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460273

Sigma-Aldrich

1,2-Bis(diphenylphosphino)benzene

97%

Sinonimo/i:

1,2-Bis(diphenylphosphanyl)benzene, dppBz, dppbe, dppben, dppbenz, dppbz, o-Phenylenebis[diphenylphosphine], o-bis(diphenylphosphino)benzene

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About This Item

Formula condensata:
C6H4[P(C6H5)2]2
Numero CAS:
Peso molecolare:
446.46
Numero MDL:
Codice UNSPSC:
12352002
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

97%

Forma fisica

solid

Impiego in reazioni chimiche

reagent type: ligand
reaction type: Baeyer-Villiger Oxidation

reagent type: ligand
reaction type: Cycloadditions

reagent type: ligand
reaction type: Reductions

Punto di fusione

183-188 °C (lit.)

Gruppo funzionale

phosphine

Stringa SMILE

c1ccc(cc1)P(c2ccccc2)c3ccccc3P(c4ccccc4)c5ccccc5

InChI

1S/C30H24P2/c1-5-15-25(16-6-1)31(26-17-7-2-8-18-26)29-23-13-14-24-30(29)32(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-24H
NFRYVRNCDXULEX-UHFFFAOYSA-N

Applicazioni

1,2-Bis(diphenylphosphino)benzene (DPPB) can be used:
  • As a chelating ligand in the synthesis of luminescent copper(I) halide complexes.
  • In the synthesis of copper-1,2-bis(diphenylphosphino)benzene catalyst which is used for the β-boration of α, β-unsaturated amide.
  • As an alternative to TMEDA for the selective cleavage of sp3 C-X bond in fluoroaromatic coupling reactions catalyzed by iron.
  • As a ligand in the synthesis of alkenylboronates from acetylenic esters.
  • To synthesize copper-diphosphine complexes which are used as homogeneous catalysts for N-formylation of a wide range of amines.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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Copper-Catalyzed Conjugate Addition of Diboron Reagents to α, β -Unsaturated Amides: Highly Reactive Copper-1, 2-Bis (diphenylphosphino) benzene Catalyst System
Chea H, et al.
Advanced Synthesis & Catalysis, 351(6), 855-858 (2009)
Copper-diphosphine complex catalysts for N-formylation of amines under 1 atm of carbon dioxide with polymethylhydrosiloxane
Motokura K, et al.
Catalysis Science & Technology, 3(9), 2392-2396 (2013)
Synthesis of Activated Alkenylboronates from Acetylenic Esters by CuH-Catalyzed 1, 2-Addition/Transmetalation
Lipshutz BH, et al.
Angewandte Chemie (International Edition in English), 47(52), 10183-10186 (2008)
Photophysical properties of highly luminescent copper (I) halide complexes chelated with 1, 2-bis (diphenylphosphino) benzene
Tsuboyama A, et al.
Inorganic Chemistry, 46(6), 1992-2001 (2007)
Copper-Catalyzed Conjugate Addition of Diboron Reagents to α, β -Unsaturated Amides: Highly Reactive Copper-1, 2-Bis (diphenylphosphino) benzene Catalyst System
Chea H, et al.
advanced synthesis and catalysis, 351(6), 855-858 (2009)

Articoli

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

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