2-Ethyl-4-methylpentanoic acid

Base Information

• Chemical Name: 2-Ethyl-4-methylpentanoic acid
• CAS No.: 108-81-6
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.214
• European Community (EC) Number: 805-613-4
• DSSTox Substance ID: DTXSID40881254
• Mol file: 108-81-6.mol

Synonyms:2-ethyl-4-methylpentanoic acid;108-81-6;Pentanoic acid, 2-ethyl-4-methyl-;Pentanoic acid,2-ethyl-4-methyl-;isobutylbutyric acid;(+-)-2-Ethyl-4-methylpentanoic acid;2-ethyl-4-methylpentanoicacid;SCHEMBL322526;DTXSID40881254;Valeric acid, 2-ethyl-4-methyl-;d-2-(2-Methylpropyl)butanoic acid;AKOS010364943;CS-0242421;EN300-248918;A1-23379;Z756391140

Chemical Property of 2-Ethyl-4-methylpentanoic acid

Chemical Property:

• Vapor Pressure: 0.0231mmHg at 25°C
• Boiling Point: 230.6°C at 760 mmHg
• Flash Point: 104.8°C
• Density: 0.924g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 144.115029749
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(CC(C)C)C(=O)O

Technology Process of 2-Ethyl-4-methylpentanoic acid

There total 9 articles about 2-Ethyl-4-methylpentanoic acid 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:

ethyl iodide (75-03-6) + lithiodianion of 4-methylvaleric acid → 2-ethyl-4-methylpentanoic acid (56640-31-4,108-81-6)

Guidance literature:

lithiodianion of 4-methylvaleric acid; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at 5 ℃; for 0.5h;

ethyl iodide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm901229s

Reference yield:

4-Methylpentanoic acid (646-07-1) + ethyl iodide (75-03-6) → 2-ethyl-4-methylpentanoic acid (56640-31-4,108-81-6)

Guidance literature:

4-Methylpentanoic acid; With lithium diisopropyl amide; In tetrahydrofuran; at -15 - -5 ℃; Inert atmosphere;

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at 5 ℃; for 0.5h;

ethyl iodide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm100170w

Reference yield:

ethyl-isobutyl-malonic acid diethyl ester (123647-93-8) → 2-ethyl-4-methylpentanoic acid (56640-31-4,108-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / H₂O; ethanol / Heating

2: 120 - 180 °C / Heating

With potassium hydroxide; In ethanol; water; 1: Hydrolysis / 2: Decarboxylation;

DOI:10.1021/tx950216s

upstream raw materials:

2-ethyl-4-methyl-pentanal

ethyl-isobutyl-malonic acid

Isobutyl bromide

ethyl iodide

Downstream raw materials:

(2S)-ethyl-4-methyl-1-pentanol

Refernces

• 1、 Hen, Naama,Bialer, Meir,Wlodarczyk, Bogdan,Finnell, Richard H.,Yagen, Boris. "Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide". experimental part. p. 4177 - 4186. Retrieved 2010/09/04.
• 2、 Bojic, Ursula,Elmazar, Mohamed M. A.,Hauck, Ralf-Siegbert,Nau, Heinz. "Further branching of valproate-related carboxylic acids reduces the teratogenic activity, but not the anticonvulsant effect". . p. 866 - 870. Retrieved 2007/10/03.