85686-00-6

Basic information

• Product Name: 1 4-BIS(DIPHENYLPHOSPHINO)BUTANE MONOOX&
• Synonyms: 1 4-BIS(DIPHENYLPHOSPHINO)BUTANE MONOOX&;1-4-Bis(diphenylphosphino)butane Monoxide;Bis(diphenylphosphino)butane monoxide;1-(Diphenylphosphino)-4-(diphenylphosphinoyl)butane
• CAS NO: 85686-00-6
• Molecular Formula: C₂₈H₂₈OP₂
• Molecular Weight: 442.468842
• Mol File: 85686-00-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 183-188 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 1 4-BIS(DIPHENYLPHOSPHINO)BUTANE MONOOX&(CAS DataBase Reference)
• NIST Chemistry Reference: 1 4-BIS(DIPHENYLPHOSPHINO)BUTANE MONOOX&(85686-00-6)
• EPA Substance Registry System: 1 4-BIS(DIPHENYLPHOSPHINO)BUTANE MONOOX&(85686-00-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 85686-00-6(Hazardous Substances Data)

Usage

General Description

1,4-Bis(diphenylphosphino)butane monooxide, also known as DPPB oxide, is a chemical compound commonly used as a ligand in coordination chemistry. It is a white solid with a molecular formula of C28H26O2P2. 1 4-BIS(DIPHENYLPHOSPHINO)BUTANE MONOOX& is known for its ability to stabilize and enhance the catalytic activity of transition metal complexes in various organic and inorganic synthesis reactions. It is commonly used in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. DPPB oxide is also used in catalytic processes such as hydrogenation, cross-coupling reactions, and various other organic transformations. Additionally, it has applications in the field of materials science and catalysis, making it a valuable compound in the field of chemical research and development.

Upstream product

• 7688-25-7 1,4-di(diphenylphosphino)-butane 
• 4151-27-3 1,4-bis(diphenylphosphinyl)butane 

Downstream Products

• 217789-76-9 PdCl₂((C₆H₅)2PC₄H₈P(O)(C₆H₅)2)2 
• 623172-42-9 [Ru(η3:η3-C10H16)Cl2(κ1-P-Ph2P(CH2)4P(=O)Ph2)] 
• 113377-83-6 Pt(CH₃)2(P(C₆H₅)2CH₂CH₂CH₂CH₂PO(C₆H₅)2)2 

Relevant articles and documents

Molybdenum-Catalyzed Deoxygenative Cyclopropanation of 1,2-Dicarbonyl or Monocarbonyl Compounds

The transition-metal-catalyzed cyclopropanation of alkenes by the decomposition of diazo compounds is a powerful and straightforward strategy to produce cyclopropanes, but is tempered by the potentially explosive nature of diazo substrates. Herein we report the Mo-catalyzed regiospecific deoxygenative cyclopropanation of readily available and bench-stable 1,2-dicarbonyl compounds, in which one of the two carbonyl groups acts as a carbene equivalent upon deoxygenation and engages in the subsequent cyclopropanation process. The use of a commercially available Mo catalyst afforded an array of valuable cyclopropanes with exclusive regioselectivity in up to 90 % yield. The synthetic utility of this method was further demonstrated by gram-scale syntheses, late-stage functionalization, and the cyclopropanation of a simple monocarbonyl compound. Preliminary mechanistic studies suggest that phosphine (or silane) acts as both a mild reductant and a good oxygen acceptor that efficiently regenerates the catalytically active Mo catalyst through reduction of the Mo-oxo complexes.

Intramolecular stabilization of the phosphine radical cation by the second phosphorus atom during the photooxidation of diphosphines:31P NMR spectroscopic analysis

Diphosphines, Ph2P(CH2)nPPh2 1 (n = 1, 2, 3, 4, and 6), were photolyzed by a xenon lamp in air. The 31P NMR spectroscopic analysis of the reaction showed that 1 is oxidized, according to first-order kinetics, to the monoxide, which is further oxidized to the dioxide. The dependence of the rate constants for the first oxidation on the chain-length n in 1 is interpreted in terms of the orientation of the p-orbitals on the two phosphorus atoms in the intermediate, the diphosphine radical cation.

Catalysis for catalysis: Synthesis of mixed phosphine-phosphine oxide ligands via highly selective, Pd-catalyzed monooxidation of bidentate phosphines

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