143562-54-3

Basic information

• Product Name: Tetrahydro-4H-Pyran-4-one
• Synonyms: 4-oxacyclohexanone; 2,3,5,6-Tetrahydro-4-pyranone; TetrahydroHpyranone; Tetrahydro-2H-pyran-4-one; 4-Tetrahydropyranylcarboxylic acid; Pyran-4-carboxylic acid, tetrahydro-; Tetrahydro-4H-pran-4-one; dihydro-2H-pyran-4(3H)-one; 4-THP; 4-OXOCYCLOHEXANONE; 4H-Pyran-4-one, tetrahydro-; Tetrahydro-4H-pyran-4-on; Tetranydropyran-4-one; oxan-4-one
• CAS NO: 143562-54-3
• Molecular Formula: C5H8 O2
• Molecular Weight: 0100.12
• EINECS: 249-967-2
• Mol File: 143562-54-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 167.5°Cat760mmHg
• Flash Point: 63.6°C
• Appearance: colorless liquid
• Density: 1.065g/cm³
• Vapor Pressure: 1.69mmHg at 25°C
• Refractive Index: 1.451-1.453
• Water Solubility: MISCIBLE
• CAS DataBase Reference: Tetrahydro-4H-Pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydro-4H-Pyran-4-one(143562-54-3)
• EPA Substance Registry System: Tetrahydro-4H-Pyran-4-one(143562-54-3)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 143562-54-3(Hazardous Substances Data)

Usage

General Description

Tetrahydro-4H-Pyran-4-one, also known as dihydro-2H-pyran-4(3H)-one, or 4-hydroxytetrahydropyran, is a small size organic compound falling under the class of oxanes. It belongs to the family of Pyrans, which are compounds containing a pyran ring, offering heterocycle properties. Tetrahydro-4H-Pyran-4-one features a cyclohexane ring and an oxygen atom, which is considered an important skeleton in chemistry due to its prevalence in many natural products. It is typically used in scientific research, particularly in the development of pharmaceuticals, biomolecules, polymers, and materials chemistry. The compound can be derived both synthetically and naturally. It has a molecular formula of C5H8O2 and a molar mass of 100.12 g·mol?1.

InChI:InChI=1/C5H8O2/c6-5-1-3-7-4-2-5/h1-4H2

Upstream product

• 2081-44-9 Tetrahydro-pyran-4-ol 
• 108-97-4 4-pyrone 
• 2919-05-3 pent-4-en-2-yn-1-ol 
• 3592-25-4 1,5-dichloropentan-3-one 
• 64769-48-8 5-ethoxy-pent-1-en-3-yne 
• 7664-93-9 sulfuric acid 
• 100960-26-7 5-acetoxy-pent-1-en-3-one 
• 84302-42-1 2,3-dihydro-4H-pyran-4-one 
• 50675-18-8 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde 
• 124-38-9 carbon dioxide 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 1194657-31-2 4-nitrosotetrahydro-2H-pyran-4-yl 2,2,2-trichloroacetate 
• 1194657-35-6 4-nitrosotetrahydro-2H-pyran-4-yl pivalate 
• 1194657-13-0 4-nitrosotetrahydro-2H-pyran-4-yl acetate 

Downstream Products

• 91332-46-6 tetrahydro-pyran-4-one-(4-nitro-phenylhydrazone) 
• 24606-03-9 tetrahydro-pyran-4-one-(2,4-dinitro-phenylhydrazone) 
• 17517-75-8 10-phenyl-3,4-dihydro-1H-pyrano[4,3-b]quinoline 
• 112799-20-9 4-Pyrrolidino-tetrahydro-4H-pyran-4-carbonitril 
• 84655-51-6 4-hydroxy-4-<2-(1-methoxy-1-phenylmethyl)phen-1-yl>-2,3,5,6-tetrahydropyran 
• 4233-18-5 bicyclohexylidene 
• 2888-11-1 1,1'-bicyclohexane-1,1'-diol 
• 80879-18-1 4-(tetrahydropyranyl)cyclohexane-1,1'-diol 
• 80879-19-2 4-Cyclohexylidene-tetrahydro-pyran 
• 80879-20-5 Octahydro-[4,4']bipyranylidene 
• 131067-76-0 3-methyl-tetrahydro-pyran-4-one 
• 243968-52-7 tert-butyl 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylate 
• 81462-07-9 4-phenyltetrahydro-2H-pyran-4-ol 
• 57155-42-7 3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one 

Relevant articles and documents

Elemental fluorine. Part 7. New oxidation methodology

Reaction of fluorine with water in the presence of acids provides new oxidants for 'in-situ' oxidation of ketones. Direct reaction of fluorine with anhydrous alcohols and 1,2-diols provides simple methodology for oxidation to corresponding secondary ketones or α-hydroxy ketones.

Tetrahydro-4 H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

This study describes our recent efforts to find an efficient and scalable route to tetrahydro-4H-pyran-4-one using the commercially available starting materials. The route scouting work and the full development of an efficient access to the target are described. This work culminated in the preparation of above 20 kg of the title compound in our pilot plant facility.

Tetrahydropyranone preparation method

The invention relates to a tetrahydropyranone preparation method, the method takes acetone and diethyl oxalate as raw materials, through steps of a ring closure reaction, a decarboxylation reaction, and a reduction reaction, three-step high-yield synthesis is realized to obtain tetrahydropyranone. The tetrahydropyranone preparation method has the advantages of high yield, low cost, and easy operation, and is suitable for industrial preparation method.

Synthesis of azasilacyclopentenes and silanols: Via Huisgen cycloaddition-initiated C-H bond insertion cascades

An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C-H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C-H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.