15212-27-8

Basic information

• Product Name: 2-BENZYLTETRAHYDROFURAN
• Synonyms: 2-BENZYLTETRAHYDROFURAN
• CAS NO: 15212-27-8
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• Mol File: 15212-27-8.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 247.3°Cat760mmHg
• Flash Point: 99.1°C
• Appearance: /
• Density: 1.026g/cm³
• Vapor Pressure: 0.041mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 2-BENZYLTETRAHYDROFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYLTETRAHYDROFURAN(15212-27-8)
• EPA Substance Registry System: 2-BENZYLTETRAHYDROFURAN(15212-27-8)

Safety Data

• Hazardous Substances Data: 15212-27-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14O/c1-2-5-10(6-3-1)9-11-7-4-8-12-11/h1-3,5-6,11H,4,7-9H2

Upstream product

• 37542-92-0 2-benzylfuran 
• 109-99-9 tetrahydrofuran 
• 908094-04-2 phenyldiazomethane 
• 93214-18-7 exo-6-Phenyl-2-oxabicyclo<3.1.0>hexane 
• 93214-18-7 endo-6-Phenyl-2-oxabicyclo<3.1.0>hexane 
• 85696-66-8 4-Chloro-5-phenyl-pentan-1-ol 
• 195874-69-2 N-((E)-5-Phenyl-pent-4-enyloxy)-selenobenzimidic acid phenyl ester 
• 230285-18-4 1-(diethylphosphatoxy)-1-phenyl-5-(N-phthalimidoxy)pentane 
• 230285-19-5 1-(diphenylphosphatoxy)-1-phenyl-5-(N-phthalimidoxy)pentane 
• 10521-91-2 5-phenylpentan-1-ol 
• 1011-62-7 5-hydroxy-1-phenylpentan-1-one 
• 230285-14-0 1-phenyl-1-(2-tetrahydropyranyloxy)-5-pentanol 
• 230285-16-2 1-phenyl-5-(N-phthalimidoxy)-1-pentanol 
• 230285-11-7 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-pentanone 

Downstream Products

• 90397-88-9 5-Iodo-1-phenyl-pentan-2-ol 
• 91130-80-2 (2,5-dibromo-pentyl)-benzene 

Relevant articles and documents

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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.

Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π-Alkene Activation

Heteroarylation of alkenes with aryl iodides was efficiently achieved with a (MeDalphos)AuCl complex through AuI/AuIII catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5-, 6-, and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox/oxidative approaches. In addition, it provides a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols.

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.