27721-02-4

Basic information

• Product Name: 1,5-Bis(diphenylphosphino)pentane
• Synonyms: 98% Ph2P(CH2)5PPh2;1,5-bis(diphenylphosphino)pent;DPPENT;5-diphenylphosphanylpentyl(diphenyl)phosphane;1,5-BIS(DIPHENYLPHOSPHINO)PENTANE;DPPPE;PENTAMETHYLENEBIS(DIPHENYLPHOSPHINE);1,5-Bis(diphenyphosphino)Pentane
• CAS NO: 27721-02-4
• Molecular Formula: C₂₉H₃₀P₂
• Molecular Weight: 440.5
• EINECS: 1312995-182-4
• Product Categories: Pyrimidines;Achiral Phosphine;Aryl Phosphine;Phosphines;Ligand;Phosphine Ligands;Synthetic Organic Chemistry;phosphine ligand
• Mol File: 27721-02-4.mol

Chemical Properties

• Melting Point: 43-47 °C(lit.)
• Boiling Point: 230 C
• Flash Point: >230 °F
• Appearance: White to light yellow/Powder to Crystals or Chunks
• Vapor Pressure: 1.04E-11mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in N,N-dimethyl formamide.
• BRN: 2953640
• CAS DataBase Reference: 1,5-Bis(diphenylphosphino)pentane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Bis(diphenylphosphino)pentane(27721-02-4)
• EPA Substance Registry System: 1,5-Bis(diphenylphosphino)pentane(27721-02-4)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-10
• Safety Statements: 26-37/39-36-16
• WGK Germany: 3
• F: 10-23
• TSCA: No
• Hazardous Substances Data: 27721-02-4(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
1,5-Bis(diphenylphosphino)pentane is used as a ligand for cross-coupling reactions, which are essential in the formation of carbon-carbon bonds in organic chemistry. Its use as a ligand enhances the efficiency and selectivity of these reactions, leading to improved catalyst productivities.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,5-bis(diphenylphosphino)pentane is utilized in the synthesis of various drugs and active pharmaceutical ingredients. Its role as a ligand in cross-coupling reactions allows for the creation of complex molecular structures with high precision.
3. Used in Manufacturing Glass Bottles:
1,5-Bis(diphenylphosphino)pentane is used in the manufacturing process of glass bottles, particularly in the production of PTFE (polytetrafluoroethylene) bottles. Its application contributes to the瓶子 (bottle) industry by enhancing the quality and performance of the final product.
4. Used in Packaging Industry:
The compound is also used in the packaging industry, specifically for the production of aluminum foil bags and cardboard drums. Its application in these packaging materials helps improve their durability and resistance to various environmental factors.
5. Used in Catalyst Formulation:
The combination of a 1,5-bis(diphenylphosphino)pentane ligand and the addition of N,N,N',N'-tetramethylethylenediamine (TMEDA) as a co-catalyst are key factors in obtaining the corresponding aryl nitriles with improved catalyst productivities and selectivities. This application is particularly relevant in the chemical and pharmaceutical industries, where the synthesis of aryl nitriles is crucial for the production of various compounds and materials.

InChI:InChI=1/C29H30P2/c1-6-16-26(17-7-1)30(27-18-8-2-9-19-27)24-14-5-15-25-31(28-20-10-3-11-21-28)29-22-12-4-13-23-29/h1-4,6-13,16-23H,5,14-15,24-25H2

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 829-85-6 diphenylphosphane 
• 628-76-2 1,5-dichloropentane 
• 7439-93-2 lithium 
• 603-35-0 triphenylphosphine 

Downstream Products

• 591-51-5 phenyllithium 
• 115241-59-3 1,5-Bis--pentamethylen 
• 15553-71-6 Mo2(CO)10(μ-P-P) 
• 99350-05-7 (μ-1,5-bis(diphenylphosphine)pentane)bis(chlorogold) 
• 138646-14-7 {(CH₂(C₂H₄P(C₆H₅)2)2)Cu}2(N₂(C(O)OC(CH₃)3)2)⁽¹⁺⁾ 
• 325781-68-8 fac-(CO)3(Ph₂P(CH₂)5PPh₂)MnH 
• 223616-25-9 ((η(4)-C6H8)Fe(CO)2)2(μ-Ph2P(CH2)5PPh2) 
• 178115-42-9 Pt6(μ6-Hg)(μ-CO)6(CO)2(μ-dpppe)2 

Relevant articles and documents

The synthesis and deep purification of GaEt3. Reversible complexation of adducts MAlk3 (M = Al, Ga, In; Alk = Me, Et) with phenylphosphines

Optimal parameters of organomagnesium technique of synthesis of triethylgallium have been defined. Various techniques of deep purification of triethylgallium to the extent required in metalorganic vapor-phase epitaxy MOVPE have been studied: by way of residue ether displacement through high-performance rectification and interaction with high pure aluminum and gallium trichloride, and by way of reversible complexation with triphenylphosphine, 1,3-bis(diphenylphosphine)propane and 1,5- bis(diphenylphosphine)pentane. Advantages and disadvantages of each technique have been identified. We have shown high performance of adduct purification technique covering trimethyl and triethyl derivatives of aluminum, gallium and indium. The structure of donor-acceptor complexes between metal alkyls and the above-mentioned phosphines have been verified using H and 31P NMR spectroscopy and X-ray studies, as well as quantum chemical calculations. Thermal stability of triethylgallium and oxidation of its adducts with phosphines have been studied.

A mild and efficient CsOH-promoted synthesis of ditertiary phosphines

A mild and efficient method for the synthesis of ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves, and DMF, various dihalides were coupled with diphenylphosphine at room temperature, and the results have demonstrated that this methodology offers a general synthetic procedure producing a variety of ditertiary phosphines in high yields.

CsOH-promoted P-alkylation: A convenient and highly efficient synthesis of tertiary phosphines

A mild and efficient method for the synthesis of tertiary phosphines and ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves and DMF at room temperature, various secondary phosphines and alkyl bromides were examined, and the results have demonstrated that this methodology offers a general synthetic procedure to produce tertiary phosphines in moderate to high yields. Optically active tertiary phosphine synthesis is also described.

Preparation of organohalosilanes

When oganohalosilanes are prepared by charging a reactor with a contact mass containing a metallic silicon powder and a copper catalyst, and introducing an organohalide-containing gas into the reactor to effect the direct reaction, a poly(organo)phosphino compound is added to the contact mass. The invention is successful in producing organohalosilanes at a significantly improved production rate without reducing the selectivity of useful silane.

Process for the preparation of substituted phenols

A process for the preparation of substituted phenols, in particular, the condensation of phenols having one or more alkyl substituents with a butadiene derivative comprising at least six carbon atoms, in particular myrcene and/or β-springene is disclosed. The cyclization, in the form of chromans, of the products obtained during this condensation and their hydrogenation in order to prepare vitamin E is also disclosed.

Radical Cations of Bis(diphenylphosphino) Derivatives (Ph2P-R-PPh2): The Formation of Localized, Cyclic, and Dimeric Configurations. An ESR and Quantum Chemical Study

A matrix ESR study on radiogenic radical cations of Ph2P-R-PPh2 derivatives with various linkers (R) is presented.The experiments show that in a frozen dichloromethane solution the radical cations can adopt localized (Ph2PR*+), cyclic , and dimeric (Ph2RP*-PRPh2+) configurations, depending on the nature of the linker.The cyclic and dimeric products are formed in the reaction of a localized cation with a second free-electron pair, resulting in an intra- or intermolecular three-electron P-P ?* bond, respectively.The formation of the cyclic structure, with a strongly bent P-P ?* bond, requires a specific proximate position of the two phosphine moieties in the precursor molecule.The mutual orientation of the two free-electron pairs of the precursors is assessed by NMR via the nJPP spin-spin coupling constant.Ab initio UHF quantum chemical calculations at the 3-21G*/SCF level support the assignments.

Process for the selective preparation of alkenecarboxylic acid derivatives

A process for the selective carbonylation of a conjugated diene by contacting with carbon monoxide in the presence of a hydroxyl-group-containing compound such as water, alcohol, phenol or carboxylic acid in liquid phase using a catalyst system formed by the combination of: (a) a palladium compound and (b) at least one organic bidentate phosphine.

Preparation of biaryl compounds

A method for the preparation of biaryl compounds is disclosed which comprises contacting an aromatic halide in the presence of a catalyst comprising zerovalent nickel, a bidentate phosphorus-containing coordinating ligand and a reducing metal in a polar, aprotic solvent system for a time and under conditions suitable for the formation of biaryl compound.