5518-52-5

Basic information

• Product Name: TRI(2-FURYL)PHOSPHINE
• Synonyms: SALOR-INT L308749-1EA;TRIS(2-FURYL)PHOSPHINE;TRI(2-FURYL)PHOSPHINE;Tri(2-furyl)phosphine,97%;Tri-2-furylphosphine,98+%;TRI-(2-FURYL)PHOSPHINE 98%;2,2',2''-Phosphinidynetrisfuran;Tri(2-furanyl)phosphine
• CAS NO: 5518-52-5
• Molecular Formula: C₁₂H₉O₃P
• Molecular Weight: 232.17
• EINECS: 1312995-182-4
• Product Categories: Ligand;Phosphine Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds;organophosphorus ligand;Aromatics;Chelating Agents & Ligands;Heterocycles;Achiral Phosphine;Aryl Phosphine
• Mol File: 5518-52-5.mol

Chemical Properties

• Melting Point: 59-64 °C(lit.)
• Boiling Point: 136 °C4 mm Hg(lit.)
• Flash Point: 136°C/4mm
• Appearance: faintly brown/solid
• Vapor Pressure: 0.00456mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive: air sensitive
• BRN: 1577564
• CAS DataBase Reference: TRI(2-FURYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRI(2-FURYL)PHOSPHINE(5518-52-5)
• EPA Substance Registry System: TRI(2-FURYL)PHOSPHINE(5518-52-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25
• WGK Germany: 3
• F: 10-23
• TSCA: No
• Hazardous Substances Data: 5518-52-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRI(2-FURYL)PHOSPHINE is used as a phosphine ligand for transition-metal mediated organic synthesis, specifically in Wittig reactions, to improve (Z) selectivity. This enhancement allows for the creation of more precise and desired products in chemical reactions.
Used in Suzuki Reaction:
In the field of cross-coupling reactions, TRI(2-FURYL)PHOSPHINE is employed as a phosphine ligand in the Suzuki reaction. This reaction is a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of complex organic molecules and pharmaceutical compounds.
Overall, TRI(2-FURYL)PHOSPHINE plays a crucial role in the advancement of organic chemistry, particularly in the development of new and efficient synthetic pathways for the production of various compounds.

Reaction

Useful ligand for C-C coupling reactions. Ligand used for the alkynylation of thioesters. Ligand used for enol ester formation. Ligand for palladium-catalyzed 3-Component coupling. Ligand for palladium-catalyzed C-C coupling reaction. Ligand for trans-olefin formation. Olefin formation from N-tosylhydrazones and benzyl halides. C-H arylation/alkenylation of 1-substituted tetrazoles.

InChI:InChI=1/C12H9O3P/c1-4-10(13-7-1)16(11-5-2-8-14-11)12-6-3-9-15-12/h1-9H

Upstream product

• 110-00-9 furan 
• 2786-02-9 2-lithiofuran 
• 472962-98-4 Ag(tris(2-furyl)phosphine)3(ONO₂) 
• 64-17-5 ethanol 
• 1186392-97-1 tris(2-furyl)phosphane-borane(1:1) 
• 1021-20-1 tris(furan-2-yl)phosphine oxide 

Downstream Products

• 95499-53-9 tri-2-furyl<3-bromo-6-(4-diethylaminophenylazo)phenyl>phosphonium bromide 
• 263720-29-2 methyl (E-3{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}prop-2-enoate) 
• 26910-78-1 methyl-tri(2-furyl)phosphonium iodide 
• 251966-59-3 1-[3-(2,4-Difluoro-benzyl)-phenyl]-ethanone 
• 195992-08-6 2,6-dinitrostyrene 
• 247174-63-6 1-(6-Allylnaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 
• 258839-91-7 4-nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-propionylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate 
• 252749-95-4 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-(2,2-dimethylpropyl)-1,2,3-triazolo[4,5-b]pyridine 

Relevant articles and documents

Synthesis of the tertiaryphosphine derivatives of iron carbonyl phosphines: preparation of tetracarbonyliron(0), pentacarbonylbisdiiron(0), tetracarbonyliron(0) and pentacarbonylbis<...

Pentacarbonyl iron reacts with this(2-furyl)phosphine (or tris(2-benzofuryl)phosphine) in the presence of sodium borohydride in refluxing n-butanol to give the title compounds.The crystal and molecular structure of pentacarbonylbis(μ-bis(2-furyl)phosphido>diiron(0) were determined by X-ray crystallography. Keywords: Iron; Dinuclear; Carbonyls; X-ray structure; Benzoferrylphosphine complex

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

PROCESS FOR PRODUCTION OF PHOSPHINE DERIVATIVE FROM PHOSPHINE OXIDE DERIVATIVE

Disclosed is a process for producing a phosphine derivative from a phosphine oxide derivative, which comprises the following steps: (I) mixing a phosphine oxide derivative represented by formula (1) with a chlorinating agent in a polar organic solvent to cause the reaction between these components; and (II-1) adding a salt of a metal having an ionization tendency equal to or lower than that of aluminum to the reaction mixture and carrying out the reductive reaction in the presence of aluminum or (II-2) subjecting the reaction mixture to electrolytic reduction, thereby producing a phosphine derivative represented by formula (2). ArnR3-nP═O (1) ArnR3-nP (2) In formulae (1) and (2), Ar represents an aryl group such as a phenyl group, a phenyl group having a substituent, a heteroaromatic ring group, and a heteroaromatic ring group having a substituent; R represents an aliphatic hydrocarbon group or an aliphatic hydrocarbon group having a substituent; and n represents an integer of 0 to 3.

Catalyst-free alcoholysis of phosphane-boranes: a smooth, cheap, and efficient deprotection procedure

Catalyst-free alcoholytic deprotection of borane-protected phosphorus compounds offers a smooth, efficient, and clean alternative to existing deprotection methods. In this paper we report our results on the general applicability of deprotecting phosphane-

Triethylborane-mediated hydrogallation and hydroindation: Novel access to organogalliums and organoindiums

Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.

A single-strand helical motif induced by self-assembly of [Ag(TFP)]+ moieties with nitrate anions - 31P NMR spectroscopic and X-ray crystal structure characterization of the complexes involved in equilibrium reactions of silver salts and TFP ligand

The ability of the ligand tris(2-furyl)phosphane (TFP) to coordinate AgI ions has been investigated. The molar ratio and the nature of the counterions used (NO3-; BF4-) affected the reaction. Moreover, equilibrium reactions were observed and the [Ag(TFP)n]+ (n = 1-4) species involved were identified by variable-temperature 31P NMR spectroscopy. The [Ag(TFP)3]BF4 complex turned out to be the more labile species in solution and it disproportionates by means of an SN2 mechanism to yield the complexes [Ag(TFP)2(H2O)]BF4 (3) and [Ag(TFP)4]BF4 (4). Most of the compounds detected in solution were isolated and characterized in the solid state. The molecular structures of the complexes [Ag(TFP)NO3] (1), [Ag(TFP)3NO3] (2), and [Ag(TFP)2(H2O)]BF4 (3) were determined by X-ray crystal structure diffraction confirming the solution characterization data. In these structures the TFP ligand was always only bonded to the metal centre by the phosphorous atom. It is noteworthy to underline that the molecular structure of complex 1 consists of an infinite single-strand helix arising from the ability of the bridging nitrate anions to connect the [Ag(TFP)]+ units. In the structure the nitrate anions are coordinated to the metal centres in unusual modes acting simultaneously as chelating and bridging ligands. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

A Wittig reaction with 2-furyl substituents at the phosphorus atom: Improved (Z) selectivity and isolation of a stable oxaphosphetane intermediate

Wittig reactions with ylides bearing one, two or three 2-furyl groups directly bound to the phosphorus atom have been studied. Greatly improved (Z)-alkene selectivities of up to 98:2 could be observed if 2-furyl groups were present. Monitoring of the reactions by NMR spectroscopy revealed only oxaphosphetane intermediates, which became more stable with increasing number of 2-furyl substituents bound to the phosphorus atom. Oxaphosphetane 10d, with three furyl groups, was successfully isolated, and the results of a crystal structure analysis are presented. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

PHOSPHORYLATION OF FURAN, 2-METHYLFURAN, AND THIOPHENE WITH PHOSPHORUS TRIBROMIDE

In the presence of pyridine phophorus tribromide is a convenient phosphorylating agent for compounds of furan and thiophene series.Preparative methods for the synthesis of phophorylated furan, 2-methylfuran, and thiophene derivatives were developed.