6581-66-4

Basic information

• Product Name: 2-METHOXYTETRAHYDROPYRAN
• Synonyms: 2-Methoxytetrahydro-2H-pyran;(R,S)-2-Methoxy-tetrahydro-pyran;2H-Pyran,tetrahydro-2-methoxy-;2-methoxy-tetrahydro-pyra;Pyran,tetrahydro-2-methoxy-;tetrahydro-2-methoxy-2h-pyra;tetrahydro-2-methoxy-2h-pyran;2-METHOXYTETRAHYDROPYRAN
• CAS NO: 6581-66-4
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• EINECS: 229-509-8
• Product Categories: Heterocyclic Building Blocks;Pyrans;Building Blocks
• Mol File: 6581-66-4.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 128-129 °C(lit.)
• Flash Point: 77 °F
• Appearance: /
• Density: 0.963 g/mL at 25 °C(lit.)
• Vapor Pressure: 12.9mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• CAS DataBase Reference: 2-METHOXYTETRAHYDROPYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXYTETRAHYDROPYRAN(6581-66-4)
• EPA Substance Registry System: 2-METHOXYTETRAHYDROPYRAN(6581-66-4)

Safety Data

• Hazard Codes: F
• Statements: 10
• Safety Statements: 16-29-33
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 2
• RTECS: UQ0300000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 6581-66-4(Hazardous Substances Data)

Usage

Preparation

To a flask equipped with a stirrer and containing 84.0 gm (1.0 mole) of 2,3-dihydropyran in the presence of 1 ml of cone, hydrochloric acid is added 32.0 gm (1.0 mole) of methanol. The reaction is exothermic and is stirred for 3 hr. Then a few pellets of sodium hydroxide are added to make the reaction basic. The mixture is directly distilled to afford 98.6 gm (85%), b.p. 125°C (760 mm Hg).

General Description

2-Methoxytetrahydropyran is methoxy-substituted tetrahydropyran. α- and β-glycosidic C1-O1 bonds of the axial and equatorial forms of 2-methoxytetrahydropyran has been investigated by ab initio conformational study. Stereochemical properties of the glycosidic linkage of 2-methoxytetrahydropyran have been studied by the quantum-chemical PCILO method. It undergoes elimination reaction in the gas phase to yield 3, 4-dihydro-2H-pyran and methanol. Proton resonance spectra of 2-methoxytetrahydropyran has been analyzed.

InChI:InChI=1/C6H12O2/c1-7-6-4-2-3-5-8-6/h6H,2-5H2,1H3

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 67-56-1 methanol 
• 5631-96-9 2-(2-chloroethoxy)-tetrahydro-2H-pyrane 
• 1927-62-4 tetrahydro-2-(benzyloxy)-2H-pyran 
• 1927-50-0 2-benzylsulfanyltetrahydropyran 
• 78633-30-4 2-Buten-1-ol Tetrahydropyranyl Ether 
• 5324-21-0 3-bromo-2-methoxy-tetrahydropyran 
• 1927-63-5 2-hexyloxy-tetrahydro-pyran 
• 2162-31-4 2-(tetrahydropyran-2-yloxy)ethanol 
• 30784-04-4 2-naphthyl tetrahydro-2H-pyran-2-yl ether 
• 54105-78-1 1-[(tetrahydro-2H-pyran-2-yl)oxy]-3-methyl-2-butene 
• 4454-05-1 2-methoxy-3,4-dihydro-2H-pyran 
• 28627-46-5 2-(tert-butylperoxy)tetrahydro-2H-pyran 

Downstream Products

• 37749-86-3 2-(Tetrahydro-2H-pyran-2-yl)-1-cyclohexanon 
• 5397-43-3 tetrahydro-2H-pyran-2-carbonitrile 
• 64042-26-8 tetrahydro-2-(phenylseleno)-2H-Pyran 
• 137469-52-4 5-Methoxy-5-phenylselanyl-pentan-1-ol 
• 20965-36-0 2-(phenylthio)tetrahydro-2H-pyran 
• 96754-03-9 2-(phenylsulfonyl)tetrahydro-2H-pyran 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 624-24-8 methyl valerate 
• 628-77-3 1,5-diiodopentane 
• 7429-25-6 2-iodotetrahydropyran 
• 74-88-4 methyl iodide 
• 142-68-7 TETRAHYDROPYRANE 
• 67-56-1 methanol 
• 22528-77-4 phenyl-2-(tetrahydro-2H-pyran-2-yl)ethanone 

Relevant articles and documents

Characterization and catalytic activity of acid-treated, size-fractionated smectites

Five layered silicates in which the octahedral sheet contained differing amounts of Al, Mg, Fe, and Li were acid leached using acid concentrations and treatment temperatures selected to produce materials in which the octahedral sheet was depopulated in a controlled, stepwise (yet comparable) manner. SAz-1 and JP are dioctahedral smectites with octahedral compositions rich in Mg and Al, respectively. SWa-1 is a ferruginous smectite and ST an iron-rich beidellite. The fifth mineral was a trioctahedral hectorite which contains almost exclusively octahedral Mg. The Br?nsted acidity and catalytic activity of the resulting materials were highest for the samples prepared with the mildest acid treatments but decreased as the octahedral sheet became increasingly depleted. Only the hectorite exhibited no catalytic activity despite the proven existence of Br?nsted acid sites. The elemental composition of the starting material did not appear to make a significant contribution to the catalytic activity for the chosen test reaction although it does play a key role in determining the seventy of the activation conditions required for the optimization of catalytic activity. Fourier transform infrared (FTIR) spectroscopy was found to be as sensitive to structural acid attack as 29Si magic angle spinning NMR and the octahedral depletion (measured using FTIR) correlated well with the acidity determined from thermal desorption of cyclohexylamine.

Sulfonic acid-functionalized LUS-1: an efficient catalyst for tetrahydropyranylation/depyranylation of alcohols

Efficient acidic functionalization of mesoporous silica LUS-1 (Laval University Silica) and its application as a recyclable heterogeneous catalyst for DHP (3,4-dihydro-2H-pyran) protection of alcohols and the subsequent removal of the corresponding protecting group have been reported. This green method offers a number of advantages such as short reaction time, good yields of protection and deprotection, simple work-up procedure, recyclable catalyst, and environmentally friendly conditions.

Aqueous-phase hydrogenation and hydrodeoxygenation of biomass-derived oxygenates with bimetallic catalysts

The reaction rate on a per site basis for aqueous-phase hydrogenation (APH) of propanal, xylose, and furfural was measured over various alumina-supported bimetallic catalysts (Pd-Ni, Pd-Co, Pd-Fe, Ru-Ni, Ru-Co, Ru-Fe, Pt-Ni, Pt-Co, and Pt-Fe) using a high-throughput reactor (HTR). The results in this paper demonstrate that the activity of bimetallic catalysts for hydrogenation of a carbonyl group can be 110 times higher than monometallic catalysts. The addition of Fe to a Pd catalyst increased the activity for hydrogenation of propanal, xylose, and furfural. The Pd1Fe3 catalyst had the highest reaction rate for APH of propanal among all catalysts tested in the HTR. The addition of Fe to the Pd catalyst increased the reaction rate for xylose hydrogenation by a factor of 51, compared to the monometallic Pd catalyst. However, no bimetallic catalyst tested in this study was more active than the monometallic Ru catalyst for hydrogenation of xylose. The Pd1Fe 3 catalyst had the highest reaction rate for APH of furfural, which was 9 times higher than the rate of the Pd catalyst. The Pd1Fe 3/Zr-P, a bimetallic bifunctional catalyst, was 14 times more active on a per site basis than a Pd/Zr-P catalyst for aqueous-phase hydrodeoxygenation (HDO) of sorbitol in a continuous flow reactor. The addition of Fe to the Pd catalyst increased the rate of C-C cleavage reactions and promoted the conversion of sorbitan and isosorbide in HDO of sorbitol. Pd1Fe 3/Zr-P also had a higher yield of gasoline-range products than the Pd/Zr-P catalyst.