(R)-3-(1-(Dimethylamino)ethyl)phenol

Base Information

• Chemical Name: (R)-3-(1-(Dimethylamino)ethyl)phenol
• CAS No.: 851086-95-8
• Molecular Formula: C10H15NO
• Molecular Weight: 165.235
• Hs Code.: 2922299090
• European Community (EC) Number: 804-866-8
• DSSTox Substance ID: DTXSID60437974
• Wikidata: Q72468962
• Mol file: 851086-95-8.mol

Synonyms:(R)-3-(1-(DIMETHYLAMINO)ETHYL)PHENOL;851086-95-8;3-[(1R)-1-(DIMETHYLAMINO)ETHYL]PHENOL;Phenol, 3-[(1R)-1-(dimethylamino)ethyl]-;3-(1-Dimethylamino)ethylphenol;ent NAP 226-90;SCHEMBL12557215;DTXSID60437974;BCP11200;MFCD06656490;AKOS006295625;AS-12937;CS-0059835;W16716;Q-101324

Chemical Property of (R)-3-(1-(Dimethylamino)ethyl)phenol

Chemical Property:

• 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.: Inert atmosphere,Room Temperature
• 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:

98%,99%, ^*data from raw suppliers

entNAP226-90 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Uses: R-Enantiomer metabolite of Rivastigmine, a brain selective acetylcholinesterase inhibitor

Technology Process of (R)-3-(1-(Dimethylamino)ethyl)phenol

There total 3 articles about (R)-3-(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: 94.0%

3-Hydroxyacetophenone (121-71-1) + dimethyl amine (124-40-3) → 3-[1-(dimethylamino)ethyl]phenol (851086-95-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; titanium(IV) isopropylate; hydrogen; iodine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; at 4 ℃; for 20h; under 30402 Torr;

DOI:10.1039/c9sc00323a

Reference yield:

3-Hydroxyacetophenone (121-71-1) + dimethyl amine (124-40-3) → 3-[1-(dimethylamino)ethyl]phenol (851086-95-8) + (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8)

Guidance literature:

With Trimethyl borate; hydrogen; iodine; acetic acid; (R)-diMe-PipPhos; In tetrahydrofuran; acetonitrile; for 20h; under 38002.6 Torr; Overall yield = 93 %; Optical yield = 88 %ee; enantioselective reaction; Autoclave;

Reference yield:

(+/-)-3-<1-(Dimethylamino)ethyl>phenol (105601-04-5) → 3-[1-(dimethylamino)ethyl]phenol (851086-95-8) + (S)-3-(1-dimethylaminoethyl)phenol (139306-10-8)

Guidance literature:

(+/-)-3-<1-(Dimethylamino)ethyl>phenol; With (1S)-10-camphorsulfonic acid; In ethanol; at 40 - 80 ℃; for 0.166667 - 1h; Resolution of racemate;

With water; sodium carbonate; Purification / work up;

upstream raw materials:

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

3-Hydroxyacetophenone

dimethyl amine

Downstream raw materials:

C₂₀H₂₆N₂O₂

Refernces

• 1、 -. "A chiral three-stage amine compound synthetic methods and use thereof". Paragraph 0030; 0033; 0034. . Retrieved 2019/05/21.