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Organic thiocyanates are hydrolyzed to thiocarbamates in the Riemschneider thiocarbamate synthesis. Electrochemical reduction typically converts thiocyanates to thioates and cyanide , although sometimes it can replace the thiocyanate group as a whole with hydride.
Thiocyanate [6] is known to be an important part in the biosynthesis of hypothiocyanite by a lactoperoxidase. [7] [8] [9] Thus the complete absence of thiocyanate or reduced thiocyanate [10] in the human body, (e.g., cystic fibrosis) is damaging to the human host defense system.
Allyl thiocyanate isomerizes to the isothiocyanate: [4] CH 2 =CHCH 2 SCN → CH 2 =CHCH 2 NCS. Isothiocyanates can be prepared by treating organic dithiocarbamate salts with lead nitrate or tosyl chloride. [5] [6] Synthesis of phenyl isothiocyanate. Isothiocyanates may also be accessed by the fragmentation reactions of 1,4,2-oxathiazoles. [7]
Methyl thiocyanate: ... it is the most important organic isothiocyanate in industry. [1] ... MITC is a building block for the synthesis of 1,3,4-thiadiazoles, ...
Sodium thiocyanate (sometimes called sodium sulphocyanide) is the chemical compound with the formula NaSCN. This colorless deliquescent salt is one of the main sources of the thiocyanate anion . As such, it is used as a precursor for the synthesis of pharmaceuticals and other specialty chemicals . [ 2 ]
TMSNCS is useful reagent in organic chemistry. It is an ambident nucleophile, able to react with various alkyl halides, acetals, aldehydes, unsaturated compounds, aziridines, oxiranes, polycyclic aromatic hydrocarbons, and acetylated hexoses to form either thiocyanate or isothiocyanate structures. [6]
Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate: [4] CH 2 =CHCH 2 Cl + KSCN → CH 2 =CHCH 2 NCS + KCl. The product obtained in this fashion is sometimes known as synthetic mustard oil. Allyl thiocyanate isomerizes to the isothiocyanate: [8] CH 2 =CHCH 2 SCN → CH 2 =CHCH 2 NCS
The first synthesis of mercury thiocyanate was probably completed in 1821 by Jöns Jacob Berzelius: HgO + 2 HSCN → Hg(SCN) 2 + H 2 O. Evidence for the first pure sample was presented in 1866 prepared by a chemist named Otto Hermes. [2] It is prepared by treating solutions containing mercury(II) and thiocyanate ions.