Ethyl 2-acetylpentanoate

Base Information

• Chemical Name: Ethyl 2-acetylpentanoate
• CAS No.: 1540-28-9
• Deprecated CAS: 123325-83-7
• Molecular Formula: C9H16O3
• Molecular Weight: 172.224
• European Community (EC) Number: 216-269-4
• NSC Number: 67958,6764
• DSSTox Substance ID: DTXSID40870885
• Nikkaji Number: J136.404I
• Mol file: 1540-28-9.mol

Synonyms:Ethyl 2-acetylpentanoate;1540-28-9;Ethyl 2-propylacetoacetate;Ethyl 2-acetylvalerate;Ethyl 2-n-propylacetoacetate;Pentanoic acid, 2-acetyl-, ethyl ester;n-Amyl acetoacetate;Ethyl alpha-propylacetoacetate;NSC 6764;EINECS 216-269-4;NSC 67958;Valeric acid, 2-acetyl-, ethyl ester;AI3-06005;Ethyl .alpha.-propylacetoacetate;2-ACETYL-PENTANOIC ACID ETHYL ESTER;Ethyl 2-propyl-3-oxobutanoate;2-Acetylvaleric acid ethyl ester;Ethyl2-acetylpentanoate;2-Acetylpentanoicacidethylester;SCHEMBL3010250;Ethyl 2-(n-propyl)acetoacetate;DTXSID40870885;NSC6764;NSC-6764;NSC67958;MFCD00048563;NSC-67958;AKOS006220441;2-Propyl-3-oxobutanoic acid ethyl ester;LS-06676;CS-0216383;FT-0633648;EN300-41607

Chemical Property of Ethyl 2-acetylpentanoate

Chemical Property:

• Vapor Pressure: 0.0934mmHg at 25°C
• Refractive Index: 1.424
• Boiling Point: 224 °C at 760 mmHg
• PKA: 12.17±0.46(Predicted)
• Flash Point: 82.4 °C
• PSA: 43.37000
• Density: 0.967 g/cm³
• LogP: 1.55480
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 172.109944368
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2-acetylpentanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)C)C(=O)OCC
• Uses: Ethyl 2-acetylpentanoate (CAS# 1540-28-9) is an intermediate in the synthesis of 3-[(Dimethylamino)methyl]-2-hexanone (D462285), derived from Ethyl Acetoacetate (E899545), which is a chemical intermediate us in the production of various analgesics, antibiotics, and antimalarial agents.

Technology Process of Ethyl 2-acetylpentanoate

There total 16 articles about Ethyl 2-acetylpentanoate 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: 80.0%

2-bromo-acrylic acid ethyl ester (5459-35-8) + 1-(trimethylsilyl)ethanone (13411-48-8) + diethylzinc (557-20-0) → ethyl 2-propylacetoacetate (1540-28-9)

Guidance literature:

In n-heptane; dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.tet.2015.09.045

Reference yield: 78.0%

ethyl acetoacetate (141-97-9) + 1-iodo-propane (107-08-4) → ethyl 2-propylacetoacetate (1540-28-9)

Guidance literature:

ethyl acetoacetate; With sodium; In ethanol; for 0.5h; Inert atmosphere; Reflux;

1-iodo-propane; for 2.5h; Reflux; Inert atmosphere;

Reference yield: 50.0%

ethyl acetoacetate (141-97-9) + propyl bromide (106-94-5) → ethyl 2-propylacetoacetate (1540-28-9)

Guidance literature:

ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 40 ℃; for 2h;

propyl bromide; In tetrahydrofuran; at 80 ℃;

DOI:10.1016/j.bioorg.2011.10.005

upstream raw materials:

ethyl acetoacetate

propyl bromide

1-iodo-propane

sodium ethyl acetylacetate enolate

Downstream raw materials:

2-propyl-acetoacetic acid p-toluidide

N,N'-bis(4-chlorophenyl)urea

6-methyl-5-propyl-2-thiouracil

N,N-diphenylurea

Refernces

• 1、 Kou, Xuezhen,Shao, Qihang,Ye, Chenghao,Yang, Guoqiang,Zhang, Wanbin. "Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters". supporting information. p. 7587 - 7597. Retrieved 2018/06/04.
• 2、 -. "ALLOSTERIC MODULATORS OF THE CANNIBINOID 1 RECEPTOR". Paragraph 0269. . Retrieved 2015/03/13.