483317-04-0

Basic information

• Product Name: 6-(2-aminophenyl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one
• Synonyms: 6-(2-aminophenyl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one
• CAS NO: 483317-04-0
• Molecular Weight: 261.368
• Mol File: 483317-04-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-(2-aminophenyl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(2-aminophenyl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one(483317-04-0)
• EPA Substance Registry System: 6-(2-aminophenyl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one(483317-04-0)

Safety Data

• Hazardous Substances Data: 483317-04-0(Hazardous Substances Data)

Upstream product

• 612-41-9 2-nitrocinnamic acid 
• 111190-24-0 3-(2-thienylthio)-3-(o-nitrophenyl)-propionic acid 
• 483317-03-9 6-(o-nitrophenyl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one 

Relevant articles and documents

Stannous chloride-mediated reductive cyclization - Rearrangement of nitroarenyl ketones

Cyclization products are produced in excellent yields from using standard reaction conditions for nitroarene reduction to aminoarene with SnCl2. Thus, 4-methyl-2-(2-nitrobenzyl)-2H-1,4-benzothiazin-3(4H)-one (2b) upon treatment with SnCl2 in ethanol did not produce the expected aniline derivative. Instead, 6-methyl-11a, 12-dihydro-6H-quino[3,2-b][1,4]benzothiazine (3) was produced in excellent yield, presumably via novel Sn (IV)-mediated amidine formation from the initial aniline reduction product. Under identical reaction conditions, 2-(2-nitrophenyl)-thiochroman-4-one (6) produces ethyl 5,11-dihydrodibenzo[b,e][1,4]thiazepin-11-ylacetate (7). A novel semipinacol rearrangement is proposed to account for this extensive skeletal rearrangement. Aniline derivative (14) (from 6 treated with FeSO4 · 7H2O) forms 12-ethoxy-11,12-dihydro-6H-6,12-methanodibenzo[b,f][1,5]thiazocine (15) upon treatment with SnCl2 in ethanol. Thiophene analogues of 6 and 14 (18 and 19, respectively) react similarly, forming the analogous thiazepine (20) and cyclic N,O-acetals (21), respectively.