6-HYDROXYCAPROIC ACID

Base Information

• Chemical Name: 6-HYDROXYCAPROIC ACID
• CAS No.: 1191-25-9
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29181998
• European Community (EC) Number: 681-173-5
• NSC Number: 617319
• UNII: 3Y3OX37NM8
• DSSTox Substance ID: DTXSID00152316
• Nikkaji Number: J262.001D
• Wikidata: Q27102678
• Metabolomics Workbench ID: 1292
• ChEMBL ID: CHEMBL2006530
• Mol file: 1191-25-9.mol

Synonyms:6-Hydroxycaproicacid;6-Hydroxyhexanoic acid;NSC 617319;e-Hydroxycaproic acid;

Chemical Property of 6-HYDROXYCAPROIC ACID

Chemical Property:

• Appearance/Colour: white low melting crystalline solid
• Vapor Pressure: 0.00078mmHg at 25°C
• Melting Point: 38-40 °C
• Refractive Index: 1.44
• Boiling Point: 272.6 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 132.9 °C
• PSA: 57.53000
• Density: 1.104 g/cm³
• LogP: 0.62370
• Storage Temp.: Freezer (-20°C)
• Water Solubility.: Soluble in water.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 80.4

Purity/Quality:

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

6-Hydroxyhexanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 24/25-45-36/37/39-26-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(=O)O)CCO
• Uses: 6-Hydroxyhexanoic acid acts as a useful reagent in synthetic chemistry. It is used as a precursor to prepare surface active monomers.

Technology Process of 6-HYDROXYCAPROIC ACID

There total 84 articles about 6-HYDROXYCAPROIC 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: 85.4%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) + 6-Hydroxyhexanoic acid (1191-25-9)

Guidance literature:

With dihydrogen peroxide; acetic acid; In water; at 70 ℃; for 1h; Reagent/catalyst;

Reference yield: 61.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + benzaldehyde (100-52-7) → hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) + 6-Hydroxyhexanoic acid (1191-25-9) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With oxygen; In benzene; at 25 ℃; for 8h;

DOI:10.1016/j.crci.2010.01.007

Reference yield: 44.0%

oxepane (592-90-5) → hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) + Adipic acid (124-04-9) + 6-Hydroxyhexanoic acid (1191-25-9)

Guidance literature:

With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetramesitylporphyrinato)ruthenium(IV); In 1,2-dichloro-ethane; at 40 ℃; for 20h; Inert atmosphere;

DOI:10.1142/S1088424615500297

upstream raw materials:

N-nitroso-6-caprolactam

adipinic acid monoethyl ester

diethyl adipate

cyclohexanone

Downstream raw materials:

hexahydro-2H-oxepin-2-one

6-iodohexanoic acid

6-hydroxy-hexanoic acid ethyl ester

2-[2-cyclohexyl-2-(5-hydroxypentanoylamino)acetylamino]-3-(3-hydroxyphenyl)propionic acid methyl ester

Refernces

• 1、 Mehta, Jignasu P.,Parmar, Digvijaysinh K.,Godhani, Dinesh R.,Nakum, Haresh D.,Desai, Nisheeth C.. "Heterogeneous catalysts hold the edge over homogeneous systems: Zeolite-Y encapsulated complexes for Baeyer-Villiger oxidation of cyclohexanone". . p. 178 - 188. Retrieved 2016.
• 2、 Dale. "". . p. 72,73. Retrieved 1965.
• 3、 Baj, Stefan,Chrobok, Anna,Siewniak, Agnieszka. "New and efficient technique for the synthesis of ε-caprolactone using KHSO5 as an oxidising agent in the presence of a phase transfer catalyst". . p. 49 - 52. Retrieved 2011.
• 4、 Patra, Astam K.,Dutta, Arghya,Bhaumik, Asim. "Mesoporous core-shell fenton nanocatalyst: A mild, operationally simple approach to the synthesis of adipic acid". . p. 12388 - 12395. Retrieved 2013.
• 5、 Stephan, Michel Massoud S.,Mohar, Barbara. "Simple preparation of highly pure monomeric ω-hydroxycarboxylic acids". . p. 481 - 483. Retrieved 2006.
• 6、 Capece, Noemi,Cavani, Fabrizio,Palombo Ferraz, Camila,Paul, Sébastien,Pietrowski, Mariusz,Sadier, Achraf,Thuriot-Roukos, Jo?lle,Wojcieszak, Robert,Zieliński, Micha?. "Aerobic oxidation of 1,6-hexanediol to adipic acid over Au-based catalysts: The role of basic supports". . p. 2644 - 2651. Retrieved 2020.
• 7、 Kuznetsov,Pervova,Yatluk. "Synthesis of E-caprolactone with stable hydrogen peroxide adducts". . p. 176 - 181. Retrieved 2013.
• 8、 Van Natta et al.. "-". . p. 455. Retrieved 1934.
• 9、 Takashima, Yoshinori,Kawaguchi, Yoshinori,Nakagawa, Shinya,Harada, Akira. "Inclusion Complex Formation and Hydrolysis of Lactones by Cyclodextrins". . p. 1122 - 1123. Retrieved 2003.
• 10、 Wu, Peng,Ruan, Juanfang,Wang, Lingling,Wu, Leilei,Wang, Yong,Liu, Yueming,Fan, Weibin,He, Mingyuan,Terasaki, Osamu,Tatsumi, Takashi. "Methodology for synthesizing crystalline metallosilicates with expanded pore windows through molecular alkoxysilylation of zeolitic lamellar precursors". . p. 8178 - 8187. Retrieved 2008.