[1-(ethoxycarbonyl)cyclopropyl]triphenylphosphanium; tetrafluoroboranuide

• ChemBase ID: 94888
• Molecular Formular: C24H24BF4O2P
• Molecular Mass: 462.2245338
• Monoisotopic Mass: 462.15430992
• SMILES: [P+](c1ccccc1)(C1(CC1)C(=O)OCC)(c1ccccc1)c1ccccc1.[B-](F)(F)(F)F
• Canonical SMILES: F[B-](F)(F)F.CCOC(=O)C1(CC1)[P+](c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H24O2P.BF4/c1-2-26-23(25)24(18-19-24)27(20-12-6-3-7-13-20,21-14-8-4-9-15-21)22-16-10-5-11-17-22;2-1(3,4)5/h3-17H,2,18-19H2,1H3;/q+1;-1
• InChIKey: RGJYRMUGSAFITK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [1-(ethoxycarbonyl)cyclopropyl]triphenylphosphanium; tetrafluoroboranuide
• IUPAC Traditional name: [1-(ethoxycarbonyl)cyclopropyl]triphenylphosphanium tetrafluoroborate
• Synonyms: (1-Carbethoxycyclopropyl)tris(phenyl)phosphonium tetrafluoroborate; [1-(Ethoxycarbonyl)cyclopropyl]tris(phenyl)phosphonium tetrafluoroborate 98%; (1-Carboethoxycyclopropyl)triphenylphosphonium tetrafluoroborate; Fuchs' Reagent; (1-Ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate; (1-乙氧基羰基环丙基)三苯基磷四氟硼酸盐

Database IDs

• CAS Number: 52186-89-7
• MDL Number: MFCD00051879
• Beilstein Number: 4650673
• PubChem SID: 162081542
• PubChem CID: 11016017

CALCULATED PROPERTIES

• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.094632
• LogD (pH = 7.4): 5.094632
• Log P: 5.094632
• Molar Refractivity: 110.1729 cm^3
• Polarizability: 43.585716 Å^3

PROPERTIES

Physical Property

• Melting Point: 173-179°C; 173-179°C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%

DETAILS

Apollo Scientific Ltd - PC2522

Fuchs Reagent

REFERENCES

• Cyclic imides e.g. Succinimide, A13503, give bridgehead lactams: Liebigs Ann. Chem., 521 (1983); for reaction scheme, see Glutarimide, L00968.
• Valuable intermediate for cycloalkenylation of compounds containing a nucleophilic center and a carbonyl group. Nucleophilic ring-opening of the cyclopropyl ring is followed by intramolecular Wittig reaction (see Appendix 1) of the intermediate carbonyl-phosphorane; e.g., with ?-keto esters, cyclopentenes are formed: J. Am. Chem. Soc., 96, 1607 (1974):
  
• With 2-formylcyclohexanones, spirocyclopentenes are obtained: J. Am. Chem. Soc., 99, 7307 (1977). Na carboxylates give 2,3-dihydrofurans: Tetrahedron Lett., 4353 (1975), and thiolcarboxylates give dihydrothiophenes, readily aromatized to thiophenes with DDQ: J. Chem. Soc., Perkin 1, 2403 (1994):