1431846-80-8

Basic information

• Product Name: (1S,2R)-2-(5-ethylthiophen-2-yl)methylamino-1-phenylpropanol
• Synonyms: (1S,2R)-2-(5-ethylthiophen-2-yl)methylamino-1-phenylpropanol
• CAS NO: 1431846-80-8
• Molecular Weight: 275.415
• Mol File: 1431846-80-8.mol

Chemical Properties

• CAS DataBase Reference: (1S,2R)-2-(5-ethylthiophen-2-yl)methylamino-1-phenylpropanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-(5-ethylthiophen-2-yl)methylamino-1-phenylpropanol(1431846-80-8)
• EPA Substance Registry System: (1S,2R)-2-(5-ethylthiophen-2-yl)methylamino-1-phenylpropanol(1431846-80-8)

Safety Data

• Hazardous Substances Data: 1431846-80-8(Hazardous Substances Data)

Upstream product

• 36880-33-8 5-ethyl-thiophene-2-carbaldehyde 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 872-55-9 2-ethylthiophene 
• 1431846-76-2 (1S,2R)-2-((5-ethylthiophen-2-yl)methyleneamino)-1-phenylpropan-1-ol 

Relevant articles and documents

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands

Abstract: Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.

Synthesis of novel thiophene-based chiral ligands and their application in asymmetric Henry reaction

Novel chiral thiolated amino alcohols were synthesized from norephedrine and thiophene carbaldehydes (methyl- or ethyl-substituted) and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide β-hydroxy nitroalkanols in high conversion (92%). The reaction was optimized in terms of the metal, solvent, temperature and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and 2-propanol as the solvent provided the best enantioselectivities (up to 96% ee) of the corresponding nitroalcohols for aliphatic aldehydes. Copyright 2013 John Wiley & Sons, Ltd. Chiral thiophene contanining amino alcohol ligands were synthesized from norephedrine and substituted 5-thiophene-2-carbaldehyde. This novel chiral ligands were used to catalyze enantioselective Henry reaction of various aldehydes and nitroalkanes in high yields with good to high enantio- and diastereoselectivities. Copyright

Synthesis of novel β-amino alcohols and their application in the catalytic asymmetric sulfoxidation of sulfides

Novel chiral norephedrine-based β-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)2 for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee.