3622-76-2

Basic information

• Product Name: 2-(Vinyloxy)ethyldimethylamine
• Synonyms: [2-(Dimethylamino)ethyl]vinyl ether;2-(Ethenyloxy)-N,N-dimethylethanamine;2-(Vinyloxy)ethyldimethylamine;N,N-Dimethyl-2-(vinyloxy)ethanamine
• CAS NO: 3622-76-2
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.20
• Mol File: 3622-76-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 215.49°C (rough estimate)
• Flash Point: 28.4°C
• Appearance: /
• Density: 0.9837 (rough estimate)
• Vapor Pressure: 16.1mmHg at 25°C
• Refractive Index: 1.4690 (estimate)
• CAS DataBase Reference: 2-(Vinyloxy)ethyldimethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Vinyloxy)ethyldimethylamine(3622-76-2)
• EPA Substance Registry System: 2-(Vinyloxy)ethyldimethylamine(3622-76-2)

Safety Data

• Hazardous Substances Data: 3622-76-2(Hazardous Substances Data)

Usage

General Description

2-(Vinyloxy)ethyldimethylamine is a chemical compound with the formula C6H13NO. It is a tertiary amine and contains both a vinyl and oxyethyl functional group. It is commonly used as a reactive intermediate in the synthesis of various organic compounds, especially in the production of polymers and resins. It is also used as a precursor in the modification of polymers for various applications, such as in the production of adhesives, coatings, and surfactants. Additionally, it is used in the manufacturing of pharmaceuticals and agrochemicals, as well as in the production of corrosion inhibitors and lubricant additives. This chemical is known to be highly toxic and should be handled with extreme caution.

InChI:InChI=1/C6H13NO/c1-4-8-6-5-7(2)3/h4H,1,5-6H2,2-3H3

Upstream product

• 2412-10-4 N,N-dimethylmorpholinium iodide 
• 69013-77-0 4,4-dimethyl-morpholinium; hydroxide 
• 1704-62-7 1-O-Dimethylaminoethyl-ethylenglykol 
• 99051-18-0 toluene-4-sulfonic acid 2-vinyloxy-ethyl ester 
• 124-40-3 dimethyl amine 
• 110-75-8 2-chloroetyl vinyl ether 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 74-86-2 acetylene 
• 24721-92-4 1-Dimethylamino-ethanol 
• 109-92-2 ethyl vinyl ether 
• 4223-11-4 ethylene glycol n-butyl vinyl diether 

Downstream Products

• 24586-04-7 trimethyl-(2-vinyloxy-ethyl)-ammonium; iodide 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 129126-43-8 1-<2-<2-(dimethylamino)ethoxy>ethenyl>-4-nitrobenzene 
• 197230-95-8 N,N-dimethyl-2-[2-(phenyl)ethenyloxy]ethanamine 
• 129126-31-4 (Z)-N,N-dimethyl-2-(styryloxy)ethanamine 
• 129126-30-3 (E)-N,N-dimethyl-2-(styryloxy)ethanamine 
• 1026309-87-4 dimethyl-[2-(1-o-tolyl-vinyloxy)-ethyl]-amine 
• 154318-66-8 4-[1-(2-Dimethylamino-ethoxy)-vinyl]-benzonitrile 
• 1282534-34-2 2-(1,2-bis(4-methoxycarbonylphenyl)ethoxy)-N,N-dimethylethanamine 
• 1282534-32-0 2-(1,2-bis(4-acetylphenyl)ethoxy)-N,N-dimethylethanamine 
• 1282534-40-0 2-(1,2-bis(3-(trifluoromethyl)phenyl)ethoxy)-N,N-dimethylethanamine 
• 1282534-37-5 2-(1,2-bis(4-(trifluoromethyl)phenyl)ethoxy)-N,N-dimethylethanamine 
• 1282534-38-6 2-(1,2-bis(4-(methylthio)phenyl)ethoxy)-N,N-dimethylethanamine 
• 1282534-33-1 2-(1,2-bis(4-formylphenyl)ethoxy)-N,N-dimethylethanamine 

Relevant articles and documents

Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a heck triarylation process

This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled tri- and diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.

Chelation-Controlled, Palladium-Catalyzed Vinylic Substitution Reactions of Vinyl Ethers. 2-Arylethanal Equivalents from Aryl Halides

The regioselectivity of palladium-catalyzed arylation reactions of a series of nitrogen-containing vinyl ethers is reported.The presence of a β-amino substituent gives a profound influence on regiochemistry.Thus, the arylation of ethene (1c) with a variety of aryl iodides and bromides provides the β-arylation products ethenyl>arenes (3) with at least 95percent selectivity and in good yields.The corresponding arylation of butoxyethene is a nonselective process giving a mixture of α- and β-substitution products.The palladium-catalyzed arylation of 1c constitutes an entry to 2-arylethanals after cleavage of the enol ether.The directing effect of the amino group is discussed in terms of chelation with the intermediate arylpalladium halide.