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401595

Sigma-Aldrich

4-(Diphenylphosphino)benzoic acid

97%

Sinônimo(s):

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

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About This Item

Fórmula linear:
(C6H5)2PC6H4CO2H
Número CAS:
2129-31-9
Peso molecular:
306.30
Número MDL:
MFCD00407264
Código UNSPSC:
12352002
ID de substância PubChem:
24865028
NACRES:
NA.22

Ensaio

97%

adequação da reação

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

pf

157-160 °C (lit.)

grupo funcional

phosphine

cadeia de caracteres SMILES

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)

chave InChI

GXMHDTPYKRTARV-UHFFFAOYSA-N

Categorias relacionadas

Descrição geral

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

Aplicação

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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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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