59463-54-6

Basic information

• Product Name: S-(cyanomethyl) O-ethyl carbonodithioate
• Synonyms: carbonodithioic acid, S-(cyanomethyl) O-ethyl ester; S-(Cyanomethyl) O-ethyl carbonodithioate
• CAS NO: 59463-54-6
• Molecular Formula: C₅H₇NOS₂
• Molecular Weight: 161.2452
• Mol File: 59463-54-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 260.7°C at 760 mmHg
• Flash Point: 111.5°C
• Density: 1.242g/cm³
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: S-(cyanomethyl) O-ethyl carbonodithioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-(cyanomethyl) O-ethyl carbonodithioate(59463-54-6)
• EPA Substance Registry System: S-(cyanomethyl) O-ethyl carbonodithioate(59463-54-6)

Safety Data

• Hazardous Substances Data: 59463-54-6(Hazardous Substances Data)

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 107-14-2 chloroacetonitrile 
• 75-15-0 carbon disulfide 
• 141-52-6 sodium ethanolate 

Downstream Products

• 58260-77-8 (Z)-3-Methyl-dodec-2-enenitrile 
• 4435-18-1 2-cyclohexylideneacetonitrile 
• 54353-77-4 (aS)-(4-methylcyclohexylidene)acetonitrile 
• 5732-88-7 cyclopentylideneacetonitrile 
• 125011-70-3 4-(methylthio)-3-phenyl-2-thioxo-4-thiazoline-5-carbonitrile 
• 736178-15-7 3-(1-benzyl-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[c]isothiazol-3-yl)-propionitrile 
• 736178-06-6 3-(1-methyl-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[c]isothiazol-3-yl)-propionitrile 
• 869667-23-2 dithiocarbonic acid S-{3-cyano-1-[(4-methoxy-phenylcarbamoyl)-methyl]-propyl} ester O-ethyl ester 

Relevant articles and documents

Xanthates as Thiol Surrogates for Nucleophilic Substitution with Aryl Halides

We herein report an unprecedented xanthate-based protocol for the preparation of aryl-alkyl thioethers. Heating xanthates with aryl halides and namely cesium carbonate in methanol provides the target thioethers in generally good yields within short reaction times. This method allows one to avoid contact with odorous thiols and also to introduce substituents of which the corresponding thiols are virtually unavailable or inconvenient in use.

A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals

Reported herein is a visible-light-mediated radical approach to the α-alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN2-based activation of alkyl halides and blue light irradiation. The resulting open-shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl halides through a traditional two-electron path. The mild reaction conditions allowed functionalization of the α position of ketones with functional groups that are not compatible with classical anionic strategies. In addition, the redox-neutral nature of this process makes it compatible with a cinchona-based primary amine catalyst, which was used to develop a rare example of enantioselective organocatalytic radical α-alkylation of ketones.

Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

A radical addition reaction and subsequent performic acid oxidation were used for the synthesis of 1-substituted taurines with diverse functionalized side-chains from N-allylphthalimide and various xanthates. The current approach shows high yields and short synthetic route and reaction time. Moreover, the current method is a convenient and practical method for the synthesis of 1-substituted taurines with different functionalized side-chains.