Isopropyl chloroformate
[CAS# 108-23-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Propyl esters
• Name: Isopropyl chloroformate
• Synonyms: Carbonochloridic acid 1-methylethyl ester
• Molecular Formula: C₄H₇ClO₂
• Molecular Weight: 122.55
• CAS Registry Number: 108-23-6
• EC Number: 203-563-2
• SMILES: CC(C)OC(=O)Cl

Properties

• Density: 0.892 (1.0 M in toluene)
• Boiling point: 105 °C
• Refractive index: 1.485
• Flash point: 43 °F

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07 Danger
• Risk Statements: H225-H302-H314-H315-H317-H318-H330
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P320-P321-P330-P332+P317-P333+P317-P362+P364-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	1	H330
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	2	H330
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H332
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H301

• Transport Information: UN 2407; UN 3286

Discovery and Applications

Isopropyl chloroformate is an organochlorine compound widely used as a reagent in organic synthesis. Its molecular formula is C4H7ClO2, and it consists of an isopropyl group attached to a chloroformate functional group. The compound is a colorless liquid with a pungent odor and is reactive due to the presence of the chloroformate group. Isopropyl chloroformate is commonly used in the formation of esters and carbamates, making it a versatile reagent in chemical processes.

The discovery and utility of isopropyl chloroformate stem from the development of chloroformate reagents in organic chemistry, which are known for their ability to facilitate esterification and carbamate formation. Isopropyl chloroformate is particularly valuable in the synthesis of pharmaceutical intermediates, where precise control over functional group introduction is required. Its reactivity with alcohols and amines makes it useful in creating esters and carbamates, key components in various drugs and agrochemicals.

One of the main applications of isopropyl chloroformate is in peptide synthesis, where it serves as a coupling reagent. In this process, the compound reacts with amino groups to form protective groups or intermediates, facilitating the sequential addition of amino acids during peptide bond formation. The ease with which isopropyl chloroformate reacts with both amines and alcohols has made it a standard reagent in laboratories involved in peptide and protein chemistry.

Isopropyl chloroformate also finds use in the production of carbamate-based pesticides and herbicides. The ability of chloroformates to form stable carbamate linkages with amines makes them essential in the design of agrochemicals, which require stability and controlled reactivity in agricultural environments. This compound's reactivity provides a pathway for creating highly effective carbamate derivatives used in protecting crops from pests.

Another application of isopropyl chloroformate is in pharmaceutical chemistry, where it aids in the synthesis of various intermediates for drug molecules. The compound's ability to introduce chloroformate groups efficiently allows for the formation of complex organic molecules with desired functional properties. This has led to its use in the development of several drug candidates and in the optimization of synthetic routes for pharmaceuticals.

Isopropyl chloroformate continues to be an important reagent in organic chemistry, offering versatile reactivity for a range of synthetic applications. Its utility in esterification, carbamate formation, and protective group chemistry ensures its ongoing relevance in industrial and academic research.

References

2010. Analysis of the Nucleophilic Solvation Effects in Isopropyl Chlorothioformate Solvolysis. International Journal of Molecular Sciences.
DOI: 10.3390/ijms11072597

2013. Determination of phenols in aqueous solutions by chromatography-mass spectrometry as isopropyl hydroxycarbonyl derivatives. Journal of Analytical Chemistry.
DOI: 10.1134/s1061934813010073

2016. Selective and full derivatization of amino group in chitosan with alkyl chloroformate of low stereo-hindrance. Macromolecular Research.
DOI: 10.1007/s13233-016-4079-4