bromotriphenylphosphanium bromide

• ChemBase ID: 295211
• Molecular Formular: C18H15Br2P
• Molecular Mass: 422.093461
• Monoisotopic Mass: 419.92781111
• SMILES: c1ccc(cc1)[P+](c1ccccc1)(c1ccccc1)Br.[Br-]
• Canonical SMILES: Br[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C18H15BrP.BrH/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H/q+1;/p-1
• InChIKey: UWGULZXZFOYYJT-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: bromotriphenylphosphanium bromide
• IUPAC Traditional name: bromotriphenylphosphanium bromide
• Synonyms: Dibromotriphenylphosphorane; Triphenylphosphine dibromide; 二溴化三苯基膦

Database IDs

• CAS Number: 1034-39-5
• EC Number: 213-855-1
• MDL Number: MFCD00000054
• Beilstein Number: 917652
• PubChem SID: 180680742
• PubChem CID: 10137025

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.108826
• LogD (pH = 7.4): 5.108826
• Log P: 5.108826
• Molar Refractivity: 90.3581 cm^3
• Polarizability: 35.064034 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: ca 260°C dec.

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: UN3261
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Product Information

• Purity: 96%

REFERENCES

• The reagent formed with DMSO at low temperatures provides an alternative to the Swern oxidation for selective conversion of alcohols to carbonyl compounds: Tetrahedron Lett., 43, 8355 (2002).
• Reagent for the conversion of alcohols and phenols to bromides in good yields: J. Org. Chem., 37, 626 (1972). Particularly useful for alcohols where sensitive functionality is present: J. Org. Chem., 49, 431 (1984); Synth. Commun., 22, 2945 (1992). Cleaves dialkyl ethers to the two alkyl bromides: J. Am. Chem. Soc., 86, 5037 (1964); J. Org. Chem., 37, 626 (1972).
• Reaction with amines gives iminophosphoranes, which have been used as a means of blocking an amino group to permit monoalkylation: Synthesis, 295 (1980). Iminophosphoranes also undergo a Wittig-like condensation with CO₂ or CS₂ to give the isocyanates or isothiocyanates respectively: Synthesis, 596 (1982):
  
• Ureas are dehydrated to carbodiimides: Liebigs Ann. Chem., 718, 24 (1968); Synthesis, 373 (1981).