cyclopropyltriphenylphosphanium bromide

• ChemBase ID: 80818
• Molecular Formular: C21H20BrP
• Molecular Mass: 383.261261
• Monoisotopic Mass: 382.04859927
• SMILES: [P+](C1CC1)(c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: C1CC1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C21H20P.BrH/c1-4-10-18(11-5-1)22(21-16-17-21,19-12-6-2-7-13-19)20-14-8-3-9-15-20;/h1-15,21H,16-17H2;1H/q+1;/p-1
• InChIKey: XMPWFKHMCNRJCL-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclopropyltriphenylphosphanium bromide
• IUPAC Traditional name: cyclopropyltriphenylphosphanium bromide
• Synonyms: NSC 110599; Cyclopropyltriphenylphosphonium bromide; cyclopropyl(triphenyl)phosphonium bromide; 环丙基三苯基溴化鏻; 溴化环丙基三苯基膦

Database IDs

• CAS Number: 14114-05-7
• EC Number: 237-970-1
• MDL Number: MFCD00011872
• Beilstein Number: 6413483; 4170278
• PubChem SID: 162067937; 24849670
• PubChem CID: 2723931

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.9895773
• LogD (pH = 7.4): 4.9895773
• Log P: 4.9895773
• Molar Refractivity: 94.4816 cm^3
• Polarizability: 37.380898 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 178-181 °C; 178-181 °C(lit.); 183-186°C

Safety Information

• Storage Warning: 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: ≥98.0% (AT); 98%
• Grade: technical
• Linear Formula: C3H5P(C6H5)3Br

DETAILS

Sigma Aldrich - 157317

Application
Wittig reagent
Used for electrolytic polarization of Zn1Studied for potential antitumor activity2Reactant for synthesis of:
• Keto halides for sequential azidation and intramolecular Schmidt reactions3
• Cycloporpylidenemethylarylethynynes4
• Dipeptides containing azabicyclo[3.1.0]hexane5Reactant for hydroalkynylation6
Packaging
25 g in glass bottle

Sigma Aldrich - 30015

Other Notes
Wittig reagent used to prepare alkylidene-cyclopropanes7,8,9
Application
Used for electrolytic polarization of Zn1Studied for potential antitumor activity2Reactant for synthesis of:
• Keto halides for sequential azidation and intramolecular Schmidt reactions3
• Cycloporpylidenemethylarylethynynes4
• Dipeptides containing azabicyclo[3.1.0]hexane5Reactant for hydroalkynylation6

REFERENCES

• Wittig salt (see Appendix 1) for the conversion of carbonyl compounds to cyclopropylidene derivatives. For use in the synthesis of the isoquinoline alkaloid (-)-mesembrine, see: J. Org. Chem., 60, 6785 (1995). Greatly improved yields in this type of reaction have been obtained with NaH in THF, in the presence of the phase-transfer catalyst TDA-1 (Tris(3,6-dioxaheptyl)amine, L13544): Tetrahedron Lett., 29, 2531 (1988).