33598-76-4

Usage

Physical state

Colorless to pale yellow liquid

Odor

Strong, sweet

Uses

a. Intermediate in the synthesis of pharmaceuticals
b. Intermediate in the synthesis of agrochemicals
c. Intermediate in the synthesis of other organic compounds
d. Solvent in various industrial processes

Hazardous properties

a. Flammability
b. Potential for skin and eye irritation upon contact

Safety precautions

Proper handling and storage required to minimize risks

InChI:InChI=1/C9H11ClO/c1-2-11-7-8-3-5-9(10)6-4-8/h3-6H,2,7H2,1H3

Upstream product

• 352-12-5 4-chlorobenzyl fluoride 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 
• 64-17-5 ethanol 
• 130774-55-9 p-Chlorobenzyl Trifluoromethanesulfinate 
• 7803-57-8 hydrazine hydrate 
• 78-39-7 Triethyl orthoacetate 
• 873-76-7 para-Chlorobenzyl alcohol 
• 2031-62-1 diethoxymethylane 
• 104-88-1 4-chlorobenzaldehyde 
• 17876-99-2 (4-chlorobenzyl)trimethylsilane 
• 1801-77-0 oxovanadium(V) ethoxydichloride 

Downstream Products

• 104-88-1 4-chlorobenzaldehyde 
• 74-84-0 ethane 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 2403-61-4 p-chlorobenzaldehyde diethyl acetal 
• 831-81-2 4-chlorophenyl(phenyl)methane 
• 712-95-8 tert-butyl 4-chlorobenzoate 

Relevant academic research and scientific papers

Reductive etherification of aldehydes photocatalyzed by dicarbonyl pentamethylcyclopentadienyl iron complexes

The reductive etherification of aldehydes can be performed by the reaction with dialkylmethylsilanes in the presence of new iron(II) piano-stool catalysts of general formula Cp*Fe(CO)2Ar (Cp * = η5-C5Me5; Ar = Ph, 4-C6H4OCH3, 4-C6H4CH 3, Fc). This transformation is promoted by UV light and affords a simple route for the preparation of unsymmetrical alkyl ethers.

New method for the synthesis of benzyl alkyl ethers mediated by FeSO 4

The synthesis of benzyl alkyl ethers from benzyl bromides and alcohols using FeSO4 as a recoverable and reusable mediator has been described without use of base and cosolvent under mild conditions.

A kinetic model for water reactivity (avoiding activities) for hydrolyses in aqueous mixtures - Selectivities for solvolyses of 4-substituted benzyl derivatives in alcohol-water mixtures

For solvolyses of various benzyl substrates in ethanol-water (EW) and methanol-water (MW) mixtures, product selectivities (S) are reported for chlorides at 75°C defined as follows using molar concentrations: S= ([ether product]/[alcohol product]) × ([water]/[alcohol solvent]). The results support earlier evidence that solvolyses of 4-nitrobenzyl substrates are S N2 processes, which are not susceptible to mechanistic changes over the whole range of solvents from water to alcohol. S values at 25 and/or 45°C in EW and MW, and additional kinetic data including kinetic solvent isotope effects (KSIE) are reported for solvolyses of 4-nitrobenzyl mesylate and tosylate. A kinetic model, explaining both rates and product, is proposed; a general medium effect due to solvent polarity is combined in one parameter with solvent effects on the nucleophilicity of the water and alcohol molecules acting as nucleophiles in SN2 reactions. According to this model, as alcohol is added to water the rate of reaction decreases due to a decrease in solvent polarity, but the nucleophilicity of water increases relative to alcohol. The availability of experimental rate and product data over the whole range of solvent compositions from alcohol to water, reveals limitations of alternative approaches using activities. Copyright

Iodine catalyzed selective O-alkylation of alcohols with orthoesters

In the present communication O-alkylation of a number of allylic and benzylic alcohols has been described.

Selective Cross Coupling via Oxovanadium(V)-Induced Oxidative Desilylation of Benzylic Silanes

Benzylic silanes bearing an electron-donating group at the ortho- or para-position underwent the oxovanadium(V)-induced one-electron oxidative desilylation due to low ionization potential, which was applied to the intermolecular regioselective coupling with allylic silanes or silyl enol ether.

THE SYNTHESIS, SOLVOLYSIS AND REARRANGEMENT OF BENZYL TRIFLUOROMETHANESULFINATES

The synthesis and reactivity of benzyl trifluoromethanesulfinates have been investigated.These esters are easily and almost quantitatively obtained by selective oxidation of the corresponding sulfenates.A study of their behavior has revealed some unique features.In sharp contrast to benzyl arenesulfinates, which undergo ethanolysis with complete sulfur-oxygen bond fission, the corresponding trifluoromethanesulfinates undergo ethanolysis with exclusive carbon-oxygen bond fission, and with a rate enhancement by a factor of 6 powers of ten.The unusual high reactivity of these esters, comparable to that of the corresponding tosylates, is discussed.A kinetic study of the solvent and substituents effects on the rate of solvolysis has been performed.Also in contrast with benzyl arenesulfinates, these esters undergo facile rearrangement to sulfone on heating in polar nonhydroxylic solvents such as acetonitrile, in high yields.The mechanisms of solvolysis and rearrangement are discussed.