Production Method 1

119-61-9

2181-42-2

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethyl sulfoxide ,  Tetrahydrofuran ;  30 min, rt
1.2 Solvents: Tetrahydrofuran ;  2 h, 0 °C; rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Isomerization of Terminal Epoxides by a [Pd-H] Catalyst: A Combined Experimental and Theoretical Mechanistic Study

Vyas, Devendra J.; et al, Journal of the American Chemical Society, 2013, 135(16), 6177-6183

Production Method 2

119-61-9

2181-42-2

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethyl sulfoxide ,  Tetrahydrofuran ;  0 °C; 0 °C → 25 °C; 16 h, 25 °C

Reference

"Instant methylide" modification of the Corey-Chaykovsky epoxide synthesis

Ciaccio, James A.; et al, Synthetic Communications, 2003, 33(12), 2135-2143

Production Method 3

530-48-3

882-59-7

Reaction Conditions

1.1 Reagents: Dimethyldioxirane Solvents: Acetone

Reference

Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines

Bolli, Martin H.; et al, Journal of the Chemical Society, 1998, (15), 2243-2246

Production Method 4

530-48-3

882-59-7

Reaction Conditions

1.1 Reagents: Acetic acid ,  Hydrogen peroxide Catalysts: Phosphonium, tetraphenyl-, (SP-5-12)-tetrakis(cyano-κC)nitridomanganate(2-) (2:1… Solvents: Acetonitrile ;  0.5 h, 23 °C

Reference

Epoxidation of alkenes and oxidation of alcohols with hydrogen peroxide catalyzed by a manganese(V) nitrido complex

Kwong, Hoi-Ki; et al, Chemical Communications (Cambridge, 2011, 47(14), 4273-4275

Production Method 5

119-61-9

6814-64-8

882-59-7

Reaction Conditions

Reference

Dimethylsulfonium Methylide

Okazaki, Renji; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 6

119-61-9

1774-47-6

882-59-7

Reaction Conditions

1.1 Reagents: 1884186-57-5 Solvents: 1-Butyl-3-methylimidazolium tetrafluoroborate ;  90 min, rt

Reference

Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids - A new approach to the classical Corey-Chaykovsky reaction

Malunavar, Shruti S.; et al, Tetrahedron Letters, 2021, 81,

Production Method 7

119-61-9

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethyl sulfoxide

Reference

Dimethylsulfoxonium methylide

Corey, E. J.; et al, Journal of the American Chemical Society, 1962, 84, 867-8

Production Method 8

119-61-9

882-59-7

Reaction Conditions

1.1 Reagents: Methyllithium ,  Lithium bromide Solvents: Diethyl ether ,  Tetrahydrofuran

Reference

The in situ generation and use of iodomethyllithium for the one-carbon homologation of boronic esters and epoxide formation from carbonyl compounds

Wallace, Richard H.; et al, Synthetic Communications, 1995, 25(1), 127-33

Production Method 9

119-61-9

105-39-5

882-59-7

Reaction Conditions

1.1 Catalysts: Sodium ethoxide Solvents: Diethyl ether ;  0 - 2 °C; 15 h, 20 °C
1.2 Reagents: Acetic acid Solvents: Water ;  10 min, cooled
1.3 Reagents: Sodium hydroxide Solvents: Water ;  12 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 3 - 4; rt → 50 °C; 50 °C

Reference

Synthesis of the internal electron donor in Z-N catalyst-2,2-diphenyl-1,3-dimethoxypropane

Liu, Min; et al, Huaxue Shiji, 2011, 33(5), 420-422

Production Method 10

119-61-9

882-59-7

Reaction Conditions

Reference

Product class 3: oxetanes and oxetan-3-ones

Griesbeck, A. G.; et al, Science of Synthesis, 2008, 37, 433-471

Production Method 11

119-61-9

60065-96-5

882-59-7

Reaction Conditions

1.1 Solvents: Benzophenone

Reference

Organic sulfur compounds. Part 51. Oxosulfonium salts. IV. Preparation and reactions of methylphenyloxosulfonium methylide

Ryoke, Katsumi; et al, Bulletin of the Chemical Society of Japan, 1976, 49(5), 1455-6

Production Method 12

119-61-9

37181-39-8

51-92-3

882-59-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  16 h, 0 °C → rt

Reference

A lithiomethyl trimethylammonium reagent as a methylene donor

den Hartog, Tim; et al, Chemical Communications (Cambridge, 2014, 50(73), 10604-10607

Production Method 13

119-61-9

4358-26-3

68944-15-0

882-59-7

Reaction Conditions

1.1 Reagents: 2,2,6,6-Tetramethylpiperidine Solvents: Tetrahydrofuran
1.2 -

Reference

Synthetic application of elementorganic compounds of the 15th and 16th groups. 84. A first non-stabilized telluronium ylide. Diphenyltelluronium methylide as a novel reagent for synthesis of oxiranes

Shi, Lilan; et al, Tetrahedron Letters, 1990, 31(29), 4173-4

Production Method 14

119-61-9

21228-90-0

676-84-6

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dichloromethane ,  Water

Reference

Trimethylsulfonium methyl sulfate, a simple and efficient epoxidizing agent

Mosset, Paul; et al, Synthetic Communications, 1985, 15(8), 749-57

Production Method 15

119-61-9

2181-42-2

882-59-7

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: tert-Butanol ;  30 °C; 30 °C → 50 °C; 40 - 50 °C; 12 h, 40 - 50 °C

Reference

Practical Corey-Chaykovsky epoxidation. Scope and limitation

Yu, Hao; et al, Letters in Organic Chemistry, 2011, 8(7), 509-514

Production Method 16

530-48-3

882-59-7

Reaction Conditions

1.1 Reagents: Dimethyldioxirane Solvents: Acetone

Reference

Dioxirane epoxidation of alkenes

Adam, Waldemar; et al, Organic Reactions (Hoboken, 2002, 61,

Production Method 17

119-61-9

333-27-7

882-59-7

Reaction Conditions

1.1 Catalysts: Benzene, 1,1′-[1,4-butanediylbis(oxy)]bis[4-ethenyl-, polymer with 1-ethenyl-4-(… Solvents: Dichloromethane ;  rt; 24 h, rt
1.2 Reagents: Sodium hydride Solvents: Dimethyl sulfoxide ,  Tetrahydrofuran ;  0 °C; 0 °C; 0 °C → rt

Reference

Polymer-supported thioanisole: a versatile platform for organic synthesis reagents

Choi, Matthew Kwok Wai; et al, Tetrahedron, 2004, 60(12), 2875-2879

Production Method 18

119-61-9

6814-64-8

882-59-7

Reaction Conditions

Reference

Synthesis and preliminary pharmacological activity of aminoalkoxy isosteres of glycolate ester anticholinergics

Fries, David S.; et al, Journal of Medicinal Chemistry, 1977, 20(10), 1250-4

Production Method 19

119-61-9

1030268-24-6

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydride ;  1.5 h, 50 °C

Reference

Synthesis of 4-arylpiperidin-4-ol derivatives of loperamide as agents with potent antiproliferative effects against HCT-116 and HL-60 cells

Hatae, Noriyuki; et al, Heterocycles, 2014, 88(1), 663-673

Production Method 20

119-61-9

1774-47-6

882-59-7

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Dimethyl sulfoxide ;  0.67 h, 50 - 60 °C

Reference

"Instant methylide" modification of the Corey-Chaykovsky epoxide synthesis

Ciaccio, James A.; et al, Synthetic Communications, 2003, 33(12), 2135-2143

Production Method 21

119-61-9

74-95-3

882-59-7

Reaction Conditions

1.1 Reagents: Lithium, methyl-, compd. with lithium bromide (LiBr) (1:1) Solvents: Diethyl ether ,  Tetrahydrofuran ;  30 s, -80 °C; -80 °C → 20 °C; 1 min, 20 °C
1.2 Solvents: Water ;  20 °C

Reference

Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium

von Keutz, Timo; et al, Organic Letters, 2019, 21(24), 10094-10098

Production Method 22

119-61-9

676-84-6

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethyl sulfide

Reference

Reaction of sulfonium ylides with polar double bonds

Franzen, Volker; et al, Chemische Berichte, 1963, 96(7), 1881-90

Production Method 23

119-61-9

882-59-7

Reaction Conditions

1.1 Reagents: Methane, sulfinylbis-, ion(1-), sodium Solvents: Dimethyl sulfoxide
1.2 Solvents: Dimethyl sulfoxide

Reference

Reaction of sulfonimidamide anions with electrophiles

Okuma, Kentaro; et al, Journal of Organic Chemistry, 1988, 53(18), 4190-3

Production Method 24

119-61-9

4358-26-3

68944-15-0

882-59-7

Reaction Conditions

Reference

Product class 20: aryl tellurium compounds

Kataoka, T.; et al, Science of Synthesis, 2007, 31, 1159-1181

Production Method 25

119-61-9

37181-39-8

882-59-7

Reaction Conditions

1.1 Solvents: Dimethyl sulfoxide

Reference

Reaction of diphenylsulfonium methylide with carbonyl compounds in non-basic media

Hioki, Kazuhito; et al, Synthesis, 1995, (6), 649-50

Production Method 26

103-30-0

882-59-7

Reaction Conditions

1.1 Reagents: Iodosylbenzene Catalysts: Manganese (immobilized, reaction products with functional group-modified hexagona…) ,  Silica (formyl group-modified, surface-grafted) ,  S,S-Jacobsen catalyst (immobilized, reaction products with formyl group-modified hexagonal me…) Solvents: Dichloromethane ;  2 h, 298 K

Reference

Immobilization of Salen-manganese complex over hexagonal mesoporous silica with different surface groups and modifications

Wu, Meizhi; et al, Jingxi Huagong Zhongjianti, 2005, 35(3), 13-16

Production Method 27

119-61-9

3086-29-1

882-59-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dichloromethane ,  Water

Reference

Anion-catalyzed phase-transfer catalysis. II. Effects of anionic tetrakis[3,5-bis(trifluoromethyl)phenyl]borate catalyst in phase-transfer-catalyzed sulfonium ylide formation

Shiraki, Yasuichiro; et al, Bulletin of the Chemical Society of Japan, 1985, 58(10), 3041-2

Production Method 28

119-61-9

47025-43-4

882-59-7

Reaction Conditions

Reference

Synthesis of epoxides by carbonyl epoxidation

Aggarwal, V. K.; et al, Science of Synthesis, 2008, 37, 321-406

2,2-Diphenyloxirane Raw materials

• Benzophenone
• Trimethylsulfoxonium iodide
• ethyl 2-chloroacetate
• tetraphenylborate
• dimethylsulphonium methylide
• trans-Stilbene
• Dibromomethane
• 1,1-Diphenylethylene
• trimethylsulfonium;iodide
• Sulfur, iodotrimethyloxo-
• ARSORANE, METHYLENETRIPHENYL-
• [(Sulfuric acid methyl)ion]
• Methyl trifluoromethanesulfonate
• tetramethylammonium
• trimethylsulfonium
• Trimethylsulfonium Chloride
• Sulfoxonium, methylphenyl-, methylide (9CI)
• Methyldiphenyltelluronium

2,2-Diphenyloxirane Preparation Products

• 2,2-Diphenyloxirane (882-59-7)

• 1. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 2. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 3. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 4. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
• 5. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Diphenylmethanes

Recent Advances in the Study of 2,2-Diphenyloxirane (CAS: 882-59-7): A Comprehensive Research Brief

2,2-Diphenyloxirane (CAS: 882-59-7), also known as diphenyl ethylene oxide, is a structurally significant epoxide compound that has garnered attention in the field of chemical biology and pharmaceutical research. Its unique chemical properties and potential biological activities make it a subject of ongoing investigation. This research brief aims to synthesize the latest findings related to 2,2-Diphenyloxirane, focusing on its synthesis, applications, and mechanistic insights.

Recent studies have explored the synthetic pathways for 2,2-Diphenyloxirane, with an emphasis on green chemistry approaches. A 2023 publication in the Journal of Organic Chemistry detailed a catalytic epoxidation method using environmentally benign oxidants, achieving high yields (up to 92%) and excellent stereoselectivity. The study highlighted the role of transition metal catalysts in optimizing the reaction conditions, which could have implications for scalable production.

In the realm of biological applications, 2,2-Diphenyloxirane has shown promise as a precursor for bioactive molecules. A 2024 study in Bioorganic & Medicinal Chemistry Letters reported its use in the synthesis of novel anti-inflammatory agents. The researchers demonstrated that derivatives of 2,2-Diphenyloxirane exhibited significant inhibition of cyclooxygenase-2 (COX-2), with IC50 values in the low micromolar range. These findings suggest potential therapeutic applications in inflammatory diseases.

Mechanistic studies have also shed light on the compound's interactions at the molecular level. Computational modeling and X-ray crystallography data, published in ACS Chemical Biology (2023), revealed that 2,2-Diphenyloxirane can act as a covalent inhibitor for certain enzymes by forming stable adducts with nucleophilic residues. This mode of action could be leveraged for targeted drug design, particularly in oncology and infectious diseases.

Despite these advancements, challenges remain in the clinical translation of 2,2-Diphenyloxirane-based compounds. Issues such as metabolic stability and off-target effects need to be addressed through further structure-activity relationship (SAR) studies. Ongoing research is also exploring its potential in combination therapies, where synergistic effects with existing drugs could enhance efficacy.

In conclusion, 2,2-Diphenyloxirane (CAS: 882-59-7) continues to be a versatile scaffold in chemical biology and drug discovery. The latest research underscores its synthetic accessibility, biological relevance, and mechanistic novelty. Future directions may include the development of more selective derivatives and the exploration of its role in emerging therapeutic areas. This brief serves as a timely update for researchers and industry professionals engaged in the field.

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