triphenyl({2-[(triphenylphosphaniumyl)methyl]phenyl}methyl)phosphanium dibromide

• ChemBase ID: 146170
• Molecular Formular: C44H38Br2P2
• Molecular Mass: 788.528042
• Monoisotopic Mass: 786.08154848
• SMILES: c1ccc(cc1)[P+](Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1.[Br-].[Br-]
• Canonical SMILES: c1ccc(c(c1)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-].[Br-]
• InChI: InChI=1S/C44H38P2.2BrH/c1-7-23-39(24-8-1)45(40-25-9-2-10-26-40,41-27-11-3-12-28-41)35-37-21-19-20-22-38(37)36-46(42-29-13-4-14-30-42,43-31-15-5-16-32-43)44-33-17-6-18-34-44;;/h1-34H,35-36H2;2*1H/q+2;;/p-2
• InChIKey: MXCBXCYGWQAOSN-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl({2-[(triphenylphosphaniumyl)methyl]phenyl}methyl)phosphanium dibromide
• IUPAC Traditional name: triphenyl({2-[(triphenylphosphaniumyl)methyl]phenyl}methyl)phosphanium dibromide
• Synonyms: (o-Phenylenedimethylene)bis[triphenylphosphonium bromide]; 1,2-Bis(triphenylphosphoniomethyl)benzene dibromide; NSC 665614; NSC 78589; o-Xylylenebis(triphenylphosphonium bromide); 邻苯二甲基联(溴化三苯基膦); 邻亚二甲苯基联(溴化三苯基膦)

Database IDs

• CAS Number: 1519-46-6
• EC Number: 216-183-7
• MDL Number: MFCD00044843
• Beilstein Number: 4121635
• PubChem SID: 162240369; 24902126
• PubChem CID: 2753326

CALCULATED PROPERTIES

• Acid pKa: 14.757154
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 10.731282
• LogD (pH = 7.4): 10.731282
• Log P: 10.731282
• Molar Refractivity: 197.6096 cm^3
• Polarizability: 77.75233 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98+%
• Linear Formula: C6H4[CH2P(C6H5)3Br]2

DETAILS

Sigma Aldrich - X1105

Packaging
5 g in glass bottle
Application
Reactant for:
• Synthesis of [6.8]3cyclacene and polyunsaturated [23] and [24]metacyclophanes1
• Selective inclusion of equatorial isomers of cyclohexane-polyols in phosphonium salt hosts2
• Photoactive platinum(II) DNA intercalator synthesis3
• Preparation of (pheynlenedivinylene)bis[pyrrole] derivatives4
• The reaction with sodium hexamethyldisilazide to form acyclic, ring, and cage AS,C compounds5
• Synthesis of styryl substituted annelated furan derivatives6

REFERENCES

• For use in the phase-transfer catalyzed synthesis of polycyclic hydrocarbons by the bis-Wittig reaction with dialdehydes, see: Synthesis, 497 (1983). For a review of the bis-Wittig reaction in the synthesis of non-benzenoid aromatic ring-systems, see: Synthesis, 765 (1975). See Appendix 1.