50972-20-8

Usage

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 
• 117972-13-1 phenyl 1-isothiocyanoethylcarbonate 
• 104483-32-1 1-bromoethyl phenyl carbonate 
• 351-80-4 phenyl fluoroformate 
• 109548-52-9 phenyl 1-thiocyanoethylcarbonate 
• 108-95-2 phenol 

Relevant academic research and scientific papers

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.

Process for the preparation of carbamates, thiocarbamates and ureas

The invention relates to a process for preparing carbamic acid derivatives of formula: STR1 in which R1 or R2 denotes a hydrogen atom or a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or heterocyclic radical, or R1 and R2 together form a ring, and Y denotes OR, SR, STR2 groups, R being a substituted or unsubstituted, saturated or unsaturated aliphatic or cycloaliphatic radical, or a substituted or unsubstituted aromatic radical, R3 and R4 denote a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or together form a ring, and R6 and R7 denote a saturated or unsaturated, substituted or unsubstituted aliphatic or cycloaliphatic radical, a hydrogen atom, an alkylthio radical or an alkyloxy radical. According to the process, a compound of formula STR3 is reacted with an α-halogenated derivative of formula STR4 at a temperature of -5° to 150° C. in the presence of an acceptor for hydrohalic acid. The carbamates, thiocarbamates or ureas obtained are very useful, especially as pesticides.

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.

Alkyl 1-Chloroalkyl Carbonates: Reagents for the Synthesis of Carbamates and Protection of Amino Groups

The synthesis of 1-chloroalkyl carbonates and their reaction with various type of amines are described.This reaction is useful for the synthesis of carbamate pesticides and for the protection of various amino groups, including amino acids.