(S)-morpholin-3-ylmethanol

Base Information

• Chemical Name: (S)-morpholin-3-ylmethanol
• CAS No.: 211053-50-8
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• European Community (EC) Number: 866-418-8
• DSSTox Substance ID: DTXSID00363824
• Nikkaji Number: J2.306.542H
• Wikidata: Q72485393
• Mol file: 211053-50-8.mol

Synonyms:(S)-morpholin-3-ylmethanol;211053-50-8;3(S)-Hydroxymethylmorpholine;[(3S)-morpholin-3-yl]methanol;(S)-3-HYDROXYMETHYLMORPHOLINE;(S)-3-(Hydroxymethyl)morpholine;(S)-3-HYDROXYMETHYL-MORPHOLINE;(S)-morpholin-3-yl-methanol;(3s)-morpholine-3-methanol;SCHEMBL18375;(3s)-morpholin-3-ylmethanol;DTXSID00363824;AMY22661;MFCD06799480;MFCD08447345;(3S)-3-Morpholinemethanol,99%e.e.;3-MORPHOLINEMETHANOL, (3S)-;AKOS015855748;DS-1894;CS-0031401;EN300-95214;A18442

Chemical Property of (S)-morpholin-3-ylmethanol

Chemical Property:

• Vapor Pressure: 0.0268mmHg at 25°C
• Melting Point: 112 °C
• Refractive Index: 1.441
• Boiling Point: 218.3 °C at 760 mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 85.9 °C
• PSA: 41.49000
• Density: 1.045 g/cm³
• LogP: -0.70410
• Storage Temp.: 2-8°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 67.4

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-Hydroxymethylmorpholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCC(N1)CO
• Isomeric SMILES: C1COC[C@@H](N1)CO
• Uses: (S)-3-Hydroxymethylmorpholine is a chemical reagent used in the synthesis of Aurora kinase inhibitors, used for their anti-tumor activity. Also used in the preparation of human epidermal growth factor receptor 1 & 2 kinase inhbitors in the treatment of solid tumors.

Technology Process of (S)-morpholin-3-ylmethanol

There total 4 articles about (S)-morpholin-3-ylmethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(S)-4-benzyl-3-(hydroxymethyl)morpholine (101376-25-4) → (S)-3-(hydroxymethyl)morpholine (211053-50-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 48h; under 2100.21 Torr;

DOI:10.1021/acs.jmedchem.9b00972

Reference yield: 87.0%

(R)-3-(tert-butyldiphenylsilyloxymethyl)morpholine (885321-34-6) → (S)-3-(hydroxymethyl)morpholine (211053-50-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2005.12.027

Reference yield:

methanesulfonic acid 2-[2-amino-3-(tert-butyl-diphenyl-silanyloxy)-propoxy]-ethyl ester → (S)-3-(hydroxymethyl)morpholine (211053-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.707 g / Et₃N; N,N-diisopropylethylamine / methanol / 4 h / 80 °C

2: 87 percent / TBAF / tetrahydrofuran

With tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetasy.2005.12.027

upstream raw materials:

(R)-3-(tert-butyldiphenylsilyloxymethyl)morpholine

(S)-4-benzyl-3-(hydroxymethyl)morpholine

(3R)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

Downstream raw materials:

(S)-3-(hydroxymethyl)morpholine-4-carboxylic acid tert-butyl ester

(3S)-3-(3-phenylprop-2-yn-1-yl)morpholine

2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-[(3S)-3-(hydroxymethyl)-morpholin-4-yl]-4-methyl-pyridine-3-carboxylic acid amide

(R)-morpholine-3,4-dicarboxylic acid 4-tert-butyl ester