16314-18-4

Basic information

• Product Name: TERT-BUTYL PROPARGYL ETHER
• Synonyms: TERT-BUTYL PROPARGYL ETHER;tert-Butyl propargyl ether,98%;tert-Butyl propargyl ether, 98% 5GR;1-Propyne,3-(1,1-dimethylethoxy)-
• CAS NO: 16314-18-4
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• Mol File: 16314-18-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 119℃
• Flash Point: 20°(68°F)
• Appearance: Clear light yellow/Liquid
• Density: 0.835
• Vapor Pressure: 13.8mmHg at 25°C
• Refractive Index: 1.417-1.419
• Storage Temp.: Flammables area
• CAS DataBase Reference: TERT-BUTYL PROPARGYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL PROPARGYL ETHER(16314-18-4)
• EPA Substance Registry System: TERT-BUTYL PROPARGYL ETHER(16314-18-4)

Safety Data

• Hazard Codes: Xi-F
• Statements: 36/37/38-11
• Safety Statements: 37/39-26-16
• HazardClass: 3
• Hazardous Substances Data: 16314-18-4(Hazardous Substances Data)

Usage

Description

TERT-BUTYL PROPARGYL ETHER is a clear light yellow liquid that serves as a versatile reactant with a terminal alkyne group, making it a valuable compound in various chemical reactions and applications.

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

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

Downstream Products

• 26826-41-5 (4-tert-Butoxy-1-ethoxy-but-2-ynyl)-benzene 
• 1005414-21-0 (S,Z)-(6-tert-butoxy-2-methylhexa-1,4-dien-3-yl)benzene 
• 1622445-89-9 (Z)-(3-(tert-butoxy)-1-(phenylthio)prop-1-en-1-yl)dimethyl(phenyl)silane 
• 1622445-90-2 (E)-(3-(tert-butoxy)-1-(phenylthio)prop-1-en-2-yl)dimethyl(phenyl)silane 
• 1622445-79-7 (3-(tert-butoxy)prop-1-yn-1-yl)(phenyl)sulfane 
• 1264670-16-7 C₁₃H₁₅ClO 
• 1251861-55-8 (R,Z)-(6-(tert-butoxy)-3-methylhexa-1,4-dien-3-yl)dimethyl(phenyl)silane 
• 95455-62-2 4-carbomethoxy-3-(2-t-butoxyethyl)2-cyclohexen-1-one 

Relevant articles and documents

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.

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.

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.