triphenyl(propan-2-yl)phosphanium iodide

• ChemBase ID: 80773
• Molecular Formular: C21H22IP
• Molecular Mass: 432.277611
• Monoisotopic Mass: 432.05038533
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)C(C)C.[I-]
• Canonical SMILES: CC([P+](c1ccccc1)(c1ccccc1)c1ccccc1)C.[I-]
• InChI: InChI=1S/C21H22P.HI/c1-18(2)22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h3-18H,1-2H3;1H/q+1;/p-1
• InChIKey: HHBXWXJLQYJJBW-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl(propan-2-yl)phosphanium iodide
• IUPAC Traditional name: isopropyltriphenylphosphanium iodide
• Synonyms: (1-Methylethyl)triphenylphosphonium iodide; NSC 140615; Isopropyltriphenylphosphonium iodide; (2-Propyl)triphenylphosphonium iodide; ISOPROPYLTRIPHENYLPHOSPHONIUM IODIDE; Isopropyltris(phenyl)phosphonium iodide; 碘化异丙基三苯膦; 异丙基三苯碘化磷鎓

Database IDs

• CAS Number: 24470-78-8
• EC Number: 246-281-5
• MDL Number: MFCD00031595
• Beilstein Number: 3599629
• PubChem SID: 162067893; 24863508
• PubChem CID: 2723783

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.297396
• LogD (pH = 7.4): 5.297396
• Log P: 5.297396
• Molar Refractivity: 96.4378 cm^3
• Polarizability: 38.127544 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 194-197 °C(lit.); 194-198°C; 195-198°C

Safety Information

• Storage Warning: Irritant/Light Sensitive/Hygroscopic/Keep Cold; Light Sensitive & Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 98%; 98+%
• Linear Formula: (CH3)2CHP(C6H5)3I

DETAILS

MP Biomedicals - 05216347

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 377481

Packaging
25 g in glass bottle
Application
Employed in Wittig1,2 and cyclopropanation reactions.2,3
Reactant for:
• Total synthesis of heliananes
• Preparation of highly substituted benzene derivatives
• Synthesis of curcuphenol and elvirol analogs via a retro-aldol reaction as fungicidal agents
• 4-substituted methoxylbenzoyl-aryl-thiazoles analogues as potent and orally bioavailable anticancer agents
• Wittig reaction

REFERENCES

• Useful precursor of isopropylidene unit by Wittig reaction with aldehydes: J. Am. Chem. Soc., 103, 2823 (1981), and ketones: J. Org. Chem., 53, 3877 (1988).
• The derived phosphorane can also add to activated double bonds to give gem-dimethyl cyclopropanes: Tetrahedron Lett., 3781 (1972). For use of tandem cyclopropanation and Wittig olefination in a synthesis of chrysanthemic acid, see: Tetrahedron Lett., 3911 (1976):