(iodomethyl)triphenylphosphanium iodide

• ChemBase ID: 143338
• Molecular Formular: C19H17I2P
• Molecular Mass: 530.120981
• Monoisotopic Mass: 529.91573317
• SMILES: c1ccc(cc1)[P+](CI)(c1ccccc1)c1ccccc1.[I-]
• Canonical SMILES: IC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[I-]
• InChI: InChI=1S/C19H17IP.HI/c20-16-21(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19;/h1-15H,16H2;1H/q+1;/p-1
• InChIKey: NAVMMSRRNOXQMJ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (iodomethyl)triphenylphosphanium iodide
• IUPAC Traditional name: (iodomethyl)triphenylphosphanium iodide
• Synonyms: NSC 116665; (Iodomethyl)triphenylphosphonium iodide; (IodoMethyl)triphenylphosphoniuM iodide; (碘甲基)三苯基碘化膦

Database IDs

• CAS Number: 3020-28-8
• MDL Number: MFCD03931274
• PubChem SID: 162237558
• PubChem CID: 10973449

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.657189
• LogD (pH = 7.4): 5.657189
• Log P: 5.657189
• Molar Refractivity: 99.8914 cm^3
• Polarizability: 39.086624 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 260-266 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-28
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C19H17I2P

DETAILS

Sigma Aldrich - 725285

Packaging
5, 10 g in glass bottle
Application
Reactant or reagent for synthesis of:
• Phosphacyclic compounds via oxidative dimerizations1
• Enamides via cross-coupling2
• Cyclopeptide alkaloids for use as antibacterial or cytotoxic agents3
• Terminal alkynes via dehydrohalogenation of aldehydes4Reactant for vinylcyclopropanation / cyclopentenation of strained alkenes using a sequential carborhodation process5Used as an olefination agent in the Lewis acid catalysis of electrocyclization of trienes6