2-Chloroethyl chloroformate
[CAS# 627-11-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 2-Chloroethyl chloroformate
• Synonyms: Chloroethyl chloroformate; beta-Chloroethyl chloroformate
• Molecular Formula: C₃H₄Cl₂O₂
• Molecular Weight: 142.97
• CAS Registry Number: 627-11-2
• EC Number: 210-982-4
• SMILES: C(CCl)OC(=O)Cl

Properties

• Density: 1.385
• Boiling point: 155-156 ºC
• Refractive index: 1.446
• Flash point: 158 ºF

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H314-H315-H319-H331-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P271-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P330-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H331
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H330
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	3	H226
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Carcinogenicity	Carc.	1A	H350
Flammable liquids	Flam. Liq.	4	H227

• Transport Information: UN 3277

Discovory and Applicatios

2-Chloroethyl chloroformate, with the chemical formula C3H3Cl2O2, is an organochlorine compound used extensively in organic synthesis. It features a chloroformate group attached to a 2-chloroethyl group, making it a valuable reagent in the preparation of various chemical derivatives. Its discovery and development have significantly influenced its applications in organic chemistry, particularly in the synthesis of esters, carbonates, and other functional groups.

The discovery of 2-chloroethyl chloroformate is linked to the broader study of chloroformates and their role in organic synthesis. Chloroformates, known for their reactivity with alcohols and amines, are key intermediates in introducing ester and carbonate functionalities into molecules. The synthesis of 2-chloroethyl chloroformate typically involves the reaction of 2-chloroethanol with phosgene, resulting in the formation of the chloroformate ester.

In organic synthesis, 2-chloroethyl chloroformate is used as a reagent for the protection of alcohols and amines. When reacted with alcohols, it forms 2-chloroethyl esters, which are stable and can be selectively removed after the desired chemical transformations are completed. Similarly, 2-chloroethyl chloroformate reacts with amines to produce 2-chloroethyl carbamates, which serve as protecting groups for amino functionalities. This protective strategy is essential for ensuring selective reactions and preventing undesired side reactions in complex syntheses.

2-Chloroethyl chloroformate also finds applications in the synthesis of pharmaceuticals and fine chemicals. Its ability to introduce carbonyl groups into molecules makes it valuable in the preparation of carbonates and carbamates, which are important functional groups in drug development and chemical manufacturing. The compound's utility extends to the synthesis of polymer precursors and specialty chemicals, highlighting its significance in various industrial applications.

In summary, 2-chloroethyl chloroformate is an important reagent in organic chemistry, offering valuable applications in the protection of functional groups and the synthesis of complex molecules. Its discovery and development have enhanced the capabilities of organic synthesis, making it a crucial tool in the preparation of pharmaceuticals, polymers, and other fine chemicals.