Benzyl chloroformate
[CAS# 501-53-1]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other protected amino acids
• Name: Benzyl chloroformate
• Synonyms: Carbobenzoxy chloride; Carbonochloride acid benzylester
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• CAS Registry Number: 501-53-1
• EC Number: 207-925-0
• SMILES: C1=CC=C(C=C1)COC(=O)Cl

Properties

• Density: 1.195
• Melting point: -18 °C
• Refractive index: 1.519
• Boiling point: 103 °C (20 mm Hg)
• Flash point: 92 °C
• Water solubility: decomposes

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS09 Danger
• Risk Statements: H314-H318-H330-H400-H410
• Safety Statements: P260-P264-P264+P265-P271-P273-P280-P284-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P320-P321-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335
Carcinogenicity	Carc.	1B	H350
Carcinogenicity	Carc.	1A	H350

• Transport Information: UN 1739

Discovery and Applications

Benzyl chloroformate, with the chemical formula C8H7ClO2, is an organofluorine compound commonly used as a reagent in organic synthesis. It consists of a benzyl group attached to a chloroformate moiety, making it a valuable tool in various chemical transformations. The discovery and development of benzyl chloroformate have significantly impacted its applications in organic chemistry, including its use in the synthesis of esters, carbonates, and other functional groups.

The discovery of benzyl chloroformate can be traced back to advancements in the chemistry of chloroformates and their derivatives. Chloroformates, known for their reactivity with alcohols and amines, have been used extensively as intermediates in organic synthesis. The introduction of the benzyl group into chloroformates provided a compound with enhanced reactivity and selectivity. The synthesis of benzyl chloroformate typically involves the reaction of benzyl alcohol with phosgene, resulting in the formation of the chloroformate ester.

In organic synthesis, benzyl chloroformate serves as a versatile reagent. One of its primary applications is in the protection of alcohols and amines during multi-step syntheses. By reacting with alcohols, benzyl chloroformate forms benzyl esters, which are stable and can be easily removed after the desired transformations are completed. Similarly, it can react with amines to form benzyl carbamates, which are used to protect amino groups during complex syntheses. This protective strategy is crucial for ensuring selective reactions and preventing undesired side reactions.

Benzyl chloroformate also plays a role in the synthesis of various 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. Additionally, it is used in the synthesis of polymer precursors and other specialty chemicals, further demonstrating its utility in the chemical industry.

In summary, benzyl chloroformate is a significant 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 an essential tool in the preparation of pharmaceuticals, polymers, and other fine chemicals.

References

2023. Stereoselective synthesis of S-norvaline and related amino acids through a common intermediate. Amino Acids.
DOI: 10.1007/s00726-023-03289-y

2022. Recent advances in therapeutical applications of the versatile hydroxypyridinone chelators. Journal of Inclusion Phenomena and Macrocyclic Chemistry.
DOI: 10.1007/s10847-021-01114-1

2021. New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP). Amino Acids.
DOI: 10.1007/s00726-021-02962-4