14774-37-9

Basic information

• Product Name: (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL
• Synonyms: (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL;(TETRAHYDRO-PYRAN-4-YL)-METHANOL;TETRAHYDROPYRAN-4-METHANOL;TERTAHYDROPYRAN-4-METHANOL;4-(Hydroxymethyl)tetrahydro-2H-pyran;4-(Hydroxymethyl)tetrahydropyr;(Tetrahydro-pyran-4-yl)-methanol ,97%;4-(Hydroxymethyl)tetrahydropyran
• CAS NO: 14774-37-9
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.15828
• Product Categories: blocks;Heterocycles;Alcohols and Derivatives;Heterocycles series;Hydroxymethyl's;Pyrans, Piperidines &Piperazines;Pyrans, Piperidines & Piperazines
• Mol File: 14774-37-9.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 105 °C
• Flash Point: 61°(142°F)
• Appearance: /
• Density: 1 g/cm³
• Vapor Pressure: 0.0259mmHg at 25°C
• Refractive Index: 1.4600
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.85±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL(14774-37-9)
• EPA Substance Registry System: (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL(14774-37-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-41-37/38
• Safety Statements: 26-36/37/39-23-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 14774-37-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Used as a reagent in the identification and optimization of pteridinone Toll-like receptor 7 agonists, which can be used for the oral treatment of viral hepatitis. 4-(Hydroxymethyl)tetrahydropyran is also a starting material for [1-[(Tetrahydro-2H-pyran-4-yl)methyl]-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone which is a drug that acts as CB2 cannabinoid receptor agonist.

InChI:InChI=1/C6H12O2/c7-5-6-1-3-8-4-2-6/h6-7H,1-5H2

Upstream product

• 36838-71-8 4-methylene-tetrahydro-pyran 
• 280-64-8 9-bora-bicyclo[3.3.1]nonane 
• 25637-18-7 4-iodotetrahydropyran 
• 50-00-0 formaldehyd 
• 130990-25-9 3-(2'-hydroxyethyl)tetrahydrofuran 
• 77-93-0 citric acid triethyl ester 
• 110238-91-0 tetrahydropyran-4-carboxylic acid methyl ester 
• 96835-17-5 ethyl tetrahydro-2H-pyran-4-carboxylate 
• 5337-03-1 tetrahydro-2H-pyran-4-carboxylic acid 
• 50675-18-8 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde 

Downstream Products

• 125552-89-8 4-(bromomethyl)tetrahydro-2H-pyran 
• 101691-65-0 toluene-4-sulfonic acid tetrahydropyran-4-ylmethyl ester 
• 50675-18-8 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde 
• 582299-19-2 2-hydroxy-1-phenyl-2-(3,4,5,6-tetrahydro-2H-pyran-4-yl) ethan-1-one 
• 582299-04-5 2-oxo-2-phenyl-1-(3,4,5,6-tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzene-1-sulfonate 
• 850429-50-4 2-(tetrahydro-2H-pyran-4-yl)acetonitrile 
• 85064-61-5 2-(tetrahydro-2H-pyran-4-yl)acetic acid 
• 279-27-6 exo-1-azabicyclo[2.2.1]heptane 
• 132291-95-3 4-(methanesulfonyloxymethyl)tetrahydropyran 
• 1191102-73-4 ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate 
• 1263420-65-0 N-Cyclopropyl-4-(8-((tetrahydro-2H-pyran-4-yl)methoxy)imidazo[1,2-a]pyrazin-3-yl)benzamide 
• 745052-93-1 2-[4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionic acid 
• 745052-97-5 ethyl 2-(4-cyclopropanesulfonyl-phenyl)-3-(tetrahydropyran-4-yl)propionate 

Relevant articles and documents

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.

Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.

Selective Hydrogenation of Carboxylic Acids to Alcohols or Alkanes Employing a Heterogeneous Catalyst

The chemoselective hydrogenation of carboxylic acids to either alcohols or alkanes is reported, employing a heterogeneous bimetallic catalyst consisting of rhenium and palladium supported on graphite. α-Chiral carboxylic acids were hydrogenated without loss of optical purity. The catalyst displays a reverse order of reactivity upon hydrogenation of different carboxylic functions with esters being less reactive than amides and carboxylic acids. This allows for chemoselective hydrogenation of an acid in the presence of an ester or an amide function.