triphenyl(prop-2-yn-1-yl)phosphanium bromide

• ChemBase ID: 138543
• Molecular Formular: C21H18BrP
• Molecular Mass: 381.245381
• Monoisotopic Mass: 380.03294921
• SMILES: C#CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: C#CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C21H18P.BrH/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h1,3-17H,18H2;1H/q+1;/p-1
• InChIKey: AFZDAWIXETXKRE-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl(prop-2-yn-1-yl)phosphanium bromide
• IUPAC Traditional name: triphenyl(prop-2-yn-1-yl)phosphanium bromide
• Synonyms: Triphenylpropargylphosphonium bromide; Triphenyl-2-propyn-1-ylphosphonium bromide; Propargyltriphenylphosphonium bromide; Propargyltriphenylphosphonium bromide; Triphenylpropargylphosphonium bromide; 炔丙基三苯基溴化磷鎓 97%; 三苯基炔丙基溴化膦; 炔丙基三苯基溴化膦

Database IDs

• CAS Number: 2091-46-5
• EC Number: 218-242-2
• MDL Number: MFCD00011811
• Beilstein Number: 3579775
• PubChem SID: 24853572; 162232798
• PubChem CID: 2724214

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.855874
• LogD (pH = 7.4): 4.855874
• Log P: 4.855874
• Molar Refractivity: 94.8014 cm^3
• Polarizability: 37.0152 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 177-180 °C; 177-180 °C(lit.); 177-182°C

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 20/21/22-36/37/38; 22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P280H-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥99.0% (NT); 97%; 98%
• Grade: purum
• Linear Formula: HC≡CCH2P(Br)(C6H5)3

DETAILS

Sigma Aldrich - 226483

Packaging
25 g in glass bottle
Application
Wittig reagent

Sigma Aldrich - 81843

Other Notes
A Wittig-reagent1

REFERENCES

• Readily undergoes additions with nucleophiles, e.g. alcohols or amines, to give 2-alkoxy or 2-alkylamino propenyl phosphonium salts. In these reactions, the reactive species is the allenic isomer, propadienyl triphenylphosphonium bromide: J. Org. Chem., 42, 200 (1977). By using a chiral alcohol, the subsequent base-promoted Wittig reaction with carbonyl compounds yields amino or alkoxy dienes which undergo face-selective Diels-Alder additions to dienophiles: J. Chem. Soc., Chem. Commun., 1785 (1995):
  
• Precursor of enynes by the Wittig reaction: Liebigs Ann. Chem., 682, 62 (1965); J. Org. Chem., 42, 200 (1977); see Appendix 1.