Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

401595

Sigma-Aldrich

4-(Diphenylphosphino)benzoic acid

97%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCR4823
MKCM8209
MKCL3468
MKCD9278
MKBW2176V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Organostannoxane-supported palladium nanoparticles. Highly efficient catalysts for suzuki-coupling reactions
Chandrasekhar V, et al.
Organometallics, 28(20), 5883-5888 (2009)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service