[2-(tert-butoxy)-2-oxoethyl]triphenylphosphanium bromide

• ChemBase ID: 147998
• Molecular Formular: C24H26BrO2P
• Molecular Mass: 457.339801
• Monoisotopic Mass: 456.0853787
• SMILES: CC(C)(C)OC(=O)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OC(C)(C)C.[Br-]
• InChI: InChI=1S/C24H26O2P.BrH/c1-24(2,3)26-23(25)19-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,19H2,1-3H3;1H/q+1;/p-1
• InChIKey: ZGLFRTJDWWKIAK-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(tert-butoxy)-2-oxoethyl]triphenylphosphanium bromide
• IUPAC Traditional name: [2-(tert-butoxy)-2-oxoethyl]triphenylphosphanium bromide
• Synonyms: NSC 82468; (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide; Carbo-tert-butoxymethyl triphenylphosphonium bromide; (叔丁氧基羰基甲基)溴化三苯基磷

Database IDs

• CAS Number: 59159-39-6
• MDL Number: MFCD00075527
• Beilstein Number: 4631405
• PubChem SID: 24862950; 162242178
• PubChem CID: 2733853

CALCULATED PROPERTIES

• Acid pKa: 19.997911
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.098072
• LogD (pH = 7.4): 5.098072
• Log P: 5.098072
• Molar Refractivity: 111.9789 cm^3
• Polarizability: 44.324696 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 178 °C (dec.)(lit.); ca 178°C dec.

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: (CH3)3CO2CCH2P(C6H5)3Br

DETAILS

Sigma Aldrich - 369047

Packaging
10, 50 g in poly bottle
Application
Reactant for:
• Rhodium-catalyzed asymmetric hydrogenation reactions1
• Wittig reaction2
• Wittig methylenation3
• Preparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via double aza-Michael addition reaction4
• Stereoselective preparation of of α-fluoro-α,β-unsaturated esters via deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydes5
• Wittig chain extension reactions6