59204-21-6

Basic information

• Product Name: Methyl (R)-2-chloro-2-phenylethanoate
• CAS NO: 59204-21-6
• Molecular Weight: 184.622
• Mol File: 59204-21-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Methyl (R)-2-chloro-2-phenylethanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (R)-2-chloro-2-phenylethanoate(59204-21-6)
• EPA Substance Registry System: Methyl (R)-2-chloro-2-phenylethanoate(59204-21-6)

Safety Data

• Hazardous Substances Data: 59204-21-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 53432-40-9 (R)-chloro-phenyl-acetic acid-chloride 
• 181026-78-8 1,1-bis(trimethylsilyloxy)-2-chloro-2-phenylethene 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 43195-94-4 (R)-2-chloro-2-phenylacetic acid 
• 1363553-28-9 (S)-methyl 2-(5,6-dimethoxyisoindolin-2-yl)-2-phenylacetate 
• 541-41-3 chloroformic acid ethyl ester 
• 21210-43-5 (S)-Methyl mandelate 
• 20698-91-3 (R)-methyl mandelate 
• 1223-44-5 4-nitrophenyl 2-phenylacetate 
• 36140-84-8 1-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenylethan-1-one 

Relevant articles and documents

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions

The asymmetric α-chlorination of activated aryl acetic acid esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammonium enolates, is best carried out under cryogenic conditions combined with a direct trapping of the activated α-chlorinated ester derivative to prevent epimerization, thus allowing for enantioselectivities of up to e.r. 99:1.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.