Isophorone oxide

Base Information

• Chemical Name: Isophorone oxide
• CAS No.: 10276-21-8
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Hs Code.: 29142990
• European Community (EC) Number: 693-050-3
• NSC Number: 63367
• DSSTox Substance ID: DTXSID00908032
• Nikkaji Number: J113.905C
• Mol file: 10276-21-8.mol

Synonyms:Isophorone oxide;10276-21-8;4,4,6-Trimethyl-7-oxabicyclo[4.1.0]heptan-2-one;4,4,5a-trimethylperhydro-1-benzoxiren-2-one;Isophorone epoxide;7-Oxabicyclo[4.1.0]heptan-2-one, 4,4,6-trimethyl-;2,3-Epoxy-3,5,5-trimethyl-1-cyclohexanone;4,4,6-TRIMETHYL-7-OXABICYCLO(4.1.0)HEPTAN-2-ONE;7-Oxabicyclo[4.1.0]heptan-2-one, 4,4,6-trimethyl-, (-)-;Isophorone oxide, 99%;SCHEMBL5432151;DTXSID00908032;ROTNQFPVXVZSRL-UHFFFAOYSA-N;NSC63367;MFCD00085465;NSC 63367;NSC-63367;AKOS016010510;2,3-Epoxy-3,5,5-trimethylcyclohexanone;AS-68074;CS-0204566;FT-0627444;FT-0627447;I0805;3,5,5-Trimethyl-2,3-epoxy-1-cyclohexanone;A18028;D91201;EN300-7405450;1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-5-one;7-Oxabicyclo[4.1.0]heptan-2-one,4,6-trimethyl-;4,4,6-Trimethyl-7-oxabicyclo[4.1.0]heptan-2-one #;Z1255475750

Chemical Property of Isophorone oxide

Chemical Property:

• Vapor Pressure: 0.212mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Boiling Point: 208.6 °C at 760 mmHg
• Flash Point: 76.5 °C
• PSA: 29.60000
• Density: 1.056 g/cm³
• LogP: 1.53300
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 220

Purity/Quality:

Isophorone oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 23-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CC(=O)C2C(C1)(O2)C)C

Technology Process of Isophorone oxide

There total 16 articles about Isophorone oxide 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: 98.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → isophorone oxide (10276-21-8)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In ethanol; at 30 - 35 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00131-4

Reference yield: 23.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → isophorone oxide (10276-21-8) + 2-methoxy-3,5,5-trimethylcyclohex-2-enone (5682-76-8)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In methanol; water; at 20 ℃; for 20h;

DOI:10.1246/cl.2010.136

Reference yield: 4.0%

(E)-1-(3,5,5-Trimethyl-cyclohex-2-enyl)-but-2-en-1-ol (178160-88-8) → isophorone oxide (10276-21-8) + rac-(E)-4-(3,5,5-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one + (Z)-1-(3,5,5-Trimethyl-cyclohex-2-enyl)-but-2-en-1-one + (E)-1-(3,5,5-Trimethyl-cyclohex-2-enyl)-but-2-en-1-one

Guidance literature:

With jones' reagent; In acetone; at -20 ℃; for 0.5h; Yields of byproduct given;

upstream raw materials:

3,5,5-Trimethylcyclohex-2-en-1-one

(E)-1-(3,5,5-Trimethyl-cyclohex-2-enyl)-but-2-en-1-ol

3,5,5-trimethylcyclohex-3-en-1-one

rac-3,5,5-Trimethyl-2-cyclohexene-1-carbaldehyde

Downstream raw materials:

2,4,4-trimethylcyclopentan-1-one

3,5,5-Trimethyl-1,2-cyclohexanedione

(+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde

2-Thiocyanato-3,5,5-trimethyl-2-cyclohexenon

Refernces

• 1、 Mandal,Borude. "An economically viable route to cis/trans-(±)-2,2-dimethyl-3-(2',2'-dichlorovinyl) cyclopropane carboxylic acid esters". . p. 111 - 120. Retrieved 1991.
• 2、 Konoike, Toshiro,Araki, Yoshitaka,Kanda, Yasuhiko. "A novel allylic hydroxylation of sterically hindered olefins by Fe-porphyrin-catalyzed mCPBA oxidation". . p. 6971 - 6974. Retrieved 1999.
• 3、 Wang, Congmin,Wang, Guoliang,Mao, Jianyong,Yao, Zhen,Li, Haoran. "Metal and solvent-free oxidation of α-isophorone to ketoisophorone by molecular oxygen". . p. 758 - 762. Retrieved 2010.
• 4、 Fraile,Garcia, Jose I.,Mayoral, Jose A.,Figueras, Francois. "Comparison of several heterogeneous catalysts in the epoxidation of α-isophorone with hydroperoxides". . p. 5995 - 5996. Retrieved 1996.
• 5、 Rissafi,Rachiqi,El Louzi,Loupy,Petit,Fkih-Tétouani. "Epoxyisophorone ring-opening: An efficient route for the introduction of functional groups at position 2 of isophorone". . p. 2761 - 2768. Retrieved 2001.
• 6、 Loeker, Frank,Leitner, Walter. "Steel-promoted oxidation of olefins in supercritical carbon dioxide using dioxygen in the presence of aldehydes". . p. 2011 - 2015. Retrieved 2000.
• 7、 Kandzia, Christof,Steckhan, Eberhard. "Electrochemical Epoxidation of Electron-Poor Olefins Using Silver Bipyridine Based Redox Mediators". . p. 3695 - 3698. Retrieved 1994.
• 8、 Tavanti, Michele,Parmeggiani, Fabio,Castellanos, J. Rubén Gómez,Mattevi, Andrea,Turner, Nicholas J.. "One-Pot Biocatalytic Double Oxidation of α-Isophorone for the Synthesis of Ketoisophorone". . p. 3338 - 3348. Retrieved 2017.
• 9、 Zhou, Yin,Tang, Rui-Ren,Song, Dan. "Novel catalytic system: N-hydroxyphthalimide/hydrotalcite-like compounds catalysing allylic carbonylation of cyclic olefins". . p. 888 - 897. Retrieved 2016.
• 10、 Baiker,Muller,Schneider,Mallat. "Epoxidation of α-isophorone with amine-modified titania-silica hybrid aerogel: Evidence for Ti-amine interaction". . p. 448 - 451. Retrieved 2000.