283589-06-0

Basic information

• Product Name: Benzeneethanamine, a-(bromomethyl)-, hydrobromide, (aS)-
• Synonyms: Benzeneethanamine, a-(bromomethyl)-, hydrobromide, (aS)-
• CAS NO: 283589-06-0
• Molecular Formula: C9H12BrN.BrH
• Molecular Weight: 295.017
• Mol File: 283589-06-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzeneethanamine, a-(bromomethyl)-, hydrobromide, (aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanamine, a-(bromomethyl)-, hydrobromide, (aS)-(283589-06-0)
• EPA Substance Registry System: Benzeneethanamine, a-(bromomethyl)-, hydrobromide, (aS)-(283589-06-0)

Safety Data

• Hazardous Substances Data: 283589-06-0(Hazardous Substances Data)

Upstream product

• 106454-69-7 N-tert-butoxycarbonyl-D-Phenylalaninol 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 141595-88-2 (R)-tert-butyl (1-bromo-3-phenylpropan-2-yl)carbamate 
• 63-91-2 L-phenylalanine 
• 3182-95-4 L-Phenylalaninol 
• 150-30-1 Phenylalanine 
• 1795-98-8 rac-phenylalaninol 

Relevant articles and documents

Chiral N-Heterocyclic Carbene Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents

Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee). The addition of HMPA to the reaction mixture as a co-solvent is critical in terms of chemical yield and enantioselectivity. A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction. Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee; see scheme). A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction.

Synthesis of chiral iminoalkyl functionalised N-heterocyclic carbenes and their use in asymmetric catalysis

A library of new chiral iminoalkyl imidazolium salts has been synthesised from amino acids using a modular design approach. Deprotonation with silver oxide yields silver carbene transfer reagents, which can be used as ligand sources in asymmetric catalysis. Preliminary testing has shown that the ligands induce enantioselectivity in the palladium-catalysed allylic alkylation of 1,3-diphenylprop-3-enyl acetate with dimethyl malonate.

Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: Chiral Mono- and Bicyclic 1,2-Thiazetidine 1,1-Dioxides from α-Amino Acids

New chiral mono- and bicyclic β-sultams, valuable building blocks for drug synthesis, have been prepared from L-Ala, L-Val, L-Leu, L-Ile, L-Phe, L-Cys, L-Ser, L-Thr, and D-penicillamine by transformation of the COOH group into a methylsulfonyl chloride function, followed by cyclization under basic conditions. Selected properties, derivatives, and reactions of the β-sultams are described.