1107610-26-3

Basic information

• Product Name: 3-(toluenesulfonyloxy)propyl thiocyanate
• CAS NO: 1107610-26-3
• Molecular Weight: 271.361
• Mol File: 1107610-26-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-(toluenesulfonyloxy)propyl thiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(toluenesulfonyloxy)propyl thiocyanate(1107610-26-3)
• EPA Substance Registry System: 3-(toluenesulfonyloxy)propyl thiocyanate(1107610-26-3)

Safety Data

• Hazardous Substances Data: 1107610-26-3(Hazardous Substances Data)

Upstream product

• 1453200-86-6 3-iodopropyl thiocyanate 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 67066-33-5 3-hydroxypropyl thiocyanate 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

Use of 3-[18F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides

3-[18F]Fluoropropanesulfonyl chloride, a recently proposed prosthetic agent for fluorine-18 labelling, was prepared in a two-step radiosynthesis via 3-[18F]fluoropropyl thiocyanate as an intermediate. Two benzenesulfonate-based radiolabelling precursors were prepared by various routes. Comparing the reactivities of 3-thiocyanatopropyl nosylate and the corresponding tosylate towards [18F]fluoride the former proved to be superior accounting for labelling yields of up to 85%. Conditions for a reliable transformation of 3-[18F]fluoropropyl thiocyanate to the corresponding sulfonyl chloride with the potential for automation have been identified. The reaction of 3-[18F]fluoropropanesulfonyl chloride with eight different aliphatic and aromatic amines was investigated and the identity of the resulting 18F-labelled sulfonamides was confirmed chromatographically by comparison with their nonradioactive counterparts. Even for weakly nucleophilic amines such as 4-nitroaniline the desired radiolabelled sulfonamides were accessible in satisfactory yields owing to systematic variation of the reaction conditions. With respect to the application of the 18F-fluoropropan-sulfonyl group to the labelling of compounds relevant as imaging agents for positron emission tomography (PET), the stability of N-(4-fluorophenyl)-3-fluoropropanesulfonamide against degradation catalysed by carboxylesterase was investigated and compared to that of the analogous fluoroacetamide.