Dimethyldioxirane

Base Information

• Chemical Name: Dimethyldioxirane
• CAS No.: 74087-85-7
• Molecular Formula: C3H6 O2
• Molecular Weight: 74.0794
• UNII: R5RAT196DJ
• DSSTox Substance ID: DTXSID90224990
• Nikkaji Number: J246.785B
• Wikipedia: Dimethyldioxirane
• Wikidata: Q762482
• Mol file: 74087-85-7.mol

Synonyms:3,3-dimethyldioxirane;dimethyldioxirane;DMDO

Chemical Property of Dimethyldioxirane

Chemical Property:

• Vapor Pressure: 3700mmHg at 25°C
• Boiling Point: -21.6±23.0 °C(Predicted)
• PSA: 25.06000
• Density: 1.004g/cm³
• LogP: 0.68430
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 74.036779430
• Heavy Atom Count: 5
• Complexity: 42.9

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OO1)C
• Uses: Dimethyldioxirane acts as a valuable oxidant for the synthesis of polyfunctional aromatic imidazolium monomers bearing epoxides.

Technology Process of Dimethyldioxirane

There total 3 articles about Dimethyldioxirane 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: 6.0%

1,1,1-trifluoro-2-propanone (421-50-1) → methyltrifluoromethyldioxirane (115464-59-0) + 3,3-dimethyldioxirane (74087-85-7)

Guidance literature:

With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; edetate disodium; sodium hydrogencarbonate; In water; at -20 ℃; under 650 - 700 Torr;

DOI:10.1021/ja00199a039

Reference yield: 5.0%

acetone (67-64-1) → 3,3-dimethyldioxirane (74087-85-7)

Guidance literature:

With potassium hydroxide; potassium sulfate; potassium hydrogensulfate; oxone; sodium hydrogencarbonate; In water; at 5 - 10 ℃; for 0.05h; pH=7.4;

Reference yield:

2,3-Dimethyl-2-butene (563-79-1) → 2,3-dimethyl-2,3-epoxybutane (5076-20-0) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3,3-dimethyl-butan-2-one (75-97-8) + 3,3-dimethyldioxirane (74087-85-7) + hydroxy-2-propanone (116-09-6) + acetone (67-64-1)

Guidance literature:

With ozone; at -254.16 - -238.16 ℃; for 19h; Irradiation; Inert atmosphere;

DOI:10.1021/jp108457w

upstream raw materials:

1,1,1-trifluoro-2-propanone

acetone

2,3-Dimethyl-2-butene

Downstream raw materials:

2,3-dihydro-2,3,5-trimethyl-2,3-epoxybenzofuran

7-chloro-2,3-dihydro-2,3-dimethyl-2,3-epoxybenzofuran

Aflatoxin B₁ 8,9-epoxide

2,3-dihydro-2,3,4-trimethyl-2,3-epoxybenzofuran

Refernces

• 1、 Tang,Abbott. "Bioactivation of a toxic metabolite of valproic acid, (E)-2-propyl-2,4- pentadienoic acid, via glucuronidation. LC/MS/MS characterization of the GSH- glucuronide diconjugates". . p. 517 - 526. Retrieved 1996.
• 2、 Duffy, Richard J.,Morris, Kay A.,Romo, Daniel. "Synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-β-lactones obtained by epoxidation of 4-alkylidene-2-oxetanones". . p. 16754 - 16755. Retrieved 2005.
• 3、 Tang,Abbott. "Characterization of thiol-conjugated metabolites of 2-propylpent-4-enoic acid (4-ene VPA), a toxic metabolite of valproic acid, by electrospray tandem mass spectrometry.". . p. 926 - 936. Retrieved 1996.
• 4、 Yang, Baohua,Liu, Wei,Chen, Kaixian,Wang, Zhengtao,Wang, Changhong. "Metabolism of diosbulbin B in vitro and in vivo in rats: Formation of reactive metabolites and human enzymes involved". . p. 1737 - 1750. Retrieved 2014.
• 5、 Ishii, Akihiko,Suzuki, Manami,Yamashita, Remi. "Preparation of a new 1,2,3-trithiolane, trans-9,10,11-trithiabicyclo[6.3.0]undecane, and its oxidation reactions". . p. 5441 - 5447. Retrieved 2006.
• 6、 Ovchinnikov,Kazakov,Khursan. "Kinetics and mechanism of the highly efficient generation of singlet oxygen in dimethyldioxirane decomposition induced by the chloride ion". . p. 42 - 53. Retrieved 2012.
• 7、 Kazakov, D. V.,Kabal'nova, N. N.,Voloshin, A. I.,Shereshovets, V. V.,Kazakov, V. P.. "Chemiluminescence during decomposition of dimethyldioxirane". . p. 1345 - 1346. Retrieved 1995.
• 8、 Nakayama, Yasuaki,Maser, Michael R.,Okita, Tatsuya,Dubrovskiy, Anton V.,Campbell, Taryn L.,Reisman, Sarah E.. "Total Synthesis of Ritterazine B". supporting information. p. 4187 - 4192. Retrieved 2021/04/06.
• 9、 Kamakura, Daiki,Todoroki, Hidenori,Urabe, Daisuke,Hagiwara, Koichi,Inoue, Masayuki. "Total Synthesis of Talatisamine". supporting information. p. 479 - 486. Retrieved 2019/11/25.