16255-53-1

Basic information

• Product Name: 1-(tert-butyl)-4-thiocyanatobenzene
• Synonyms: 1-(tert-butyl)-4-thiocyanatobenzene
• CAS NO: 16255-53-1
• Molecular Weight: 191.297
• Mol File: 16255-53-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(tert-butyl)-4-thiocyanatobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(tert-butyl)-4-thiocyanatobenzene(16255-53-1)
• EPA Substance Registry System: 1-(tert-butyl)-4-thiocyanatobenzene(16255-53-1)

Safety Data

• Hazardous Substances Data: 16255-53-1(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 7252-86-0 4-tert-butylthioanisole 
• 253185-03-4 tert-butylbenzene 
• 1147550-11-5 ammonium thiocyanate 
• 2396-68-1 4-t-butylbenzenethiol 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 7605-48-3 bis(4-tert-butylphenyl)disulfide 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 1122-85-6 phenyl cyanate 

Downstream Products

• 10570-47-5 diethyl (4-(tert-butyl)benzoyl)phosphonate 
• 80783-57-9 1-tert-butyl-4-[(trifluoromethyl)sulfanyl]benzene 

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.

Direct Photocatalytic S-H Bond Cyanation with Green cN Source

Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green CN sources is demonstrated. This transformation features nontoxic and inexpensive CN sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions. It leads to the construction of various thiocyanates and some medicinally and biologically active thiocyanate-containing molecules.

General and practical formation of thiocyanates from thiols

A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.