16133-83-8

Basic information

• Product Name: 2-phenyl-tetrahydrofuran
• Synonyms: 2-phenyl-tetrahydrofuran;2-phenyloxolane
• CAS NO: 16133-83-8
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• Mol File: 16133-83-8.mol

Chemical Properties

• Melting Point: 91-92 °C
• Boiling Point: 105 °C(Press: 14 Torr)
• Appearance: /
• Density: 1.037 g/cm3(Temp: 15 °C)
• CAS DataBase Reference: 2-phenyl-tetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-tetrahydrofuran(16133-83-8)
• EPA Substance Registry System: 2-phenyl-tetrahydrofuran(16133-83-8)

Safety Data

• Hazardous Substances Data: 16133-83-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-phenyl-tetrahydrofuran is used as a solvent and intermediate in the synthesis of pharmaceuticals and other organic compounds, contributing to the development of new drugs and medicines.
Used in Cosmetics and Perfumery:
PT is used as a component in some consumer products such as perfumes and cosmetics, where its unique properties enhance the fragrance and texture of these products.
Used in Bio-based Fuels and Renewable Chemicals Production:
2-phenyl-tetrahydrofuran is used as a precursor in the production of bio-based fuels and renewable chemicals, leveraging its unique structure to contribute to sustainable and eco-friendly alternatives to traditional fossil fuels.
Safety Precautions:
It is important to handle 2-phenyl-tetrahydrofuran with care, as it can be harmful if ingested or inhaled, and may cause skin and eye irritation upon contact. Proper safety measures should be taken during its use and storage to minimize potential health risks.

Upstream product

• 770-36-5 4-phenylbuta-3-en-1-ol 
• 503-30-0 trimethylene oxide 
• 67-56-1 methanol 
• 908094-04-2 phenyldiazomethane 
• 1191-99-7 2,3-dihydro-2H-furan 
• 108-86-1 bromobenzene 
• 120346-80-7 tetrahydro-2-(phenylsulphonyl)furan 
• 3360-41-6 4-phenyl-butan-1-ol 
• 4850-50-4 1-phenyl-butane-1,4-diol 
• 36866-66-7 5-phenyloxolan-2-ol 
• 124468-98-0 4-trimethylsiloxybutyrophenone 
• 100-52-7 benzaldehyde 
• 1073-05-8 1,3,2-dioxathiane 2,2-dioxide 
• 591-50-4 iodobenzene 

Downstream Products

• 107686-18-0 4-Phenyl-hept-5-yn-1-ol 
• 107686-17-9 1-ethenyl-(4-hydroxy-1-phenyl-1-butyl)cyclohexane 
• 107686-16-8 4-phenyl-6-heptene-1-ol 
• 71052-93-2 1-phenyl-1,4-dibromobutane 
• 87372-61-0 2-phenyl-2-allyltetrahydrofuran 
• 1469994-83-9 trimethyl(2-phenyltetrahydrofuran-2-yl)silane 
• 1469994-84-0 2-phenyl-2-(tributylstannyl)tetrahydrofuran 
• 1469994-85-1 2-phenyl-2-(phenylthio)tetrahydrofuran 
• 1469994-88-4 2-(2-phenyltetrahydrofuran-2-yl)propan-2-ol 
• 1469994-91-9 2-phenyltetrahydrofuran-2-carbaldehyde 
• 1469994-92-0 diphenyl(2-phenyltetrahydrofuran-2-yl)phosphine 
• 60507-03-1 acetophenone-d1 
• 1469994-82-8 2-deuterio-2-phenyltetrahydrofuran 
• 39755-03-8 4-hydroxy-1-phenyl-butan-1-one 

Relevant articles and documents

Oxidation of Unsaturated Aliphatic and Arylalkyl Alcohols by Peroxydisulphate. Intramolecular Cyclization of Alkoxyl Radicals

Oxidation of unsaturated aliphatic and arylalkyl alcohols by the sodium peroxydisulphate-silver salt system has benn studied.Both classes of alcohols lead to cyclic ethers through different pathways.The ratio of five- to six-membered cyclic ethers was est

Direct C-H bond activation of ethers and successive C-C bond formation with benzene by a bifunctional palladium-titania photocatalyst

Palladium-loaded titanium oxide was found to work as a bifunctional photocatalyst for functionalization of benzene with ether upon photoirradiation, without using any special reagents. The metal-loaded TiO2 photocatalyst activated a C-H bond of ethers and the heterogeneous Pd metal nanoparticle catalyst promoted the successive C-C bond formation between benzene and the radical species. In this reaction, benzene reacted very selectively with the α-carbon of various ethers at least in the initial stage of the reaction. Kinetic and ESR studies revealed a detailed mechanism for the reaction.

An unprecedented coupling reaction of arylmagnesium compounds with tetrahydrofuran providing 2-aryltetrahydrofuran mediated by an iodoalkane- EtMgBr system

An extremely facile coupling reaction between arylmagnesium compounds and THF by means of an iodoalkane-EtMgBr system provides 2- aryltetrahydrofurans. One-pot synthesis of 2thienyltetrahydrofuran is achieved from thiophene and THF using this coupling reaction.

Radical C(sp3)-H Heck-type Reaction of N-Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols

We report the first radical C(sp3)-H Heck-type reaction of aliphatic alcohols for selective δ- and ?-alkenol synthesis by photoredox catalysis. N-Alkoxybenzimidoyl chlorides are developed as novel alkoxyl radical precursors with tunable redox potentials. Various alkenols can be constructed by the inert C(sp3)-H Heck-type reaction of 4-cyano-N-alkoxybenzimidoyl chlorides with styrene derivatives under redox-neutral conditions, which can be performed on the gram scale and can be easily derivatized.

An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans

The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.

Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Br?nsted acid catalyst

A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Br?nsted acid. Computational prediction of the pKa value of BSI indicated its classification as a strong Br?nsted acid. BSI catalyzed the h

C1-Symmetric Binap Derivative Featuring Single Diferrocenylphosphino-Donor Moiety

A C1-symmetric chiral bisphosphine, FcPh-Binap (1), which possesses a single diferrocenylphosphino moiety together with a conventional Ph2P-substituent, was prepared in enantiomerically pure forms. Ligand 1 is sterically less demanding than Fc-Segphos (A)

H3PO2-Catalyzed Intramolecular Stereospecific Substitution of the Hydroxyl Group in Enantioenriched Secondary Alcohols by N-, O-, and S-Centered Nucleophiles to Generate Heterocycles

The direct intramolecular stereospecific substitution of the hydroxyl group in enantiomerically enriched secondary benzylic, allylic, propargylic, and alkyl alcohols was successfully accomplished by phosphinic acid catalysis. The hydroxyl group was displaced by O-, S-, and N-centered nucleophiles to provide enantioenriched five-membered tetrahydrofuran, pyrrolidine, and tetrahydrothiophene as well as six-membered tetrahydroquinolines and chromanes in up to a 99% yield and 100% enantiospecificity with water as the only byproduct. Mechanistic studies using both experiments and calculations have been performed for substrates generating 5-membered heterocycles. Rate studies show dependences in a catalyst, an internal nucleophile, and an electrophile, however, independence in an external nucleophile, an electrophile, or water. Kinetic isotope effect studies show an inverse KIE of kH/kD = 0.79. Furthermore, phosphinic acid does not promote SN1 reactivity. Computational studies support a bifunctional role of the phosphinic acid in which activation of both nucleofuge and nucleophile occurs in a bridging SN2-type transition state. In this transition state, the acidic hydrogen of phosphinic acid protonates the leaving hydroxyl group simultaneously as the oxo group partially deprotonates the nucleophile. Thereby, phosphinic acid promotes the substitution of the nonderivatized hydroxyl group in enantioenriched secondary alcohols by uncharged nucleophiles with conservation of the chirality from the alcohol to the heterocycle.

Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)-H and C(sp2)-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

Site- And enantiodifferentiating C(sp3)-H oxidation enables asymmetric access to structurally and stereochemically diverse saturated cyclic ethers

A manganese-catalyzed site- and enantiodifferentiating oxidation of C(sp3)-H bonds in saturated cyclic ethers has been described. The mild and practical method is applicable to a range of tetrahydrofurans, tetrahydropyrans, and medium-sized cyclic ethers with multiple stereocenters and diverse substituent patterns in high efficiency with extremely efficient site- and enantiodiscrimination. Late-stage application in complex biological active molecules was further demonstrated. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity. The ability to employ ether substrates as the limiting reagent, together with a broad substrate scope, and a high level of chiral recognition, represent a valuable demonstration of the utility of asymmetric C(sp3)-H oxidation in complex molecule synthesis.