4-Methyl-4-nitropentanenitrile

Base Information

• Chemical Name: 4-Methyl-4-nitropentanenitrile
• CAS No.: 16507-00-9
• Molecular Formula: C6H10N2O2
• Molecular Weight: 142.158
• European Community (EC) Number: 667-496-4
• DSSTox Substance ID: DTXSID90397714
• Nikkaji Number: J738.268E
• Wikidata: Q82199277
• Mol file: 16507-00-9.mol

Synonyms:4-methyl-4-nitropentanenitrile;16507-00-9;4-NITRO-4-METHYLVALERONITRILE;4-methyl-4-nitro-valeronitrile;4-methyl-4-nitrovaleronitrile;SCHEMBL3184264;DTXSID90397714;NBEZXTYDFSHDFX-UHFFFAOYSA-N;AKOS006272598;CS-0239811;EN300-219382

Chemical Property of 4-Methyl-4-nitropentanenitrile

Chemical Property:

• Boiling Point: 105-107 °C(Press: 1 Torr)
• PSA: 69.61000
• Density: 1.095 g/cm3(Temp: 25 °C)
• LogP: 1.86868
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 172

Purity/Quality:

95% ^*data from raw suppliers

4-Nitro-4-methylvaleronitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CCC#N)[N+](=O)[O-]

Technology Process of 4-Methyl-4-nitropentanenitrile

There total 4 articles about 4-Methyl-4-nitropentanenitrile 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: 85.0%

2-nitropropane (79-46-9) + acrylonitrile (107-13-1,25014-41-9) → 4-methyl-4-nitrovaleronitrile (16507-00-9)

Guidance literature:

With potassium carbonate; In acetonitrile;

DOI:10.1016/j.mencom.2007.06.016

Reference yield:

2-nitropropane (79-46-9) + acrylonitrile (107-13-1,25014-41-9) + 2-nitro-benzaldehyde (552-89-6) → 4-methyl-4-nitrovaleronitrile (16507-00-9) + (R*)-2-[(S*)-hydroxy(2-nitrophenyl)methyl]-4-methyl-4-nitropentanenitrile + (R*)-2-[(R*)-hydroxy(2-nitrophenyl)methyl]-4-methyl-4-nitropentanenitrile

Guidance literature:

With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; In dimethyl sulfoxide; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tet.2021.132329

Reference yield:

2-nitropropane (79-46-9) + cetyltrimethylammonium chloride (112-02-7,79728-63-5) + acrylonitrile (107-13-1,25014-41-9) → 4-methyl-4-nitrovaleronitrile (16507-00-9)

Guidance literature:

In sodium hydroxide;

upstream raw materials:

2-nitropropane

acrylonitrile

cetyltrimethylammonium chloride

2-nitro-benzaldehyde

Downstream raw materials:

5,5-dimethyl-2-pyrrolidone

4-methyl-4-nitropentanoic acid

2-amino-5,5-dimethylpyrroline 1-oxide

isocapronitrile

Refernces

• 1、 Bosica, Giovanna,Polidano, Kurt. "Solvent-Free Henry and Michael Reactions with Nitroalkanes Promoted by Potassium Carbonate as a Versatile Heterogeneous Catalyst". . . Retrieved 2017/07/11.
• 2、 Mistryukov, Electron A.. "Imidazolium salts as specific catalysts for Michael addition to nitroalkanes: a structure-catalyst efficiency relationship". . p. 230 - 231. Retrieved 2008/03/12.