5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone

Base Information

• Chemical Name: 5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone
• CAS No.: 56980-94-0
• Molecular Formula: C₁₅H₂₄N₂O₃
• Molecular Weight: 280.367
• DSSTox Substance ID: DTXSID50972460
• Mol file: 56980-94-0.mol

Synonyms:56980-94-0;5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone;CCRIS 4210;1-[5-amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]ethanone;N-112;5-Amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]acetophenone;3-acetyl-4-[3-(1,1-dimethylethylamino)-2-hydroxy-propoxy]aniline;1-(5-Amino-2-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)ethanone;Ethanone, 1-(5-amino-2-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)-;1-{5-Amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}ethan-1-one;1-[5-Amino-2-[(2RS)-3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]phenyl]ethanone;SCHEMBL10365460;DTXSID50972460;LS-67117;FT-0661625

Chemical Property of 5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone

Chemical Property:

• Vapor Pressure: 1.02E-09mmHg at 25°C
• Boiling Point: 472.1°Cat760mmHg
• Flash Point: 239.3°C
• PSA: 84.58000
• Density: 1.107g/cm³
• LogP: 2.57130
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 280.17869263
• Heavy Atom Count: 20
• Complexity: 315

Purity/Quality:

98%min ^*data from raw suppliers

5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C=CC(=C1)N)OCC(CNC(C)(C)C)O

Technology Process of 5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone

There total 12 articles about 5-Amino-2-(3-(tert-butylamino)-2-hydroxypropoxy)acetophenone 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: 92.0%

1-{2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-nitrophenyl}ethan-1-one (329722-32-9) → 1-{5-amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}ethan-1-one (56980-94-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; under 1034.32 Torr;

DOI:10.1021/op000297l

Reference yield:

1-[2-(3-tert-butylamino-2-hydroxy-propoxy)-5-nitro-phenyl]-ethanone (329722-32-9) → 1-[5-amino-2-(3-tert-butylamino-2-hydroxy-propoxy)-phenyl]-ethanone (56980-94-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; at 20 ℃; under 1034.3 Torr;

DOI:10.1016/j.tet.2005.01.074

Reference yield:

allyl 2-acetyl-4-nitrophenyl ether (850427-85-9) → 1-[5-amino-2-(3-tert-butylamino-2-hydroxy-propoxy)-phenyl]-ethanone (56980-94-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / (DHQD)2-PHAL; OsO₄; K₂CO₃ / K₂Fe(CN)6 / 2-methyl-propan-2-ol; H₂O; toluene / 0 °C

2.1: SOCl₂; Et₃N / CH₂Cl₂ / 0 °C

3.1: 932 mg / RuCl₃*3H₂O; NaIO₄ / acetonitrile; H₂O / 0 °C

4.1: LiBr / tetrahydrofuran / 25 °C

4.2: aq. H₂SO₄ / diethyl ether / 25 °C

4.3: 85 percent / K₂CO₃ / methanol / 2 h / 0 °C

5.1: H₂O / 1 h / Heating

6.1: H₂ / Pd/C / 20 °C / 1034.3 Torr

With ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; hydrogen; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; palladium on activated charcoal; K₂Fe(CN)6; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2005.01.074

upstream raw materials:

1-[2-(3-tert-butylamino-2-hydroxy-propoxy)-5-nitro-phenyl]-ethanone

allyl 2-acetyl-4-nitrophenyl ether

(2S)-3-(2-acetyl-4-nitrophenoxy)-1,2-epoxypropane

(S)-3-(2'-acetyl-4'-nitrophenoxy)-1,2-propanediol

Refernces

• 1、 Joshi, Ramesh A.,Gurjar, Mukund K.,Tripathy, Narendra K.,Chorghade, Mukund S.. "A new and improved process for celiprolol hydrochloride". . p. 176 - 178. Retrieved 2013/09/07.