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401595

Sigma-Aldrich

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
MDL number:
MFCD00407264
UNSPSC Code:
12352002
PubChem Substance ID:
24865028
NACRES:
NA.22

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR4823
MKCM8209
MKCL3468
MKCD9278
MKBW2176V

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Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water
Parisot S, et al.
Tetrahedron Letters, 43(41), 7397-7400 (2002)
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)
Organostannoxane-supported palladium nanoparticles. Highly efficient catalysts for suzuki-coupling reactions
Chandrasekhar V, et al.
Organometallics, 28(20), 5883-5888 (2009)
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)
Janine Broda et al.
Advanced healthcare materials, 5(24), 3118-3128 (2016-11-20)
As the size of nanoparticles (NPs) is in the range of biological molecules and subcellular structures, they provide new perspectives in biomedicine. This work presents studies concerning the cellular uptake and distribution of phosphine-stabilized cytotoxic 1.4 nm sized AuNPs and

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