1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one

Product Name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
CAS No.: 63106-93-4
Chemical Name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Synonyms: Milnacipran HCl PI-1;5-phenyl-3-oxabicyclo[3.1.0]hexan-4-one;2-oxo-iphenyl-3-oxbicyclo｛3.1.0｝-hexane;2-oxo-1phenyl-3-oxbicyclo｛3.1.0｝-hexane;1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one;2–Oxo-1phenyl-3-oxbicyclo{3.1.0}-hexane2;3-Oxabicyclo[3.1.0]hexan-2-one, 1-phenyl-;2-Oxo-1-phenyl-3-oxabicyclo[3.1.0]-hexane;(1R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one;(1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE
CBNumber: CB01008935
Molecular Formula: C11H10O2
Formula Weight: 174.2
MOL File: 63106-93-4.mol

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1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Property

Melting point:: 49-50 °C
Boiling point:: 119 °C(Press: 0.1 Torr)
Density: 1.300±0.06 g/cm3(Predicted)
storage temp.: Hygroscopic, Refrigerator, under inert atmosphere
solubility: Chloroform, Methanol
form: Solid
color: White to Off-White
InChI: InChI=1S/C11H10O2/c12-10-11(6-9(11)7-13-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChIKey: WZGFIZUMKYUMRN-UHFFFAOYSA-N
SMILES: C12(C3=CC=CC=C3)C(C1)COC2=O

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Safety

HS Code: 2918300090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: P336115
Product name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 25g
Price: $65
Updated: 2021/12/16

TRC

Product number: P336115
Product name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 50g
Price: $95
Updated: 2021/12/16

Usbiological

Product number: 286612
Product name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 25g
Price: $333
Updated: 2021/12/16

AK Scientific

Product number: J51001
Product name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 1g
Price: $10
Updated: 2021/12/16

AK Scientific

Product number: J51001
Product name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 5g
Price: $25
Updated: 2021/12/16

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1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical Properties,Usage,Production

Uses

Intermediate in the synthesis of Milnacipran (M344600) an antidepressant. A selective norepinephrine and serotonin reuptake inhibitor approved for the management of fibromyalgia.

Reactions

1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (1POX) is a monomer that belongs to the class of cyclopropane compounds and can be used in the synthesis of polymers. It has been shown to react with benzene, irradiation, monoxide, oxiranyl, acetonitrile and trimeric dyes to form reactive intermediates such as ketones and carboxylic acids. These intermediates can undergo photolysis to produce products such as ketones and carboxylic acids. The wavelength of the light used for photolysis can influence the product formation.

Synthesis

140-29-4

106-89-8

63106-93-4

1. To a solvent mixture of toluene (26.0 kg) and N,N'-dimethyl-2-imidazolidinone (94.9 kg), 60% sodium hydride (27.2 kg, 683 mol) was slowly added, followed by benzeneacetonitrile (40.2 kg, 343 mol). After the dropwise addition was completed at 10 to 20 °C, stirring was continued for 2 h. The mixture was then mixed into the solvent mixture at the same temperature range. 2. A mixture of 1-chloro-2,3-epoxypropane (31.7 kg, 343 mol) and toluene (26.0 kg) was added dropwise over the same temperature range and stirring was continued until the feedstock was completely gone. 3. Upon completion of the reaction, methanol (22.0 kg) and water (120.6 kg) were added for washing followed by phase separation. 4. 24% aqueous potassium hydroxide (159.1 kg) and tetrabutyl ammonium sulfate (1.1 kg) were added to the organic layer and heated under reflux conditions. 5. After removal of the organic phase by phase separation, toluene (69.6 kg) and 35% hydrochloric acid (78.7 kg) were added to the aqueous phase and stirred at 60-70 °C for 2 hours. 6. Phase separation was performed again to separate the organic phase, which was washed twice with 8% aqueous sodium bicarbonate and twice with water in turn. 7. The washed organic layer was concentrated under reduced pressure to give 40.7 kg of 1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one as a pale yellow oil in 68.1% yield. 8. The resulting 1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one oily substance was cooled to induce crystallization.

Structure and conformation

1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (1POX) is also a substrate for cyclopropane ring formation reactions, which are known for their high reactivity due to the stability of this ring system. The carbonyl group on 1POX is electron withdrawing and stabilizes the planar geometry of 1POX.

References

[1] Patent: WO2005/123709, 2005, A1. Location in patent: Page/Page column 6-7
[2] Patent: EP1767522, 2007, A1. Location in patent: Page/Page column 3
[3] Patent: US2012/165339, 2012, A1. Location in patent: Page/Page column 22-23
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4648 - 4664

1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Preparation Products And Raw materials

Raw materials

Preparation Products

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1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Suppliers

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View Lastest Price from 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one manufacturers

Jinan Ruitong Biotech Co., Ltd.

Product: 2-Oxo-1-phenyl-3-oxabicyclo [3.1.0]-hexane 63106-93-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1
Release date: 2025-08-27

Taizhou Creating Bio-pharm co., ltd.

Product: (1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE 63106-93-4
Price: US $0.00/KG
Min. Order: 1KG
Purity: 0.99
Supply Ability: 10TONS
Release date: 2025-06-06

Shaanxi Xianhe Biotech Co., Ltd

Product: (1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE 63106-93-4
Price: US $0.00/KG
Min. Order: 1KG
Purity: 0.99
Supply Ability: 1000KG
Release date: 2025-04-17

63106-93-4, 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-oneRelated Search:

4'-Hydroxyacetophenone Benzyl alcohol TPP (1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE 1-Phenyl-1-cyclopropanecarboxylic acid MILNACIPRAN HYDROCHLORIDE

(1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE

2-Oxo-1-phenyl-3-oxabicyclo[3.1.0]-hexane

1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one

(1R,2S)-rel-2-Oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane

2–Oxo-1phenyl-3-oxbicyclo{3.1.0}-hexane2

Milnacipran HCl PI-1

2-oxo-1phenyl-3-oxbicyclo｛3.1.0｝-hexane

2-oxo-iphenyl-3-oxbicyclo｛3.1.0｝-hexane

5-phenyl-3-oxabicyclo[3.1.0]hexan-4-one

Cis(±)-1-phenyl-2-oxo-3-oxa bicyclo[3.1.0]hexane (Racemate) (63106-93-4)

3-Oxabicyclo[3.1.0]hexan-2-one, 1-phenyl-

(1R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

(1S,1R)-(5R,5S)-1-Phenyl-2-oxo-3-oxabicyclo[3.1.0]hexane

63106-93-4