7205-94-9

Basic information

• Product Name: CHLOROMETHYL PHENYL SULFOXIDE
• Synonyms: CHLOROMETHYL PHENYL SULFOXIDE;[(chloromethyl)sulphinyl]benzene;[(Chloromethyl)sulfinyl]benzene;Phenyl (chloromethyl) sulfoxide;Benzene, ((chloromethyl)sulfinyl)-;Einecs 230-580-2;Chloromethyl phenyl sulfoxide >=97.0%
• CAS NO: 7205-94-9
• Molecular Formula: C₇H₇ClOS
• Molecular Weight: 174.65
• EINECS: 230-580-2
• Product Categories: Organic Building Blocks;Sulfoxides;Sulfur Compounds
• Mol File: 7205-94-9.mol

Chemical Properties

• Melting Point: 33-35 °C
• Boiling Point: 109-111 °C0.01 mm Hg
• Flash Point: 100 °C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: −20°C
• BRN: 1617664
• CAS DataBase Reference: CHLOROMETHYL PHENYL SULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROMETHYL PHENYL SULFOXIDE(7205-94-9)
• EPA Substance Registry System: CHLOROMETHYL PHENYL SULFOXIDE(7205-94-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7205-94-9(Hazardous Substances Data)

Usage

Uses

1. Used in the Synthesis of 1-Chloroalkyl Sulfoxides:
Chloromethyl phenyl sulfoxide is used as a starting material for the synthesis of 1-chloroalkyl sulfoxides, which are important intermediates in organic chemistry.
2. Used in the Synthesis of Alkyl Sulfoxides:
It serves as a precursor for the synthesis of alkyl sulfoxides, which are valuable compounds in the pharmaceutical and chemical industries due to their diverse applications.
3. Used as a Thiol Ester Acyl Anion Equivalent:
Chloromethyl phenyl sulfoxide is utilized as a thiol ester acyl anion equivalent in organic synthesis, providing a versatile route to various target molecules.
4. Stereospecific Hydroxyalkylation:
The unusual stereochemical specificity of chloromethyl phenyl sulfoxide has been investigated for stereospecific hydroxyalkylation reactions, which are crucial in the development of enantiomerically pure compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 4496, 1968 DOI: 10.1021/ja01018a078Synthesis, p. 831, 1986Tetrahedron Letters, 17, p. 613, 1976

InChI:InChI=1/C7H7ClOS/c8-6-10(9)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 186581-53-3 diazomethane 
• 4972-29-6 benzenesulphinyl chloride 
• 60-29-7 diethyl ether 
• 7205-91-6 phenylthiomethyl chloride 
• 100-68-5 methyl-phenyl-thioether 
• 1193-82-4 racemic methyl phenyl sulfoxide 

Downstream Products

• 7205-98-3 chloromethyl phenyl sulfone 
• 21849-29-6 2-chloro-1,1-diphenyl-2-(phenylsulfinyl)ethanol 
• 70872-74-1 (1-chloro-octane-1-sulfinyl)-benzene 
• 70872-73-0 (1-chloro-decane-1-sulfinyl)-benzene 
• 70872-72-9 (1-chloro-tridecane-1-sulfinyl)-benzene 
• 70872-71-8 (1-chloro-heptadecane-1-sulfinyl)-benzene 
• 70872-70-7 2-(2-Benzenesulfinyl-2-chloro-ethyl)-1-chloro-4-methoxy-benzene 
• 67087-40-5 S-chloromethyl S-phenyl sulfoximine 
• 21849-27-4 1-(Phenylsulfinylchlormethyl)-cyclohexanol 
• 29626-90-2 1-chloro-2-phenylethyl phenyl sulfoxide 
• 70872-75-2 1-chloroheptyl phenyl sulfoxide 
• 405516-51-0 (E)-1-chloro-4-phenyl-1-(phenylsulfinyl)but-3-ene-2-ol 
• 273748-98-4 1-Benzenesulfinyl-1-chloro-4-phenyl-butan-2-ol 
• 38042-52-3 2-chloro-2-(phenylsulfinyl)-1-phenyl-1-ethanone 

Relevant articles and documents

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

Selectivity switch in the aerobic oxygenation of sulfides photocatalysed by visible-light-responsive decavanadate

Nanometre-sized metal oxides are promising species for the development of visible-light-responsive photocatalysts for the selective transformation of organic functional groups. In this article, we report that decavanadate ([V10O28]6-, V10) behaved as an efficient visible-light-responsive photocatalyst in the product-selective oxygenation of sulfides achieved using O2 (1 atm) as the green oxidant. In particular, we revealed that visible-light-responsive photocatalysis of V10 showed remarkable activity for the oxygenation of structurally diverse sulfides to form the corresponding sulfones using O2 in methyl ethyl ketone (MEK). Furthermore, by simply adding water to the reaction mixture, the product selectivity of sulfide oxygenation can be significantly switched toward the production of sulfoxides, without concomitant loss of photocatalytic activity. Based on experimental evidence, we inferred the following mechanistic steps for this photocatalytic system: the aerobic oxygenation of sulfides to form the corresponding sulfoxides initiated by a visible-light-induced photoredox reaction of V10. As for the formation of sulfones, MEK-derived peroxide species as the co-catalysts are probably involved in the oxygenation of sulfoxides to sulfones. The selectivity switch of the V10-photocatalysed reaction brought about by water addition is most likely achieved by suppressing the formation of MEK-derived peroxide species. This journal is

Sulfone compound (by machine translation)

[Problem] to safely and conveniently, highly selective, sulfide compound producing a sulfone compound. [Solution] pH is 9 - 12 under, water or water-insoluble solvent or an aromatic hydrocarbon-based solvent mixture, sodium hypochlorite is used as oxidizing agent, (1) (2) from the compound represented by the formula sulfide sulfone compound represented by the formula manufacturing method. (R1 And R2 Are each independently an alkyl, aryl, aralkyl, heteroaryl)[Drawing] no (by machine translation)

Chemoselective Oxidation of Sulfides to Sulfoxides with Urea-Hydrogen Peroxide Complex Catalysed by Diselenide

A highly selective catalytic oxidation system has been developed for the conversion of sulfides into the corresponding sulfoxides using urea-hydrogen peroxide as stoichiometric oxidant in the presence of a catalytic quantity of diphenyl diselenide.

On the nature of the chain-extending species in organolithium initiated stereospecific reagent-controlled homologation reactions using α-chloroalkyl aryl sulfoxides

The reaction of an organolithium with an α-chloroalkyl aryl sulfoxide ostensibly generates an α-chloroalkyllithium by sulfoxide-lithium exchange, but the actual identity of the chain-extending species in chlorosulfoxide-based StReCH reactions is not certain. To explore this issue, racemic 2-cyclohexyl (4R?,5R?)-4,5-diphenyl-1,3,2-dioxaborolane was homologated by treatment with scalemic (S)-chloromethyl phenyl sulfoxide and n-BuLi (THF, -78 °C). The reaction proceeded without a detectable level of kinetic resolution, a finding consistent with chloromethyllithium being the active chain-extending species rather than a chiral sulfurane intermediate.

Enantioselective aziridination of cyclic enals facilitated by the fluorine-iminium ion Gauche effect

The enantioselective, organocatalytic aziridination of small, medium and macro-cyclic enals is reported using (S)-2-(fluorodiphenyl methyl)-pyrrolidine. Central to the reaction design is the reversible formation of a β-fluoroiminium ion intermediate, which is pre-organised on account of the fluorine-iminium ion gauche effect. This conformational effect positions the fluorine substituent synclinal-endo to the electropositive nitrogen centre thus benefiting from favourable stereoelectronic and electrostatic interactions (σC-H→σC-F*; F δ-···N+). Consequently, one of the shielding groups on the fluorine-bearing carbon atom is positioned above the π-system, forming the basis of an enantioinduction strategy. Treatment of this intermediate with a "nitrene" source furnished a series of novel, optically active aziridines (e.r. up to 99.5:0.5). Further derivatisation of the product aziridines gives facile access to various amino acid derivatives, including β-fluoroamino acids. Crystallographic analyses of both the aziridines and their derivatives are disclosed. Copyright

ELECTROPHILIC REAGENTS FOR MONOHALOMETHYLATION,THEIR PREPARATION AND THEIR USES

The invention provides a compound of formula A, B, C or D, methods for making them, intermediates therefor, and their use in making organic biologically active compounds: (Formula (A)). Wherein: ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R1, R2, R3, R4, R5, R6, R7, R8, R9, R1O are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates ? Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate; or (Formula (B)). Wherein: X = F, CI, Br, I, sulfonate esters, phosphate esters or other another leaving group; and R1, R2, R3, R4, R5 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino and R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates; and R12 = resin, naphthalene or substituted naphthalene Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 = R7 = R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate and when X = F and R1= R2 = R3 = R4= R5 = H and R12 = poly(styrene-co- divinylbenzene) and R11 = triflate or tetrafluoroborate; or (Formula (C)). Wehrein ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R13 = naphthalene or substituted naphthalene ? R6, R7, R8, R9, R10 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alcoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates: or (Formula (D)) X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group R13 = naphthalene or substituted naphthalene R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates carbonates R12 = resin, naphthalene or substituted naphthalene.

A general and selective zinc-catalyzed oxidation of sulfides to sulfoxides

A general zinc-catalyzed oxidation of sulfides to sulfoxides has been developed. All the reactions proceeded at room temperature. Hydrogen peroxide was used as a green oxidant. Twenty-one examples of sulfoxides were prepared in moderate to excellent yields.

Ammonium bromide as an effective and viable catalyst in the oxidation of sulfides using nitro urea and silica sulfuric acid

A new catalytic method for the chemoselective oxidation of sulfides to the sulfoxides has been studied. A variety of dialkyl, alkylaryl and diaryl sulfides were subjected to the oxidation reaction by a mixture of nitro urea, derived from urea nitrate, silica sulfuric acid (SiO2-OSO3H) and catalytic amounts of ammonium bromide in CH2Cl2 at room temperature.

VO(acac)2-catalyzed oxidation of sulfoxides to sulfones using chlorine dioxide

The catalytic effect of VO(acac)2 in the oxidation of sulfoxides to sulfones with chlorine dioxide was found.