16212-05-8

Basic information

• Product Name: Allyl phenyl sulfone
• Synonyms: ALLYL PHENYL SULFONE;ALLYL PHENYL SULPHONE;ALLYLSULFONYLBENZENE;(allylsulphonyl)benzene;Phenyl allyl sulfone.;(2-propenylsulfonyl)-benzen;Allyl Phenyl sulone;sulfone, allyl phenyl
• CAS NO: 16212-05-8
• Molecular Formula: C₉H₁₀O₂S
• Molecular Weight: 182.24
• EINECS: 240-338-8
• Product Categories: Phenyls & Phenyl-Het;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Phenyls & Phenyl-Het;Organic Building Blocks;Sulfones;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 16212-05-8.mol

Chemical Properties

• Boiling Point: 110-113 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colourless to faintly yellow liquid
• Density: 1.189 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000456mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Light Sensitive
• BRN: 1863561
• CAS DataBase Reference: Allyl phenyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl phenyl sulfone(16212-05-8)
• EPA Substance Registry System: Allyl phenyl sulfone(16212-05-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: WR2400000
• F: 8-10
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 16212-05-8(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
Allyl phenyl sulfone is used as a key intermediate in the synthesis of various organic compounds due to its ability to undergo isomerization by nonionic proazaphosphatrane catalysts under mild reaction conditions.
2. Used in Pharmaceutical Industry:
Allyl phenyl sulfone is used as a building block for the synthesis of marine eicosanoid bacillariolides I-III, which have potential applications in the development of new drugs and therapeutic agents.
3. Used in Polymer Industry:
Allyl phenyl sulfone can be utilized as a monomer in the production of polymers, particularly those with specific properties such as heat resistance or chemical stability.
4. Used in Electrochemistry:
Allyl phenyl sulfone is used as a substrate in electrocatalytic additions to vinyl sulfones, catalyzed by an electrogenerated base. This application can lead to the development of new electrochemical processes and materials.
5. Used in Research and Development:
Due to its unique chemical properties, allyl phenyl sulfone can be employed in research and development for the discovery of new reactions, catalysts, and materials with potential applications in various industries.

InChI:InChI=1/C9H10O2S/c1-2-8-12(10,11)9-6-4-3-5-7-9/h2-7H,1,8H2

Upstream product

• 5296-64-0 allyl phenyl thioether 
• 873-55-2 sodium benzenesulfonate 
• 106-95-6 allyl bromide 
• 556-56-9 allyl iodid 
• 3066-75-9 allyl diethyl phosphate 
• 591-87-7 Allyl acetate 
• 35466-83-2 allyl methyl carbonate 
• 28691-72-7 (E)-1-propenyl phenyl sulfone 
• 19206-69-0 allyl diphenyl phosphate 
• 16308-68-2 allyl phenyl carbonate 
• 107-18-6 allyl alcohol 
• 618-41-7 Benzenesulfinic acid 
• 98-09-9 benzenesulfonyl chloride 
• 14370-82-2 allyl phenyl selenide 

Downstream Products

• 28975-80-6 Phenyl-propenyl-sulfon 
• 2674-25-1 [(2,3-dibromopropyl)sulfonyl]benzene 
• 28691-72-7 (E)-1-propenyl phenyl sulfone 
• 77657-92-2 2-bromo-1-(phenylsulfonyl)propane 
• 13630-97-2 (2,3-dichloro-propyl)-phenyl sulfone 
• 53893-41-7 1,3-bis-benzenesulfonyl-propane 
• 32133-86-1 4,4'-(1-benzenesulfonylmethyl-ethane-1,2-diyl)-bis-morpholine 
• 592-76-7 1-Heptene 
• 2114-42-3 allylcyclohexane 
• 98351-34-9 (1-Benzenesulfonyl-allyl)-trimethyl-silane 
• 67902-88-9 3-((E)-3-Benzenesulfonyl-allyl)-cyclohexanone 
• 78828-40-7 1-(1-Benzenesulfonyl-allyl)-cyclohex-2-enol 
• 78828-33-8 3-(1-Benzenesulfonyl-allyl)-cyclohexanone 
• 78828-35-0 5-Benzenesulfonyl-4,4-dimethyl-hept-6-en-2-one 

Relevant articles and documents

A convenient method for the synthesis of β,γ-unsaturated sulfones through zinc-mediated C-S coupling reaction

Through zinc-mediated coupling reaction of allylic bromides with alkane- or arenesulfonyl chlorides, β,γ-unsaturated sulfones were obtained with moderate to good yields.

A new attachment/cleavage strategy: Polymer-bound allylic sulfones in a solid-phase route to trisubstituted olefins

By tethering allyl sulfone to polystyrene (3-steps from polystyrene beads consisting of lithiation, sulfination, and allylation), trisubstituted olefins can be generated by Cα-sulfone alkylation and subsequent resin cleavage by S(N)2' nucleophilic displacement of sulfinate.

Organic oxidations promoted in vortex driven thin films under continuous flow

With increasing concerns for the environmental impact of chemical manufacturing, reagents and processes that align with the principles of green chemistry are essential. The fundamental oxidation of organic substrates is no exception and in this report three distinct modes of green oxidation are demonstrated in a vortex fluidic device (VFD) under continuous flow: aerobic oxidation, oxidation using chlorine bleach, and oxidation using hydrogen peroxide. The VFD, which is a thin film microfluidic platform, revealed clear advantages in these oxidations in comparison to traditional batch reactor processing: Efficient mass transfer of gases in the dynamic thin film increased the rate of aerobic oxidations, and the intense micromixing allowed multi-phase oxidations to proceed efficiently, obviating the need for organic solvents and phase transfer catalysts. In addition, the rapid dissipation of heat in the VFD also improved the safety profile and stereoselectivity for exothermic oxidations.

Design, Multigram Synthesis, and in Vitro and in Vivo Evaluation of Propylamycin: A Semisynthetic 4,5-Deoxystreptamine Class Aminoglycoside for the Treatment of Drug-Resistant Enterobacteriaceae and Other Gram-Negative Pathogens

Infectious diseases due to multidrug-resistant pathogens, particularly carbapenem-resistant Enterobacteriaceae (CREs), present a major and growing threat to human health and society, providing an urgent need for the development of improved potent antibiotics for their treatment. We describe the design and development of a new class of aminoglycoside antibiotics culminating in the discovery of propylamycin. Propylamycin is a 4′-deoxy-4′-alkyl paromomycin whose alkyl substituent conveys excellent activity against a broad spectrum of ESKAPE pathogens and other Gram-negative infections, including CREs, in the presence of numerous common resistance determinants, be they aminoglycoside modifying enzymes or rRNA methyl transferases. Importantly, propylamycin is demonstrated not to be susceptible to the action of the ArmA resistance determinant whose presence severely compromises the action of plazomicin and all other 4,6-disubstituted 2-deoxystreptamine aminoglycosides. The lack of susceptibility to ArmA, which is frequently encoded on the same plasmid as carbapenemase genes, ensures that propylamycin will not suffer from problems of cross-resistance when used in combination with carbapenems. Cell-free translation assays, quantitative ribosome footprinting, and X-ray crystallography support a model in which propylamycin functions by interference with bacterial protein synthesis. Cell-free translation assays with humanized bacterial ribosomes were used to optimize the selectivity of propylamycin, resulting in reduced ototoxicity in guinea pigs. In mouse thigh and septicemia models of Escherichia coli, propylamycin shows excellent efficacy, which is better than paromomycin. Overall, a simple novel deoxy alkyl modification of a readily available aminoglycoside antibiotic increases the inherent antibacterial activity, effectively combats multiple mechanisms of aminoglycoside resistance, and minimizes one of the major side effects of aminoglycoside therapy.

Highly porous conjugated polymers for selective oxidation of organic sulfides under visible light

High surface area porous conjugated polymers were synthesized via the high internal phase emulsion polymerization technique and micropore engineering as efficient heterogeneous photocatalysts for highly selective oxidation of organic sulfides to sulfoxides under visible light. This journal is the Partner Organisations 2014.

Polyvinylpolypyrrolidone-supported boron trifluoride (PVPP-BF3): Highly efficient catalyst for chemoselective oxygenation of sulfides to sulfones by H2O2

A highly efficient method for the oxidation of sulfides to sulfones using polyvinylpolypyrrolidone-supported boron trifluoride (PVPP-BF3) in the presence of (35%) hydrogen peroxide has been developed. This procedure cleanly oxidizes dialkyl and alkyl aryl sulfides to the corresponding sulfones in excellent yields at room temperature.

Oxidation of sulfides including DBT using a new vanadyl complex of a non-innocent o-aminophenol benzoxazole based ligand

Reaction of a non-innocent o-aminophenol benzoxazole based ligand HLBAP with VOCl3 afforded a vanadyl complex, VOLBIS (SQ), in which SQ is a 2,4-di-tert-butylsemiquinone produced from hydrolysis of HLBAP. The crystal structure of VOLBIS (SQ) exhibits an octahedral geometry with the VO2+ center coordinated by two nitrogen and one oxygen atoms of LBAP and two oxygen atoms of SQ. Electrochemical studies showed quasi-reversible metal-centered reduction and ligand-centered oxidation of complex. The magnetic moment of VOLBIS (SQ) is consistent with the spin-only value expected for S?=?1/2 system. The neutral species of VOLBIS (SQ) is EPR active, which is consistent with a paramagnetic electronic ground state (S?=?1/2). This result is in accordance with the vanadyl (IV) moiety surrounded by tridentate iminobenzosemiquinonate anion radical (HLBIS)?- and benzosemiquinone ligand (SQ)?. The theoretical calculations confirm the experimental results. Furthermore, we present the optimal conditions for maximum efficiency of sulfide oxidation for oxidative desulfurization with hydrogen peroxide and 6 times reusability of catalyst for sulfoxidation of dibenzothiophene.

Indium-mediated Coupling Reaction of Sulfonyl Chlorides with Alkyl Bromides in Water. A Facile Synthesis of Sulfones

Indium-mediated coupling of alkyl bromides with aromatic sulfonyl chlorides gives the corresponding sulfones in aqueous media with moderate to good yields.

A convenient synthesis of sulfones using zinc mediated coupling reaction of sulfonyl chlorides with alkyl halides in aqueous media

An efficient procedure for the preparation of sulfones has been developed through a simple reaction of aromatic sulfonyl chlorides with suitable alkyl halides mediated by commercial zinc powder in aqueous media at 0 °C ~ room temperature.

COMPOSITES, METHODS AND USES THEREOF

The present invention relates, in general terms, to methods of catalysing a reaction, including the steps of contacting a chemical entity comprising a sulphide moiety with a composite and an oxidant. The composite acts as a heterogeneous catalyst to oxidise the sulphide moiety. The present invention also relates to composites, methods of synthesising the composites and its use as a catalyst thereof.