3088-44-6

Basic information

• Product Name: 3-ALLYLOXYPROPIONITRILE
• Synonyms: 3-ALLYLOXYPROPIONITRILE;B-ALLYLOXYPROPIONITRILE;BETA-ALLYLOXYPROPIONITRILE;3-allyloxypropannitril;3-allyloxy-propionitril;3-(Allyloxy)propiononitrile;3-prop-2-enoxypropanenitrile
• CAS NO: 3088-44-6
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• Product Categories: monomer
• Mol File: 3088-44-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 208.27°C (rough estimate)
• Flash Point: 82.9°C
• Appearance: /
• Density: 1.0656 (rough estimate)
• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: 1.4420 (estimate)
• CAS DataBase Reference: 3-ALLYLOXYPROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ALLYLOXYPROPIONITRILE(3088-44-6)
• EPA Substance Registry System: 3-ALLYLOXYPROPIONITRILE(3088-44-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3088-44-6(Hazardous Substances Data)

Usage

General Description

3-allyloxypropionitrile is a chemical compound with the formula C6H9NO, and it is commonly referred to as 3-allyloxypropionitrile. It is an organic compound that contains an α,β-unsaturated nitrile group. It is commonly used in the pharmaceutical industry for the synthesis of various biologically active compounds due to its versatile reactivity. It can also be used as an intermediate in the production of other chemicals and has potential applications in the field of organic synthesis. However, it should be handled with care as it is considered to be harmful if ingested, inhaled, or absorbed through the skin, and may cause irritation to the eyes and skin.

InChI:InChI=1/C6H9NO/c1-2-5-8-6-3-4-7/h2H,1,3,5-6H2

Upstream product

• 20907-32-8 sodium allyloxide 
• 107-13-1 acrylonitrile 
• 107-18-6 allyl alcohol 

Downstream Products

• 55629-55-5 3-<3-(Methylphenylsilyl)-propoxy>-propionitril 
• 55629-61-3 3-[3-(Ethyl-phenyl-silanyl)-propoxy]-propionitrile 
• 55629-56-6 3-[3-(Benzyl-methyl-silanyl)-propoxy]-propionitrile 
• 55629-63-5 3-<3-(Diphenylsilyl)-propoxy>-propionitril 
• 55629-59-9 3-{3-[Methyl-((E)-styryl)-silanyl]-propoxy}-propionitrile 
• 55629-57-7 3-[3-(Methyl-phenethyl-silanyl)-propoxy]-propionitrile 
• 55629-58-8 3-{3-[Methyl-(3-phenyl-propyl)-silanyl]-propoxy}-propionitrile 
• 127764-29-8 3-(3-triphenylstannyl-propoxy)-propionitrile 
• 55629-65-7 Acetic acid 3-{[3-(2-cyano-ethoxy)-propyl]-methyl-phenethyl-silanyl}-propyl ester 
• 22577-15-7 3-(allyloxy)propionic acid 

Relevant articles and documents

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

Electron-rich triarylphosphines, namely 4-(methoxyphenyl)diphenylphosphine (MMTPP) and tris(4-trimethoxyphenyl)phosphine (TMTPP), outperform commonly used triphenylphosphine (TPP) in catalyzing oxa-Michael additions. A matrix consisting of three differently strong Michael acceptors and four alcohols of varying acidity was used to assess the activity of the three catalysts. All test reactions were performed with 1 mol % catalyst loading, under solvent-free conditions and at room temperature. The results reveal a decisive superiority of TMTPP for converting poor and intermediate Michael acceptors such as acrylamide and acrylonitrile and for converting less acidic alcohols like isopropanol. With stronger Michael acceptors and more acidic alcohols, the impact of the more electron-rich catalysts is less pronounced. The experimental activity trend was rationalized by calculating the Michael acceptor affinities of all phosphine-Michael acceptor combinations. Besides this parameter, the acidity of the alcohol has a strong impact on the reaction speed. The oxidation stability of the phosphines was also evaluated and the most electron-rich TMTPP was found to be only slightly more sensitive to oxidation than TPP. Finally, the catalysts were employed in the oxa- Michael polymerization of 2-hydroxyethyl acrylate. With TMTPP polymers characterized by number average molar masses of about 1200 g/mol at room temperature are accessible. Polymerizations carried out at 80°C resulted in macromolecules containing a considerable share of Rauhut-Currier-type repeat units and consequently lower molar masses were obtained.

An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans

An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.

Preparation of 3-(n-alkenoxy)propanoic acids

3-(n-Alkenoxy)propanoic acids have been prepared by reaction of alkenols with tert-butyl acrylate (catalyzed by Triton B or n-butyl lithium) followed by cleavage of the tert-butyl group by CF3COOH or KO2.