3-[(1S)-1-(Dimethylamino)ethyl]phenol

Base Information

• Chemical Name: 3-[(1S)-1-(Dimethylamino)ethyl]phenol
• CAS No.: 139306-10-8
• Molecular Formula: C10H15NO
• Molecular Weight: 165.235
• Hs Code.: 29222990
• European Community (EC) Number: 478-670-2,691-246-3
• UNII: 1608PLR9ZO
• DSSTox Substance ID: DTXSID60161005
• Wikidata: Q27095312
• Metabolomics Workbench ID: 148997
• Mol file: 139306-10-8.mol

Synonyms:3-(1-dimethylaminoethyl)phenol;NAP 226-90;NAP-226-90;NAP226-90

Chemical Property of 3-[(1S)-1-(Dimethylamino)ethyl]phenol

Chemical Property:

• Appearance/Colour: off-white to pale yellow crystal
• Vapor Pressure: 0.0233mmHg at 25°C
• Melting Point: 87-88 °C
• Refractive Index: 1.539
• Boiling Point: 241.3 °C at 760 mmHg
• PKA: 9.86±0.10(Predicted)
• Flash Point: 97.2 °C
• PSA: 23.47000
• Density: 1.021 g/cm³
• LogP: 2.01480
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 165.115364102
• Heavy Atom Count: 12
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

NAP226-90 ^*data from reagent suppliers

Safty Information:

• Statements: 36-43
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC=C1)O)N(C)C
• Isomeric SMILES: C[C@@H](C1=CC(=CC=C1)O)N(C)C
• Recent ClinicalTrials: A Phase I/II Clinical Study of SAF-189s in Non-small Cell Lung Cancer (NSCLC) Patients
• Description: NAP 226-90 is a metabolite of rivastigmine that is formed by hydrolysis.
• Uses: S-Enantiomer metabolite of Rivastigmine, a brain selective acetylcholinesterase inhibitor NAP 226-90 (Rivastigmine EP Impurity A; Rivastigmin USP Related Compound C) is a S-Enantiomer metabolite of Rivastigmine, a brain selective acetylcholinesterase inhibitor.

Technology Process of 3-[(1S)-1-(Dimethylamino)ethyl]phenol

There total 46 articles about 3-[(1S)-1-(Dimethylamino)ethyl]phenol 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: 97.0%

S-(-)-[1-(3-methoxyphenyl)ethyl]-N,N-dimethylamine (889443-69-0) → (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8)

Guidance literature:

S-(-)-[1-(3-methoxyphenyl)ethyl]-N,N-dimethylamine; With water; hydrogen bromide; at 100 ℃; for 10h; Sealed tube;

With potassium carbonate; In water;

DOI:10.1021/jo900784g

Reference yield: 92.0%

(S)-(1-(3-methoxymethoxy)phenyl)-N,N-dimethylethanamine (1243322-14-6) → (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; for 0.0333333h;

DOI:10.1039/c0cc00585a

Reference yield: 90.0%

3-[(S)-1-(methylamino)ethyl]phenol (894079-42-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8)

Guidance literature:

With formic acid; In water; at 70 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1080/00397911.2010.527425

upstream raw materials:

formaldehyd

3-acetylphenyl acetate

C₁₀H₁₅NO*C₁₀H₁₆O₄S

(+/-)-3-<1-(Dimethylamino)ethyl>phenol

Downstream raw materials:

C₁₉H₂₄N₂O₂

S-rivastigmine-atomoxetine

C₂₀H₂₆N₂O₂

S-rivastigmine-l-amphetamine

Refernces

• 1、 Abdur-Rashid, Kamaluddin,Abdur-Rashid, Kareem,Dasgupta, Tara,Jia, Wenli,Lorraine, Shannen,Maragh, Paul. "Biaryl diphosphine ligands and their ruthenium complexes: Preparation and use for catalytic hydrogenation of ketones". . . Retrieved 2020/07/10.
• 2、 -. "Synthetic method of rivastigmine chiral intermediate". . . Retrieved 2020/07/15.