Definition
Isobutyramide, also known as 2‑methylpropanamide, is an organic compound belonging to the class of aliphatic amides. Its chemical formula is C₄H₉NO and it is the amide derivative of isobutyric (2‑methylpropanoic) acid.
Overview
Isobutyramide appears as a white, crystalline solid that is readily soluble in water and polar organic solvents such as ethanol. It is employed as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and polymer precursors. The compound is catalogued under CAS 124‑34‑7 and has a molar mass of 87.12 g·mol⁻¹.
Etymology/Origin
The name “isobutyramide” derives from its parent acid, isobutyric acid (2‑methylpropanoic acid). The prefix “iso‑” indicates the presence of a branched (methyl‑substituted) carbon chain, while the suffix “‑amide” denotes the functional group –C(=O)NH₂ that replaces the hydroxyl group of the corresponding carboxylic acid.
Characteristics
| Property | Value / Description |
|---|---|
| IUPAC name | 2‑Methylpropanamide |
| Synonyms | Isobutyl amide, 2‑Methyl‑propionamide |
| Molecular formula | C₄H₉NO |
| Molar mass | 87.12 g·mol⁻¹ |
| Physical state | White crystalline solid |
| Melting point | 130–133 °C (reported) |
| Boiling point | Decomposes before boiling; decomposition observed near 225 °C |
| Solubility | Highly soluble in water; miscible with ethanol and methanol |
| Density | Approximately 1.13 g·cm⁻³ at 20 °C |
| pKa (conjugate acid) | ~−0.5 (characteristic of amide functional groups) |
| Safety | Classified as an irritant; handling requires gloves and eye protection. Material Safety Data Sheet (MSDS) recommends avoidance of inhalation and contact with skin or eyes. |
Related Topics
- Butyramide – the straight‑chain analogue (CH₃CH₂CH₂C(=O)NH₂).
- Isobutyric acid – the parent carboxylic acid (2‑methylpropanoic acid).
- Amides – a functional group class characterized by a carbonyl attached to a nitrogen atom.
- Organic synthesis – Isobutyramide serves as a building block for various nitrogen‑containing compounds.
- Polyamide precursors – Certain polyamides incorporate isobutyramide‑derived monomers.
All presented data are derived from established chemical reference sources and peer‑reviewed literature.