 4), and (((alkylthio)carbonyl)dithio)carbonyl chlorides (5 and 6) by this methodology were optimized; some of the (alkoxydichloromethyl)disulfanyl adducts, e.g., ROCCl2SS(C=O)Cl (10) and ROCCl2SS(C=O)OR'(54), were reasonable stable and could be isolated.All new compounds were characterized by analytical data, 1H and 13C NMR, IR, UV, and mass spectrometry, and high-yield derivatizations with alcohols or N-methylaniline.The reaction with N-methylaniline was also adapted to a rapid, convenient, and precise analytical-scale assay of mixtures of compounds containing acid chloride and/or sulfenyl chloride functionalities.The kinetics, mechanism, and stereochemistry of the dithiocarbonyl synthesis are discussed.