Methyl 3-oxotetradecanoate

Base Information

• Chemical Name: Methyl 3-oxotetradecanoate
• CAS No.: 22348-97-6
• Molecular Formula: C15H28 O3
• Molecular Weight: 256.386
• Hs Code.: 2918300090
• European Community (EC) Number: 244-929-1
• UNII: 5JZD9UC56Q
• DSSTox Substance ID: DTXSID10176881
• Nikkaji Number: J206.360C
• Wikidata: Q83047216
• Mol file: 22348-97-6.mol

Synonyms:Methyl 3-oxotetradecanoate;22348-97-6;Tetradecanoic acid, 3-oxo-, methyl ester;EINECS 244-929-1;3-oxo-Tetradecanoic Acid Methyl Ester;Methyl 3-oxomyristate;Methyl beta-ketomyristate;5JZD9UC56Q;SCHEMBL1376494;DTXSID10176881;3-Oxotetradecanoic acid methyl ester;MFCD00673474;AKOS015901948;PROPANEDIOICACIDMONOPOTASSIUMSALT;BS-22393;CS-0169302;FT-0628842;H11047;J-014658

Chemical Property of Methyl 3-oxotetradecanoate

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Melting Point: 29-30oC
• Boiling Point: 296.9°Cat760mmHg
• PKA: 10.65±0.46(Predicted)
• Flash Point: 121.5°C
• PSA: 43.37000
• Density: 0.926g/cm³
• LogP: 4.03950
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 256.20384475
• Heavy Atom Count: 18
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-Oxotetradecanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(=O)CC(=O)OC
• Uses: Methyl 3-Oxotetradecanoate (cas# 22348-97-6) is a compound useful in organic synthesis.

Technology Process of Methyl 3-oxotetradecanoate

There total 26 articles about Methyl 3-oxotetradecanoate 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%

methanol (67-56-1) + 5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (736177-64-3) → methyl 3-oxotetradecanoate (22348-97-6)

Guidance literature:

for 2h; Heating;

DOI:10.1016/j.bmc.2004.04.001

Reference yield: 86.0%

n-dodecanoyl chloride (112-16-3) + monomethyl monopotassium malonate (38330-80-2) → methyl 3-oxotetradecanoate (22348-97-6)

Guidance literature:

monomethyl monopotassium malonate; With triethylamine; magnesium chloride; In acetonitrile; at 10 - 25 ℃; for 2.5h; Inert atmosphere;

n-dodecanoyl chloride; With triethylamine; In acetonitrile; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.031

Reference yield: 81.0%

n-dodecanoyl chloride (112-16-3) + acetic acid methyl ester (79-20-9) → methyl 3-oxotetradecanoate (22348-97-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -65 ℃; for 0.5h;

DOI:10.1021/ja00258a039

upstream raw materials:

n-dodecanoyl chloride

sodium ethyl acetylacetate enolate

tetradec-1-ene-1,3-dione-1-dimethylacetal

2-acetyl-3-oxo-tetradecanoic acid ethyl ester

Downstream raw materials:

3-hydroxytetradecanoic acid

3-oxomyristic acid

(R)-3-hydroxytetradecanoic acid

tridecan-2-one

Refernces

• 1、 -. "Intermediate, synthesis and application of vaccine adjuvant MPLA". Paragraph 0121-0124. . Retrieved 2021/10/27.
• 2、 -. "Intermediate, synthesis and application of vaccine adjuvant MPLA". Paragraph 0262-0263; 0265-0268. . Retrieved 2021/10/27.