O-ethyl carbonodithioate

Base Information

• Chemical Name: O-ethyl carbonodithioate
• CAS No.: 151-01-9
• Molecular Formula: C3H6OS2
• Molecular Weight: 122.212
• Hs Code.: 2905199090
• Nikkaji Number: J238.939H
• Mol file: 151-01-9.mol

Synonyms:Ethyl xanthate;Carbonodithioic acid, O-ethyl ester;O-ethyl carbonodithioate;ZOOODBUHSVUZEM-UHFFFAOYSA-M;STK367788;AKOS005206997

Chemical Property of O-ethyl carbonodithioate

Chemical Property:

• Vapor Pressure: 18.2mmHg at 25°C
• Melting Point: 140 °C
• Refractive Index: 1.548
• Boiling Point: 120.5 °C at 760mmHg
• PKA: 3.19±0.60(Predicted)
• Flash Point: 26.7 °C
• PSA: 91.12000
• Density: 1.181 g/cm³
• LogP: 1.78530
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 120.97818213
• Heavy Atom Count: 6
• Complexity: 47.2

Purity/Quality:

99% ^*data from raw suppliers

ETHYL XANTHATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=S)[S-]
• General Description: **O-Ethyl hydrogen dithiocarbonate (also known as ethylxanthate or O-ethyl dithiocarbonate)** is a xanthate derivative commonly used in organic synthesis, particularly in radical reactions and as a precursor for functional group transformations. It serves as a versatile reagent for inter-molecular radical additions to olefins and reductive cleavage processes, often demonstrating efficiency in transferring xanthate groups under mild conditions. Its applications include the ortho-substitution of anilines and indoline synthesis, where it participates in radical additions followed by desulfurization or cyclization. The compound is compatible with various functional groups, though its reactivity may vary depending on the substrate (e.g., secondary xanthates perform better than primary ones). Its utility is further enhanced by its solubility and ease of monitoring in reactions using spectroscopic techniques. *(Note: The paragraph synthesizes key insights from the provided abstracts without referencing the literature directly.)*

Technology Process of O-ethyl carbonodithioate

There total 28 articles about O-ethyl carbonodithioate 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%

→ O-ethyl hydrogen dithiocarbonate (151-01-9)

Guidance literature:

Reference yield: 97.0%

→ AK + O-ethyl hydrogen dithiocarbonate (151-01-9)

Guidance literature:

Reference yield: 53.0%

→ 7-[(Methylthio)carbonothioyloxy]-10-desacetyloxybaccatin + O-ethyl hydrogen dithiocarbonate (151-01-9)

Guidance literature:

upstream raw materials:

carbon disulfide

diethyl ether

potassium ethyl xanthogenate

ethanol

Downstream raw materials:

carbon disulfide

ethanol

3,5-bis-benzylmercapto-[1,2,4]thiadiazole

1-(2-methoxy-phenyl)-dithiobiuret

Refernces

Xanthates and solid-phase chemistry. A new soluble polymer analogue of Wang resin

10.1016/S0040-4020(02)00526-4

The research focuses on the synthesis and application of a new soluble polymer analogue of Wang resin in solid-phase chemistry, specifically for inter-molecular radical additions of xanthates onto olefins. The experiments compared the new resin with a classical Wang resin, examining the efficiency of radical transfer and cleavage conditions. Reactants included xanthates, olefins, and the new soluble polymer, with reactions monitored using 'H NMR spectroscopy for easy tracking of the reaction progress. The analyses involved various techniques such as 'H and "C NMR, infrared spectroscopy, mass spectrometry, HPLC, and TLC to characterize the reactants, intermediates, and final products. The study demonstrated that the new soluble polymer provided better results for radical transfer, preserved the efficient cleavage conditions of the Wang linker, and allowed for easier monitoring of reactions compared to the classical Wang resin.

A practical method for the reductive cleavage of the sulfide bond in xanthates

10.1016/0040-4039(96)01253-1

The research describes a practical method for the reductive cleavage of the sulfide bond in xanthates, with the purpose of removing the xanthate group from various synthetic targets that do not contain sulfur. The process involves heating xanthates in 2-propanol in the presence of equimolar amounts of dilauroyl peroxide, which is added in small portions. This method is advantageous because it does not require high dilution or slow addition of reagents, unlike traditional stannane-based radical reactions. The study concludes that this approach is efficient, particularly for secondary xanthates, and demonstrates tolerance to a variety of functional groups commonly encountered in organic synthesis. However, limitations were observed with primary xanthates, where large amounts of peroxide were needed and yields were poor.

A new approach for the ortho-substitution of anilines and for the synthesis of indolines

10.1016/j.tetlet.2004.04.111

The study presents a new method for the ortho-substitution of anilines and the synthesis of indolines. The process begins with a radical addition of a xanthate to a vinyl sulfanilide, leading to the formation of a dihydrobenzoisothiazole dioxide structure. This intermediate loses sulfur dioxide upon heating to yield a 2-substituted aniline. In some instances, the presence of DBU during heating induces the formation of an indoline. The vinyl sulfanilides are prepared from 2-chloroethylsulfonyl chloride and anilines. The xanthates used in the radical addition can be benzylic, tertiary, or substituted with electrophilic groups like nitriles, ketones, or ketoesters. The study explores various substituents on the nitrogen and the aromatic ring, finding that electron-withdrawing groups facilitate the formation of indolines. The method is notable for its use of readily available starting materials and reagents, and its potential to access compounds that are difficult to obtain through classical approaches.