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401595

4-(Diphenylphosphino)benzoic acid

97%

Synonym(s):

(4-Carboxyphenyl)diphenylphosphine, Diphenyl(p-carboxyphenyl) phosphine, p-(Diphenylphosphino)benzoic acid

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About This Item

Linear Formula:
(C6H5)2PC6H4CO2H
CAS Number:
2129-31-9
Molecular Weight:
306.30
NACRES:
NA.22
PubChem Substance ID:
24865028
UNSPSC Code:
12352002
MDL number:
MFCD00407264
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Quality Level

100

assay

97%

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

mp

157-160 °C (lit.)

functional group

phosphine

SMILES string

OC(=O)c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI

1S/C19H15O2P/c20-19(21)15-11-13-18(14-12-15)22(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14H,(H,20,21)

InChI key

GXMHDTPYKRTARV-UHFFFAOYSA-N

General description

4-(Diphenylphosphino)benzoic acid is a phosphine ligand that is employed in palladium-catalyzed cross-coupling and Suzuki cross-coupling reactions.

Application

4-(Diphenylphosphino)benzoic acid can be used as a ligand in the synthesis of:
  • Organostannoxane-supported palladium nanoparticles. The resulting catalysts show high activity and selectivity in Suzuki-coupling reactions.
  • Polymetallic ruthenium-zinc complex catalyst for the hydrogenation of levulinic acid to γ-valerolactone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4236
MKCR4823
MKCM8209
MKCL3468
MKCD9278

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Homogeneous polymetallic ruthenium(II)^zinc(II) complexes: robust catalysts for the efficient hydrogenation of levulinic acid to ?-valerolactone
Amenuvor G, et al.
Catalysis Science & Technology, 8(9), 2370-2380 (2018)
Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water
Parisot S, et al.
Tetrahedron Letters, 43(41), 7397-7400 (2002)
Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model
Trost BM, et al.
Accounts of Chemical Research, 39(10), 747-760 (2006)
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Global Trade Item Number

SKUGTIN
401595-5G04061833314104
401595-1G04061826663080