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Fluoromethyl phenyl sulfone serves as a key precursor in the synthesis of vinyl fluorides, where it is converted in situ into diethyl 1-fluoro-1-(phenylsulfonyl)methanephosphonate, a reactive intermediate for the Horner-Wittig reaction with aldehydes and ketones. The resulting α-fluoro-α,β-unsaturated sulfones are subsequently reduced to yield vinyl fluorides, demonstrating Fluoromethyl phenyl sulfone's utility in a versatile and efficient synthetic route.

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  • 20808-12-2 Structure
  • Basic information

    1. Product Name: Fluoromethyl phenyl sulfone
    2. Synonyms: FLUOROMETHYL PHENYL SULFONE;FLUOROMETHYLSULFONYLBENZENE;Phenyl Fluoromethyl Sulfone;Fluoromethanesulfonyl-benzene
    3. CAS NO:20808-12-2
    4. Molecular Formula: C7H7FO2S
    5. Molecular Weight: 174.19
    6. EINECS: N/A
    7. Product Categories: Biochemistry;Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Reagents for Oligosaccharide Synthesis;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
    8. Mol File: 20808-12-2.mol
  • Chemical Properties

    1. Melting Point: 53 °C
    2. Boiling Point: 314.332 °C at 760 mmHg
    3. Flash Point: 143.903 °C
    4. Appearance: /
    5. Density: 1.275 g/cm3
    6. Vapor Pressure: 0.000866mmHg at 25°C
    7. Refractive Index: 1.501
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: soluble in Methanol
    10. CAS DataBase Reference: Fluoromethyl phenyl sulfone(CAS DataBase Reference)
    11. NIST Chemistry Reference: Fluoromethyl phenyl sulfone(20808-12-2)
    12. EPA Substance Registry System: Fluoromethyl phenyl sulfone(20808-12-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 20808-12-2(Hazardous Substances Data)

20808-12-2 Usage

Chemical Description

Fluoromethyl Phenyl Sulfone has a phenyl group attached to a sulfone group and a fluoromethyl group.

Check Digit Verification of cas no

The CAS Registry Mumber 20808-12-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,8,0 and 8 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 20808-12:
(7*2)+(6*0)+(5*8)+(4*0)+(3*8)+(2*1)+(1*2)=82
82 % 10 = 2
So 20808-12-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H7FO2S/c8-6-11(9,10)7-4-2-1-3-5-7/h1-5H,6H2

20808-12-2 Well-known Company Product Price

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  • TCI America

  • (F0341)  Fluoromethyl Phenyl Sulfone  >98.0%(GC)

  • 20808-12-2

  • 1g

  • 1,690.00CNY

  • Detail
  • TCI America

  • (F0341)  Fluoromethyl Phenyl Sulfone  >98.0%(GC)

  • 20808-12-2

  • 5g

  • 5,800.00CNY

  • Detail

20808-12-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name fluoromethylsulfonylbenzene

1.2 Other means of identification

Product number -
Other names fluoromethanesulfonyl-benzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:20808-12-2 SDS

20808-12-2Relevant articles and documents

Novel process for synthesizing 2 -fluorocyclopropylamine with high selectivity and asymmetric synthesis

-

Paragraph 0049-0051, (2021/10/13)

A novel highly selective asymmetric synthesis process of 2 -fluorocyclopropylamine (Structural I). The method provided by the invention uses 1 - fluorine -1 - benzene (propylene) sulfonyl methane and chiral epichlorohydrin to construct chiral cyclopropane under basic conditions, and a new synthetic route not only achieves a special cis-trans selectivity, but also has a highly specific stereoselectivity. The synthesis route is efficient, the reaction condition is mild, the method is suitable for large industrial production in a green environment, 2 -fluorocyclopropylamine production cost is greatly reduced.

Highly stereoselective monofluoroolefination: Facile access to (E)-α-fluorinated arylvinyl sulfones from trifluoromethyl α-fluorinated arylsulfonyl gem-diols

Fang, Xiang,Zhou, Jun,Wang, Wang,Yang, Xueyan,Wu, Fanhong

, (2020/04/28)

An excellent stereoselective direct synthesis of trisubstituted (E)-α-fluorinated arylvinyl sulfones employing trifluoromethyl α-fluorinated arylsulfonyl gem-diols and aryl aldehydes under mild reaction conditions has been developed, which affords α-fluorinated arylvinyl sulfones in high yields with E-isomer only. The desired products can be further transformed into more useful fluoroolefins through debenzenesulfonyl process.

Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding

Poteat, Christopher M.,Lindsay, Vincent N. G.

supporting information, p. 2912 - 2915 (2019/03/17)

The direct and selective α-mono-bromination of alkyl sulfones was achieved through base-mediated electrophilic halogenation. The appropriate combination of solvent and electrophilic bromine source was found to be critical to control the nature of the products formed, where reagent-solvent halogen bonding is proposed to control the selectivity via alteration of the effective size of the electrophilic bromine source. Conversely, the α,α-di-brominated sulfones were selectively obtained in good yields following polyhalogenation followed by selective de-halogenation during workup. Both procedures can be applied on gram scale, and the mono-halogenation was successfully extended to the fully selective α-chlorination, α-iodination and α-fluorination of alkyl sulfones.

AZETIDINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF

-

Paragraph 0225; 0227, (2018/08/29)

The present invention relates to an azetidine derivative for use as a Janus kinase (JAK) inhibitor, a drug composition comprising same, a preparation method therefor, and a use thereof in the treatment of JAK-related diseases comprising, for example, infl

Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates: Probing the Fluorine Effect

Xing, Bo,Ni, Chuanfa,Hu, Jinbo

, p. 206 - 212 (2018/02/06)

A copper-mediated di- and monofluoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesulfinate reagents provides aryl difluoromethyl (or monofluoromethyl) sulfones in good yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the following order: CH2FSO2Na > CF2HSO2Na > CF3SO2Na.

BICYCLIC AZA COMPOUNDS AS MUSCARINIC M1 RECEPTOR AGONISTS

-

, (2014/04/04)

This invention relates to compounds (Formula (1)) that are agonists of the muscarinic M1 receptor and which are useful in the treatment of muscarinic M1 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and

Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding

Champagne, Pier Alexandre,Pomarole, Julien,Therien, Marie-Eve,Benhassine, Yasmine,Beaulieu, Samuel,Legault, Claude Y.,Paquin, Jean-Francois

supporting information, p. 2210 - 2213 (2013/06/26)

It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H 2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.

Nucleophilic fluoroalkylation of α,β-unsaturated carbonyl compounds with α-fluorinated sulfones: Investigation of the reversibility of 1,2-additions and the formation of 1,4-adducts

Shen, Xiao,Ni, Chuanfa,Hu, Jinbo

, p. 2043 - 2051 (2013/01/15)

A detailed investigation of the reactions of PhSO2CF 2H and PhSO2CH2F with (E)-chalcone (=(E)-1,3-diphenylprop-2-en-1-one) at low temperatures revealed that these two reactions were kinetically controlled, and the ratios of 1,2- vs. 1,4-adducts, which did not change much over time at these temperatures, reflect the relative rates of the two reaction pathways. The controlled experiments of converting the PhSO2CF2- and PhSO2CHF-substituted 1,2-adducts to 1,4-adducts showed that these isomerizations are not favored due to the low stability and hard-soft nature of PhSO2CF2- and PhSO2CHF- anions. Moreover, taking advantage of the remarkable stability and softness of (PhSO2)2CF - anion, an efficient thermodynamically controlled isomerization of (PhSO2)2CF-substituted 1,2-adduct to 1,4-adduct was achieved for the first time. Copyright

Chemistry of trichlorofluromethane: Synthesis of chlorofluromethyl phenyl sulfone and fluoromethyl phenyl sulfone and some of their reactions

Saikia,Tsuboi

, p. 643 - 647 (2007/10/03)

It was observed that the reaction of CFCl3 with thiophenoxide gave only 10% of the corresponding thioether. On the other hand, these thioethers could be prepared in excellent yield from diaryl disulfides and CFCl3 in the presence of sodium hydroxymethanesulfinate in aqueous DMF at 4 atm pressure of nitrogen. Dechlorination of the thioether (PhSCFCl2) with different reducing agents were studied. Most of the reducing agents eliminated both fluorine and chlorine functionalities or gave the hydrolyzed products. But its sulfone on treatment with Zinc in methanol gave monochlorofluoromethyl and fluoromethyl phenyl sulfone in good yields. Darzens reaction of these compounds was also studied.

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