10317-13-2

Basic information

• Product Name: 3-phenyloxetane
• Synonyms: 3-phenyloxetane;Oxetane, 3-phenyl-;beta,beta'-Epoxycumene
• CAS NO: 10317-13-2
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.1751
• Mol File: 10317-13-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 55-56℃
• Boiling Point: 82-85℃ (4 Torr)
• Flash Point: 78.978 °C
• Appearance: /
• Density: 1.063 g/cm³
• Vapor Pressure: 0.219mmHg at 25°C
• Refractive Index: 1.5386 (589.3 nm 20℃)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-phenyloxetane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyloxetane(10317-13-2)
• EPA Substance Registry System: 3-phenyloxetane(10317-13-2)

Safety Data

• Hazardous Substances Data: 10317-13-2(Hazardous Substances Data)

Usage

General Description

3-Phenyloxetane is a colorless liquid with a molecular formula of C9H10O. It is a chemical compound that belongs to the class of oxetanes, which are cyclic organic compounds containing a three-membered ring. 3-Phenyloxetane is mainly used as a building block in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It is also used in the manufacturing of flavors and fragrances. However, it is important to handle 3-Phenyloxetane with care, as it is classified as a flammable liquid and a hazardous chemical. Additionally, it may cause irritation to the skin, eyes, and respiratory system, so proper safety precautions should be observed when working with this compound.

InChI:InChI=1/C9H10O/c1-2-4-8(5-3-1)9-6-10-7-9/h1-5,9H,6-7H2

Upstream product

• 1570-95-2 2-phenylpropane-1, 3-diol 
• 26272-85-5 3-iodooxetane 
• 98-80-6 phenylboronic acid 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 780-69-8 triethoxyphenylsilane 
• 40893-99-0 3-bromo-2-phenyl-propan-1-ol 

Downstream Products

• 40893-99-0 3-bromo-2-phenyl-propan-1-ol 
• 184682-45-9 3-(4-nitrophenyl)oxetane 
• 189572-01-8 2-(4-nitrophenyl)-1,3-O-dinitropropanediol 
• 6274-58-4 3-chloro-2-phenyl-1-propanol 
• 571206-65-0 (S)-3-azido-2-phenyl-1-propanol 
• 571206-58-1 (R)-3-bromo-2-phenyl-1-propanol 

Relevant articles and documents

Palladium-catalyzed hiyama cross-couplings of arylsilanes with 3-Iodoazetidine: Synthesis of 3-arylazetidines

The first palladium-catalyzed Hiyama cross-coupling reactions of arylsilanes with 3-iodoazetidine were described. The protocol provides a convenient access to a variety of useful 3-arylazetidines which are of great interest in pharmaceutical laboratories in moderate to good yields (30%-88%). In addition, this strategy has the advantage of easy operation and mild reaction conditions.

Catalytic One-Pot Oxetane to Carbamate Conversions: Formal Synthesis of Drug Relevant Molecules

Oxetanes are versatile building blocks in drug-related synthesis to induce property-modulating effects. Whereas related oxiranes are widely used in coupling chemistry with carbon dioxide (CO2) to afford value-added commodity chemicals, oxetane/CO2couplings remain extremely limited despite the recent advances in the synthesis of these four-membered heterocycles. Here we report an effective one-pot three-component reaction (3CR) strategy for the coupling of (substituted) oxetanes, amines and CO2to afford a variety of functionalized carbamates with excellent chemoselectivity and good yields. The process is mediated by an aluminium-based catalyst under relatively mild conditions and the developed catalytic methodology can be applied to the formal synthesis of two pharmaceutically relevant carbamates with the 3CR being a key step. (Figure presented.).

A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Br?nsted- And Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings

Generality in asymmetric catalysis can be manifested in dramatic and valuable ways, such as high enantioselectivity across a wide assortment of substrates in a given reaction (broad substrate scope) or as applicability of a given chiral framework across a variety of mechanistically distinct reactions (privileged catalysts). Reactions and catalysts that display such generality hold special utility, because they can be applied broadly and sometimes even predictably in new applications. Despite the great value of such systems, the factors that underlie generality are not well understood. Here, we report a detailed investigation of an asymmetric hydrogen-bond-donor catalyzed oxetane opening with TMSBr that is shown to possess unexpected mechanistic generality. Careful analysis of the role of adventitious protic impurities revealed the participation of competing pathways involving addition of either TMSBr or HBr in the enantiodetermining, ring-opening event. The optimal catalyst induces high enantioselectivity in both pathways, thereby achieving precise stereocontrol in fundamentally different mechanisms under the same conditions and with the same chiral framework. The basis for that generality is analyzed using a combination of experimental and computational methods, which indicate that proximally localized catalyst components cooperatively stabilize and precisely orient dipolar enantiodetermining transition states in both pathways. Generality across different mechanisms is rarely considered in catalyst discovery efforts, but we suggest that it may play a role in the identification of so-called privileged catalysts.