Phenyl acetoacetate

Base Information

• Chemical Name: Phenyl acetoacetate
• CAS No.: 6864-62-6
• Molecular Formula: C10H10 O3
• Molecular Weight: 178.188
• Hs Code.: 2918300090
• European Community (EC) Number: 229-963-7
• DSSTox Substance ID: DTXSID00218729
• Nikkaji Number: J265.936K
• Wikidata: Q83095633
• Mol file: 6864-62-6.mol

Synonyms:Phenyl acetoacetate;phenyl 3-oxobutanoate;6864-62-6;EINECS 229-963-7;phenyl3-oxobutanoate;O-acetoacetyl-phenol;SCHEMBL329955;3-Oxobutyric acid phenyl ester;DTXSID00218729;MFCD03792524;MFCD24390719;BS-24627;F12019

Chemical Property of Phenyl acetoacetate

Chemical Property:

• Vapor Pressure: 0.00258mmHg at 25°C
• Melting Point: 42.5 °C
• Boiling Point: 286.8°C at 760 mmHg
• PKA: 9.73±0.46(Predicted)
• Flash Point: 124.6°C
• PSA: 43.37000
• Density: 1.133g/cm³
• LogP: 1.57110
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

Phenyl3-oxobutanoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)OC1=CC=CC=C1

Technology Process of Phenyl acetoacetate

There total 8 articles about Phenyl acetoacetate 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%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + phenol (108-95-2,27073-41-2) → phenyl acetoacetate (6864-62-6)

Guidance literature:

In xylene; at 150 ℃; for 0.5h;

DOI:10.1021/jo00214a006

Reference yield: 85.0%

ethyl acetoacetate (141-97-9) + phenol (108-95-2,27073-41-2) → phenyl acetoacetate (6864-62-6)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide; for 0.0111111h; Reagent/catalyst; Microwave irradiation;

DOI:10.1080/00397911.2020.1750033

Reference yield: 78.0%

n-butanethiol (109-79-5) + 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) → phenyl acetoacetate (6864-62-6)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 145 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol5005643

upstream raw materials:

4-methyleneoxetan-2-one

phenol

2,2,6-trimethyl-4H-1,3-dioxin-4-one

tert-butyl acetoacetate

Downstream raw materials:

(2S,3aR,7R,7aS)-7-Hydroxy-2-methyl-2-phenoxycarbonylmethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

(2R,3aR,7R,7aS)-7-Hydroxy-2-methyl-2-phenoxycarbonylmethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

1,3-Dimethyl-6-oxo-2-phenyl-2,6-dihydro-cyclohepta[c]pyrrole-5-carboxylic acid phenyl ester

7-hydroxy-4-methyl-chromen-2-one

Refernces

• 1、 Chityala, Yadaiah,Duguta, Govardhan,Kamatala, Chinna Rajanna,Muddam, Bhooshan,Mukka, Satish Kumar. "N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters". supporting information. p. 1641 - 1655. Retrieved 2020/05/25.
• 2、 Xin, Dongyue,Burgess, Kevin. "A chemoselective route to β-enamino esters and thioesters". supporting information. p. 2108 - 2110. Retrieved 2014/05/06.