(bromomethyl)triphenylphosphanium bromide

• ChemBase ID: 148354
• Molecular Formular: C19H17Br2P
• Molecular Mass: 436.120041
• Monoisotopic Mass: 433.94346117
• SMILES: c1ccc(cc1)[P+](CBr)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: BrC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C19H17BrP.BrH/c20-16-21(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19;/h1-15H,16H2;1H/q+1;/p-1
• InChIKey: YFTMLUSIDVFTKU-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (bromomethyl)triphenylphosphanium bromide
• IUPAC Traditional name: (bromomethyl)triphenylphosphanium bromide
• Synonyms: NSC 193751; (Bromomethyl)triphenylphosphonium bromide; (Bromomethyl)triphenylphosphonium bromide; (溴甲基)三苯基溴化磷

Database IDs

• CAS Number: 1034-49-7
• EC Number: 213-857-2
• MDL Number: MFCD00011864
• Beilstein Number: 3579901
• PubChem SID: 24856314; 162242530
• PubChem CID: 2733422

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.226911
• LogD (pH = 7.4): 5.226911
• Log P: 5.226911
• Molar Refractivity: 94.6427 cm^3
• Polarizability: 36.872368 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 234-236 °C(lit.); 234-239 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-28
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (AT); 95+%; 98%
• Grade: purum
• Linear Formula: BrCH2P(Br)(C6H5)3

DETAILS

Sigma Aldrich - 269158

Packaging
5, 25 g in glass bottle
Application
Reactant or reagent for synthesis of:
• Vernonia allenes and sesquiterpenoids1
• Monohalovinylated pyrethoids with insecticidal activity2
• Vitamin D analogs with anticancer activity3Reactant for:
• Asymmetric substitution affecting optical properties of boradiazaindacene dyes4
• Carbanionic rearrangements of halomethylenecyclobutanes5Used for diferrocenyl molecular wires6

Sigma Aldrich - 17626

Other Notes
Wittig reagent for the synthesis of bromoalkenes; alkynes can also be obtained from aldehydes7,8,9,10
Application
Reactant or reagent for synthesis of:
• Vernonia allenes and sesquiterpenoids1
• Monohalovinylated pyrethoids with insecticidal activity2
• Vitamin D analogs with anticancer activity3Reactant for:
• Asymmetric substitution affecting optical properties of boradiazaindacene dyes4
• Carbanionic rearrangements of halomethylenecyclobutanes5Used for diferrocenyl molecular wires6