Ethyl 4-(3-nitrophenyl)-4-oxobutanoate

Base Information

• Chemical Name: Ethyl 4-(3-nitrophenyl)-4-oxobutanoate
• CAS No.: 75227-18-8
• Molecular Formula: C₁₂H₁₃NO₅
• Molecular Weight: 251.239
• Hs Code.: 2918300090
• NSC Number: 162048
• DSSTox Substance ID: DTXSID80303788
• Wikidata: Q82049249
• Mol file: 75227-18-8.mol

Synonyms:75227-18-8;ethyl 4-(3-nitrophenyl)-4-oxobutanoate;ETHYL 4-(3-NITROPHENYL)-4-OXOBUTYRATE;MFCD02261329;NSC162048;DTXSID80303788;AKOS010910718;NSC-162048;ETHYL4-(3-NITROPHENYL)-4-OXOBUTYRATE

Chemical Property of Ethyl 4-(3-nitrophenyl)-4-oxobutanoate

Chemical Property:

• Vapor Pressure: 1.49E-05mmHg at 25°C
• Boiling Point: 366.2°C at 760 mmHg
• Flash Point: 155.6°C
• PSA: 89.19000
• Density: 1.241g/cm³
• LogP: 2.64400
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 251.07937252
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

97% ^*data from raw suppliers

Ethyl4-(3-nitrophenyl)-4-oxobutyrate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCC(=O)C1=CC(=CC=C1)[N+](=O)[O-]

Technology Process of Ethyl 4-(3-nitrophenyl)-4-oxobutanoate

There total 2 articles about Ethyl 4-(3-nitrophenyl)-4-oxobutanoate 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:

3-nitro-benzaldehyde (99-61-6) + ethyl acrylate (140-88-5,9003-32-1) → (E)-ethyl 4-hydroxy-4-(3-nitrophenyl)but-2-enoate (1417403-43-0) + ethyl 4-(3-nitrophenyl)-4-oxobutanoate (75227-18-8)

Guidance literature:

With P(p-CH₃OC₆H₄)3; In chloroform; at 60 ℃; for 24h; Overall yield = 70 %;

DOI:10.1080/00397911.2011.610551

Reference yield:

ethyl 3-iodopropanoate (6414-69-3) + m-nitrobenzoic acid chloride (121-90-4) → ethyl 4-(3-nitrophenyl)-4-oxobutanoate (75227-18-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc copper;

DOI:10.1246/cl.1998.881

Reference yield:

ethyl 4-(3-nitrophenyl)-4-oxobutanoate (75227-18-8) → (R)-3-(3-nitrophenyl)cyclopentanone

Guidance literature:

Multi-step reaction with 3 steps

1: t-BuOK

2: DIBAL-H

3: ClO₄ / CH₂Cl₂ / 2 h

With ClO4; potassium tert-butylate; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1246/cl.1998.881

upstream raw materials:

ethyl 3-iodopropanoate

m-nitrobenzoic acid chloride

3-nitro-benzaldehyde

ethyl acrylate

Downstream raw materials:

4-(3-nitro-phenyl)-pent-4-enal

Refernces

• 1、 Fujio, Masakazu,Tanaka, Masakazu,Wu, Xiao-Ming,Funakoshi, Kazuhisa,Sakai, Kiyoshi,Suemune, Hiroshi. "ortho-halogeno substituents effect in asymmetric cyclization of 4-aryl-4-pentenals using a rhodium catalyst". . p. 881 - 882. Retrieved 2007/10/03.