Phenyl chloroformate
[CAS# 1885-14-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Phenyl esters
• Name: Phenyl chloroformate
• Synonyms: Carbonochloridic acid phenyl ester
• Molecular Formula: C₇H₅ClO₂
• Molecular Weight: 156.57
• CAS Registry Number: 1885-14-9
• EC Number: 217-547-8
• SMILES: C1=CC=C(C=C1)OC(=O)Cl

Properties

• Density: 1.248
• Melting point: -28 °C
• Boiling point: 188-189 °C
• Refractive index: 1.51-1.512
• Flash point: 80 °C
• Water solubility: hydrolysis

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H290-H302-H314-H315-H317-H318-H330-H335
• Safety Statements: P234-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P320-P321-P330-P332+P317-P333+P317-P362+P364-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	1	H330
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	5	H313
Flammable liquids	Flam. Liq.	4	H227
Skin corrosion	Skin Corr.	1C	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

• Transport Information: UN 2746

Discovery and Applications

Phenyl chloroformate, with the chemical formula C6H5O2Cl, is an important organic compound widely used in chemical synthesis and industrial applications. It was first synthesized in the late 19th century as part of studies into esters and their reactivity. The compound is an ester of phenol and chloroformic acid, featuring a phenyl group attached to the chloroformate moiety.

The synthesis of phenyl chloroformate typically involves the reaction of phenol with phosgene (COCl2) in the presence of a base. This process produces phenyl chloroformate along with hydrochloric acid as a byproduct. The reaction is carried out under controlled conditions to manage the reactivity of phosgene, a highly toxic compound.

Phenyl chloroformate is primarily utilized as a reagent in organic synthesis. One of its major applications is in the preparation of carbamates from amines. This reaction is valuable in the pharmaceutical and agricultural industries, where carbamates are used as pesticides, herbicides, and pharmaceutical agents. The ability of phenyl chloroformate to react with amines to form carbamates is harnessed to create a variety of compounds with diverse biological activities.

In addition to its role in the synthesis of carbamates, phenyl chloroformate is used as a protective reagent in the synthesis of peptides and other organic molecules. It can be employed to temporarily protect amino groups in peptide synthesis, allowing for selective reactions at other functional sites. This application is crucial in the production of peptides and proteins, which are important in pharmaceuticals and biotechnology.

Phenyl chloroformate also serves as a reagent in the synthesis of other organic compounds, including esters and anhydrides. Its reactivity with alcohols and acids allows for the formation of various derivatives that are used in different chemical processes.

Despite its utility, phenyl chloroformate must be handled with care due to its reactive and potentially hazardous nature. It is important to use appropriate safety measures to manage its reactivity and to handle phosgene, which is highly toxic. Proper storage and handling protocols are essential to ensure safe usage in laboratory and industrial settings.

Overall, phenyl chloroformate is a versatile reagent with significant applications in organic synthesis. Its discovery and development have contributed to advances in chemical manufacturing and pharmaceutical production, highlighting its importance in various chemical processes.

References

2020. Novel method for the synthesis of lenvatinib using 4-nitrophenyl cyclopropylcarbamate and their pharmaceutical salts. Chemical Papers, .
DOI: 10.1007/s11696-020-01402-z

2023. Optimization of the regioselective synthesis of mixed cellulose 3,5-dimethylphenyl and α-phenylethyl carbamate selectors as separation phases for chiral HPLC. Cellulose, .
DOI: 10.1007/s10570-022-05007-5