2637-35-6

Basic information

• Product Name: pyridin-2-yl thiocyanate
• Synonyms: Pyridin-2-yl thiocyanate; thiocyanic acid, 2-pyridinyl ester
• CAS NO: 2637-35-6
• Molecular Formula: C₆H₄N₂S
• Molecular Weight: 136.1744
• Mol File: 2637-35-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 266.9°C at 760 mmHg
• Flash Point: 115.2°C
• Density: 1.27g/cm³
• Vapor Pressure: 0.00843mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: pyridin-2-yl thiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: pyridin-2-yl thiocyanate(2637-35-6)
• EPA Substance Registry System: pyridin-2-yl thiocyanate(2637-35-6)

Safety Data

• Hazardous Substances Data: 2637-35-6(Hazardous Substances Data)

Upstream product

• 127878-51-7 S-(pyridin-2-yl) 4-methylbenzenesulfonothioate 
• 151-50-8 potassium cyanide 
• 18438-38-5 2-methylsulfanyl-pyridine 
• 7677-24-9 trimethylsilyl cyanide 
• 2637-34-5 2-Sulfanylpyridine 
• 506-68-3 bromocyane 

Downstream Products

• 1052174-83-0 2-((difluoro(phenylsulfonyl)methyl)thio)pyridine 
• 51290-79-0 2-(benzylthio)pyridine 
• 3111-54-4 2-phenylsulfanylpyridine 

Relevant articles and documents

Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates

Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.

Electrophilic cyanations. I. Synthesis of thiocyanato-heteroarenes and tosylheteroarenes from mercapto-heteroarenes using p-toluenesulfonyl cyanide

Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).