4-Hydroxycyclohexanone

Base Information

• Chemical Name: 4-Hydroxycyclohexanone
• CAS No.: 13482-22-9
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 2914400090
• European Community (EC) Number: 620-210-1
• DSSTox Substance ID: DTXSID00337621
• Nikkaji Number: J99.913J
• Wikidata: Q72483592
• Mol file: 13482-22-9.mol

Synonyms:4-Hydroxycyclohexanone;13482-22-9;4-hydroxycyclohexan-1-one;4-Hydroxy-cyclohexanone;Cyclohexanone, 4-hydroxy-;4-hydroxycyclohexanon;4-Hydroxy Cyclohexanone;1-Hydroxy-4-oxocyclohexane;4-Hydroxy Cyclohexanone-d4;MFCD02093817;p-Hydroxycyclohexanone;4-Oxocyclohexan-1-ol;4hydroxycyclohexanone;4-hydroxy-cyclohexan-1-one;SCHEMBL148906;DTXSID00337621;AMY17986;CS-D0911;AKOS006344707;PB40354;SY005938;FT-0646905;FT-0669349;EN300-93773;J-006609;J-515521

Chemical Property of 4-Hydroxycyclohexanone

Chemical Property:

• Vapor Pressure: 0.016mmHg at 25°C
• Melting Point: -1 °C
• Refractive Index: 1.5
• Boiling Point: 226.28 °C at 760 mmHg
• PKA: 14.62±0.20(Predicted)
• Flash Point: 91.392 °C
• PSA: 37.30000
• Density: 1.142 g/cm³
• LogP: 0.49040
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 88.7

Purity/Quality:

99.9% ^*data from raw suppliers

4-Hydroxycyclohexanone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)CCC1O

Technology Process of 4-Hydroxycyclohexanone

There total 55 articles about 4-Hydroxycyclohexanone 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: 96.0%

1,4-Cyclohexanedione (637-88-7) → 4-hydroxycyclohexanone (13482-22-9)

Guidance literature:

With [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); formic acid; triethylamine; In acetonitrile; at 20 ℃;

DOI:10.1002/ejoc.201300338

Reference yield: 93.0%

1,4-Cyclohexanediol (556-48-9) → 4-hydroxycyclohexanone (13482-22-9) + 1,4-Cyclohexanedione (637-88-7)

Guidance literature:

With sodium bromate; sodium hydrogensulfite; In water; acetonitrile; at 20 ℃; for 6h;

DOI:10.1246/bcsj.70.2561

Reference yield: 82.0%

hydroquinone (123-31-9,8027-02-9) → 4-hydroxycyclohexanone (13482-22-9)

Guidance literature:

With sodium formate; sodium hydroxide; In water; at 120 ℃; pH=12;

DOI:10.1016/j.mcat.2021.111613

upstream raw materials:

4-(1-oxoethyl)-1-cyclohexanone

1,4-Cyclohexanediol

2,3-dioxabicyclo<2.2.2>octane

(1S,4R)-Cyclohex-2-ene-1,4-diol

Downstream raw materials:

4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone

(+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol

trans-1-(5-Hydroxy-2-oxo-cyclohexyliden)-2-(2,2-dimethyl-cyclohexyliden)-ethan

4-(trimethylsiloxy)cyclohexanone

Refernces

• 1、 Kularatne, Ruvanthi N.,Washington, Katherine E.,Bulumulla, Chandima,Calubaquib, Erika L.,Biewer, Michael C.,Oupicky, David,Stefan, Mihaela C.. "Histone Deacetylase Inhibitor (HDACi) Conjugated Polycaprolactone for Combination Cancer Therapy". . p. 1082 - 1089. Retrieved 2018.
• 2、 Astakhov, Grigorii S.,Bilyachenko, Alexey N.,Korlyukov, Alexander A.,Levitsky, Mikhail M.,Shul'Pina, Lidia S.,Bantreil, Xavier,Lamaty, Frédéric,Vologzhanina, Anna V.,Shubina, Elena S.,Dorovatovskii, Pavel V.,Nesterov, Dmytro S.,Pombeiro, Armando J. L.,Shul'Pin, Georgiy B.. "High-Cluster (Cu9) Cage Silsesquioxanes: Synthesis, Structure, and Catalytic Activity". . p. 11524 - 11529. Retrieved 2018.
• 3、 Konopelski, Joseph P.,Deng, Hongbo,Schiemann, Kai,Keane, Joseph M.,Olmstead, Marilyn M.. "Stereoselective conjugate addition directed by an enantiomerically pure ketal. Preparation of the cyclohexanone fragment of N-methylwelwitindolinone C isothiocyanate". . p. 1105 - 1107. Retrieved 1998.
• 4、 Fetizon et al.. "-". . p. 1102. Retrieved 1969.
• 5、 Kelly, David R.,Bansal, Harjinder,Morgan. "The mechanism of the tertiary amine catalysed isomerisation of endoperoxides to hydroxyketones: Synthesis and chemistry of the intermediate postulated in the peroxide attack mechanism". . p. 9331 - 9333. Retrieved 2002.
• 6、 Bonnet, Marc,Geneste, Patrick,Rodrigues, Marcel. "Liquid-Phase Catalytic Hydrogenation of 1,4-Cyclohexanedione: Activity and Selectivity". . p. 40 - 43. Retrieved 1980.
• 7、 Campana, Filippo,Ferlin, Francesco,Silvetti, Matteo,Trombettoni, Valeria,Vaccaro, Luigi,Valentini, Federica. "POLITAG-Pd(0) catalyzed continuous flow hydrogenation of lignin-derived phenolic compounds using sodium formate as a safe H-source". . . Retrieved 2021/07/09.
• 8、 Bergander, Klaus,Glorius, Frank,Heusler, Arne,Wollenburg, Marco. "Trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives". . p. 11365 - 11370. Retrieved 2020/11/24.