2039-85-2

Usage

Uses

Used in Electronics Industry:
3-Chlorostyrene is used as an electron resist for direct device fabrication. Its unique chemical properties make it a promising candidate in the development of advanced materials for the electronics industry. The application reason is that 3-Chlorostyrene can be utilized in the production of high-quality electron resists, which are essential for creating intricate patterns and structures on semiconductor wafers during the manufacturing process of microelectronic devices.
Used in Chemical Synthesis:
3-Chlorostyrene is also used as a building block in the synthesis of various organic compounds. Its reactivity and the presence of the chlorine atom make it a versatile starting material for the production of a wide range of chemicals, including pharmaceuticals, agrochemicals, and specialty chemicals. The application reason is that 3-Chlorostyrene can undergo various chemical reactions, such as substitution, addition, and elimination, to form a diverse array of products with different functional groups and molecular structures.
Used in Polymer Industry:
3-Chlorostyrene can be used as a monomer in the polymer industry to produce a variety of polymers with specific properties. The application reason is that the presence of the chlorine atom in the styrene molecule can influence the polymer's physical and chemical properties, such as its solubility, reactivity, and thermal stability. These polymers can be used in various applications, including coatings, adhesives, and plastics.

Preparation

1-(m-Chlorophenyl)ethanol is reacted with potassium hydrogen sulfate in the presence of p-tert-butylcatechol to give m-chlorostyrene.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1180, 1948 DOI: 10.1021/ja01183a088Organic Syntheses, Coll. Vol. 3, p. 204, 1955

Synthesis Reference(s)

Synthetic Communications, 11, p. 405, 1981 DOI: 10.1080/00397918108064307

InChI:InChI=1/C8H7Cl/c1-2-7-4-3-5-8(9)6-7/h2-6H,1H2

Upstream product

• 7073-93-0 m-chlorocumene 
• 587-04-2 m-Chlorobenzaldehyde 
• 19493-09-5 Methylenetriphenylphosphorane 
• 120121-01-9 1-(m-Chlorophenyl)ethanol 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 67-66-3 chloroform 
• 71-43-2 benzene 
• 74-85-1 ethene 
• 625-99-0 3-iodochlorobenzene 
• 20697-04-5 3-chlorostyrene oxide 
• 67-71-0 dimethylsulfone 
• 873-63-2 m-chlorobenzyl alcohol 
• 2039-86-3 3-bromostyrene 
• 766-83-6 m-chlorophenylacetylene 

Downstream Products

• 16633-45-7 trans-2-(3-chlorophenyl)-cyclopropanecarboxylic acid 
• 42866-88-6 1-chloro-3-(2,2-dimethoxyethyl)benzene 
• 39791-83-8 5-(3-chloro-phenyl)-2-[1-(3-chloro-phenyl)-2-nitro-ethoxy]-3,3-dinitro-isoxazolidine 
• 58519-38-3 1,4-Dinitro-5-(m-chlorphenyl)-bicyclo<2.2.2>oct-2-en 
• 30010-80-1 1-Chloro-3-(1,2-dichloro-ethyl)-benzene 
• 84508-62-3 2-bromo-1-(3-chlorophenyl)-1,1-dimethoxyethane 
• 109332-87-8 2-bromo-1-(3-chlorophenyl)-1-methoxyethane 
• 109275-37-8 1-(2-Bromo-1-chloro-ethyl)-3-chloro-benzene 
• 127510-49-0 1-chloro-3-(2,2-dibromocyclopropyl)benzene 
• 152713-96-7 1-Chloro-3-(2,2-dichloro-3,3-difluoro-cyclobutyl)-benzene 
• 77871-28-4 1-(m-chlorophenyl)-2,2-bis(ethoxycarbonyl)cyclopropane 
• 620-16-6 3-chloroethylbenzene 
• 947732-85-6 3-chloro-α-methylphenylacetaldehyde 
• 96999-60-9 1-(2-Bromo-1-phenylselanyl-ethyl)-3-chloro-benzene 

Relevant academic research and scientific papers

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Switchable Chemoselectivity of Reactive Intermediates Formation and Their Direct Use in A Flow Microreactor

A chemoselectivity switchable microflow reaction was developed to generate reactive and unstable intermediates. The switchable chemoselectivity of this reaction enables a selection for one of two different intermediates, an aryllithium or a benzyl lithium, at will from the same starting material. Starting from bromo-substituted styrenes, the aryllithium intermediates were converted to the substituted styrenes, whereas the benzyl lithium intermediates were engaged in an anionic polymerization. These chemoselectivity-switchable reactions can be integrated to produce polymers that cannot be formed during typical polymerization reactions.

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.

Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Metal-free and base-free decarboxylation of substituted cinnamic acids in a deep eutectic solvent

A metal-free and base-free strategy was developed in DES to synthesize styrenes for the first time by decarboxylation of cinnamic acid derivatives, which provided a renewable and cost efficiently protocol to access various styrenes including those with functional groups such as 4-vinylphenol and 1-chloro-4-vinylbenzene.

Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.

Palladium-catalyzed proaromatic C(Alkenyl)-H olefination: Synthesis of densely functionalized 1,3-dienes

An example of proaromatic C(alkenyl)-H olefination is reported. This protocol utilized a free carboxylic acid as a directing group for C(alkenyl)-H activation of 1,4-cyclohexadiene and coupled with various alkenes. Direct and sequential bisolefinations of proaromatic acids were achieved. The synthetic applicability has been exhibited by [4 + 2] cycloaddition and decarboxylative aromatization of the resulting proaromatic 1,3-dienes. Additionally, several kinetic studies also have been carried out to elucidate the reaction mechanism.

Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus

Antibiotic resistance among clinically significant bacterial pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. As a part of continuing effort to develop antibacterial agents, we rationally designed and synthesized two series of 4,5-dihydroisoxazol-5-yl and 4,5-dihydroisoxazol-3-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compound A16 possessing the 4,5-dihydroisoxazol-5-yl group showed outstanding antibacterial activity (MIC, ≤0.125–0.5 μg/mL) against various testing strains, including methicillin-resistant, penicillin-resistant and clinical isolated S. aureus strains. Besides, further mouse infection model revealed that A16 could be effective in vivo and non-toxic to Hela cells. Finally, a detailed discussion of structure-activity relationships was conducted, referring to the docking results. It is worth noting that substituting a 4,5-dihydroisoxazole ring for the isoxazole ring not only broadened the antibacterial spectrum but also resulted in a significant increase in antibacterial activity against S. aureus strains. Taken together, these results suggest a promising chemotype for the development of new FtsZ-targeting bactericidal agents.

Nitrogen-fixing of ultrasmall Pd-based bimetallic nanoclusters on carbon supports

Synthesis of supported Pd-based bimetallic catalysts is of great importance in the heterogeneous catalysis field owing to their optimal geometric and electronic effects. Downsizing active metals to ultrasmall nanocluster (2-reduction at 400–500 °C. Through the nitrogen-fixing strategy, we prepare 9 sub-2 nm Pd-based bimetallic nanocluster catalysts by conventional impregnation process. The prepared supported bimetallic Pd-Pb nanocluster catalyst exhibit a high turnover frequency of 1092 h?1 for the semihydrogenation of phenylacetylene under a mild condition (30 °C, 5 bar H2), along with a high selectivity of >93% to styrene, demonstrating the alloying and small-size effects in the bimetallic nanocluster catalysts.