Allyl chloroformate
[CAS# 2937-50-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Allyl chloroformate
• Synonyms: prop-2-enyl carbonochloridate
• Molecular Formula: C₄H₅ClO₂
• Molecular Weight: 120.5
• CAS Registry Number: 2937-50-0
• EC Number: 220-916-6
• SMILES: C=CCOC(=O)Cl

Properties

• Density: 1.136
• Boiling point: 74 °C (720 mmHg)
• Refractive index: 1.422
• Flash point: 31 °C

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06 Danger
• Risk Statements: H226-H301-H314-H330
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P270-P271-P280-P284-P301+P316-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P320-P321-P330-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	3	H301
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1A	H314
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Allyl chloroformate is an organic compound with the chemical formula C4H5ClO2. It is a member of the chloroformate family, which includes compounds known for their reactivity and versatility in organic synthesis. Allyl chloroformate is a colorless liquid with a pungent odor, and it is used primarily as a reagent in chemical reactions involving esterification and carbamoylation.

The discovery of allyl chloroformate emerged from the broader investigation into chloroformates and their applications. Chloroformates are known for their utility in introducing functional groups into organic molecules, particularly in the synthesis of esters and carbamates. Allyl chloroformate was synthesized by the reaction of allyl alcohol with phosgene, a common method for preparing chloroformates. This compound's distinct reactivity is attributed to the presence of both the chloroformate and allyl groups, which enhance its utility in various chemical transformations.

In organic synthesis, allyl chloroformate serves as a valuable reagent for the formation of esters and carbamates. It reacts with alcohols to produce allyl esters, which are important intermediates in the synthesis of complex organic compounds. Additionally, allyl chloroformate can be used to prepare carbamates from amines, a reaction that is useful in creating protective groups or modifying biological molecules. The allyl group in allyl chloroformate offers additional reactivity, allowing for further transformations such as cross-coupling reactions or polymerizations.

The applications of allyl chloroformate extend to several industrial and research areas. In the pharmaceutical industry, it is employed in the synthesis of active pharmaceutical ingredients (APIs) and intermediates. Its ability to introduce ester and carbamate functionalities makes it valuable in the development of new drugs and therapeutic compounds. In the field of polymer chemistry, allyl chloroformate is used in the preparation of functionalized polymers with specific properties, such as increased reactivity or improved solubility.

Furthermore, allyl chloroformate is utilized in the synthesis of agrochemicals and other specialty chemicals. Its reactivity allows for the creation of diverse chemical structures, contributing to the development of novel compounds with desired properties. Research into new applications and methods involving allyl chloroformate continues, highlighting its significance as a versatile reagent in organic synthesis.

References

2024, Synthetic studies on the tetrasubstituted D-ring of cystobactamids lead to potent terephthalic acid antibiotics, _Communications Chemistry_, 7(1)
DOI: https://doi.org/10.1038/s42004-024-01337-6

2013, Kinetic Studies that Evaluate the Solvolytic Mechanisms of Allyl and Vinyl Chloroformate Esters, _International Journal of Molecular Sciences_, 14(4)
DOI: https://doi.org/10.3390/ijms14047286

2014, Synthesis of N-Allyloxycarbonyl 3,5-Dihydroxyphenylglycine via Photochemical Wolff Rearrangement-Nucleophilic Addition Sequence in a Micro-Flow Reactor, _Journal of Flow Chemistry_, 4(4)
DOI: https://doi.org/10.1556/jfc-d-14-00015