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460273

Sigma-Aldrich

1,2-Bis(diphenylphosphino)benzene

97%

Synonym(s):

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

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About This Item

Linear Formula:
C6H4[P(C6H5)2]2
CAS Number:
13991-08-7
Molecular Weight:
446.46
MDL number:
MFCD00014081
UNSPSC Code:
12352002
PubChem Substance ID:
24869673
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

reagent type: ligand
reaction type: Baeyer-Villiger Oxidation
reagent type: ligand
reaction type: Cycloadditions
reagent type: ligand
reaction type: Reductions

mp

183-188 °C (lit.)

functional group

phosphine

SMILES string

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

InChI key

NFRYVRNCDXULEX-UHFFFAOYSA-N

Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Iron-catalysed fluoroaromatic coupling reactions under catalytic modulation with 1, 2-bis (diphenylphosphino) benzene
Hatakeyama T, et al.
Chemical Communications (Cambridge, England), 351(10), 1216-1218 (2009)
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)
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 & Catalysis, 351(6), 855-858 (2009)
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Articles

Baeyer-Villiger Oxidation Reaction

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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