638013

4-Diphenylphosphanylbenzoic acid, 2-(trimethylsilyl)ethyl ester solution

0.5 M in THF

• Empirical Formula (Hill Notation): C₂₄H₂₇O₂PSi
• CAS Number: 566190-45-2
• Molecular Weight: 406.53
• MDL number: MFCD07369722
• UNSPSC Code: 12352108
• PubChem Substance ID: 24882904

Properties

• reaction suitability: reaction type: Buchwald-Hartwig Cross Coupling Reaction; reaction type: Heck Reaction; reaction type: Hiyama Coupling; reaction type: Negishi Coupling; reaction type: Sonogashira Coupling; reaction type: Stille Coupling; reaction type: Suzuki-Miyaura Coupling; reagent type: ligand
• concentration: 0.5 M in THF
• density: 0.925 g/mL at 25 °C
• functional group: phosphine
• SMILES string: C[Si](C)(C)CCOC(=O)c1ccc(cc1)P(c2ccccc2)c3ccccc3
• InChI: 1S/C24H27O2PSi/c1-28(2,3)19-18-26-24(25)20-14-16-23(17-15-20)27(21-10-6-4-7-11-21)22-12-8-5-9-13-22/h4-17H,18-19H2,1-3H3
• InChI key: QTYUNPJLGFKKRV-UHFFFAOYSA-N

Description

Application

4-Diphenylphosphanyl-benzoic acid 2-trimethylsilanyl-ethyl ester (DPPBE) was developed as an efficient alternative to triphenylphosphine in the Mitsunobu reaction since the phosphine oxide formed during the reaction can be easily removed during workup.

Reagent for:

• Synthesis of alkenes
• Methylation of aldehydes
• Mitsunobu reactions

Safety Information

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H225,H319,H335,H351
• pcodes: P210 - P280 - P305 + P351 + P338 - P370 + P378 - P403 + P235
• Hazard Classifications: Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
• target_organs: Respiratory system
• supp_hazards: EUH019
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: -4.0 °F - closed cup
• flash_point_c: -20 °C - closed cup