16314-18-4

Usage

Uses

Used in Chemical Synthesis:
TERT-BUTYL PROPARGYL ETHER is used as a reactant for the preparation of ether and amine-functionalized internal vinylboronates. This is achieved through copper-NHC-catalyzed hydroboration of alkyne, propargyl alcohols, and amines.
Used in Stereoselective Synthesis:
In the field of stereoselective synthesis, TERT-BUTYL PROPARGYL ETHER is used as a key component in the chemoselective and stereoselective preparation of vicinal diboronates. This is accomplished via a one-pot copper-catalyzed sequential hydroboration of alkyne in the presence of a chiral N-heterocyclic carbene ligand.
Used in Pharmaceutical Industry:
TERT-BUTYL PROPARGYL ETHER is used as an intermediate in the synthesis of various pharmaceutical compounds, taking advantage of its versatile reactivity and the ability to form complex molecular structures.
Used in Material Science:
In the material science industry, TERT-BUTYL PROPARGYL ETHER is utilized in the development of new materials with specific properties, such as improved strength, flexibility, or chemical resistance, by incorporating its unique structural features into the material's composition.

InChI:InChI=1/C7H12O/c1-5-6-8-7(2,3)4/h1H,6H2,2-4H3

Upstream product

• 16253-83-1 2-bromo-3-tert-butoxy-propene 
• 107-19-7 propargyl alcohol 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 32038-79-2 hydroxy acetylene 
• 507-19-7 t-butyl bromide 

Downstream Products

• 26826-41-5 (4-tert-Butoxy-1-ethoxy-but-2-ynyl)-benzene 
• 133958-07-3 3-tert-Butoxy-2-methoxy-thiophene 
• 133958-05-1 3-tert-Butoxy-2-tert-butyl-thiophene 
• 145278-41-7 (E)-phenyl-2-tert-butoxy-3-<(trimethylsilyl)methylidene>-5-hexene 
• 95455-62-2 4-carbomethoxy-3-(2-t-butoxyethyl)2-cyclohexen-1-one 
• 1005414-21-0 (S,Z)-(6-tert-butoxy-2-methylhexa-1,4-dien-3-yl)benzene 
• 1251861-55-8 (R,Z)-(6-(tert-butoxy)-3-methylhexa-1,4-dien-3-yl)dimethyl(phenyl)silane 

Relevant academic research and scientific papers

Metabolic depropargylation and its relationship to aldehyde dehydrogenase inhibition in vivo

The relationship between metabolic depropargylation in vitro to inhibition of the low K(m) aldehyde dehydrogenase (AIDH) of rat liver mitochondria in vivo was determined for a number of compounds bearing a propargyl substituent on nitrogen or oxygen. Only those compounds which enzymatically released the highly reactive α, β-acetylenic aldehyde, propiolaldehyde, when incubated in vitro with phenobarbital-induced rat liver microsomes, e.g., tripropargylamine (4), pargyline (1a), and N-propargylbenzylamine (1b), significantly elevated blood acetaldehyde levels when administered in vivo. Mitochondrial AlDH activity in these animals was corresponding reduced to ≤20% that of control animals. Compounds that did not inhibit mitochondrial AlDH activity to this degree did not produce significant levels of propiolaldehyde when incubated with microsomes. Thus, for this series of compounds, metabolic depropargylation is a requirement for AlDH inhibitory activity in vivo.

Highly regioselective hydrosilylation of unsymmetric alkynes using a phenylthio directing group

Cobalt-assisted hydrosilylation of acetylenes is particularly interesting in organic synthesis since alkynyl group functionalization can give way to more useful substructures. This study aims to answer the general question of how to control hydrosilylatio

A convenient synthesis of tert-butyl ethers under microwave condition

Synthesis of tert-butyl ethers from various alcohols and substituted phenols can be achieved using tert-butyl bromide in the presence of basic lead carbonate as a catalyst under microwave irradiation in absence of solvent. The catalyst is easily recovered via filtration and reused up to three times without appreciable loss of activity.

Efficient synthesis of tert-butyl ethers under solvent-free conditions

A simple and efficient synthesis of tert-butyl ethers from various alcohols and substituted phenols using tert-butyl bromide in the presence of basic lead carbonate as a catalyst. The catalyst is easily recovered via filtration and can be reused up to three times without appreciable loss of activity. Copyright Taylor & Francis Group, LLC.

Hydrolysis and Alcoholysis of Esters of o-Nitrobenzenesulfonic Acid

The rate of solvolysis of esters of o-nitrobenzenesulfonic acid with water and C1-C4 alcohols is satisfactorily described by two-parametric Hammett-Taft equation with predominating effect of the electronic factor σ*. The effect of the structure of the hydrocarbon rest in the sulfonic ester group does not fit to this relationship.

3,5-disubstituted 2-isoxazolines and isoxazoles, agents containing them and their use

Novel 3,5-disubstituted 2-isoxazolines and isoxazoles and novel pharmaceuticals are described which are suitable, in particular, for the prophylaxis and/or treatment of pathological, neurodegenerative disorders in humans and animals. Processes for the preparation of these 3,5-disubstituted 2-isoxazolines and isoxazolines and isoxazoles are additionally indicated.

MILD PROTECTION AND DEPROTECTION OF ALCOHOLS AS TER-BUTYL ETHERS IN THE FIELD OF PHEROMONE SYNTHESIS

α,ο-Halohydrins and ο-acetylenic alcohols are protected as t-butyl ethers by reaction with isobutene and an acid catalyst : Amberlyst H-15. t-Butyl ethers are, in turn, cleaved to acetates by Ac2O and 10 percent FeCl3 in Et2O solvent.Under these mild conditions conjugated dieneic systems are neither destroyed nor isomerized.

REACTION OF 1-PROPYN-3-OL WITH ALCOHOLS

The reaction of propargyl alcohol with primary alcohols in the presence of metal complex catalysts leads to 2,5-dialkoxy-2,5-dimethyl-1,4-dioxanes.In contrast to primary alcohols, condensation to form 3-alkoxy- or 3-aryloxypyronines is the first step of the reaction of trimethyl-, dimethylethyl-, and triphenylcarbinols with propargyl alcohol.In the case of alkylcarbinols, these pyronines undergo hydration of the triple bond and cleavage of alkoxyacetones.One of the products of the reaction of propargyl alcohol with trimethyl- and dimethylcarbinols is 2,5-di(2-propynoxy)-2,5-dimethyl-1,4-dioxane.The same product was isolated upon heating propargyl alcohol in ether in the presence of HgO + (C2H5)2O.BF3.