20638-52-2

Basic information

• Product Name: 4-phenyl-tetrahydro-2H-pyran
• Synonyms: 4-phenyl-tetrahydro-2H-pyran
• CAS NO: 20638-52-2
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.22826
• Mol File: 20638-52-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 49-50 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Boiling Point: 253.5°C at 760 mmHg
• Flash Point: 102.9°C
• Appearance: /
• Density: 1.003g/cm³
• Vapor Pressure: 0.029mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 4-phenyl-tetrahydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenyl-tetrahydro-2H-pyran(20638-52-2)
• EPA Substance Registry System: 4-phenyl-tetrahydro-2H-pyran(20638-52-2)

Safety Data

• Hazardous Substances Data: 20638-52-2(Hazardous Substances Data)

Usage

General Description

4-phenyl-tetrahydro-2H-pyran is a chemical compound with the molecular formula C12H14O. It is a heterocyclic compound that contains a tetrahydropyran ring with a phenyl group attached at the 4-position. 4-phenyl-tetrahydro-2H-pyran is commonly used as a building block in organic synthesis and medicinal chemistry, and it has been found to have potential biological activities, including anti-bacterial and anti-fungal properties. 4-phenyl-tetrahydro-2H-pyran has also been studied for its potential use in the development of new drugs and pharmaceuticals. Additionally, it is utilized as a fragrance ingredient in the perfume industry due to its pleasant and sweet aroma.

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

Upstream product

• 829-27-6 3-phenylpentane-1,5-diol 
• 1768-64-5 4-chlorotetrahydro-2H-pyran 
• 98-80-6 phenylboronic acid 
• 25637-18-7 4-iodotetrahydropyran 
• 100-59-4 phenylmagnesium chloride 
• 1202-81-9 4-phenyltetrahydro-2H-pyran-4-carbonitrile 
• 140-29-4 phenylacetonitrile 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 100-58-3 phenylmagnesium bromide 
• 1078-58-6 diphenylzinc 
• 5337-03-1 tetrahydro-2H-pyran-4-carboxylic acid 
• 71-43-2 benzene 
• 4165-96-2 3-phenylglutaric acid 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 

Downstream Products

• 27070-24-2 (3-bromo-1-(2-bromoethyl)-propyl)benzene 
• 1276024-95-3 methyl 4-(tetrahydro-2H-pyran-4-yl)benzoate 
• 1276024-96-4 (4-tetrahydropyran-4-yl-phenyl)methanol 
• 1276024-97-5 4-(tetrahydro-2H-pyran-4-yl)benzaldehyde 
• 19015-37-3 1-(phenylmethyl)-4-phenylpiperidine 

Relevant articles and documents

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

General C(sp2)-C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts

Cross-electrophile coupling (XEC) of alkyl and aryl halides promoted by electrochemistry represents an attractive alternative to conventional methods that require stoichiometric quantities of high-energy reductants. Most importantly, electroreduction can readily exceed the reducing potentials of chemical reductants to activate catalysts with improved reactivities and selectivities over conventional systems. This work details the mechanistically-driven development of an electrochemical methodology for XEC that utilizes redox-active shuttles developed by the energy-storage community to protect reactive coupling catalysts from overreduction. The resulting electrocatalytic system is practical, scalable, and broadly applicable to the reductive coupling of a wide range of aryl, heteroaryl, or vinyl bromides with primary or secondary alkyl bromides. The impact of overcharge protection as a strategy for electrosynthetic methodologies is underscored by the dramatic differences in yields from coupling reactions with added redox shuttles (generally >80%) and those without (generally 20%). In addition to excellent yields for a wide range of substrates, reactions protected from overreduction can be performed at high currents and on multigram scales.

Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers

Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.