1-(2-Amino-5-hydroxyphenyl)propan-1-one

Base Information

• Chemical Name: 1-(2-Amino-5-hydroxyphenyl)propan-1-one
• CAS No.: 35364-15-9
• Molecular Formula: C9H11 N O2
• Molecular Weight: 165.192
• European Community (EC) Number: 680-346-2
• Nikkaji Number: J2.256.793D
• Mol file: 35364-15-9.mol

Synonyms:1-(2-amino-5-hydroxyphenyl)propan-1-one;35364-15-9;1-(2-amino-5-hydroxyphenyl)-1-propanone;1-Propanone,1-(2-amino-5-hydroxyphenyl)-;SCHEMBL459040;BCP32212;MFCD16877176;AKOS015890633;SY316861;1-(2-Amino-5-hydroxyphenyl)propane-1-one;F70655;A1-05708;2-Amino-5-Hydroxypropiophenone

Chemical Property of 1-(2-Amino-5-hydroxyphenyl)propan-1-one

Chemical Property:

• Melting Point: 144.5-144.9 °C
• Boiling Point: 363.9±32.0 °C(Predicted)
• PKA: 9.35±0.18(Predicted)
• PSA: 63.32000
• Density: 1.195±0.06 g/cm3(Predicted)
• LogP: 2.14830
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

1-(2-Amino-5-hydroxyphenyl)propan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C1=C(C=CC(=C1)O)N
• Uses: 1-(2-Amino-5-hydroxyphenyl)propan-1-one is a useful synthetic intermediate. It is used in the asymmetrical synthesis of (S)-4-ethyl-6,7,8,10- tetrahydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a key intermediate for synthesis of irinotecan and other camptothecin analogs. It is also used in the synthesis of E-?ring-?modified (RS)?-?camptothecin analogs as antitumor agents.

Technology Process of 1-(2-Amino-5-hydroxyphenyl)propan-1-one

There total 17 articles about 1-(2-Amino-5-hydroxyphenyl)propan-1-one 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-(5-hydroxy-2-nitrophenyl)propan-1-one (453518-19-9) → 2'-amino-5'-hydroxypropiophenone (35364-15-9)

Guidance literature:

With sodium dithionite; water; sodium carbonate; at 20 ℃; for 1h;

DOI:10.1080/00397911.2012.658947

Reference yield: 84.0%

1-(5-benzyloxy-2-nitrophenol)-2-propen-1-one (453518-18-8) → 2'-amino-5'-hydroxypropiophenone (35364-15-9)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethyl acetate; at 0 - 25 ℃; for 13h;

Reference yield: 76.0%

→ 2'-amino-5'-hydroxypropiophenone (35364-15-9)

Guidance literature:

upstream raw materials:

1-(5-benzyloxy-2-nitrophenol)-2-propen-1-one

1-(5-hydroxy-2-nitrophenyl)propan-1-one

ethyl bromide

2-amino-5-methoxybenzonitrile

Downstream raw materials:

7-ethyl-10-hydroxycamptothecin

4,11-diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione

2'-amino-5'-tert-butoxycarbonyloxypropiophenone

irinotecan

Refernces

• 1、 Rao, A. V. Rama,Rao, Ramakrishna,Yadav,Khagga, Mukkanti. "Scalable synthetic route to 2-amino-5-hydroxypropiophenone: Efficient formal synthesis of irinotecan". . p. 1661 - 1667. Retrieved 2013/05/21.
• 2、 -. "Method of Synthesizing Key Intermediates for the Production of Camptothecin Derivatives". Page/Page column 3; 5. . Retrieved 2008/12/08.