(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one

Product Name: (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
CAS No.: 96847-53-9
Chemical Name: (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Synonyms: Milnacipran Hydrochloride Impurity 2;(1S,5R)-1-Pheny-3-oxabicyclo[3.1.0]hexan-2-one;cis-(-)-1-Phenyl-2-oxo-3-oxabicyclo[3.1.0]hexane;(1S,5R)-2-Oxo-1-phenyl-3-oxa bicyclo[3.1.0]hexane;(1S,5R)-1-phenyl-2-oxo-3-oxa bicyclo[3.1.O ]hexane;(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-oneacid;3-Oxabicyclo[3.1.0]hexan-2-one, 1-phenyl-, (1S,5R)-;cis-(-)-1-Phenyl-2-oxo-3-oxabicyclo[3.1.0]hexane 98%;(1S,5R)-1-phenyl-2-oxo-3-oxa bicyclo[3.1.0]hexane (96847-53-9)
CBNumber: CB42714693
Molecular Formula: C11H10O2
Formula Weight: 174.2
MOL File: 96847-53-9.mol

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(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Property

Boiling point:: 340.0±21.0 °C(Predicted)
Density: 1.300±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
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/t9-,11+/m0/s1
InChIKey: WZGFIZUMKYUMRN-GXSJLCMTSA-N
SMILES: [C@@]12(C3=CC=CC=C3)[C@@]([H])(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

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: P336118
Product name: (1S,5R)-rel-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 250mg
Price: $45
Updated: 2021/12/16

TRC

Product number: P336118
Product name: (1S,5R)-rel-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 500mg
Price: $60
Updated: 2021/12/16

AK Scientific

Product number: 1580CS
Product name: (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 5g
Price: $108
Updated: 2021/12/16

SynQuest Laboratories

Product number: 2H25-1-74
Product name: cis-(-)-1-Phenyl-2-oxo-3-oxabicyclo[3.1.0]hexane
Packaging: 10g
Price: $108
Updated: 2021/12/16

AK Scientific

Product number: 1580CS
Product name: (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Packaging: 10g
Price: $132
Updated: 2021/12/16

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(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical Properties,Usage,Production

Synthesis

51594-55-9

140-29-4

63106-93-4

General procedure for the synthesis of 1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one from levulinic epichlorohydrin and phenylacetonitrile: 28 g of sodium amide (0.682 mol) was suspended in 400 ml of toluene, and 85.5 g of a toluene solution of phenylacetonitrile (0.729 mol) was slowly added with vigorous stirring and at 0-5 °C. The reaction mixture was stirred continuously at 0°C for at least 1 hour. Subsequently, 27 g of levulinic epichlorohydrin (0.292 mol) dissolved in 40 ml of toluene was added while the reaction temperature was controlled at 100 °C. After the addition was completed, the reaction mixture was stirred at 50°C for at least 2 hours. After completion of the reaction, the reaction solution was slowly poured into 240 ml of water for hydrolysis, keeping the temperature between 5-40°C. The hydrolyzed solution was concentrated, 115 g of 30% sodium hydroxide solution was added and the mixture was heated to 95°C to promote hydrolysis of the nitro functional groups. The reaction mixture was washed twice with 190 ml of toluene and the toluene phase was discarded. After addition of 270 ml of toluene, the aqueous phase was separated by acidification with 25% hydrochloric acid solution to the appropriate pH. Subsequently, the mixture was heated to 60°C and kept for at least 3 hours. After decantation, the toluene phase containing the target lactone was washed with 10 ml of water and neutralized with 10% sodium carbonate solution to pH 8. Finally, the toluene phase was washed with 140 ml of water and concentrated to give 38 g of intermediate lactone 3.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2834 - 2837
[2] Patent: US2012/165339, 2012, A1. Location in patent: Page/Page column 25-26
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8838 - 8858,21
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8838 - 8858
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6371 - 6385

(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Preparation Products And Raw materials

Raw materials

Preparation Products

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(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Suppliers

China 65 India 8 United Kingdom 3 United States 4 Global 80

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Lynnchem

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View Lastest Price from (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one manufacturers

Jinan Ruitong Biotech Co., Ltd.

Product: (1S,5R)-1-phenyl-2-oxo-3-oxa bicyclo[3.1.O ]hexane 96847-53-9
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1
Release date: 2025-08-27

Shaanxi Dideu New Materials Co. Ltd

Product: (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one 96847-53-9
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 10000KGS
Release date: 2025-02-18

Zhuozhou Wenxi import and Export Co., Ltd

Product: (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one 96847-53-9
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-26

96847-53-9, (1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-oneRelated Search:

Milnacipran Hydrochloride (1S-cis)-Milnacipran Hydrochloride Sertraline hydrochloride

(1S,5R)-1-phenyl-2-oxo-3-oxa bicyclo[3.1.0]hexane (96847-53-9)

cis-(-)-1-Phenyl-2-oxo-3-oxabicyclo[3.1.0]hexane

Milnacipran Hydrochloride Impurity 2

cis-(-)-1-Phenyl-2-oxo-3-oxabicyclo[3.1.0]hexane 98%

3-Oxabicyclo[3.1.0]hexan-2-one, 1-phenyl-, (1S,5R)-

(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-oneacid

(1S,5R)-2-Oxo-1-phenyl-3-oxa bicyclo[3.1.0]hexane

(1S,5R)-1-Pheny-3-oxabicyclo[3.1.0]hexan-2-one

(1S,5R)-1-phenyl-2-oxo-3-oxa bicyclo[3.1.O ]hexane

96847-53-9