36625-67-9

Basic information

• Product Name: 3-nitropyridine-2-carboxaldehyde thiosemicarbazone
• CAS NO: 36625-67-9
• Molecular Weight: 225.231
• Mol File: 36625-67-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-nitropyridine-2-carboxaldehyde thiosemicarbazone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitropyridine-2-carboxaldehyde thiosemicarbazone(36625-67-9)
• EPA Substance Registry System: 3-nitropyridine-2-carboxaldehyde thiosemicarbazone(36625-67-9)

Safety Data

• Hazardous Substances Data: 36625-67-9(Hazardous Substances Data)

Upstream product

• 10261-94-6 3-nitropyridine-2-carboxaldehyde 
• 79-19-6 thiosemicarbazide 
• 65156-92-5 (E)-N,N-dimethyl-2-(3-nitropyridin-2-yl)ethenamine 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 18699-87-1 2-methyl-3-nitropyridine 

Downstream Products

• 143621-35-6 3-aminopyridine-2-carboxaldehyde thiosemicarbazone 

Relevant articles and documents

Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)

Palladium-catalyzed cross-coupling of methylboronic acid with 2-chloro- 3-nitropyridine produced 2-methyl-3-nitropyridine 4 in one step in high yield. Oxidation of 4 with selenium dioxide gave aldehyde 5. Alternatively, condensation of 4 with DMFDMA followed by oxidation gave 5 in a two step higher yielding conversion. Subsequent direct coupling of 5 with thiosemicarbazide followed by reduction of the nitro group using stannous chloride or sodium sulfide provided 3-AP (3). Reduction with sodium hydrosulfite gave 3-HAP (8). Finally a route which avoids the reduction of a nitro function was devised. Thus direct coupling of styrene with 2-chloro-3- aminopyridine 9 under Heck reaction conditions gave 16 which was converted to 17, oxidized to the aldehyde 18 and converted to 3-AP (3) with in situ deblocking of the t-Boc functionality.