14372-67-9

Basic information

• Product Name: 3-methoxyphenyl thiocyanate
• Synonyms: 3-Methoxyphenyl thiocyanate; m-Methoxyphenyl thiocyanate; Thiocyanic acid, 3-methoxyphenyl ester; Thiocyanic acid, m-methoxyphenyl ester
• CAS NO: 14372-67-9
• Molecular Formula: C₈H₇NOS
• Molecular Weight: 165.2123
• Mol File: 14372-67-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 272.1°C at 760 mmHg
• Flash Point: 118.4°C
• Density: 1.2g/cm³
• Vapor Pressure: 0.0062mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 3-methoxyphenyl thiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxyphenyl thiocyanate(14372-67-9)
• EPA Substance Registry System: 3-methoxyphenyl thiocyanate(14372-67-9)

Safety Data

• Hazardous Substances Data: 14372-67-9(Hazardous Substances Data)

Upstream product

• 15570-12-4 3-methoxybenzenethiol 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 
• 536-90-3 m-Anisidine 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 10365-98-7 3-methoxyphenylboronic acid 
• 333-20-0 potassium thioacyanate 
• 17333-78-7 3-methoxyphenyldiazonium ion 
• 1111-67-7 copper(I) thiocyanate 

Downstream Products

• 1333375-76-0 1-[(difluoromethyl)thio]-3-methoxybenzene 
• 97675-15-5 1-(methoxy)-3-[(trifluoromethyl)thio]benzene 
• 3097-21-0 1,3-dimethyl-1,3-dihydrobenzimidazol-2-one 
• 59014-89-0 bis(3-methoxyphenyl)disulfide 

Relevant articles and documents

Triphenylbismuth Dichloride-Mediated Conversion of Thioamides to Nitriles

Thioamides were efficiently converted to nitriles using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process was also successfully extended to the synthesis of cyanamides starting from the corresponding thioureas and of thiocyanates from dithiocarbamates.

One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)

An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.

Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ

A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups - a largely unexplored substituent with highly promising properties - into drug-like molecules. A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts.