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
• Article Data: 30

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

Description

Chloromethyl phenyl sulfoxide is an organic compound with synthetic potential and exhibits unusual stereochemical specificity. It is known for its role in the preparation of various chemical compounds and its unique stereochemical properties.

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

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

Downstream Products

• 21849-29-6 2-chloro-1,1-diphenyl-2-(phenylsulfinyl)ethanol 
• 21849-27-4 1-(Phenylsulfinylchlormethyl)-cyclohexanol 
• 273748-98-4 1-Benzenesulfinyl-1-chloro-4-phenyl-butan-2-ol 
• 102104-43-8 [(1-chloro-4-penten-1-yl)sulfinyl]benzene 
• 121000-76-8 1-[chloro (phenylsulfinyl)methyl]-2-cyclohexene-1-ol 
• 145663-76-9 1-cyclodecanol 
• 6099-23-6 1-(phenylsulfinyl)acetophenone 
• 128867-15-2 2-Benzenesulfinyl-2-chloro-1-phenyl-ethanol 
• 128867-22-1 1-(phenylsulfinyl)butan-2-one 
• 128867-07-2 1-Benzenesulfinyl-1-chloro-butan-2-ol 
• 145663-77-0 1-cyclododecanol 
• 111036-61-4 2-Benzenesulfinyl-1-oxa-spiro[2.11]tetradecane 
• 64190-25-6 1-cyclopentanol 
• 145663-81-6 1--1-phenylethanol 

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.

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)

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.