829-23-2

Usage

General Description

Benzenemethanol, a-(chloromethyl)-, acetate is a chemical compound with the molecular formula C9H9ClO2. It is derived from benzenemethanol and acetic acid, and is used in various industrial and chemical applications. The compound is known for its reactivity and ability to undergo various chemical reactions, making it useful in the synthesis of other compounds and materials. It is also used as a solvent and in the production of pharmaceuticals, fragrances, and flavorings. However, it is important to handle this chemical with caution, as it can be hazardous if not handled properly.

Upstream product

• 108-24-7 acetic anhydride 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 532-27-4 1-chloroacetophenone 
• 100-42-5 styrene 
• 64-19-7 acetic acid 
• 93-56-1 phenylethane 1,2-diol 
• 40635-66-3 2-acetoxy-2-methylpropanoyl chloride 
• 96-09-3 styrene oxide 
• 75-36-5 acetyl chloride 
• 90352-14-0 Toluene-4-sulfonic acid 2-chloro-1-phenyl-ethyl ester 
• 70111-05-6 (S)-2-chloro-1-phenylethanol 
• 127-19-5 N,N-dimethyl acetamide 
• 141-78-6 ethyl acetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 70111-05-6 (S)-2-chloro-1-phenylethanol 
• 56751-12-3 2-chloro-1-phenylethanol 
• 33942-01-7 (-)-(R)-2-Chloro-1-phenyl-1-acetoxyethane 

Relevant academic research and scientific papers

Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization

Racemic phenylethyl halohydrins acetates containing several groups attached to the aromatic ring were resolved via hydrolysis reaction in the presence of lipase B from Candida antarctica (Novozym 435). In all cases, the kinetic resolution was highly selective (E > 200) leading to the corresponding (S)-β-halohydrin with ee > 99 %. However, the time required for an ideal 50 % conversion ranged from 15 min for 2,4-dichlorophenyl chlorohydrin acetate to 216 h for 2-chlorophenyl bromohydrin acetate. Six chlorohydrins and five bromohydrins were evaluated, the latter being less reactive. For the β-brominated substrates, steric hindrance on the aromatic ring played a crucial role, which was not observed for the β-chlorinated derivatives. To shed light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data obtained for β-chlorinated substrates suggested that physical aspects such as high hydrophobicity or induced change in the conformation of the enzymatic active site are more relevant aspects when compared to steric hindrance effects.

Immobilization of Amano lipase from Pseudomonas fluorescens on silk fibroin spheres: an alternative protocol for the enantioselective synthesis of halohydrins

The search for a new, efficient, cheaper and sustainable matrix for lipase immobilization is a growing area in biotechnology. Amano lipase from Pseudomonas fluorescens was immobilized on silk fibroin spheres and used in the enzymatic kinetic resolution of halohydrins, to obtain optically active epoxides (up to 99% ee), important precursors in the synthesis of derivative antifungal azoles. This paper reinforces the versatility of silk fibroin as a support for heterogeneous catalysts.

Intermolecular Halogenation/Esterification of Alkenes with N-Halosuccinimide and Acetic Acid Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

1,4-Diazabicyclo[2.2.2]octane (DABCO) is a suitable Lewis base that acts as an organocatalyst in the activation of N-chlorosuccinimide (NCS) towards the chlorination of alkenes. The chloriranium ion formed from NCS and the alkene, can be intermolecularly opened by a nucleophile, such as acetic acid, to produce highly functionalized trans-chloro esters in high yields. The protocol is also applied to the synthesis of chlorohydrins and chloro ethers using water or methanol as nucleophiles instead of acetic acid. Brominated analogs can also be synthesized from alkenes and N-bromosuccinimide (NBS) in the presence of various basic catalysts. However, the reaction patterns seem to be remarkably different. The catalytic performance of bases in the bromoesterification of alkenes was found to be strongly affected by their Br?nsted basicity, suggesting that acetyl hypobromite, formed in situ from NBS and acetic acid, acts as a real brominating agent in these systems. (Figure presented.).

Highly enantioselective acylation of chlorohydrins using Amano AK lipase from P. fluorescens immobilized on silk fibroin-alginate spheres

Aromatic, allylic, and aliphatic compounds containing a chlorohydrin group were selected as substrates for the enzymatic kinetic resolution mediated by Amano AK lipase from Pseudomonas fluorescens immobilized in silk friboin-alginate spheres. Thus, the en

Catalyst-free, direct, high regio- and chemoselective conversion of epoxides to vicinal haloesters under mild, neutral, and solvent-free conditions

A catalyst-free, high regio- and chemoselective method is described for the mild conversion of wide varieties of epoxides directly to their corresponding vicinal haloesters using quaternary ammonium halides R4N +X- (X equa

Addition of halide to π-bond directly from aqueous NaX solution: A general strategy for installation of two different functional groups

Activation of π-bond with organic Lewis acid and cationic surfactant mediated direct transfer of halides to alkyne and alkene are demonstrated to afford α,α-dihaloketones and other valuable synthons with outstanding selectivities.

An algorithm for the deconvolution of mass spectrosopic patterns in isotope labeling studies. Evaluation for the hydrogen-deuterium exchange reaction in ketones

(Graph Presented) An easy to use computerized algorithm for the determination of the amount of each labeled species differing in the number of incorporated isotope labels based on mass spectroscopic data is described and evaluated. Employing this algorithm, the microwave-assisted synthesis of various α-labeled deuterium ketones via hydrogen-deuterium exchange with deuterium oxide was optimized with respect to time, temperature, and degree of labeling. For thermally stable ketones the exchange of α-protons was achieved at 180°C within 40-200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75-94 h to 40-200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols.

Trichloroisocyanuric Acid as a Cohalogenating Reagent: An Efficient Transformation of Alkenes into Chlorohydrins, β-Chloroethers and β-Chloroacetates

The preparation of diverse β-chloroethers, β-chloroacetates, and chlorohydrins is efficiently achieved under mild conditions by reaction of alkenes with trichloroisocyanuric acid (0.34 mol equiv) in alcohols (MeOH, EtOH, i-PrOH, t-BuOH), acetic acid or aqueous acetone, respectively.

Efficient and Regioselective Conversion of Epoxides into Vicinal Chloroesters with TiCl4 and Imidazole in Ethyl Acetate

Epoxides can be cleaved easily in EtOAc with TiCl4 in the presence of imidazole to afford β-chloroesters with excellent yields and regioselectivity.

A facile 1,2-acetoxychlorination reaction of olefins by using the N,N-dimethtylacetamide/hydrogen chloride/m-chloroperbenzoic acid (or oxone) system

Various alkenes underwent 1,2-acetoxychlorination by dimethylacetamide (DMA)/HCl/m-CPBA (or Oxone) system in good yields.