Isobutyl chloroformate
Chemical Additives 2025-03-19
Isobutyl chloroformate is an organic compound with the chemical formula C₅H₉ClO₂. It consists of a chloroformate group (-OCOCl) attached to an isobutyl group (-CH₂CH(CH₃)₂). This structure makes it an ester of chloroformic acid and isobutanol, combining the properties of esters and acyl chlorides.
Isobutyl chloroformate is widely used as a reagent in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It is valued for its ability to introduce the chloroformate group into target molecules, which is useful in the synthesis of carbamates, carbonates, and other derivatives. It is also employed in peptide coupling reactions and the modification of biomolecules.
The compound is typically a clear, colorless to pale yellow liquid with a pungent odor. It is highly reactive, moisture-sensitive, and can cause severe irritation to the skin, eyes, and respiratory system. Proper handling, including the use of personal protective equipment (PPE) and working in a fume hood, is essential. It should be stored in a cool, dry place, away from moisture and incompatible materials.
ISOBUTYL CHLOROFORMATE: TECHNICAL DATA SHEET
| Category | Specifications |
|---|---|
| Chemical Name | Isobutyl Chloroformate |
| CAS No. | 543-27-1 |
| Molecular Formula | C₅H₉ClO₂ |
| Appearance | Colorless to pale yellow liquid |
| Odor | Pungent, irritating |
| Boiling Point | 125-128°C |
| Density (20°C) | 1.05-1.07 g/cm³ |
| Flash Point | 25°C (closed cup) |
Key Properties
| Property | Performance Data |
|---|---|
| Reactivity | Highly reactive with nucleophiles (e.g., amines, alcohols) |
| Solubility | Soluble in organic solvents (ether, benzene) |
| Refractive Index | 1.405-1.410 (20°C) |
| Vapor Pressure | 10 mmHg (20°C) |
Applications
| Industry | Primary Uses |
|---|---|
| Pharmaceuticals | Intermediate for carbamates/ureas |
| Agrochemicals | Pesticide synthesis |
| Peptide Synthesis | Carboxyl group activator |
| Polymer Chemistry | Monomer modification |
Safety & Handling
| Parameter | Requirements |
|---|---|
| GHS Classification | H225. H302. H314. H331 |
| Storage | Sealed, dry, inert atmosphere (N₂), <0°C |
| PPE | Acid-resistant gloves, face shield, fume hood |
References:
Handbook of Reagents for Organic Synthesis
NFPA 704: 3-2-1 (Health-Fire-Reactivity)
