Methyl 3-(4-chlorophenyl)-3-oxopropanoate

Base Information

• Chemical Name: Methyl 3-(4-chlorophenyl)-3-oxopropanoate
• CAS No.: 22027-53-8
• Molecular Formula: C10H9 Cl O3
• Molecular Weight: 212.633
• Hs Code.: 2918300090
• European Community (EC) Number: 627-449-0
• DSSTox Substance ID: DTXSID70967631
• Nikkaji Number: J1.248.316C
• Wikidata: Q82950238
• Mol file: 22027-53-8.mol

Synonyms:methyl 3-(4-chlorophenyl)-3-oxopropanoate;Methyl 4-chlorobenzoylacetate;22027-53-8;53101-00-1;Methyl (4-chlorobenzoyl)acetate;Methyl(4-chlorobenzoyl)acetate;SCHEMBL1531237;DTXSID70967631;OIPOJEDRCKVDJK-UHFFFAOYSA-N;AMY14647;XAA02753;AB7497;MFCD00216520;AKOS001471540;p-chloro-benzoylacetic acid methyl ester;AS-11472;A4734;BB 0296200;CS-0067987;FT-0655111;FT-0676499;EN300-30884;methyl 3-(4-chlorophenyl)-3-keto-propanoate;3-(4-chlorophenyl)-2-methyl-3-oxopropanoic acid;J-014432;3-(4-chlorophenyl)-3-oxopropionic acid methyl ester;Z317040222

Chemical Property of Methyl 3-(4-chlorophenyl)-3-oxopropanoate

Chemical Property:

• Vapor Pressure: 0.00123mmHg at 25°C
• Melting Point: 42-46 °C(lit.)
• Refractive Index: 1.528
• Boiling Point: 100-106°C 0,2mm
• PKA: 9.54±0.25(Predicted)
• Flash Point: 125.5°C
• PSA: 43.37000
• Density: 1.255g/cm³
• LogP: 2.08580
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 212.0240218
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-(4_Chlorophenyl)-3-oxopropanoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(=O)C1=CC=C(C=C1)Cl
• Uses: Reactant involved in:Oxidative coupling with aminopyridinesEnantioselective hydrogenation of unprotected β-enamine estersIntramolecular cyclizationOxidative alkylation of benzylic C-H bondsTandem oxidative coupling and annulation of phenols

Technology Process of Methyl 3-(4-chlorophenyl)-3-oxopropanoate

There total 11 articles about Methyl 3-(4-chlorophenyl)-3-oxopropanoate 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: 97.0%

para-chloroacetophenone (99-91-2) + carbonic acid dimethyl ester (616-38-6) → methyl 3-(4-chlorophenyl)-3-oxopropanoate (22027-53-8)

Guidance literature:

With sodium hydride; In toluene; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.7b01706

Reference yield: 70.0%

4-chlorobenzaldehyde (104-88-1) + methyl diazoacetate (6832-16-2) → methyl 3-(4-chlorophenyl)-3-oxopropanoate (22027-53-8)

Guidance literature:

With Cu(II)-Mont K 10 clay; In benzene; at 80 ℃; for 2h;

DOI:10.1039/a905028k

Reference yield: 60.0%

magnesium monomethyl malonate + para-chlorobenzoic acid (74-11-3) → methyl 3-(4-chlorophenyl)-3-oxopropanoate (22027-53-8)

Guidance literature:

para-chlorobenzoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 10h;

magnesium monomethyl malonate; In tetrahydrofuran; at 20 ℃; for 18h; Further stages.;

DOI:10.1002/adsc.200390021

upstream raw materials:

4-chloro-benzoyl chloride

acetoacetic acid methyl ester

4-chlorobenzaldehyde

methyl diazoacetate

Downstream raw materials:

N-(p-Chlorphenyl)-p-chlorbenzoyl-acetamid

C₁₉H₁₆ClNO₂

methyl 3-(4-chlorophenyl)-3-(phenylamino)acrylate

dimethyl 2,4-bis(4-chlorobenzoyl)pentanedioate

Refernces

• 1、 Wu, Jun,Hou, Zhipeng,Wang, Yan,Chen, Liping,Lian, Chengxi,Meng, Qingfei,Zhang, Chaoying,Li, Xiufen,Huang, Longjiang,Yu, Haibo. "Discovery of 7-alkyloxy- [1,2,4] triazolo[1,5-a] pyrimidine derivatives as selective positive modulators of GABAA1 and GABAA4 receptors with potent antiepileptic activity". . . Retrieved 2021/12/20.
• 2、 -. "AZOLE DERIVATIVES, AND AGRICULTURAL AND HORTICULTURAL CHEMICALS AND INDUSTRIAL MATERIAL PROTECTING AGENTS". Paragraph 0119. . Retrieved 2021/02/13.