Fluorobis(phenylsulfonyl)methane

Base Information

• Chemical Name: Fluorobis(phenylsulfonyl)methane
• CAS No.: 910650-82-7
• Molecular Formula: C13H11FO4S2
• Molecular Weight: 314.358
• Hs Code.: 29350090
• European Community (EC) Number: 804-334-5
• Nikkaji Number: J2.337.800K
• Mol file: 910650-82-7.mol

Synonyms:fluorobis(phenylsulfonyl)methane

Chemical Property of Fluorobis(phenylsulfonyl)methane

Chemical Property:

• Melting Point: 114-115℃ (hexane )
• Boiling Point: 539.6±50.0 °C(Predicted)
• PSA: 85.04000
• Density: 1.408±0.06 g/cm3(Predicted)
• LogP: 4.34890
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 314.00827934
• Heavy Atom Count: 20
• Complexity: 456

Purity/Quality:

98%Min ^*data from raw suppliers

FLUOROBIS-(PHENYLSULFONYL)METHANE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)C(F)S(=O)(=O)C2=CC=CC=C2
• Uses: (Fluoromethylenedisulfonyl)dibenzene is a nucleophilic fluoromethylating agent.

Technology Process of Fluorobis(phenylsulfonyl)methane

There total 10 articles about Fluorobis(phenylsulfonyl)methane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1-bromo-1-fluorobis(phenylsulfonyl)methane → 1-fluoro-1,1-bis(phenylsulfonyl)methane (910650-82-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 6h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

Reference yield: 96.0%

[fluoro(phenylsulfinyl)methylsulfonyl]benzene (1151549-59-5) → 1-fluoro-1,1-bis(phenylsulfonyl)methane (910650-82-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo900320b

Reference yield: 95.0%

fluoromethyl phenyl sulfone (20808-12-2) + phenylsulfonyl fluoride (368-43-4) → 1-fluoro-1,1-bis(phenylsulfonyl)methane (910650-82-7)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1016/j.jfluchem.2010.07.006

upstream raw materials:

bis(phenylsulfonyl)methane

α-fluoro-α-phenylthio-α-phenylsulfonylmethane

[fluoro(phenylsulfinyl)methylsulfonyl]benzene

fluoromethyl phenyl sulfone

Downstream raw materials:

Acetic acid (1R,4S)-4-(bis-benzenesulfonyl-fluoro-methyl)-cyclopent-2-enyl ester

Refernces

Efficient nucleophilic fluoromethylation and subsequent transformation of alkyl and benzyl halides using fluorobis(phenylsulfonyl)methane

10.1021/ol8029627

The study presents an efficient method for nucleophilic fluoromethylation of alkyl and benzyl halides using fluorobis(phenylsulfonyl)methane (1) as a versatile reagent. The researchers achieved stereospecific one-pot synthesis of fluorovinyl compounds such as fluorostyrylsulfones, fluorocinnamates, and fluorochalcones using benzyl halides. The methodology was extended to synthesize R-substituted fluoroalkane derivatives through selective reductive desulfonylation. The study highlights the importance of fluorine in modifying the physicochemical and pharmacokinetic properties of drug molecules. The researchers used mild bases like potassium carbonate in DMF or cesium carbonate in acetonitrile to generate the soft carbanion [R-fluorobis(phenylsulfonyl)methide] from R-fluorobis(phenylsulfonyl)methane, which then reacted with primary alkyl iodides and bromides to produce alkylated products in moderate to excellent yields. For benzyl halides, the reaction led to the formation of fluorovinyl sulfones, indicating a second elimination step. The study also explored reductive desulfonylation using a Mg/HOAc/NaOAc system for monodesulfonylation and a Mg/MeOH system for didesulfonylation, yielding R-fluoro-R-(phenylsulfonyl)alkanes and R-fluoroalkanes, respectively.