5-Oxohexanenitrile

Base Information

• Chemical Name: 5-Oxohexanenitrile
• CAS No.: 10412-98-3
• Molecular Formula: C6H9NO
• Molecular Weight: 111.144
• Hs Code.: 2926909090
• European Community (EC) Number: 233-884-3
• UNII: DD734N7VC5
• DSSTox Substance ID: DTXSID5065065
• Nikkaji Number: J56.070G
• Wikidata: Q81991953
• Mol file: 10412-98-3.mol

Synonyms:5-Oxohexanenitrile;5-Ketohexanenitrile;10412-98-3;Hexanenitrile, 5-oxo-;5-Oxohexanonitrile;4-Acetylbutyronitrile;5-oxo-hexanenitrile;MFCD00010671;DD734N7VC5;EINECS 233-884-3;AI3-26936;5-oxocapronitrile;methyl 3-cyanopropyl ketone;UNII-DD734N7VC5;SCHEMBL329262;DTXSID5065065;.GAMMA.-ACETOBUTYRONITRILE;AKOS006221641;NS-01010;SY051847;CS-0446855;FT-0636701;K0029;D91224;A896279

Chemical Property of 5-Oxohexanenitrile

Chemical Property:

• Vapor Pressure: 0.0549mmHg at 25°C
• Refractive Index: 1.4310-1.4350
• Boiling Point: 233.8°Cat760mmHg
• Flash Point: 107.8°C
• PSA: 40.86000
• Density: 0.941g/cm³
• LogP: 1.26928
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 111.068413911
• Heavy Atom Count: 8
• Complexity: 120

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Ketohexanenitrile >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CCCC#N
• Uses: 5-Oxohexanonitrile is used as a reagent in many chemical reactions. It is reported to undergo electroreduction to give the corresponding intermolecularly coupled product.

Technology Process of 5-Oxohexanenitrile

There total 30 articles about 5-Oxohexanenitrile 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: 97.0%

1-cyclopropylethanol (765-42-4) + P-toluenesulfonyl cyanide (19158-51-1) → 5-oxohexanenitrile (10412-98-3)

Guidance literature:

With benzophenone; In acetonitrile; at 20 ℃; for 10h; chemoselective reaction; Inert atmosphere; UV-irradiation;

DOI:10.1021/ol202659e

Reference yield: 96.9%

ethyl 2-(2-cyanoethyl)-3-oxobutanoate (10444-33-4) → 5-oxohexanenitrile (10412-98-3)

Guidance literature:

With sodium carbonate; In water; for 4h; Heating;

DOI:10.1248/cpb.34.893

Reference yield: 92.0%

hex-5-enenitrile (5048-19-1) → 5-oxohexanenitrile (10412-98-3)

Guidance literature:

With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 80 ℃; for 40h; under 4560 Torr;

DOI:10.1002/anie.200502886

upstream raw materials:

1-chloro-4-(1,3-dioxolane)-n-pentane

sodium cyanide

ethyl 2-(2-cyanoethyl)-3-oxobutanoate

acrylonitrile

Downstream raw materials:

2-Methylcyclopentanone

2-methyl-2-hydroxycyclopentanone

(S)-6-methyl-tetrahydro-pyran-2-one

5-hexanolide

Refernces

• 1、 Mitsudome, Takato,Umetani, Takuya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi. "Highly efficient Wacker oxidation catalyzed by heterogeneous Pd montmorillonite under acid-free conditions". . p. 1425 - 1428. Retrieved 2006.
• 2、 Luethy,C. et al.. "-". . p. 6211 - 6217. Retrieved 1978.
• 3、 Haley, Hannah M. S.,Payer, Stefan E.,Papidocha, Sven M.,Clemens, Simon,Nyenhuis, Jonathan,Sarpong, Richmond. "Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids". supporting information. p. 4732 - 4740. Retrieved 2021/04/07.
• 4、 Liang, Shengzong,Jasinski, Jacek,Hammond, Gerald B.,Xu, Bo. "Supported Gold Nanoparticle-Catalyzed Hydration of Alkynes under Basic Conditions". supporting information. p. 162 - 165. Retrieved 2015/07/28.