Description
Specifications Table
Product Name – Pivaloyl chloride
Quantity/Pack Size – 100 ml
Form – Liquid
Grade – Synthesis Grade (98%+)
Application – Acylation reagent, protecting group synthesis
Product Overview
Pivaloyl chloride is a highly reactive acyl chloride derivative of pivalic acid, widely recognized for its role in organic synthesis. This colorless to pale yellow liquid exhibits a sharp, pungent odor characteristic of acyl chlorides and boasts a purity level exceeding 98%, making it suitable for demanding chemical transformations. The compound’s sterically hindered structure imparts unique reactivity patterns, particularly in the formation of tert-butyl esters and amides, which are valuable intermediates in pharmaceutical and fine chemical synthesis. Its moisture sensitivity necessitates careful handling under anhydrous conditions, typically in a fume hood with proper ventilation. The reagent demonstrates excellent solubility in common organic solvents like dichloromethane, THF, and toluene, while remaining immiscible with water. Pivaloyl chloride’s relatively high boiling point of 105°C provides stability during reactions, though it requires storage at temperatures between 2-8°C to maintain optimal shelf life. The compound’s reactivity profile includes rapid hydrolysis in aqueous environments, making it particularly useful for introducing the pivaloyl protecting group in peptide synthesis and other sensitive applications where steric bulk is advantageous.
FAQs
1. What precautions should be taken when handling pivaloyl chloride?
Always work in a well-ventilated fume hood wearing appropriate PPE including gloves, goggles, and a lab coat. The compound is highly corrosive and reacts violently with water, releasing hydrogen chloride gas. Use glassware that has been thoroughly dried and maintain anhydrous conditions throughout handling and storage.
2. Can pivaloyl chloride be used as a substitute for acetyl chloride?
While both are acyl chlorides, pivaloyl chloride introduces a tert-butyl group that provides significantly greater steric hindrance. This makes it unsuitable as a direct substitute for acetyl chloride in most applications, though it may be preferred in specific cases where the bulkier pivaloyl group offers advantages in selectivity or stability of the resulting products.
3. What is the typical shelf life of unopened pivaloyl chloride?
When stored properly at 2-8°C in its original sealed container, pivaloyl chloride maintains its specified purity for approximately 12 months from the date of manufacture. The container should be kept tightly closed and protected from moisture at all times to prevent degradation.
4. How should pivaloyl chloride waste be disposed of?
Never dispose of pivaloyl chloride in regular waste streams. The compound should be carefully neutralized by slow addition to a cold, dilute sodium bicarbonate solution in a fume hood, followed by proper chemical waste disposal procedures according to local environmental regulations and institutional safety protocols.
5. What solvents are most compatible with pivaloyl chloride for reactions?
The reagent shows excellent solubility in anhydrous solvents like dichloromethane, tetrahydrofuran, and toluene. These solvents are typically preferred for reactions involving pivaloyl chloride as they provide good solubility while maintaining the anhydrous conditions required for optimal reactivity and product formation.
