diphenyliodanium chloride

• ChemBase ID: 103221
• Molecular Formular: C12H10ClI
• Molecular Mass: 316.56527
• Monoisotopic Mass: 315.951576
• SMILES: [Cl-].[I+](c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)[I+]c1ccccc1.[Cl-]
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyliodanium chloride
• IUPAC Traditional name: diphenyliodanium chloride
• Synonyms: DPI; NSC 134275; Diphenyliodonium chloride; DIPHENYLIODONIUM CHLORIDE; 二苯基碘酰氯; 二苯氯化碘鎓,

Database IDs

• CAS Number: 1483-72-3
• EC Number: 216-049-8
• MDL Number: MFCD00011909
• Beilstein Number: 3574977
• Merck Index: 147464
• PubChem SID: 24866949; 162090445
• PubChem CID: 73870

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.5634055
• LogD (pH = 7.4): 4.5634055
• Log P: 4.5634055
• Molar Refractivity: 64.8948 cm^3
• Polarizability: 28.086405 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 233-235 °C (subl.)(lit.); 233-235°C (sublimes); ca 230°C dec.

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Light Sensitive
• RTECS: NN6651666
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36; 26-36/37-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ~97%; ≥98.0% (AT); 98+%
• Linear Formula: (C6H5)2I+Cl-

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

REFERENCES

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