methyltriphenylphosphanium bromide

• ChemBase ID: 9453
• Molecular Formular: C19H18BrP
• Molecular Mass: 357.223981
• Monoisotopic Mass: 356.03294921
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)C.[Br-]
• Canonical SMILES: C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C19H18P.BrH/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19;/h2-16H,1H3;1H/q+1;/p-1
• InChIKey: LSEFCHWGJNHZNT-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: methyltriphenylphosphanium bromide
• IUPAC Traditional name: methyltriphenylphosphanium bromide
• Synonyms: Methyl (triphenyl)phosphonium bromide; Methyltriphenylphosphonium bromide; Methyl(triphenyl)phosphonium bromide; Methyltriphenylphosphonium bromide; 甲基三苯基溴化膦; 甲基三苯基溴化磷鎓

Database IDs

• CAS Number: 1779-49-3
• EC Number: 217-218-9
• MDL Number: MFCD00011804
• Beilstein Number: 3599467
• PubChem SID: 24847941; 160972760
• PubChem CID: 74505

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.731569
• LogD (pH = 7.4): 4.731569
• Log P: 4.731569
• Molar Refractivity: 87.172 cm^3
• Polarizability: 34.434486 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear
• Melting Point: 230-233 °C; 230-233°C; 230-234 °C(lit.); 230-234°C; 231-234°C

Safety Information

• Storage Warning: Hygroscopic; Irritant/Harmful/Hygroscopic
• European Hazard Symbols: Nature polluting (N); X; Harmful (Xn)
• UN Number: UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/21/22; 22-36/37/38-51/53
• Safety Statements: 26-36/37-57; 36/37
• TSCA Listed: true; 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332; H302-H315-H319-H335-H411-H401
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (NT); 98%; 98+%
• Grade: purum
• Linear Formula: CH3P(C6H5)3Br

DETAILS

MP Biomedicals - 05204606

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 130079

Application
Used widely for methylenation via the Wittig reaction
Wittig olefination salt employed recently in a synthesis of an enyne which, via ring closing metathesis, provided a benzazepine ring system.
Packaging
25, 100, 500 g in poly bottle

Sigma Aldrich - 69495

Other Notes
Wittig reagent; activated ylide by double deprotonation1

REFERENCES

• Precursor of Wittig ylide for methylenation of carbonyl compounds (see Appendix 1). See, e.g.: Org. Synth. Coll., 5, 751 (1973). A simplified procedure using K₂CO₃ in triglyme has been reported: Synth. Commun., 22, 513 (1992).
• Where the ylide is insufficiently reactive, a further proton can be removed by s-BuLi or t-BuLi, and the resulting lithio ylide reacted with hindered ketones such as fenchone: J. Am. Chem. Soc., 104, 4724 (1982). Reaction of the lithio ylide with an epoxide generates a new ylide, with which Wittig olefination of aldehydes gives trans-homoallylic alcohols (same ref.):