4,4-Dimethoxybutyronitrile

Base Information

• Chemical Name: 4,4-Dimethoxybutyronitrile
• CAS No.: 14618-78-1
• Molecular Formula: C6H11 N O2
• Molecular Weight: 129.159
• Hs Code.: 29269090
• European Community (EC) Number: 238-658-8
• UNII: J3WU6C9R93
• DSSTox Substance ID: DTXSID3065796
• Nikkaji Number: J57.752I
• Wikidata: Q72467810
• Mol file: 14618-78-1.mol

Synonyms:14618-78-1;4,4-Dimethoxybutanenitrile;4,4-Dimethoxybutyronitrile;3-Cyanopropionaldehyde dimethyl acetal;Butanenitrile, 4,4-dimethoxy-;3-Cyano propionaldehyde dimethyl acetal;3-CYANOPROPIONALDEHYDEDIMETHYLACETAL;Cyanopropionaldehyde dimethyl acetal;4,4'-Dimethoxybutyronitrile;J3WU6C9R93;EINECS 238-658-8;.beta.-Cyanopropionaldehyde dimethylacetal;4-dimeth-oxybutyronitrile;UNII-J3WU6C9R93;4,4-Dimethoxybutanenitrile #;SCHEMBL441892;Butanenitril, 4,-dimethyloxy-;AMY751;DTXSID3065796;3-Cyanopropionaldehyde dimethylacetal;3-cyanopropanaldehyde dimethyl acetal;MFCD00019883;3-cyano-propionaldehyde dimethylacetal;AKOS015851546;BUTYRONITRILE, 4,4-DIMETHOXY-;CS-W002123;DS-1556;3-Cyanopropionaldehyde dimethyl acetal, 98%;FT-0637115;EN300-1738124;J-008201

Chemical Property of 4,4-Dimethoxybutyronitrile

Chemical Property:

• Melting Point: -119.1°C
• Refractive Index: n20/D 1.419(lit.)
• Boiling Point: 201.4°Cat760mmHg
• Flash Point: 89.4°C
• PSA: 42.25000
• Density: 0.963g/cm³
• LogP: 0.90908
• Water Solubility.: Soluble in water
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

98% ^*data from raw suppliers

4,4-Dimethoxybutanenitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(CCC#N)OC
• Uses: 4,4-Dimethoxybutanenitrile is a reagent in the stereoselective preparation of aziridines.

Technology Process of 4,4-Dimethoxybutyronitrile

There total 11 articles about 4,4-Dimethoxybutyronitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

3-bromopropanal dimethyl acetal (36255-44-4) + sodium cyanide (143-33-9,25596-52-5) → 4,4-dimethoxybutanenitrile (14618-78-1)

Guidance literature:

With tributyl-amine; In water; for 2h; Heating;

DOI:10.1021/jo00324a058 DOI:10.1021/jo00249a008

Reference yield:

methanol (67-56-1) + carbon monoxide (201230-82-2) + acrylonitrile (107-13-1,25014-41-9) → 2-methylglutaronitrile (4553-62-2) + 4,4-dimethoxybutanenitrile (14618-78-1) + propiononitrile (107-12-0)

Guidance literature:

With dicobalt octacarbonyl; hydrogen; In methanol; at 100 ℃; for 8h; under 129287 Torr; Product distribution; Mechanism; var. catalysts, time and temp.;

DOI:10.1016/0022-328X(83)80026-6

Reference yield:

methanol (67-56-1) + carbon monoxide (201230-82-2) + acrylonitrile (107-13-1,25014-41-9) → 4-oxobutanenitrile (3515-93-3) + 4,4-dimethoxybutanenitrile (14618-78-1) + 3-cyano-propionic acid methyl ester (4107-62-4) + methyl 2-cyanopropionate (14618-77-0)

Guidance literature:

With hydrogen; cobalt carbonyls; at 110 ℃; for 1h; under 217517 Torr; Further byproducts given;

upstream raw materials:

3-bromopropanal dimethyl acetal

potassium cyanide

methanol

4-oxobutanenitrile

Downstream raw materials:

4-aminobutyraldehyde dimethyl acetal

4-methyl-7H-pyrrazolo[2,3-d]pyrimidine

(Z)-4-oxodec-7-enal

5-fluoro-1H-pyrrolo[2,3‐b]pyridine

Refernces

• 1、 Gribble,Switzer,Soll. "A biomimetic approach to the Elaeocarpus alkaloids. Syntheses of (±)-Elaeokanine A, (±)-Elaeokanine C, (±)-Elaeocarpidine, and (±)-Tarennine". . p. 3164 - 3170. Retrieved 2007/10/02.
• 2、 Katsnel'son,Del'nik,Kagna,Leenson. "FORMATION OF THE ACETAL OF beta -CYANOPROPIONALDEHYDE IN THE PRESENCE OF COBALT CARBONYLS.". . p. 2514 - 2517. Retrieved 2007/10/02.