304669-40-7

Basic information

• Product Name: Benzenemethanol, 2-(3,4-dihydro-2H-pyran-6-yl)-
• CAS NO: 304669-40-7
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol File: 304669-40-7.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, 2-(3,4-dihydro-2H-pyran-6-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 2-(3,4-dihydro-2H-pyran-6-yl)-(304669-40-7)
• EPA Substance Registry System: Benzenemethanol, 2-(3,4-dihydro-2H-pyran-6-yl)-(304669-40-7)

Safety Data

• Hazardous Substances Data: 304669-40-7(Hazardous Substances Data)

Usage

Composition

It consists of a benzene ring attached to a 2-(3,4-dihydro-2H-pyran-6-yl) group.

Reactivity

The compound exhibits unique reactivity due to the presence of the 2-(3,4-dihydro-2H-pyran-6-yl) group, making it versatile in chemical reactions.

Applications

Commonly used as a building block in organic synthesis.
Employed in the pharmaceutical and agrochemical industries for synthesizing various compounds and active ingredients.

Safety Precautions

It is crucial to handle this chemical with care.
Following proper safety guidelines is essential to mitigate health hazards associated with its handling.

Upstream product

• 18982-54-2 o-bromobenzyl alcohol 
• 109669-45-6 (3,4-dihydro-2H-6-pyranyl)tributyltin 
• 5159-41-1 2-iodobenzyl alcohol 
• 304669-35-0 [2-(5,6-dihydro-4H-pyranyl)]dimethylsilanol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 82466-12-4 2-bromobenzyl acetate 
• 1025707-93-0 2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization Reactions

Mechanistic and computational studies were conducted to elucidate the mechanism and the origins of enantiocontrol for asymmetric chiral phosphoric acid-catalyzed spiroketalization reactions. These studies were designed to differentiate between the SN1-like, SN2-like, and covalent phosphate intermediate-based mechanisms. The chiral phosphoric acid-catalyzed spiroketalization of deuterium-labeled cyclic enol ethers revealed a highly diastereoselective syn-selective protonation/nucleophile addition, thus ruling out long-lived oxocarbenium intermediates. Hammett analysis of the reaction kinetics revealed positive charge accumulation in the transition state (ρ = -2.9). A new computational reaction exploration method along with dynamics simulations supported an asynchronous concerted mechanism with a relatively short-lived polar transition state (average lifetime = 519 ± 240 fs), which is consistent with the observed inverse secondary kinetic isotope effect of 0.85. On the basis of these studies, a transition state model explaining the observed stereochemical outcome has been proposed. This model predicts the enantioselective formation of the observed enantiomer of the product with 92% ee, which matches the experimentally observed value.

Two-step one-pot synthesis of benzoannulated spiroacetals by Suzuki-Miyaura coupling/acid-catalyzed spiroacetalization

Substituted benzoannulated spiroacetals were prepared from (2-haloaryl)alkyl alcohols and dihydropyranyl or dihydrofuranyl pinacol boronates using a Suzuki-Miyaura coupling followed by an acid-catalyzed spirocyclization. Application of the reaction to a glycal boronate provides an approach to annulated spiroacetals in enantiopure form.

Mild and general cross-coupling of (α-alkoxyvinyl)silanols and -silyl hydrides

(Matrix presented) (α-Alkoxyvinyl)silanols and (α-alkoxyvinyl)silyl hydrides are efficiently converted to aryl vinyl ethers by a palladium(0)-catalyzed cross-coupling reaction with aryl halides in the presence of tetrabutylammonium fluoride or hydroxide.

A Palladium Mediated Spiroketal Synthesis

The synthesis of a variety of spiroketal-containing systems is outlined, utilising a palladium catalysed coupling reaction in the pivotal carbon-carbon bond forming step.