4-Methyl-5-oxopentanenitrile
Description
4-Methyl-5-oxopentanenitrile (CAS RN: 3619-38-3) is an organic compound with the molecular formula C₆H₉NO and an average molecular mass of 111.144 g/mol . Its structure features a five-carbon chain containing a ketone group at the fifth position and a nitrile group at the terminal end, with a methyl substituent at the fourth carbon. This compound is used in organic synthesis as an intermediate for pharmaceuticals, agrochemicals, and specialty chemicals due to its reactive nitrile and ketone functionalities .
Comparison with Similar Compounds
Comparison with Structurally Similar Compounds
4,4-Dimethyl-5-oxopentanenitrile
- Molecular Formula: C₇H₁₁NO
- Molecular Weight : 125.17 g/mol
- Structural data (SMILES: CC(C)(CCC#N)C=O) highlight its branched aliphatic chain, which may influence solubility and boiling point .
5-(4-Fluorophenyl)-5-oxopentanoic Acid
- Molecular Formula : C₁₁H₉FO₃
- Molecular Weight : 210.20 g/mol
- Key Differences :
- Applications: Likely used in drug discovery, particularly for nonsteroidal anti-inflammatory agents or enzyme inhibitors.
5-(Methylsulfanyl)pentanenitrile
- Molecular Formula : C₆H₉NS
- Molecular Weight : 127.21 g/mol
- Key Differences: Replacement of the ketone group with a methylsulfanyl (-S-CH₃) moiety.
- Applications : May serve as a precursor for thioether-containing polymers or ligands in catalysis.
Comparative Data Table
| Compound | Molecular Formula | Molecular Weight (g/mol) | Functional Groups | Key Structural Features | Potential Applications |
|---|---|---|---|---|---|
| 4-Methyl-5-oxopentanenitrile | C₆H₉NO | 111.14 | Nitrile, Ketone | Linear chain, methyl branch | Organic synthesis intermediates |
| 4,4-Dimethyl-5-oxopentanenitrile | C₇H₁₁NO | 125.17 | Nitrile, Ketone | Branched chain, two methyl groups | Stabilized intermediates |
| 5-(4-Fluorophenyl)-5-oxopentanoic Acid | C₁₁H₉FO₃ | 210.20 | Carboxylic Acid, Ketone | Fluorophenyl ring | Pharmaceutical agents |
| 5-(Methylsulfanyl)pentanenitrile | C₆H₉NS | 127.21 | Nitrile, Thioether | Sulfur incorporation | Catalysis, polymer chemistry |
Research Findings and Functional Insights
- Reactivity :
- The nitrile group in this compound facilitates nucleophilic additions (e.g., hydrolysis to amides or carboxylic acids), while the ketone enables condensation reactions .
- In contrast, the methylsulfanyl group in 5-(methylsulfanyl)pentanenitrile may participate in thiol-ene click chemistry or act as a leaving group in substitution reactions .
- Physicochemical Properties :
Properties
Molecular Formula |
C6H9NO |
|---|---|
Molecular Weight |
111.14 g/mol |
IUPAC Name |
4-methyl-5-oxopentanenitrile |
InChI |
InChI=1S/C6H9NO/c1-6(5-8)3-2-4-7/h5-6H,2-3H2,1H3 |
InChI Key |
WZGRZLPEJDJMAI-UHFFFAOYSA-N |
Canonical SMILES |
CC(CCC#N)C=O |
Origin of Product |
United States |
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