103-17-3

Usage

Uses

Used in Agriculture:
Chlorbenside is used as an acaricide for the control of eggs and larvae of red spider mites. Its effectiveness in managing these pests helps protect crops and maintain agricultural productivity.

Hazard

Skin irritant.

Health Hazard

Low to moderate toxicity in experimentalanimals from oral administration; chroniceffects may produce liver and kidney injuryin humans.LD50 oral (rat): 2000 mg/kg.

InChI:InChI=1/C13H10Cl2S/c14-11-3-1-10(2-4-11)9-16-13-7-5-12(15)6-8-13/h1-8H,9H2

Upstream product

• 18803-44-6 sodium p-chlorothiophenolate 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 106-54-7 p-Chlorothiophenol 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 4351-54-6 cyclohexyl formate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 7047-28-1 (4-chloro-benzyl)-(4-chloro-phenyl)-sulfoxide 
• 622-98-0 4-chloro(ethylbenzene) 
• 622-95-7 4-chlorobenzyl bromide 
• 19350-69-7 4-chlorobenzaldehyde p-toluenesulfonylhydrazone 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Downstream Products

• 7082-99-7 (4-chloro-benzyl)-(4-chloro-phenyl)-sulfone 
• 7047-28-1 (4-chloro-benzyl)-(4-chloro-phenyl)-sulfoxide 
• 134164-38-8 4-chlorophenylbis(4-chlorobenzyl)sulfonium tetrafluoroborate 

Relevant academic research and scientific papers

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.

Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation

A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.

Synthesis of Air-stable, Odorless Thiophenol Surrogates via Ni-Catalyzed C?S Cross-Coupling

Thiophenols are versatile synthetic intermediates whose practical appeal is marred by their air sensitivity, toxicity and extreme malodor. Herein we report an efficient catalytic method for the preparation of S-aryl isothiouronium salts, and demonstrate that these air-stable, odorless solids serve as user-friendly sources of thiophenols in synthesis. Diverse isothiouronium salts featuring synthetically useful functionality are readily accessible by nickel-catalyzed C?S cross-coupling of (hetero)aryl iodides and thiourea. Convenient, chromatography-free isolation of these salts is achieved by precipitation, allowing the methodology to be applied directly to large scales. Thiophenols are liberated from the corresponding isothiouronium salts upon treatment with a weak base, enabling an in situ release/S-functionalization strategy that entirely negates the need to isolate, purify or manipulate these noxious reagents.

Sequential one-pot addition of excess aryl-grignard reagents and electrophiles to O-alkyl thioformates

The sequential addition of aromatic Grignard reagents to O-alkyl thioformates proceeded to completion within 30s to give aryl benzylic sulfanes in good yields. This reaction may begin with the nucleophilic attack of the Grignard reagent onto the carbon atom of the O-alkyl thioformates, followed by the elimination of ROMgBr to generate aromatic thioaldehydes, which then react with a second molecule of the Grignard reagent at the sulfur atom to form arylsulfanyl benzylic Grignard reagents. To confirm the generation of aromatic thioaldehydes, the reaction between O-alkyl thioformates and phenyl Grignard reagent was carried out in the presence of cyclopentadiene. As a result, hetero-Diels-Alder adducts of the thioaldehyde and the diene were formed. The treatment of a mixture of the thioformate and phenyl Grignard reagent with iodine gave 1,2-bis(phenylsulfanyl)-1,2-diphenyl ethane as a product, which indicated the formation of arylsulfanyl benzylic Grignard reagents in the reaction mixture. When electrophiles were added to the Grignard reagents that were generated insitu, four-component coupling products, that is, O-alkyl thioformates, two molecules of Grignard reagents, and electrophiles, were obtained in moderate-to-good yields. The use of silyl chloride or allylic bromides gave the adducts within 5min, whereas the reaction with benzylic halides required more than 30min. The addition to carbonyl compounds was complete within 1min and the use of lithium bromide as an additive enhanced the yields of the four-component coupling products. Finally, oxiranes and imines also participated in the coupling reaction. Into the melting pot: The addition of excess aryl Grignard reagents and electrophiles to O-alkyl thioformates gives aryl sulfanes through four-component coupling reactions (see scheme). These reactions may involve the formation of aromatic thioaldehydes and aryl-benzylic Grignard reagents as intermediates. For addition to carbonyl compounds, the use of lithium halides as an additive enhanced the efficiency of the reaction. Copyright

Synthesis of thioethers via metal-free reductive coupling of tosylhydrazones with thiols

A metal-free procedure for the synthesis of thioethers is described via the base-promoted reductive coupling of tosylhydrazones with thiols through an insertion of a carbene into the S-H bond.

Polymer-supported reactions in organic synthesis: Part II-Synthesis of some sulphides

Thiophenoxide ions supported on Amberlite IRA-900 (chloride from) have been treated with arylalkyl halides as well as with aryl helides to get sulphides which are useful in crop protection.Isolation of pure products by simple filtration and evaporation is an important feature of this method.

Araliphatic sulfonium and their use

Sulfonium salts of the formulae I to IV STR1 in which A is C1 -C12 alkyl, C3 -C8 cycloalkyl, C4 -C10 cycloalkylalkyl, phenyl which is unsubstituted or mono- or polysubstituted by C1 -C8 alkyl, C1 -C4 alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, Ar, Ar1 and Ar2, independently of one another, are each unsubstituted or mono- or polysubstituted phenyl, or naphthyl which is unsubstituted or mono- or polysubstituted each arylene is an unsubstituted or mono- or polysubstituted phenylene or unsubstituted or mono- or polysubstituted naphthylene and Q? is SbF6-, AsF6- or SbF5 OH- are valuable curing agents and curing accelerators in the heat-curing of cationically polymerizable compounds, preferably epoxy resins.

Isotope effects in nucleophilic substitution reactions. IV. The effect of changing a substituent at the α carbon on the structure os SN2 transition states

Kinetic studies, secondary α-deuterium kinetic isotope effects, primary chlorine kinetic isotope effects (1), Hammett ρ values determined by changing the substituent in the nucleophile, and activation parameters have been used to determine the detailed (relative) structures of the transition states for the S2 reactions between para-substituted benzyl chlorides and thiophenoxide ion.A rationale for the U-shaped Hammett ρ plots observed when para-substituted benzyl compounds react with negatively charged nucleophiles is also presented.

Alkyl 4-[o-(substituted methyleneamino)phenyl]-3-thioallophanates

Various alkyl 4-[o-(substituted methyleneamino)phenyl] 3-thioallophanates are useful as fungicides and mite ovicides. The compounds are prepared by reacting alkyl 4-(o-aminophenyl)-3-thioallophanates with aldehydes or trialkyl orthoformates. Some of the compounds are prepared by further reacting the reaction product of an alkyl 4-(o-aminophenyl)-3-thioallophanate and a trialkyl orthoformate with a primary or secondary amine. Exemplary species are methyl 4-[o-(o-fluorobenzylideneamino)phenyl]-3-thioallophanate, methyl 4-[o-(4-methylbenzylideneamino)phenyl]-3-thioallophanate and methyl 4-[o-(2-furfurylideneamino)phenyl]-3-thioallophanate.