(4-bromobutyl)triphenylphosphanium bromide

• ChemBase ID: 140114
• Molecular Formular: C22H23Br2P
• Molecular Mass: 478.199781
• Monoisotopic Mass: 475.99041137
• SMILES: c1ccc(cc1)[P+](CCCCBr)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: BrCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C22H23BrP.BrH/c23-18-10-11-19-24(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H/q+1;/p-1
• InChIKey: BJDNCJGRAMGIRU-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-bromobutyl)triphenylphosphanium bromide
• IUPAC Traditional name: (4-bromobutyl)triphenylphosphanium bromide
• Synonyms: NSC 84071; (4-Bromobutyl)triphenylphosphonium bromide; (4-溴丁基)三苯基溴化膦

Database IDs

• CAS Number: 7333-63-3
• MDL Number: MFCD00031636
• Beilstein Number: 3812291
• PubChem SID: 162234358; 24856454
• PubChem CID: 2733851

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.0550985
• LogD (pH = 7.4): 6.0550985
• Log P: 6.0550985
• Molar Refractivity: 109.058 cm^3
• Polarizability: 42.377728 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 206-212°C; 210-213 °C(lit.)

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; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: Br(CH2)4P(C6H5)3Br

DETAILS

Sigma Aldrich - 272132

Packaging
25 g in glass bottle
Application
Reactant involved in:
• Azidification1
• C-H activation and β -elimination to product an eight-membered ring system2
• 1,3-Dipolar cycloaddition of azides onto alkenes 3
• Stereoselective SmI2-mediated coupling of unsaturated carbonyl compounds and aldehydes4
• Synthesis of D-labeled methylenecyclobutane5
• Coupling reactions6

REFERENCES

• Is converted by t-BuOK to cyclobutylidene triphenylphosphorane, which provides methylenecyclobutene by Wittig reaction with formaldehyde, or bicyclobutylidene by oxidation with oxygen: Synthesis, 299 (1987):