14618-78-1

Basic information

• Product Name: 3-CYANOPROPIONALDEHYDE DIMETHYL ACETAL
• Synonyms: 4,4-dimethoxy-butanenitril;4,4-Dimethoxybutanenitrile;4,4-dimethoxy-Butanenitrile;Butanenitril,4,-dimethyloxy-;Butanenitrile, 4,4-dimethoxy-;Cyanopropionaldehydedimethylacetal;3-CYANOPROPIONALDEHYDE DIMETHYL ACETAL;4,4-DIMETHOXYBUTYRONITRILE
• CAS NO: 14618-78-1
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• EINECS: 238-658-8
• Product Categories: straight chain compounds
• Mol File: 14618-78-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: -119.1°C
• Boiling Point: 90-91 °C14 mm Hg(lit.)
• Flash Point: 193 °F
• Appearance: /
• Density: 0.992 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.419(lit.)
• Water Solubility: Soluble in water
• CAS DataBase Reference: 3-CYANOPROPIONALDEHYDE DIMETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANOPROPIONALDEHYDE DIMETHYL ACETAL(14618-78-1)
• EPA Substance Registry System: 3-CYANOPROPIONALDEHYDE DIMETHYL ACETAL(14618-78-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: 3276
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• Hazardous Substances Data: 14618-78-1(Hazardous Substances Data)

Usage

Uses

4,4-Dimethoxybutanenitrile is a reagent in the stereoselective preparation of aziridines.

Upstream product

• 36255-44-4 3-bromopropanal dimethyl acetal 
• 151-50-8 potassium cyanide 
• 67-56-1 methanol 
• 3515-93-3 4-oxobutanenitrile 
• 864686-42-0 (E,Z)-4-methoxy-3-butenonitrile 
• 143-33-9 sodium cyanide 
• 201230-82-2 carbon monoxide 
• 107-13-1 acrylonitrile 

Downstream Products

• 945950-37-8 4-methyl-7H-pyrrazolo[2,3-d]pyrimidine 
• 41031-87-2 (Z)-4-oxodec-7-enal 
• 866319-00-8 5-fluoro-1H-pyrrolo[2,3‐b]pyridine 
• 58697-03-3 3-(5,5-dimethyl-1,3-dioxanyl)-propionaldehyde 

Relevant articles and documents

Biomimetic approach to Elaeocarpus alkaloids. A synthesis of (±)-elaeocarpidine

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RESISTANCE OF ACRYLONITRILE AND OF ITS HYDROFORMYLATION PRODUCTS TO THERMAL AND CATALYTIC ACTION.

The study of the resistance of acrylonitrile and its hydroformylation products to thermal and catalytic action showed that at 120 degree and 30 MPa pressure in presence of cobalt carbonyls acrylonitrile does not undergo polymerization in presence of an inhibitor (hydroquinone); beta -cyanopropionaldehyde and its dimethyl acetal are stable when the process is conducted in methanol, but in nonpolar solvents (benzene) beta -cyanopropionaldehyde polymerizes. The use of methanol during storage and oxidative treatment of the products of acrylonitrile hydroformylation stabilizes beta -cyanopropionaldehyde.

LIGAND EFFECTS IN THE HYDROFORMYLATION OF ACRYLONITRILE BY COBALT CARBONYL

The hydroformylation of acrylonitrile (VCN) using Co2(CO)8/L (L = HN(CH2CN)2, , Me2N(CH2)2NMeH, PPh3, and PCy3) has been examined in methanol solvent.Four reaction pathways are observed which are dependent on L.With no L or with L = HN(CH2CN)2, the reaction produces the desired acetal (MeO)2CHCH2CH2CN.For the more basic amines the reactin produces ca. 50percent yields of hydrodimerization products NCCHMe(CH2)2CN/NC(CH2)4CN in a 10/1 ratio and an ca. 30percent yield of the hydrogenation product CH3CH2CN.These reactions are shown to be metal catalyzed.The main reactionfor Co2(CO)8/PR3 catalyzed systems appears to be a classical Michael addition reaction of the solvent, methanol, with acrylonitrile to give MeOCH2CH2CN.Evidence is given to show that this reaction is catalyzed by phosphine which has dissociated under reaction conditions and not by a ligated cobalt complex.