CAS 1483-72-3|diphenyliodanium chloride|DIPHENYLIODONIUM CHLORIDE|diphenyliodanium chloride|NSC 134275|Diphenyliodonium chloride|二苯基碘酰氯|DPI|二苯氯化碘鎓,

General Information

Structure

Molecular Formula

C₁₂H₁₀ClI

Molecular Mass

316.56527

Exact Mass

315.951576

Charge

InChI

InChI=1S/C12H10I.ClH/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;1H/q+1;/p-1

InChIKey

RSJLWBUYLGJOBD-UHFFFAOYSA-M

Canonic Smiles

c1ccc(cc1)[I+]c1ccccc1.[Cl-]

Isomeric Smiles

[Cl-].[I+](c1ccccc1)c1ccccc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

4.5634055

LogD (pH = 7.4)

4.5634055

Log P

4.5634055

Molar Refractivity

64.8948

Polarizability

28.086405

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

diphenyliodanium chloride

IUPAC Traditional name

diphenyliodanium chloride

Synonyms

DIPHENYLIODONIUM CHLORIDEDiphenyliodonium chlorideNSC 134275二苯基碘酰氯DPI二苯氯化碘鎓,

Names and Identifiers

Registration numbers

CAS Number

EC Number

PubChem SID

PubChem CID

MDL Number

Beilstein Number

Merck Index

Registration numbers

Properties

Physical Property

Melting Point

233-235°C (sublimes)

233-235 °C (subl.)(lit.)

ca 230°C dec.

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150976

Phenylation reagent.
Purity: ~97%

Sigma Aldrich

43088

Other Notes
Reagent used for electrophilic phenylation, e.g. of malonates and dithiocarboxylates8,9,10
Packaging
5, 25 g in glass bottle
Application
Reactant for:
• Copper-catalyzed cross coupling reactions of purines and diaryliodonium salts1
• Synthesis of acetylenic arylselenides2
• Sonogashira coupling reactions for the preparation of aryl alkynes3
• C-H functionalization for synthesis of (arylmethylene)oxindoles4
• Arylation of anilines5
• Studies on the visible-light photosensitive system-dlourescein yellow-bis(di-Ph iodonium)6
• Investigating the properties of direct and sensitized photolysis of dispersed photoacid generators7

Molecule Details

References

PubChem Literature

From Data Sources

• For reviews of polyvalent iodine compounds in organic synthesis, see: Synthesis, 709 (1984); Chem. Rev., 96, 1123 (1996). For monographs, see: A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, N.Y. (1992); A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego (1996).

• Diphenyliodonium salts are widely used as photoinitiators for cationic polymerization: Macromolecules, 10, 1307 (1977); review: Adv. Polym. Sci., 62, 1 (1982).

• C-Phenylation of the anions derived from malonic esters, ?-keto esters and arylacetic esters: J. Org. Chem., 28, 714 (1963). Arylation of ketones: J. Org. Chem., 31, 4315 (1966). ?-Diketones can be arylated either as monoanions: Tetrahedron, 8, 49 (1960); J. Am. Chem. Soc., 84, 2819 (1962), or as dianions: J. Org. Chem., 29, 3514 (1964), where reaction occurs at the more reactive (terminal) carbon; see, e.g. (1-phenylation of 2,4-pentanedione): Org. Synth. Coll., 6, 928 (1988). For arylation of Grignard reagents and cyanide ion, see: J. Am. Chem. Soc., 75, 2708 (1953), and of nitro-compounds: J. Org. Chem., 28, 1424 (1963); 29, 2108 (1964). Other reactions reported include: O-Phenylation of aryloxides: J. Chem. Soc., 2645 (1961), alkoxides and oximes: J. Org. Chem., 40, 3010 (1975); 36, 1780 (1971); S-Phenylation of sulfides: J. Org. Chem., 36, 233 (1971); N-Phenylation of heterocycles: Tetrahedron, 1, 145 (1957); J. Org. Chem., 39, 2710 (1974).

• They are also useful phenylating agents for a variety of anions:

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

IUPAC name

diphenyliodanium chloride

IUPAC Traditional name

diphenyliodanium chloride

Synonyms

DIPHENYLIODONIUM CHLORIDEDiphenyliodonium chlorideNSC 134275二苯基碘酰氯DPI二苯氯化碘鎓,

Registration numbers

CAS Number

EC Number

PubChem SID

PubChem CID

MDL Number

Beilstein Number

Merck Index

Properties

Physical Property

Melting Point

233-235°C (sublimes)

233-235 °C (subl.)(lit.)

ca 230°C dec.

Molecule Details

MP Biomedicals

02150976

Phenylation reagent.
Purity: ~97%

Sigma Aldrich

43088

References

PubChem Literature

From Data Sources

• Diphenyliodonium salts are widely used as photoinitiators for cationic polymerization: Macromolecules, 10, 1307 (1977); review: Adv. Polym. Sci., 62, 1 (1982).

• They are also useful phenylating agents for a variety of anions:

Bioactivity

PubChem BioAssay

Molecule

ID:103221