77897-23-5

Basic information

• Product Name: (S)-3-BENZYLMORPHOLINE
• Synonyms: (3S)-3-Benzylmorpholine;(S)-3-(Phenylmethyl)morpholine;(S)-3-BENZYLMORPHOLINE;3-Benzylmorpholine;(S)-3-BenzylMorpholine HCl;(3S)-3-(phenylmethyl)-Morpholine
• CAS NO: 77897-23-5
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• Product Categories: pharmacetical
• Mol File: 77897-23-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 280.014 °C at 760 mmHg
• Flash Point: 110.773 °C
• Appearance: /
• Density: 1.031 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-3-BENZYLMORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-BENZYLMORPHOLINE(77897-23-5)
• EPA Substance Registry System: (S)-3-BENZYLMORPHOLINE(77897-23-5)

Safety Data

• Hazardous Substances Data: 77897-23-5(Hazardous Substances Data)

Usage

General Description

(S)-3-Benzylmorpholine is a chemical compound that belongs to the morpholine family and is characterized by a morpholine ring structure with a benzyl group attached to one of the nitrogen atoms. It is a chiral compound, meaning it has distinct left- and right-handed forms, with the (S)-enantiomer being the specific version with a left-handed configuration. (S)-3-BENZYLMORPHOLINE has applications in organic synthesis and as a building block for the production of pharmaceuticals, agrochemicals, and other fine chemicals. It can also act as a ligand in coordination chemistry and catalysis, contributing to its utility in various chemical processes and reactions. Additionally, (S)-3-Benzylmorpholine may also be used in research and development of new compounds and materials.

InChI:InChI=1/C11H15NO/c1-2-4-10(5-3-1)8-11-9-13-7-6-12-11/h1-5,11-12H,6-9H2/t11-/m0/s1

Upstream product

• 101250-48-0 (S)-5-benzylmorpholin-3-one 
• 7684-27-7 3-benzylmorpholine 
• 1251331-87-9 2-((3-phenylprop-2-yn-1-yl)oxy)ethan-1-amine 
• 1643771-08-7 (2S)-(4aR,9aS)-6-bromo-3-oxo-2,3,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-4(4aH)-yl 2-methoxy-2-phenylacetate 
• 1643770-97-1 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-methoxy-2-phenylacetate 
• 1643771-03-2 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate 
• 1643771-02-1 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-3-phenylpropanoate 
• 1643771-04-3 (4aR,9aS)-6-bromo-3-oxo-2,3,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-4(4aH)-yl 2-phenylacetate 
• 1643771-01-0 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-azido-3-phenylpropanoate 
• 1643771-00-9 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-methoxy-3-phenylpropanoate 
• 1643770-99-3 (R)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-fluoro-3-(4-methoxyphenyl)propanoate 
• 1643770-98-2 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-ethyl-2-phenylacetate 
• 1643771-12-3 (S)-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-methoxy-2-phenylacetate 
• 1643771-09-8 (S)-2-oxo-3,4-dihydroquinolin-1(2H)-yl 2-methoxy-2-phenylacetate 

Downstream Products

• 1346682-08-3 benzyl (3R)-3-benzylmorpholine-4-carboxylate 
• 1417827-03-2 (S)-benzyl 3-benzylmorpholine-4-carboxylate 
• 39968-33-7 1-hydroxy-7-aza-benzotriazole 
• 1417826-89-1 (S)-1-(3-benzylmorpholino)-3-phenylpropan-1-one 
• 26198-19-6 6-chloro-1-hydroxybenzotriazole 
• 1394957-71-1 (4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one 
• 1643770-69-7 2-((2S)-1-((3S)-3-benzylmorpholino)-1-oxo-3-phenylpropan-2-yl)isoindoline-1,3-dione 
• 1643770-68-6 benzyl ((S)-1-((S)-3-benzylmorpholino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 1643770-67-5 (S)-2-azido-1-((S)-3-benzylmorpholino)-3-phenylpropan-1-one 
• 1643770-66-4 (S)-1-((S)-3-benzylmorpholino)-2-methoxy-3-phenylpropan-1-one 
• 1643770-64-2 (S)-1-((S)-3-benzylmorpholino)-2-phenylbutan-1-one 
• 1643770-65-3 C₂₁H₂₄FNO₃ 
• 1643770-62-0 (2R)-1-((3S)-3-benzylmorpholino)-2-methoxy-2-phenylethanone 

Relevant articles and documents

Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights to Realize the Enantioselective Synthesis of Piperazines

An efficient and practical catalytic approach for the enantioselective synthesis of 3-substituted morpholines through a tandem sequential one-pot reaction employing both hydroamination and asymmetric transfer hydrogenation reactions is described. Starting from ether-containing aminoalkyne substrates, a commercially available bis(amidate)bis(amido)Ti catalyst is utilized to yield a cyclic imine that is subsequently reduced using the Noyori-Ikariya catalyst, RuCl [(S,S)-Ts-DPEN] (η6-p-cymene), to afford chiral 3-substituted morpholines in good yield and enantiomeric excesses of >95%. A wide range of functional groups is tolerated. Substrate scope investigations suggest that hydrogen-bonding interactions between the oxygen in the backbone of the ether-containing substrate and the [(S,S)-Ts-DPEN] ligand of the Ru catalyst are crucial for obtaining high ee's. This insight led to a mechanistic proposal that predicts the observed absolute stereochemistry. Most importantly, this mechanistic insight allowed for the extension of this strategy to include N as an alternative hydrogen bond acceptor that could be incorporated into the substrate. Thus, the catalytic, enantioselective synthesis of 3-substituted piperazines is also demonstrated.

Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles

A novel amine oxidase (AO)/imine reductase (IRED) system was developed for the deracemization of racemic amines. By combining (R)-6-hydroxy-d-nicotine oxidase (6-HDNO) with an (R)-IRED, a panel of racemic 2-substituted piperidines and pyrrolidines were deracemized to yield the (S)-amines in high yields and enantiomeric excess values. Other N-heterocycles were deracemized with monoamine oxidase (MAO-N) or 6-HDNO in combination with ammonia borane, which allowed comparison of the two enzyme deracemization approaches with that involving a chemical reducing agent.

KINETIC RESOLUTION OF CHIRAL AMINES

The present invention refers to a method for the kinetic resolution of a chiral primary or secondary amine by treating the amine with a chiral, hydroxamic acid derived reagent of the formula (I). These chiral reagents are particularly useful for the kinetic resolution of cyclic amines and may be generated in situ in the presence of an N-heterocyclic carbene, thus allowing for a catalytic reaction.