Difluoroiodotoluene

Base Information

• Chemical Name: Difluoroiodotoluene
• CAS No.: 371-11-9
• Molecular Formula: C7H7 F2 I
• Molecular Weight: 256.034
• European Community (EC) Number: 689-018-3
• UNII: 3R9W1C8C84
• Nikkaji Number: J1.189.573E
• Wikidata: Q27257935
• Mol file: 371-11-9.mol

Synonyms:371-11-9;p-(Difluoroiodo)toluene;Difluoroiodotoluene;4-IODOTOLUENE DIFLUORIDE;Difluoroiodotoluene [MI];Difluoro(4-methylphenyl)iodine;4-Methyl-1-(difluoroiodo)benzene;Benzene, 1-(difluoriodo)-4-methyl-;difluoro-(4-methylphenyl)-lambda3-iodane;3R9W1C8C84;p-iodotoluene difluoride;UNII-3R9W1C8C84;1-(Difluoriodo)-4-methylbenzene;Iodine, difluoro(4-methylphenyl)-;SCHEMBL582973;AKOS007929934;difluoro(4-methylphenyl)-lambda3-iodane;CS-0179659;EN300-299836;Q27257935

Chemical Property of Difluoroiodotoluene

Chemical Property:

• Melting Point: 102-106 °C
• PSA: 0.00000
• LogP: 3.44000
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 255.95605
• Heavy Atom Count: 10
• Complexity: 97.8

Purity/Quality:

97% ^*data from raw suppliers

4-IODOTOLUENE DIFLUORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)I(F)F
• General Description: 4-Iodotoluene difluoride (DFIT) is a hypervalent iodine reagent that serves as an efficient fluorinating agent and oxidant in organic synthesis. It facilitates the generation of electrophilic phenylselenium species when combined with diphenyldiselenide, enabling the phenylselenofluorination of alkenes and internal alkynes with high stereo- and regioselectivity. DFIT is particularly useful for mild and selective fluorination reactions, though its effectiveness varies with substrate type, as terminal alkynes only undergo selenation rather than fluoroselenation. This reagent expands synthetic strategies for incorporating fluorine into organic frameworks, making it valuable for constructing bioactive molecules and complex natural products.

Technology Process of Difluoroiodotoluene

There total 8 articles about Difluoroiodotoluene 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: 97.0%

1-iodosyl-4-methylbenzene (69180-59-2) → 4-(difluoroiodo)toluene (371-11-9)

Guidance literature:

With hydrogen fluoride; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200400659

Reference yield: 91.0%

4-tolyl iodide (624-31-7) → 4-(difluoroiodo)toluene (371-11-9)

Guidance literature:

With Selectfluor; triethylamine tris(hydrogen fluoride); In [D₃]acetonitrile; at 20 ℃; for 22h; Reagent/catalyst; Concentration; Schlenk technique; Inert atmosphere; Darkness;

DOI:10.1021/acs.joc.7b01671

Reference yield: 66.0%

4-dichloroiodanyl-toluene (19028-26-3) → 4-(difluoroiodo)toluene (371-11-9)

Guidance literature:

With hydrogen fluoride; mercury(II) oxide; In dichloromethane; for 2h;

DOI:10.1039/b209079a

upstream raw materials:

1-iodosyl-4-methylbenzene

4-tolyl iodide

4-dichloroiodanyl-toluene

1-(diacetoxyiodo)-4-methylbenzene

Downstream raw materials:

C₁₈H₂₆ClF₂I

(E)-(2-fluoro-10-methoxycarbonyl-1-decenyl)(4-methylphenyl)iodonium fluoride

C₁₆H₂₁F₂I

Refernces

Phenylselenofluorination of alkenes and alkynes promoted by difluoroiodotoluene and diphenyldiselenide

10.1055/s-2004-832827

The study explores a phenylselenofluorination method for alkenes and alkynes using difluoroiodotoluene (DFIT) and diphenyldiselenide (PhSeSePh). DFIT, acting as a fluorinating agent, oxidizes PhSeSePh to generate an electrophilic phenylselenium species in situ. This species then reacts with alkenes and internal alkynes to form phenylselenofluorinated products. The method is efficient and mild, achieving high stereo- and regioselectivity. Various alkenes and internal alkynes were successfully transformed into the desired products, with yields ranging from 58% to 92%. Terminal alkynes, however, only underwent hydrogen substitution by the PhSe group, indicating that their reactivity is independent of the hypervalent iodine structure used. The study demonstrates a promising approach for introducing fluorine atoms into organic molecules, with potential applications in the synthesis of complex natural products and bioactive compounds.

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