16696-83-6

Basic information

• Product Name: methyl dithiocarbamate
• CAS NO: 16696-83-6
• Molecular Formula: C₂H₅NS₂
• Molecular Weight: 107.1978
• Mol File: 16696-83-6.mol

Chemical Properties

• Boiling Point: 182.7°C at 760 mmHg
• Flash Point: 64.3°C
• Density: 1.273g/cm³
• Vapor Pressure: 0.8mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: methyl dithiocarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl dithiocarbamate(16696-83-6)
• EPA Substance Registry System: methyl dithiocarbamate(16696-83-6)

Safety Data

• Hazardous Substances Data: 16696-83-6(Hazardous Substances Data)

Upstream product

• 556-64-9 methyl thiocyanate 
• 2253-44-3 O,O-dibutyldithiophosphoric acid 
• 107-56-2 O,O-diisopropyl hydrogen phosphorodithioate 
• 2253-43-2 O_.O-Dipropyl-dithyophosphat 
• 105748-59-2 brassinin 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 

Downstream Products

• 716371-78-7 (2-methylsulfanyl-4-phenyl-thiazol-5-yl)-acetic acid 
• 857419-85-3 1,5-di-pyrrol-2-yl-3-thia-pentane-1,5-dione 
• 16696-88-1 acetyl dithiocarbamic acid methyl ester 
• 21406-30-4 N-Benzoylamino-dithiokohlensaeuremethylester 
• 2103-86-8 2-methylmercapto-4-phenylthiazole 
• 54167-88-3 N-(2-methylsulfanyl-4-phenyl-thiazol-5-yl)-acetamide 
• 54486-11-2 (2-methylsulfanyl-4-phenyl-thiazol-5-yl)-carbamic acid methyl ester 
• 59009-69-7 methyl N-(tosylmethyl)dithiocarbamate 
• 82646-26-2 4-amino-2-methylthio-5-phenylthiazolium benzenesulfonate 
• 134812-29-6 3-(2-Methylsulfanyl-thiazol-4-yl)-phenylamine 
• 91516-55-1 2-(2'-methylthiothiazol-4'-yl)-5-phenylpyrazine 
• 91516-59-5 2-(2'-methylthiothiazol-4'-yl)-6-phenylpyrazine 
• 91516-48-2 2-(2'-methylthiothiazol-4'-yl)-3-phenylpyrazine 
• 333-20-0 potassium thioacyanate 

Relevant articles and documents

Brassinin oxidase mediated transformation of the phytoalexin brassinin: Structure of the elusive co-product, deuterium isotope effect and stereoselectivity

Brassinin oxidase, a fungal detoxifying enzyme that mediates the conversion of the phytoalexin brassinin into indole-3-carboxaldehyde, is the first enzyme described to date that catalyzes the transformation of a dithiocarbamate group into an aldehyde equivalent. Brassinin is an essential phytoalexin due to its antifungal activity and its role as biosynthetic precursor of other phytoalexins produced in plants of the family Brassicaceae (common name crucifer). In this report, the isolation, structure determination and synthesis of the elusive co-product of brassinin transformation by brassinin oxidase, S-methyl dithiocarbamate, the syntheses of dideuterated and (R) and (S) monodeuterated brassinins, kinetic analyses of isotope effects and chemical modifications of brassinin oxidase are described. The reaction of [1′-2H 2]brassinin was found to be slowed by a kinetic isotope effect of 5.3 on the value of kcat/Km. This result indicates that the hydride/hydrogen transfer step preceding brassinin transformation is rate determining in the overall reaction. In addition, the use of (R) and (S)-[1′-2H]brassinins as substrates indicated that the hydride/hydrogen transfer step is ca. 88% stereoselective for the pro-R hydrogen. A detailed chemical mechanism of the enzymatic transformation of brassinin is proposed.

REACTIONS OF DIALKYL DITHIOPHOSPHORIC AND DIPHENYLDITHIOPHOSPHORIC ACIDS WITH THIOCYANATES

The interaction between phosphorus(IV) dithio acid partial esters and thiocyanates proceeds with initial formation of addition products to the CN bond.These adducts are either split by the second molecule of dithio acid to S-alkyl dithiocarbamates and tetraalkyl trithiophosphates or rearrange into dialkyl N-thiophosphoryldithiocarbamates.The latter easily split off the thiols and convert to isothiocyanatothiophosphates.A number of thiophosphorylated and diphosphorylated thioureas were synthesized by the reaction of isothiocyanatothiophosphates with amines and α-aminoalkylphosphonates.