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

• 7684-27-7 3-benzylmorpholine 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 77363-90-7 (4E,6E)-2-hydroxy-2-methyl-7-phenylhepta-4,6-dien-3-one 
• 1417827-02-1 C₂₂H₂₅NO₂ 
• 207120-52-3 (S)-2-chloro-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide 
• 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 

Downstream Products

• 1346682-08-3 benzyl (3R)-3-benzylmorpholine-4-carboxylate 
• 1417827-03-2 (S)-benzyl 3-benzylmorpholine-4-carboxylate 

Relevant articles and documents

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.

Diastereoselective synthesis of tetrasubstituted propargylamines via hydroamination and metalation of 1-alkynes and their enantioselective conversion to trisubstituted chiral allenes

Reaction of cyclic secondary amines with 1-alkynes and copper(I) chloride at 110-120 °C gives the corresponding alkynylcopper complex, which adds to the iminium ion intermediate formed in situ by hydroamination of 1-alkynes to give the corresponding propargylamine derivatives in up to 94% yield and 99% regioselectivity. The diastereomerically pure chiral propargylamines were obtained in 23-89% yield using optically active 2-benzyl morpholine and N-methyl camphanyl piperazine. These chiral propargylamines are readily converted to the corresponding trisubstitued chiral allenes in 71-89% yields with up to 99% ee upon reaction with ZnBr2 at 120 °C. The results are discussed considering mechanisms involving diastereoselective addition of alkynylcopper complex formed in situ to iminium ions formed in situ regioselectively to produce the corresponding propargylamines, which in turn give the chiral allenes with very high enantioselectivity via an intramolecular 1,5-hydrogen shift in the presence of zinc bromide.

Amine-promoted asymmetric (4+2) annulations for the enantioselective synthesis of tetrahydropyridines: A traceless and recoverable auxiliary strategy

Gone, without a trace: The in situ reaction of 2-(acetoxymethyl)buta-2,3- dienoate and a secondary amine produces a 2-methylene-3-oxobutanoate equivalent that can be used in asymmetric [4+2] annulations with N-tosylimines to provide tetrahydropyridines in