458569-33-0

Basic information

• Product Name: 5-bromopyridin-3-yl 4-methylbenzenesulfonate
• Synonyms: 5-bromopyridin-3-yl 4-methylbenzenesulfonate
• CAS NO: 458569-33-0
• Molecular Weight: 328.186
• Mol File: 458569-33-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-bromopyridin-3-yl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromopyridin-3-yl 4-methylbenzenesulfonate(458569-33-0)
• EPA Substance Registry System: 5-bromopyridin-3-yl 4-methylbenzenesulfonate(458569-33-0)

Safety Data

• Hazardous Substances Data: 458569-33-0(Hazardous Substances Data)

Upstream product

• 74115-13-2 5-bromopyridine-3-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 458569-34-1 5-methylpyridin-3-yl 4-methylbenzenesulfonate 

Relevant articles and documents

Synthesis of 3-[(2S)-azetidin-2-ylmethoxy]-5-[11C]-methylpyridine, an analogue of A-85380, via a Stille coupling

3-[(2S)-azetidin-2-ylmethoxy]-5-[11C]-methylpyridine (5d), which might be a novel ligand for nicotinic receptors, was synthesized via coupling [11C]iodomethane with tert-butyl (2S)-2-({[5-(trimethylstannyl)pyridin-3-yl]oxy}methyl) azetidine-1-carboxylate (4) at 80°C for 5 min with tri-o-tolylphosphine-bound, unsaturated palladium(O), followed by deprotection using trifluoroacetic acid (TFA). The previous problem (solid-phase extraction before injection on semi-preparative LC) with automation of Stille coupling reactions has been overcome. In a typical experiment, 0.46 GBq of 5d was obtained from 5.2GBq of [11C]iodomethane. The decay-corrected radiochemical yield was 39% (based on the quantity [11C]iodomethane trapped). The synthesis time was 43 min from end of radionuclide production. During a production condition using 36 μAh of proton beam irradiation, a specific radioactivity of 50 GBq/ μmol of the final product was obtained in biological buffer. Copyright