2,3-Epoxy-1-cyclohexanol

Base Information

• Chemical Name: 2,3-Epoxy-1-cyclohexanol
• CAS No.: 1192-78-5
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.144
• Mol file: 1192-78-5.mol

Synonyms:1,2-Epoxy-3-hydroxycyclohexane;2,3-Epoxycyclohexanol; 2-Cyclohexen-1-ol epoxide; 2-Cyclohexen-1-ol oxide; NSC524037

Chemical Property of 2,3-Epoxy-1-cyclohexanol

Chemical Property:

• Vapor Pressure: 0.0129mmHg at 25°C
• Boiling Point: 229.9°Cat760mmHg
• Flash Point: 111.5°C
• PSA: 32.76000
• Density: 1.224g/cm³
• LogP: 0.29860

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3-Epoxy-1-cyclohexanol

There total 67 articles about 2,3-Epoxy-1-cyclohexanol 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%

Cyclohex-2-enol (822-67-3) → 2,3-epoxycyclohexanol (1192-78-5,26828-72-8,26828-73-9,72029-31-3,89064-04-0,92841-93-5,120522-60-3,126059-76-5,127379-33-3) + cyclohexenone (930-68-7)

Guidance literature:

With 6C₁₆H₃₆N⁽¹⁺⁾*2Zn⁽²⁺⁾*4Na⁽¹⁺⁾*[Bi₂Zn₂(ZnW₉O₃₄)2]^(14-); urea hydrogen peroxide adduct; In acetonitrile; at 70 ℃; for 2h;

DOI:10.1021/acscatal.5b00066

Reference yield: 85.0%

Cyclohex-2-enol (822-67-3) → 2,3-epoxycyclohexanol (1192-78-5,26828-72-8,26828-73-9,72029-31-3,89064-04-0,92841-93-5,120522-60-3,126059-76-5,127379-33-3) + 7-oxabicyclo[4.1.0]heptan-2-one (6705-49-3) + cyclohexenone (930-68-7)

Guidance literature:

With tert.-butylhydroperoxide; 3 A molecular sieve; zircornium(IV) n-propoxide; In dichloromethane; at -20 ℃; for 24h;

DOI:10.1021/jo9518720

Reference yield: 41.0%

cyclohexene (110-83-8) → (1R*,2R*,3S*)-2,3-epoxycyclohexanol (1192-78-5,26828-72-8,26828-73-9,72029-31-3,89064-04-0,92841-93-5,120522-60-3,126059-76-5,127379-33-3) + cyclohexenone (930-68-7) + cyclohexane-1,2-epoxide (286-20-4) + Cyclohex-2-enol (822-67-3)

Guidance literature:

With oxygen; bis(acetylacetonate)oxovanadium; In 1,1,2-trichloroethane; at 60 ℃; under 760 Torr;

DOI:10.1021/jo01303a018

upstream raw materials:

7-oxabicyclo[4.1.0]heptan-2-one

cyclohexen-1-ol

1,1,3,3-tetrachloropropanone

Cyclohex-2-enol

Downstream raw materials:

(1S,2R,3R)-1-Isocyano-2,3-bis-trimethylsilanyloxy-cyclohexane

(±)-(1R,2S,6S)-2-(benzyloxy)-7-oxabicyclo[4,1,0]heptane

racemic cis-1-benzyloxy-7-oxabicyclo[4.1.0]heptane

(1S*,2S*,3S*)-(±)-3-chlorocyclohexane-1,2-diol

Refernces

• 1、 Antonioletti, R.,Bonadies, F.,Locati, L.,Scettri, A.. "Zeolite-Catalyzed Epoxidation Of Allylic Alcohols". . p. 3205 - 3206. Retrieved 1992.
• 2、 Rezaeifard, Abdolreza,Haddad, Reza,Jafarpour, Maasoumeh,Hakimi, Mohammad. "Catalytic epoxidation activity of keplerate polyoxomolybdate nanoball toward aqueous suspension of olefins under mild aerobic conditions". . p. 10036 - 10039. Retrieved 2013.
• 3、 Brussaard, Yvonne,Olbrich, Falk,Schaumann, Ernst. "Synthesis and structural characterization of molybdenum(VI) and iron(II) coordination compounds with S-alkyl-N-methyl-S-(2-pyridyl)sulfoximines and catalytic epoxidation activity of the molybdenum complexes". . p. 13160 - 13166. Retrieved 2013.
• 4、 Kuznetsova,Kuznetsova,Yakovina,Zudin,Bal’zhinimaev. "Effect of Transition Metal Compounds on the Cyclohexene Oxidation Catalyzed by N-Hydroxyphthalimide". . p. 735 - 743. Retrieved 2018.
• 5、 Bellucci, Giuseppe,Chiappe, Cinzia,Pucci, Laura,Gervasi, Pier Giovanni. "The mechanism of oxidation of allylic alcohols to α,β-unsaturated ketones by cytochrome P450 a". . p. 871 - 874. Retrieved 1996.
• 6、 Ichihara, Junko. "Solvent-free epoxidation using a tungstic acid catalyst on fluoroapatite". . p. 695 - 697. Retrieved 2001.
• 7、 Zwettler, Niklas,Schachner, J?rg A.,Belaj, Ferdinand,M?sch-Zanetti, Nadia C.. "Hydrogen bond donor functionalized dioxido-molybdenum(VI) complexes as robust and highly efficient precatalysts for alkene epoxidation". . p. 209 - 219. Retrieved 2017.
• 8、 Pierre,Chautemps. "". . p. 4371,4372. Retrieved 1972.
• 9、 Jalilian, Fariba,Yadollahi, Bahram,Riahi Farsani, Mostafa,Tangestaninejad, Shahram,Amiri Rudbari, Hadi,Habibi, Rouhollah. "Catalytic performance of Keplerate polyoxomolybdates in green epoxidation of alkenes with hydrogen peroxide". . p. 70424 - 70428. Retrieved 2015.
• 10、 Fujii, Hideaki,Oshima, Koichiro,Utimoto, Kiitiro. "Stereoselective Reduction of α,β-Epoxy Ketones into erythro-α,β-Epoxy Alcohols with Sodium Borohydride in the Presence of Calcium Chloride". . p. 967 - 970. Retrieved 1992.