5-Oxopentanenitrile

Base Information

• Chemical Name: 5-Oxopentanenitrile
• CAS No.: 3350-74-1
• Molecular Formula: C5H7NO
• Molecular Weight: 97.1167
• European Community (EC) Number: 861-178-0
• DSSTox Substance ID: DTXSID20467136
• Nikkaji Number: J1.891.558H
• Wikidata: Q82293938
• Mol file: 3350-74-1.mol

Synonyms:5-oxopentanenitrile;3350-74-1;Pentanenitrile, 5-oxo-;4-cyanobutanal;DTXSID20467136;FNEARBHZFXEPFD-UHFFFAOYSA-N;AKOS020740933;SB85408;EN300-183140

Chemical Property of 5-Oxopentanenitrile

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 97.052763847
• Heavy Atom Count: 7
• Complexity: 89.5

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC=O)CC#N

Technology Process of 5-Oxopentanenitrile

There total 2 articles about 5-Oxopentanenitrile 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: 16.0%

carbon monoxide (201230-82-2) + but-3-enenitrile (109-75-1) → but-2-enenitrile (4786-20-3,627-26-9) + 5-oxopentanenitrile (3350-74-1) + 3-methyl-4-oxo-butyronitrile

Guidance literature:

With Rh(acac)(CO)2; 3,3',5,5'-tetra(2,4-difluorophenyl)-2,2',6,6'-tetra((di-1-pyrrolylphosphino)oxy)-1,1'-biphenyl; hydrogen; In toluene; at 100 ℃; for 0.5h; under 3800.26 Torr; regioselective reaction; Autoclave;

DOI:10.1002/chem.201201396

Reference yield:

crotononitrile (4786-20-3,627-26-9) + carbon monoxide (201230-82-2) → propyl cyanide (109-74-0) + 5-oxopentanenitrile (3350-74-1) + 3-methyl-4-oxo-butyronitrile

Guidance literature:

With hydrogen; dicobalt octacarbonyl; In toluene; at 100 ℃; for 4h; under 67506.8 Torr; Further Variations:; Catalysts; Solvents; Product distribution;

DOI:10.1002/adsc.200390053

Reference yield: 81.0%

formic acid (64-18-6) + 5-oxopentanenitrile (3350-74-1) + benzonitrile (100-47-0) + N-[2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl]amine (108342-87-6,120029-97-2,120030-03-7) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-4-cyano-1-phenylcarbamoyl-butyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112023-01-5) + 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((S)-4-cyano-1-phenylcarbamoyl-butyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (112023-01-5)

Guidance literature:

With zinc chloride diethyl ether; In tetrahydrofuran; at -25 ℃; for 24h;

DOI:10.1021/ja00210a084

upstream raw materials:

crotononitrile

carbon monoxide

but-3-enenitrile

Downstream raw materials:

N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-α-amino-5-cyano-pentanoic acid-N'-tert-butyl-amide

N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-5-cyano-pentanoic acid-N'-tert-butyl-amide

6-Benzenesulfonyl-5-hydroxy-hexanenitrile

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-4-cyano-1-phenylcarbamoyl-butyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester