3-[1-Hydroxy-2-(methylamino)ethyl]phenol

Base Information

• Chemical Name: 3-[1-Hydroxy-2-(methylamino)ethyl]phenol
• CAS No.: 1477-63-0
• Deprecated CAS: 532-38-7
• Molecular Formula: C9H13 N O2
• Molecular Weight: 167.208
• European Community (EC) Number: 215-810-1,216-034-6
• UNII: RH8FKZ05H0
• DSSTox Substance ID: DTXSID20859037
• Nikkaji Number: J28.485H
• Wikidata: Q27288122
• ChEMBL ID: CHEMBL31457
• Mol file: 1477-63-0.mol

Synonyms:dl-Mesatone;3-[1-Hydroxy-2-(methylamino)ethyl]phenol;dl-Phenylephrine;1477-63-0;R,S-Phenylephrine;(+-)-Neosynephrine;(+-)-Phenylephrine;(+/-)-phenylephrine;EINECS 216-034-6;UNII-RH8FKZ05H0;RH8FKZ05H0;(+-)-m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol;3-(1-hydroxy-2-(methylamino)ethyl)phenol;Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (+-)-;BENZYL ALCOHOL, m-HYDROXY-alpha-((METHYLAMINO)METHYL)-, (+-)-;Benzenemethanol, 3-hydroxy-a-[(methylamino)methyl]-;(1)-3-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol;(R)-3-Hydroxy-alpha-[(methylamino)methyl]benzenemethanol hydrochloride;1416-03-1;Phenylephrine,(+/-);Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-;BENZENEMETHANOL, 3-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-;l -phenylephrine;3-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol;(.+/-.)-Neosynephrine;(.+/-.)-Phenylephrine;SCHEMBL4712;1-(3-hydroxyphenyl)-2-(methylamino)ethan-1-ol;TimTec1_001987;Oprea1_728868;CHEMBL31457;(+/-)-NEOSYNEPHRINE;Benzyl alcohol, m-hydroxy-.alpha.-((methylamino)methyl)-, (-)-;m-Hydroxyphenylmethylaminoethanol;DTXSID20859037;CHEBI:182853;PHENYLEPHRINE, (+/-)-;BDBM162129;HMS1539K07;BBL028092;PDSP1_001109;PDSP2_001093;STL301903;AKOS004111099;NCGC00015825-03;AM100259;LS-43026;LS-43030;VS-08664;3-(1-Hydroxy-2-methylamino-ethyl)-phenol;FT-0603248;3-[1-Hydroxy-2-(methylamino)ethyl]phenol #;(S)-3-OH-[(methylamino)methyl]benzyl alcohol;1-(3-Hydroxyphenyl)-2-(N-methylamino)ethanol;(+/-)-3-OH-[(methylamino)methyl]benzyl alcohol;1-(3-HYDROXYPHENYL)-2-METHYLAMINOETHANOL;L000677;m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol;W-109574;W-109670;3-Hydroxy-.alpha.-((methylamino)methyl)benzyl alcohol;Q27288122;Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-;Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-;(+-)-3-hydroxy-alpha-[(methylamino)methyl]benzyl alcohol;(.+/-.)-m-Hydroxy-.alpha.-((methylamino)methyl)benzyl alcohol;Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (.+.)-;Benzyl alcohol, m-hydroxy-.alpha.-[(methylamino)methyl]-, (.+.)-;BENZENEMETHANOL, 3-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (+/-)-;Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (.+/-.)-;Benzyl alcohol, m-hydroxy-.alpha.-((methylamino)methyl)-, (.+/-.)-

Chemical Property of 3-[1-Hydroxy-2-(methylamino)ethyl]phenol

Chemical Property:

• Boiling Point: 341.1°Cat760mmHg
• Flash Point: 163.4°C
• Density: 1.159g/cm³
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 167.094628657
• Heavy Atom Count: 12
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(C1=CC(=CC=C1)O)O

Technology Process of 3-[1-Hydroxy-2-(methylamino)ethyl]phenol

There total 16 articles about 3-[1-Hydroxy-2-(methylamino)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: 82.0%

N-[2-(3-hydroxyphenyl)-2-oxo-ethyl]-N-methyl-acetamide (1262121-47-0) → Phenylephrine (1477-63-0) + C11H15NO3 (1262121-49-2)

Guidance literature:

With C₆₅H₇₆Cl₂N₄O₆P₂Ru; hydrogen; potassium hydroxide; In water; isopropyl alcohol; at 63 ℃; for 3h; under 22502.3 - 23252.3 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1016/j.tetasy.2010.09.013

Reference yield: 67.0%

1-(3-methoxymethoxy-phenyl)-2-methylamino-ethanol (1089675-34-2) → Phenylephrine (1477-63-0)

Guidance literature:

1-(3-methoxymethoxy-phenyl)-2-methylamino-ethanol; With hydrogenchloride; water; In methanol; for 0.5h; Heating / reflux;

With ammonia; water; In methanol; dichloromethane;

Reference yield:

→ Phenylephrine (1477-63-0)

Guidance literature:

With ethanol; nickel; at 40 ℃; Hydrogenation;

upstream raw materials:

5-(3-benzyloxy-phenyl)-3-methyl-oxazolidin-2-one

1-(3-hydroxyphenyl)-2-nitro-ethanol

2-(benzyl(methyl)amino)-1-(3'-hydroxyphenyl)ethanone hydrochloride

1-(3-methoxymethoxy-phenyl)-2-methylamino-ethanol

Downstream raw materials:

2-Methyl-4,6-dihydroxy-1,2,3,4-tetrahydroisoquinoline

N-acetyl-1-(3-hydroxyphenyl)-2-methylaminoethanol

phenylephrine hydrochloride

(+)-1-acetoxy-1-(3-acetoxy-phenyl)-2-methylamino-ethane

Refernces

• 1、 McGarrity, John F.,Zanotti-Gerosa, Antonio. "A feasibility study on the synthesis of phenylephrine via ruthenium-catalyzed homogeneous asymmetric hydrogenation". experimental part. p. 2479 - 2486. Retrieved 2011/02/22.