1-Phenylethyl acetoacetate

Base Information

• Chemical Name: 1-Phenylethyl acetoacetate
• CAS No.: 40552-84-9
• Deprecated CAS: 134174-91-7
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Hs Code.: 2918300090
• European Community (EC) Number: 254-973-3
• DSSTox Substance ID: DTXSID30885807
• Nikkaji Number: J332.448F
• Mol file: 40552-84-9.mol

Synonyms:1-Phenylethyl acetoacetate;1-PHENYLETHYL 3-OXOBUTANOATE;40552-84-9;alpha-Methylbenzyl acetoacetate;Butanoic acid, 3-oxo-, 1-phenylethyl ester;EINECS 254-973-3;alpha-Phenylacetessigester;SCHEMBL3320374;DTXSID30885807;(rac)-1-phenylethyl 3-oxobutanoate;3-Oxobutyric acid 1-phenylethyl ester;AKOS024323859;LS-46392

Chemical Property of 1-Phenylethyl acetoacetate

Chemical Property:

• Vapor Pressure: 0.00263mmHg at 25°C
• Boiling Point: 286.5°Cat760mmHg
• Flash Point: 121.9°C
• PSA: 43.37000
• Density: 1.087g/cm³
• LogP: 2.26990
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

98%Min ^*data from raw suppliers

ALPHA-METHYL-BENZYL-3-OXOBUTYRATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)OC(=O)CC(=O)C
• Uses: 1-Phenylethyl 3-Oxobutanoate is an intermediate for the synthesis of cis-Crotoxyphos (C818825), which is an insecticide.

Technology Process of 1-Phenylethyl acetoacetate

There total 9 articles about 1-Phenylethyl 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: 99.0%

1-Phenylethanol (98-85-1,13323-81-4) + ethyl acetoacetate (141-97-9) → 1-phenylethyl acetoacetate (40552-84-9)

Guidance literature:

With rhizopus niveus lipase; Pseudomonas sp. lipoprotein lipase; Candida antarctica lipase B immobilized on acrylic resin; Carica papaya protease; In toluene; at 40 ℃; for 48h; Enzymatic reaction;

DOI:10.1002/ejoc.201500676

Reference yield: 97.0%

1-Phenylethanol (98-85-1,13323-81-4) + acetoacetic acid methyl ester (105-45-3) → 1-phenylethyl acetoacetate (40552-84-9)

Guidance literature:

sulfated tin oxide; In ethyl acetate; toluene; Petroleum ether;

Reference yield: 94.0%

tert-butyl acetoacetate (1694-31-1) + 1-Phenylethanol (98-85-1,13323-81-4) → 1-phenylethyl acetoacetate (40552-84-9)

Guidance literature:

With rhizopus niveus lipase; Pseudomonas sp. lipoprotein lipase; Candida antarctica lipase B immobilized on acrylic resin; Carica papaya protease; In toluene; at 40 ℃; for 48h; Enzymatic reaction;

DOI:10.1002/ejoc.201500676

upstream raw materials:

1-phenylethyl acetate

4-methyleneoxetan-2-one

1-Phenylethanol

diketene

Downstream raw materials:

(R)-1-phenylethyl-(S)-3-hydroxybutanoate

1-phenylethyl 3-hydroxybutanoate

(S)-1-phenylethyl acetoacetate

(R)-1-phenylethyl acetoacetate

Refernces

• 1、 Wisniewska, Catalina,Koszelewski, Dominik,Zysk, Malgorzata,Klossowski, Szymon,Zdlo, Anna,Brodzka, Anna,Ostaszewski, Ryszard. "Enzymatic Synergism in the Synthesis of β-Keto Esters". . p. 5432 - 5437. Retrieved 2015/08/24.
• 2、 Garrett, Christine E.,Fu, Gregory C.. "Nucleophilic catalysis with π-bound nitrogen heterocycles: Synthesis of the first ruthenium catalysts and comparison of the reactivity and the enantioselectivity of ruthenium and iron complexes". . p. 7479 - 7483. Retrieved 2007/10/03.