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638013

Sigma-Aldrich

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:
566190-45-2
Molecular Weight:
406.53
MDL number:
MFCD07369722
UNSPSC Code:
12352108
PubChem Substance ID:
24882904

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

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

Signal Word

Danger

Hazard Statements

H225,H319,H335,H351

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-4.0 °F - closed cup

Flash Point(C)

-20 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

638013-BULK:
638013-VAR:
638013-25ML:4548173224725
638013-5ML:4548173224732

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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