4-Oxohexanoic acid

Base Information

• Chemical Name: 4-Oxohexanoic acid
• CAS No.: 1117-74-4
• Molecular Formula: C6H10 O3
• Molecular Weight: 130.144
• Hs Code.: 2918300090
• European Community (EC) Number: 620-812-4
• DSSTox Substance ID: DTXSID20912252
• Nikkaji Number: J12.314E
• Wikidata: Q63392356
• Metabolomics Workbench ID: 1533
• Mol file: 1117-74-4.mol

Synonyms:4-oxohexanoic acid;1117-74-4;4-oxo-hexanoic acid;Hexanoic acid, 4-oxo-;4-keto-n-caproic acid;MFCD00068854;4-oxohexanoate;4-oxohexanoicacid;LMFA01060009;SCHEMBL462905;DTXSID20912252;CHEBI:180089;CLJBDOUIEHLLEN-UHFFFAOYSA-N;AMY30226;AKOS003382263;AS-57457;SY270773;CS-0207493;D93322;EN300-149328;Q63392356;Z838955680

Chemical Property of 4-Oxohexanoic acid

Chemical Property:

• Vapor Pressure: 0.00517mmHg at 25°C
• Melting Point: 36-37 °C
• Boiling Point: 255°Cat760mmHg
• PKA: 4.77±0.17(Predicted)
• Flash Point: 122.3°C
• PSA: 54.37000
• Density: 1.09g/cm³
• LogP: 0.83030
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-OXOHEXANOIC ACID AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=O)CCC(=O)O

Technology Process of 4-Oxohexanoic acid

There total 65 articles about 4-Oxohexanoic 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: 83.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + C14H18O2Si → 4-oxohexanoic acid (1117-74-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 0 ℃; for 3h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.1c01284

Reference yield: 82.0%

2-morpholino-butyronitrile (69905-96-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 4-oxohexanoic acid (1117-74-4)

Guidance literature:

2-morpholino-butyronitrile; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

acrylic acid methyl ester; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 81.0%

hexan-4-olide (695-06-7) → 4-oxohexanoic acid (1117-74-4)

Guidance literature:

hexan-4-olide; With sodium hydroxide; In ethanol;

With sodium hypochlorite; In aq. phosphate buffer; at 20 ℃; for 20h;

DOI:10.1039/c8cc04532a

upstream raw materials:

hexan-4-olide

hydrogen cyanide

2-methyl-3-butenal

methyl 4-oxohexanoate

Downstream raw materials:

3-(3-methyl-1H-indol-2-yl)propanoic acid

3-[1-(4-chlorobenzyl)-3-methylindol-2-yl]propionic acid

4-chlorobenzylamine trifluoroacetate

4-oxo-hexanoyl chloride

Refernces

• 1、 Nhu Lam, Mila,Dudekula, Dastagiri,Durham, Bri,Collingwood, Noah,Brown, Eric C.,Nagarajan, Rajesh. "Insights into β-ketoacyl-chain recognition for β-ketoacyl-ACP utilizing AHL synthases". . p. 8838 - 8841. Retrieved 2018.
• 2、 Ballini, Roberto,Petrini, Marino. "Facile and Inexpensive Synthesis of 4-Oxoalkanoic Acids from Primary Nitroalkanes and Acrolein". . p. 1024 - 1026. Retrieved 1986.
• 3、 Schick, Hans,Ludwig, Ralf. "An Efficient Approach to β-Oxoadipate Derivatives and γ-Oxo Acids by the Reformatsky Reaction of Ethyl α-Bromoalkanoates with Succinic Anhydride". . p. 369 - 370. Retrieved 1992.
• 4、 Paju, Anne,Laos, Marit,J?gi, Artur,P?ri, Malle,J??laid, Raissa,Pehk, T?nis,Kanger, T?nis,Lopp, Margus. "Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones". . p. 4491 - 4493. Retrieved 2006.
• 5、 Ariyoshi, Shoma,Sakaguchi, Kazuhiko,Nishimura, Takahiro. "Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β-Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones". . p. 11884 - 11894. Retrieved 2021/09/02.