Production Method 1

357952-84-2

97466-49-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Diethyl ether ,  Water ;  3 h, rt

Reference

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Shi, Zhanglin; Shen, Chaoren ; Dong, Kaiwu, Chemistry - A European Journal, 2021, 27(72), 18039-18042

Production Method 2

1073-67-2

97466-49-4

Reaction Conditions

1.1 Catalysts: Manganese dichloride ,  5,10,15,20-Tetrakis[(1S)-1-methyl-3-phenyl-2-(phenylmethyl)propyl]-21H,23H-porph… Solvents: Dichloromethane ;  rt; 30 min, rt
1.2 Reagents: Iodosylbenzene ;  2 h, rt

Reference

Asymmetric epoxidation of alkenes catalyzed by novel chiral porphyrin metal complexes

Sakthipriya, Pachiannan; Ananthi, Nallamuthu, Journal of Porphyrins and Phthalocyanines, 2016, 20(6), 730-737

Production Method 3

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: Sodium hypochlorite Catalysts: Pyridine N-oxide ,  Benzaldehyde, 3,3′,3′′-[1,3,5-triazine-2,4,6-triyltris(4,1-piperazinediylmethyle… (manganese complexes) Solvents: Dichloromethane ,  Water ;  6 h, 0 °C

Reference

Self-Supported Chiral Polymeric Mn(III) Salen Complexes as Highly Active and Recyclable Catalysts for Epoxidation of Nonfunctionalized Olefins

Roy, Tamal; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Abdi, Sayed H. R.; Bajaj, Hari C., ChemPlusChem, 2015, 80(6), 1038-1044

Production Method 4

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: Disodium ethylenediaminetetraacetate ,  8-Azoniabicyclo[3.2.1]octane, 3-fluoro-8,8-dimethyl-2-oxo-, (1S,3R,5R)-, 1,1,1-t… Solvents: Acetonitrile
1.2 Reagents: Sodium bicarbonate ,  Potassium peroxymonosulfate sulfate (2KHSO5.KHSO4.K2SO4)
1.3 Solvents: Water

Reference

Chiral Fluoro Ketones for Catalytic Asymmetric Epoxidation of Alkenes with Oxone

Denmark, Scott E.; Matsuhashi, Hayao, Journal of Organic Chemistry, 2002, 67(10), 3479-3486

Production Method 5

179065-35-1

97466-49-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water

Reference

Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water

Wang, Hai-Yang; Huang, Kun; De Jesus, Melvin; Espinosa, Sandraliz; Pinero-Santiago, Luis E.; et al, Tetrahedron: Asymmetry, 2016, 27(2-3), 91-100

Production Method 6

937-20-2

97466-49-4

Reaction Conditions

1.1 Reagents: Isopropanol Catalysts: Alcohol dehydrogenase Solvents: Isopropanol ;  20 - 40 °C
1.2 Reagents: Sodium hydroxide Solvents: Water

Reference

Enzymatic synthesis of carbo- and heterocyclic aryl oxiranes

Wisdom, Richard; Meudt, Andreas, Speciality Chemicals Magazine, 2007, 27(8), 32-33

Production Method 7

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: Sodium hypochlorite Catalysts: Manganese, chloro[[2,2′-[(1S,2S)-1,2-cyclohexanediylbis[(nitrilo-κN)methylidyne]… (zeolite MCM-41 supported) Solvents: Dichloromethane ;  12 h, pH 11.5, 0 °C

Reference

New immobilized chiral Mn(III) salen complexes on pyridine N-oxide-modified MCM-41 as effective catalysts for epoxidation of nonfunctionalized alkenes

Kureshy, Rukhsana I.; Ahmad, Irshad; Khan, Noor-ul H.; Abdi, Sayed H. R.; Singh, Surendra; et al, Journal of Catalysis, 2005, 235(1), 28-34

Production Method 8

1073-67-2

97466-49-4

Reaction Conditions

1.1 Catalysts: Titanium isopropoxide ,  (1S,1′′S)-3,3′′-[(1R,2R)-1,2-Cyclohexanediylbis(iminomethylene)]bis[2′-methoxy[1… Solvents: Dichloromethane ;  rt; 30 min, rt
1.2 Catalysts: Water ;  30 min, rt
1.3 Reagents: Hydrogen peroxide Solvents: Water ;  9 h, rt

Reference

Synthesis of salan (salalen) ligands derived from binaphthol for titanium-catalyzed asymmetric epoxidation of olefins with aqueous H2O2

Xiong, Donglu; Wu, Mei; Wang, Shoufeng; Li, Fuwei; Xia, Chungu; et al, Tetrahedron: Asymmetry, 2010, 21(3), 374-378

Production Method 9

147254-28-2

97466-49-4

Reaction Conditions

1.1 Reagents: Tricyclohexylphosphine Catalysts: Diisopropyl azodicarboxylate Solvents: Tetrahydrofuran

Reference

Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Weissman, Steven A.; Rossen, Kai; Reider, Paul J., Organic Letters, 2001, 3(16), 2513-2515

Production Method 10

1073-67-2

97466-49-4

Reaction Conditions

1.1 Catalysts: Methyltrioxorhenium ,  (4S,4′S)-2,2′-(1,3-Phenylene)bis[4,5-dihydro-4-phenyloxazole] Solvents: Dichloromethane ;  > 1 min, rt
1.2 Reagents: Hydrogen peroxide Solvents: Water ;  19 h, rt

Reference

Catalytic Epoxidations with Pyridinebis(oxazoline)-Methyltrioxorhenium Complexes and Nitrogen-Containing Catalyst Systems

Kiersch, Konstanze; Li, Yuehui; Junge, Kathrin; Szesni, Normen; Fischer, Richard; et al, European Journal of Inorganic Chemistry, 2012, 2012(36), 5972-5978

Production Method 11

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: Peracetic acid Catalysts: (OC-6-33-A)-[[N1(S),N2(S),1R,2R]-N1,N2-Dimethyl-N1,N2-bis[(2-pyridinyl-κN)methyl… Solvents: Acetonitrile ;  3 h, 2 °C

Reference

Non-Heme Manganese Complexes Catalyzed Asymmetric Epoxidation of Olefins by Peracetic Acid and Hydrogen Peroxide

Ottenbacher, Roman V.; Bryliakov, Konstantin P.; Talsi, Evgenii P., Advanced Synthesis & Catalysis, 2011, 353(6), 885-889

Production Method 12

97466-49-4

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Ethanol ;  rt
1.2 Reagents: Sodium bicarbonate

Reference

Highly Efficient Route for Enantioselective Preparation of Chlorohydrins via Dynamic Kinetic Resolution

Traeff, Annika; Bogar, Krisztian; Warner, Madeleine; Baeckvall, Jan-E., Organic Letters, 2008, 10(21), 4807-4810

Production Method 13

357952-84-2

97466-49-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Diethyl ether ,  Water

Reference

Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones

Cho, Byung Tae; Yang, Weon Ki; Choi, Ok Kyung, Journal of the Chemical Society, 2001, (2001), 1204-1211

Production Method 14

104-88-1

37181-39-8

97466-49-4

Reaction Conditions

1.1 Reagents: N′′′-[P,P-Bis(dimethylamino)-N-(1,1-dimethylethyl)phosphinimyl]-N,N,N′,N′,N′′,N′… Solvents: Tetrahydrofuran ;  1 h, -78 °C; -78 °C → rt

Reference

Highly enantioselective ylide-mediated synthesis of terminal epoxides

Piccinini, Alessandro; Kavanagh, Sarah A.; Connon, Stephen J., Chemical Communications (Cambridge, 2012, 48(63), 7814-7816

Production Method 15

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: Isobutyraldehyde ,  Pyridine N-oxide ,  Oxygen Catalysts: Ruthenium, aquachloro[[3,3′-[(1,2-diphenyl-1,2-ethanediyl)bis[(nitrilo-κN)ethyli… Solvents: Dichloromethane

Reference

Chiral Ru(III) metal complex-catalyzed aerobic enantioselective epoxidation of styrene derivatives with co-oxidation of aldehyde

Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Iyer, P., Journal of Molecular Catalysis A: Chemical, 1997, 124(2-3), 91-97

Production Method 16

536-38-9

97466-49-4

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; 0.5 h, 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran ,  Water ;  2 h, rt

Reference

Chiral Epoxides via Borane Reduction of 2-Haloketones Catalyzed by Spiroborate Ester: Application to the Synthesis of Optically Pure 1,2-Hydroxy Ethers and 1,2-Azido Alcohols

Huang, Kun; Wang, Haiyang; Stepanenko, Viatcheslav; De Jesus, Melvin; Torruellas, Carilyn; et al, Journal of Organic Chemistry, 2011, 76(6), 1883-1886

Production Method 17

477761-19-6

97466-49-4

Reaction Conditions

1.1 Reagents: Triethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  1 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  10 h, rt

Reference

Facile synthesis of enantiopure 1,2-diols and terminal epoxides from chiral β-hydroxy sulfides

Cho, Byung Tae; Choi, Ok Kyoung; Kim, Dong Jun, Bulletin of the Korean Chemical Society, 2003, 24(7), 1023-1025

Production Method 18

357952-84-2

97466-49-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  2 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

The Stereoselective Oxidation of para-Substituted Benzenes by a Cytochrome P450 Biocatalyst

Chao, Rebecca R.; Lau, Ian C.-K.; Coleman, Tom; Churchman, Luke R.; Child, Stella A.; et al, Chemistry - A European Journal, 2021, 27(59), 14765-14777

Production Method 19

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: NAD ,  Oxygen Catalysts: Alcohol dehydrogenase ,  Styrene monooxygenase Solvents: Isopropanol ,  Water ;  24 h, 25 °C

Reference

Efficient biocatalysis for the production of enantiopure (S)-epoxides using a styrene monooxygenase (SMO) and Leifsonia alcohol dehydrogenase (LSADH) system

Toda, Hiroshi; Imae, Ryouta; Itoh, Nobuya, Tetrahedron: Asymmetry, 2012, 23(22-23), 1542-1549

Production Method 20

1073-67-2

97466-49-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: Titanium, [μ-[3,3′-bis[[[2-[[[2-(hydroxy-κO)[1,1′-biphenyl]-3-yl]methyl]amino-κN… Solvents: Dichloromethane ,  Water ;  100 min, rt; 9 h, rt

Reference

Biaryl-Bridged Salalen Ligands and Their Application in Titanium-Catalyzed Asymmetric Epoxidation of Olefins with Aqueous H2O2

Xiong, Donglu; Hu, Xiaoxue; Wang, Shoufeng; Miao, Cheng-Xia; Xia, Chungu; et al, European Journal of Organic Chemistry, 2011, 2011(23), 4289-4292

(2S)-2-(4-chlorophenyl)oxirane Raw materials

• 4-Chlorobenzaldehyde
• 2-bromo-1-(4-chlorophenyl)ethan-1-one
• 2,4'-Dichloroacetophenone
• 1,2-Ethanediol, 1-(4-chlorophenyl)-, 2-(4-methylbenzenesulfonate), (1S)-
• (S)-2-broMo-1-(4-chlorophenyl)ethanol
• 1,2-Ethanediol, 1-(4-chlorophenyl)-, (1S)-
• p-Chlorostyrene
• (αS)-4-Chloro-α-[[(4-methylphenyl)thio]methyl]benzenemethanol

(2S)-2-(4-chlorophenyl)oxirane Preparation Products

• (2S)-2-(4-chlorophenyl)oxirane (97466-49-4)

• 1. An amorphous lanthanum–iridium solid solution with an open structure for efficient water splitting?
  Wei Sun,Chenglong Ma,Xinlong Tian,Jianjun Liao,Ji Yang,Chengjun Ge,Weiwei Huang J. Mater. Chem. A, 2020,8, 12518-12525
• 2. An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay?
  Suji Lee,Min Su Han Chem. Commun., 2021,57, 9450-9453
• 3. Aluminium alkyl and aryloxide complexes of pyrazine and bipyridines: synthesis and structure?
  Doug Ogrin,Laura H. van Poppel,Simon G. Bott,Andrew R. Barron Dalton Trans., 2004, 3689-3694
• 4. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543
• 5. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Chlorobenzenes

• 53631-04-2((3-Chlorophenyl)oxirane)
• 2788-86-5(2-(4-chlorophenyl)oxirane)
• 20697-04-5(2-(3-Chlorophenyl)oxirane)
• 646041-19-2(Benzene, 1-chloro-4-[(1R)-1-methoxyethyl]-)
• 646041-14-7(Benzene, 1-chloro-4-[(1S)-1-methoxyethyl]-)
• 78982-97-5(Oxirane, (3,5-dichlorophenyl)-)
• 28291-10-3(Oxirane,2-(4-chlorophenyl)-3-phenyl-, (2R,3R)-rel-)
• 115648-90-3((S)-(3-Chlorophenyl)oxirane)
• 62600-71-9((R)-(+)-3-Chlorostyrene Oxide)
• 21019-51-2((R)-2-(4-Chlorophenyl)oxirane)