Meluadrine

Base Information

• Chemical Name: Meluadrine
• CAS No.: 134865-33-1
• Molecular Formula: C₁₂H₁₈ClNO₂
• Molecular Weight: 243.733
• UNII: FYC8314117
• DSSTox Substance ID: DTXSID8048810
• Nikkaji Number: J755.206H
• Wikidata: Q27278292
• NCI Thesaurus Code: C66083
• ChEMBL ID: CHEMBL2104709
• Mol file: 134865-33-1.mol

Synonyms:Meluadrine;Meluadrine [INN];134865-33-1;UNII-FYC8314117;4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-3-chlorophenol;FYC8314117;DTXSID8048810;NCGC00183842-01;(-)-(R)-alpha-((tert-Butyl-amino)methyl)-2-chloro-4-hydroxybenzyl alcohol;(-)-(R)-alpha-((tert-Butylamino)methyl)-2-chloro-4-hydroxybenzyl alcohol;Benzenemethanol,2-chloro-a-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-,(aR)-;D0P0TR;SCHEMBL120043;CHEMBL2104709;DTXCID1028736;Tox21_113287;CAS-134865-33-1;Q27278292;(-)-(R)-.ALPHA.-((TERT-BUTYLAMINO)METHYL)-2-CHLORO-4-HYDROXYBENZYL ALCOHOL;(aR)-2-Chloro-a-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-benzenemethanol

Chemical Property of Meluadrine

Chemical Property:

• Vapor Pressure: 7.55E-07mmHg at 25°C
• Boiling Point: 392°Cat760mmHg
• PKA: 8.85±0.31(Predicted)
• Flash Point: 190.9°C
• PSA: 52.49000
• Density: 1.184g/cm³
• LogP: 2.85800
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 243.1026065
• Heavy Atom Count: 16
• Complexity: 218

Purity/Quality:

MELUADRINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NCC(C1=C(C=C(C=C1)O)Cl)O
• Isomeric SMILES: CC(C)(C)NC[C@@H](C1=C(C=C(C=C1)O)Cl)O

Technology Process of Meluadrine

There total 6 articles about Meluadrine 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: 35.0%

1-[4-(benzyloxy)-2-chlorophenyl]-2-(tert-butylamino)ethanol (67759-10-8) → (-)-α-[(tert-Butylamino)methyl]-2-chloro-4-hydroxybenzyl alcohol (58020-43-2,134865-33-1)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20 ℃; for 0.5h; under 3800.26 Torr;

DOI:10.1134/S1070428020030045

Reference yield:

3-monochlorophenol (108-43-0) → (-)-α-[(tert-Butylamino)methyl]-2-chloro-4-hydroxybenzyl alcohol (58020-43-2,134865-33-1)

Guidance literature:

Multi-step reaction with 5 steps

2: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / acetonitrile

3: potassium tert-butylate / dimethyl sulfoxide / 0.5 h / 5 - 20 °C

4: water / 3 h / Reflux

5: 5%-palladium/activated carbon; hydrogen / ethanol / 0.5 h / 20 °C / 3800.26 Torr

With 5%-palladium/activated carbon; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; In ethanol; water; dimethyl sulfoxide; acetonitrile; 1: |Reimer-Tiemann Phenol Formylation / 3: |Johnson-Corey-Chaykovsky Reaction;

DOI:10.1134/S1070428020030045

Reference yield:

2-chloro-4-hydroxybenzaldehyde (56962-11-9) → (-)-α-[(tert-Butylamino)methyl]-2-chloro-4-hydroxybenzyl alcohol (58020-43-2,134865-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / acetonitrile

2: potassium tert-butylate / dimethyl sulfoxide / 0.5 h / 5 - 20 °C

3: water / 3 h / Reflux

4: 5%-palladium/activated carbon; hydrogen / ethanol / 0.5 h / 20 °C / 3800.26 Torr

With 5%-palladium/activated carbon; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; In ethanol; water; dimethyl sulfoxide; acetonitrile; 2: |Johnson-Corey-Chaykovsky Reaction;

DOI:10.1134/S1070428020030045

upstream raw materials:

3-monochlorophenol

2-chloro-4-hydroxybenzaldehyde

4-(benzyloxy)-2-chlorobenzaldehyde

1-[4-(benzyloxy)-2-chlorophenyl]-2-(tert-butylamino)ethanol

Refernces

• 1、 -. "Optically active benzyl alcohol compound and pharmaceutical composition". . . Retrieved 2008/06/13.