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Merck
CN

638013

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

0.5 M in THF

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About This Item

Empirical Formula (Hill Notation):
C24H27O2PSi
CAS Number:
Molecular Weight:
406.53
UNSPSC Code:
12352108
PubChem Substance ID:
MDL number:
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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

SMILES string

C[Si](C)(C)CCOC(=O)c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI key

QTYUNPJLGFKKRV-UHFFFAOYSA-N

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

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

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-4.0 °F - closed cup

flash_point_c

-20 °C - closed cup

Regulatory Information

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Removable phosphine reagents for the Mitsunobu reaction.
Yoakim C, et al.
Synlett, 2003(04), 0473-0476 (2003)

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