DifluoroiodoMethyl phenyl sulfone

Product Name: DifluoroiodoMethyl phenyl sulfone
CAS No.: 802919-90-0
Chemical Name: DifluoroiodoMethyl phenyl sulfone
Synonyms: DifluoroiodoMethyl phenyl sulfone;(difluoroiodomethylsulfonyl)benzene;Benzene, [(difluoroiodomethyl)sulfonyl]-
CBNumber: CB82709840
Molecular Formula: C7H5F2IO2S
Formula Weight: 318.08
MOL File: 802919-90-0.mol

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DifluoroiodoMethyl phenyl sulfone Property

Boiling point:: 312.4±42.0 °C(Predicted)
Density: 1.975±0.06 g/cm3(Predicted)
storage temp.: 2-8°C(protect from light)
Appearance: White to off-white Solid

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Safety

Safety Statements: 24/25
HS Code: 29309090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Frontier Specialty Chemicals

Product number: JK1711633
Product name: Difluoroiodomethylphenylsulfone
Purity: 98%
Packaging: 250mg
Price: $72
Updated: 2021/12/16

AK Scientific

Product number: 8573AJ
Product name: Difluoroiodomethylphenylsulfone
Packaging: 250mg
Price: $162
Updated: 2021/12/16

AK Scientific

Product number: 8573AJ
Product name: Difluoroiodomethylphenylsulfone
Packaging: 1g
Price: $358
Updated: 2021/12/16

Apolloscientific

Product number: PC911469
Product name: [(Difluoroiodomethyl)sulfonyl]benzene
Purity: 98%
Packaging: 1g
Price: $475
Updated: 2021/12/16

Ambeed

Product number: A264821
Product name: ((Difluoroiodomethyl)sulfonyl)benzene
Purity: 98%
Packaging: 100mg
Price: $60
Updated: 2021/12/16

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DifluoroiodoMethyl phenyl sulfone Chemical Properties,Usage,Production

Description

A visible light-catalysed direct and regioselective (phenylsulfonyl) difluoromethylation of imidazo[1,2-A]pyridines and benzo[d]-imidazo[2,1-b]thiazoles was carried out by DifluoroiodoMethyl phenyl sulfone under mild conditions. This synthetic methodology enables the introduction of a CF2SO2Ph group in an efficient and regioselective reaction through C-H bond functionalization with a broad substrate scope in good to excellent yields.

Uses

Iododifluoromethyl phenyl sulfone can be used for the difluoromethylation of alkenes and alkynes initiated by triethylborane/air or arenediazonium salt/titanium chloride in moderate to good yields.

Reactions

(1) Difluoromethylation of terminal alkenes and alkynes.

Synthesis

1535-65-5

802919-90-0

Difluoromethyl phenyl sulfone (192 mg, 1 mmol) and elemental iodine (508 mg, 4 mmol) were dissolved in DMF (4 mL) in a Schlenk flask under argon protection. The system was cooled to -30 °C and a solution of t-BuOK (448 mg, 4 mmol) in DMF (4 mL) was added slowly dropwise via syringe. The reaction temperature was maintained between -30 °C and -20 °C with continuous stirring for 1 h. The reaction progress was monitored by 19F NMR tracking. Upon completion of the reaction, the reaction was quenched by the addition of 1N HCl aqueous solution (5 mL) at -50 °C, followed by slow warming to room temperature. Saturated aqueous NaCl solution (10 mL) was added and the reaction mixture was extracted with ether (15 mL x 3). The organic phases were combined, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9:1) to afford the target product difluoroiodomethyl phenyl sulfone (294 mg, 92% yield), which is a colorless solid and turns red easily when exposed to light. The product characterization data were as follows: 1H NMR (500 MHz, CDCl3): δ 7.63 (t, J = 7.4 Hz, 2H), 7.79 (t, J = 7.4 Hz, 1H), 7.99 (d, J = 7.5 Hz, 2H); 13C NMR (125 MHz, CDCl3): δ 102.5 (t, J = 355 Hz), 128.1, 129.7, 131.3, 136.1; 19F NMR (470 MHz, CDCl3): δ -52.2; MS (EI, m/z): 318 (M+), 177, 142, 127; HRMS (EI): m/z calcd for C7H5F2IO2S (M+) 317.9023, found 317.9013. found 317.9013.

References

[1] GUO-JIE YIN; W. F; Mei Zhu. Visible-light mediated regioselective (phenylsulfonyl)difluoromethylation of fused imidazoles with iododifluoromethyl phenyl sulfone[J]. Heterocyclic Communications, 2017. DOI:10.1515/hc-2017-0101.
[2] YA LI. Radical (Phenylsulfonyl)difluoromethylation with Iododifluoromethyl Phenyl Sulfone[J]. The Journal of Organic Chemistry, 2007. DOI:10.1021/jo070618s.

DifluoroiodoMethyl phenyl sulfone Preparation Products And Raw materials

Raw materials

Preparation Products

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802919-90-0, DifluoroiodoMethyl phenyl sulfoneRelated Search:

DifluoroiodoMethyl phenyl sulfone

(difluoroiodomethylsulfonyl)benzene

Benzene, [(difluoroiodomethyl)sulfonyl]-

802919-90-0

C7H5F2IO2S