50972-20-8

Basic information

• Product Name: Phenyl 1-Chloroethyl Carbonate
• Synonyms: 1-Chloroethyl Phenyl Carbonate;Carbonic Acid 1-Chloroethyl Phenyl Ester;Phenyl 1-Chloroethyl Carbonate
• CAS NO: 50972-20-8
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.61896
• Product Categories: Aromatics;Intermediates
• Mol File: 50972-20-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 67-68 °C(Press: 0.15 Torr)
• Appearance: /
• Density: 1.240±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Phenyl 1-Chloroethyl Carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 1-Chloroethyl Carbonate(50972-20-8)
• EPA Substance Registry System: Phenyl 1-Chloroethyl Carbonate(50972-20-8)

Safety Data

• Hazardous Substances Data: 50972-20-8(Hazardous Substances Data)

Usage

Description

Phenyl 1-Chloroethyl Carbonate, also known as Carbonic Acid 1-Chloroethyl Phenyl Ester, is an aryl chloroalkyl carbamate that serves as a versatile chemical intermediate in the synthesis of carbamate pesticides and for the protection of various amino groups, including amino acids.

Uses

Used in Pesticide Synthesis:
Phenyl 1-Chloroethyl Carbonate is used as a chemical intermediate for the synthesis of carbamate pesticides. It plays a crucial role in the production of these pesticides, which are widely used in agriculture to control pests and protect crops.
Used in Amino Group Protection:
Phenyl 1-Chloroethyl Carbonate is used as a protecting agent for a variety of amino groups, including amino acids. This application is particularly important in the field of organic synthesis and pharmaceutical chemistry, where the protection of amino groups is necessary to prevent unwanted side reactions and ensure the successful synthesis of desired compounds.

Upstream product

• 75-07-0 acetaldehyde 
• 1885-14-9 phenyl chloroformate 
• 50893-53-3 carbonochloridic acid 1-chloro-ethyl ester 
• 108-95-2 phenol 

Downstream Products

• 16641-71-7 1-(phenoxycarbonyl)piperidine 
• 109548-52-9 phenyl 1-thiocyanoethylcarbonate 
• 108-95-2 phenol 
• 351-80-4 phenyl fluoroformate 
• 104483-32-1 1-bromoethyl phenyl carbonate 
• 117972-13-1 phenyl 1-isothiocyanoethylcarbonate 

Relevant articles and documents

A Simple Conversion of 1-Chloroethyl Carbonates to Fluoroformates: Value in the Preparation of Tertiary Alkyl Fluoroformates

When the economical and easily available 1-chloroalkyl carbonates (RCHClOCO2R') are heated neat or in solution with KF in the pesence of 18-crown-6 catalyst, they fragment to aldehydes (RCHO) and fluoroformates (FCO2R').If the system is evacuated during reaction and either or both products are removed as formed, then the process is driven to completion and fluoroformates are isolated in good yield.The new methodology (which exemplifies an unusual conversion of an ester to an acid halide) is especially valuable in the synthesis of important tertiary alkyl fluoroformates and benzyl fluoroformate (with R as CH3 in the carbonate): tert-butyl fluoroformate (BOC-F, 84percent yield), tert-amyl fluoroformate (83percent), 1-adamantyl fluoroformate (76percent), benzyl fluoroformate (60percent).Boc-F previously has been recommended as a superior reagent for the preparation of Boc-amino acids, but earlier routes to this reagent have been expensive and impractical.When R in the carbonate reactant is Cl3C, the reaction proceeds cleanly without the 18-crown-6 catalyst (Boc-F in 79percent yield).This latter variation is most useful on a small industrial scale.

A Convenient New Route to 1-Haloalkyl Carbonates

Alkyl (or alkenyl or aryl) 1-haloalkyl carbonates are conveniently prepared by reaction of an aldehyde with an alkyl (or alkenyl or aryl) carbonohalidate (haloformate) in the presence of a catalyst.