4-Benzyl Albuterol

Base Information

• Chemical Name: 4-Benzyl Albuterol
• CAS No.: 56796-66-8
• Molecular Formula: C20H27 N O3
• Molecular Weight: 329.439
• European Community (EC) Number: 260-385-8
• UNII: 2092ANO5GJ
• DSSTox Substance ID: DTXSID90866591
• Nikkaji Number: J267.108E
• Wikidata: Q27253447
• Mol file: 56796-66-8.mol

Synonyms:4-Benzyl Albuterol;56796-66-8;Salbutamol Impurity I;1-(4-(Benzyloxy)-3-(hydroxymethyl)phenyl)-2-(tert-butylamino)ethanol;2-(tert-butylamino)-1-[3-(hydroxymethyl)-4-phenylmethoxyphenyl]ethanol;EINECS 260-385-8;UNII-2092ANO5GJ;4-(benzyloxy)-alpha-[[tert-butylamino]methyl]-m-xylene-alpha,alpha'-diol;2092ANO5GJ;4-(Benzyloxy)-alpha-((tert-butylamino)methyl)-m-xylene-alpha,alpha'-diol;(1RS)-2-[(1,1-Dimethylethyl)amino]-1-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]ethanol;(1RS)-2-((1,1-DIMETHYLETHYL)AMINO)-1-(4-(BENZYLOXY)-3-(HYDROXYMETHYL)PHENYL)ETHANOL;Salbutamol EP Impurity I;SCHEMBL4667082;DTXSID90866591;BCP15728;ZGA60768;1-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-(tert-butylamino)ethan-1-ol;AKOS024323971;SALBUTAMOL IMPURITY I [EP IMPURITY];FT-0662669;SALBUTAMOL SULFATE IMPURITY I [EP IMPURITY];Q27253447;1-(4-BENZYLOXY-3-HYDROXYMETHYL-PHENYL)-2-(TERT BUTYLAMINO)ETHANOL;1-(4-BENZYLOXY-3-HYDROXYMETHYL-PHENYL)-2-(TERT. BUTYLAMINO)ETHANOL;(+/-)-1-(4-(BENZYLOXY)-3-(HYDROXYMETHYL)PHENYL)-2-(TERT-BUTYLAMINO)ETHANOL;3-(Hydroxymethyl)-alpha-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)benzenemethanol;4-benzyl salbutamol;Rosiglitazone Impurity I (Pharmeuropa);1,3-BENZENEDIMETHANOL, .ALPHA.1-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-(PHENYLMETHOXY)-

Chemical Property of 4-Benzyl Albuterol

Chemical Property:

• Boiling Point: 510.1°Cat760mmHg
• PKA: 13.97±0.20(Predicted)
• Flash Point: 262.3°C
• PSA: 61.72000
• Density: 1.12g/cm³
• LogP: 3.57030
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 329.19909372
• Heavy Atom Count: 24
• Complexity: 349

Purity/Quality:

99.9% ^*data from raw suppliers

4-BenzylAlbuterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)NCC(C1=CC(=C(C=C1)OCC2=CC=CC=C2)CO)O
• Uses: 4-Benzyl Albuterol is used as the Salbutamol precursor. Impurity of Rosiglitazone Maleate Imp A (Pharmeuropa).

Technology Process of 4-Benzyl Albuterol

There total 7 articles about 4-Benzyl Albuterol 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: 90.0%

methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(benzyloxy) benzoate (174607-70-6) → α1-[[(1,1-dimethylethyl)amino]methyl]-4-(benzyloxy)-1,3-benzenedimethanol (56796-66-8)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152126

Reference yield:

diacetate salt of (S)-salbutamol (1005420-25-6) + diacetate salt of (R)-salbutamol (1005420-26-7) → α1-[[(1,1-dimethylethyl)amino]methyl]-4-(benzyloxy)-1,3-benzenedimethanol (56796-66-8)

Guidance literature:

With sodium hydroxide; water; at 80 - 85 ℃; for 15 - 16h;

Reference yield:

5-acetyl-2-benzyloxybenzoic acid methyl ester (27475-09-8) → α1-[[(1,1-dimethylethyl)amino]methyl]-4-(benzyloxy)-1,3-benzenedimethanol (56796-66-8)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen bromide; water; dimethyl sulfoxide / acetonitrile / 4 h / 40 - 60 °C / Inert atmosphere

2: Isopropyl acetate / 2.5 h / 40 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol / 2.33 h / 20 - 35 °C / Inert atmosphere

4: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 60 °C / Inert atmosphere

With sodium tetrahydroborate; water; hydrogen bromide; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In methanol; Isopropyl acetate; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2020.152126

upstream raw materials:

diacetate salt of (S)-salbutamol

diacetate salt of (R)-salbutamol

5-acetyl-2-benzyloxybenzoic acid methyl ester

methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(benzyloxy) benzoate

Downstream raw materials:

4-nitro tartranilic acid salt of (R)-isomer of 4-benzyl salbutamol

2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol

diacetate salt of (S)-salbutamol

diacetate salt of (R)-salbutamol

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF OPTICALLY PURE R (-) SALBUTAMOL AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS". Page/Page column 11. . Retrieved 2008/06/13.