CHLOROMETHYL PIVALATE

China [CN]

Basic Information

Chinese Name: Chloromethyl Pivalate

English Name: Chloromethyl Pivalate

Molecular Formula: C₆H₁₁ClO₂

Molecular Weight: 150.60

CAS Number: 18897-41-1

Structural Characteristics

The molecule is formed by the esterification of pivaloic acid (trimethylacetic acid) and chloromethanol, with the following structural characteristics:

Acyl Group: Pivaloyl ((CH₃)₃C-CO-), in which the tert-butyl group ((CH₃)₃C-) is a bulky alkyl group, which provides steric hindrance and protects the stability of the ester group, reducing the possibility of hydrolysis or other nucleophilic reactions.

Ester Group: Chloromethyl Ester (-OCH₂Cl), in which the chlorine atom is directly attached to the methylene group adjacent to the oxygen, forming a highly reactive alkyl chloride structure, which is the core reactive site of the molecule.

This combination of a bulky acyl group and a highly reactive chloromethyl group imparts both stability (resistance to hydrolysis) and selective reactivity (the chloromethyl group is easily substituted), making it a commonly used protecting group and building block in organic synthesis.

Physical and Chemical Properties

Appearance: Typically a colorless, transparent liquid with a slight ester-like odor.

Boiling Point: Approximately 145-148°C (at atmospheric pressure), or 45-47°C/10 mmHg (under reduced pressure), allowing for easy purification by distillation.

Density: Approximately 1.01 g/cm³ (20°C, experimental value).

Refractive Index: n20/D approximately 1.417-1.419 (reflects the molecular optical properties).

Solubility: Sparingly soluble in water, readily soluble in organic solvents such as ether, acetone, dichloromethane, and toluene, and has good compatibility with most non-polar and weakly polar solvents. Stability: Stable at room temperature. The steric hindrance of the tert-butyl group significantly reduces the hydrolysis rate of the ester group (it is more resistant to water and weak acids and bases than ordinary esters). However, it will still hydrolyze under strong alkaline conditions. The chloromethyl group is susceptible to substitution reactions under the action of nucleophiles. It should be sealed and stored in a cool, dry place.

Chemical Properties