1636-14-2

Usage

Uses

Used in Chemical Synthesis:
BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as an electron-withdrawing cocatalyst in rhodium-catalyzed hydroformylation reactions. This application is crucial for the selective production of aldehydes from olefins and carbon monoxide, which are essential building blocks in the synthesis of various chemicals and pharmaceuticals.
Used in Catalyst Preparation:
In the field of catalysis, BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as a ligand precatalyst for Heck coupling reactions. These reactions are important for the formation of carbon-carbon bonds in the synthesis of complex organic molecules, including pharmaceuticals and advanced materials.
Used in Palladium Chiral P-N Ligand Complexes:
BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as a reactant for the preparation of palladium chiral P-N ligand complexes. These complexes are essential for regioand stereo-selective dimerization reactions, which are crucial in the synthesis of enantiomerically pure compounds with specific biological activities.
Used in Suzuki-Miyaura Coupling:
BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is also used in the preparation of palladium tautomeric ferrocenylphosphinites as catalysts for Suzuki-Miyaura coupling. This cross-coupling reaction is widely employed in the synthesis of biaryl compounds, which are found in various pharmaceuticals, agrochemicals, and advanced materials.
Used in Michaelis-Arbuzov Rearrangement:
In the field of organophosphorus chemistry, BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as a reactant in trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement of phosphinites and phosphites. This rearrangement is an important method for the synthesis of various phosphonate and phosphinate derivatives with potential applications in pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C14H25N2P/c1-5-15(6-2)17(16(7-3)8-4)14-12-10-9-11-13-14/h9-13H,5-8H2,1-4H3

Upstream product

• 644-97-3 Dichlorophenylphosphine 
• 109-89-7 diethylamine 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 23708-47-6 1,4-bis(bromomagnesium)butane 
• 30540-36-4 3,4-dimethyl-1-phenylphosphole 
• 1073-47-8 phenyldibromophosphine 
• 685-83-6 bis(diethylamino)chlorophosphine 
• 591-51-5 phenyllithium 

Downstream Products

• 879362-21-7 phenylphosphonous acid bis-(3-methyl-3H-benzothiazol-2-ylideneamide) 
• 19858-95-8 2-phenyl-1,3,2-oxazaphospholidine 
• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 1885-79-6 2-phenyl-3-methyl-1,3,2-oxazaphospholidine 
• 59612-17-8 (2-phenyl-[1,3,2]oxazaphospholidin-3-yl)-phosphonic acid diethyl ester 
• 19858-88-9 3-(4-methoxy-phenyl)-2-phenyl-[1,3,2]oxazaphospholidine 
• 19853-56-6 2-phenyl-3-p-tolyl-[1,3,2]oxazaphospholidine 
• 19853-57-7 3-(4-chloro-phenyl)-2-phenyl-[1,3,2]oxazaphospholidine 
• 13231-65-7 C₁₈H₃₃NO₄P₂ 
• 13231-64-6 C₁₈H₃₃NO₃P₂S 
• 55054-77-8 1,5-dimethyl-3-phenyl-[1,2,4,5,3]tetrazaphosphepane 
• 4526-14-1 --anhydrid 
• 55054-74-5 1,4-diisopropyl-3-phenyl-[1,2,4,3]triazaphosphinane 
• 55054-75-6 1,4-dibutyl-3-phenyl-[1,2,4,3]triazaphosphinane 

Relevant academic research and scientific papers

General synthesis and binding affinity of position-selective phosphonodiester- and phosphotriester-incorporated oligodeoxyribonucleotides

Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.

Chiral macrocyclic N2P2 ligands and Iron(II): A marriage of interest

The N2P2 macrocyclic ligands (5S,8S,13E,14aS,18aS, 19E)-5,8-diphenyl-5,6,7,8,14a,15,16,17,18,18a-decahydrotribenzo[b,f,l][1,4,8,11] diazadiphosphacyclotetradecine ((1S,4S,9S,10S)-1a) and (5E,7R,8R,9E,15S,18S)-7, 8,15,18-tetraphenyl-7,8,15,16,17,18-hexahydrodibenzo[f,l][1,4,8,11] diazadiphosphacyclotetradecine ((1S,4S,9R,10R)-1b) were prepared by condensing the new, enantiomerically pure synthon 2,2′-((1S,1′S)-ethane-1,2- diylbis(phenylphosphinediyl))dibenzaldehyde ((S,S)-8), prepared in six steps from (2R,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine-2-borane (3)), with (1S,2S)-cyclohexane-1,2-diamine and (1R,2R)-1,2-diphenylethane-1,2- diamine under high-dilution conditions. The opposite enantiomers of the diamines gave oligomeric products. The stereospecificity of the macrocyclization reaction is explained by conformational analysis based on the X-ray structures of (1S,4S,9S,10S)-1a and (1S,4S,9R,10R)-1b. The corresponding diamino macrocycles (1S,4S,9S,10S)-2a and (1S,4S,9R,10R)-2b were prepared by reduction of the imine moiety of (1S,4S,9S,10S)-1a and (1S,4S,9R,10R)-1b, respectively. Macrocycles (1S,4S,9S,10S)-1a, (1S,4S,9R,10R)-1b, and (1S,4S,9S,10S)-2a react with [Fe(OH2)6](BF4)2 in acetonitrile to give the corresponding stable, diamagnetic bis(acetonitrile) complexes [Fe(MeCN)2(1)](BF4)2 (9a and 9b) and [Fe(MeCN)2(2a)](BF4)2 (10a). Complex 9a exists as a 3:1 mixture of trans and λ-cis-β isomers, whereas 9b and 10a adopt the λ-cis-β configuration exclusively. The bis(acetonitrile) complexes are versatile precursors and were used to prepare the bromocarbonyl analogues [FeBr(CO)(1)]BPh4 (11a and 11b).

The reactivity of arylphosphorus acid amides under Birch reduction conditions

Several classes of arylphosphorus acid amides have been tested in reactions with alkali metal solutions in liquid ammonia. The outcomes of such reactions depend on the structures of the starting materials. Generally, two processes-Birch reduction or cleavage of the P-aryl bond-can be operative. Diarylphosphinic amides tend to undergo double Birch reduction to afford bis(cyclohexadienyl)phosphinic amides. Copyright

An unconventional synthesis of dibromophosphines

Dibromophosphines, RPBr2, are obtained by reaction of tetrabromomethane with 7-substituted 7-phosphanorbornenes in toluene at ca. 100 °C. The phosphanorbornenes are obtained in situ by cycloaddition of N-phenylmaleimide with 1-substituted 3,4-d

Homometathesis and cross-metathesis coupling of phosphine-borane templates with electron-rich and electron-poor olefins

Ruthenium-catalysed olefin cross-metathesis can be used to synthesise structurally diverse acyclic phosphines protected as their borane complexes. Homodimerisations have been investigated and proved successful only for the allyl-substituted borane-protected phosphines. In the presence of various olefinic partners, allyl-substituted P templates reacted in cross-couplings to give predominantly the E products but traces of the Z isomers were always detected in the crude reaction mixtures. In contrast, cross-metathesis of vinyl-substituted phosphine boranes took place with exclusive E-selectivity. Although the conversions were consistently very good to excellent, the yields of purified products were often significantly lower suggesting that some of the newly formed compounds are prone to decompose upon purification.

Exploring the coordination chemistry and reactivity of dialkylamino- and bis(dialkylamino)-phosphines in the coordination sphere of metals

The coordination chemistry of a range of dialkylamino- and bis(dialkylamino)-phosphines, RxP(NR′2) 3-x (x = 1 or 2; R = Cl, Me, Ph, C6F5; R′ = Et, Pri), 1-7, has been studied and the resulting Group 6 tetracarbonyl and platinum dichloride bis(phosphine) complexes fully characterised. Subsequently, the reactivity of the P-N bonds of the metal-bound phosphines was probed. Treatment of R″OH (R″ = Me, Et, allyl) solutions of the bis(dialkylaminodiphenylphosphine) complexes with anhydrous HCl gas led to substitution of NR′2 by OR″; the resulting P-alkoxy complexes were isolated in excellent yields. Acidification of ethylene glycol solutions of the aminophosphine complexes afforded the corresponding bis(chlorodiphenylphosphine) derivatives. Following reaction of trans-[W(CO)4(P{NEt2}Ph2)2] with either aqueous HCl or H2SO4, trans-[W(CO) 4(P{OH}Ph2)2] could be isolated as its dichloromethane solvate in excellent yield (81%). Reactions of the bis(bis{dialkylamino} phenylphosphine) complexes under identical conditions yielded a range of unidentified products. Reactions of ligands 1-7 with [{RhCl(CO)2}2] and elemental selenium have been undertaken and the products used to assess the phosphines' donor capabilities. Depending on the substituents at phosphorus, either trans-diphosphine or cis-dicarbonyl complexes result from reaction with [{RhCl(CO)2} 2]. The sterically demanding phosphine P(NPr2 i)2Ph (5) proved unreactive towards complexation with metals, although its selenide could be prepared and isolated. In order to probe the observed lack of oxidation or complexation the molecular structure P(NPr2i)2(C6F5) has been determined by X-ray crystallography. The Royal Society of Chemistry 2003.

Formation of diastereoisomerically pure oxazaphospholes and their reaction to chiral phosphane-borane adducts

Starting with achiral phosphines and (1S,2S)-2-(methylamino)-1- phenylpropan-1-ol ((+)-pseudoephedrine) or (1R,2S)-2-(methylamino)-1- phenylpropan-1-ol ((-)-ephedrine), as chiral auxiliaries, diastereoisomerically pure oxazaphospholes were prepared (Schem

Reaktionen koordinierter Liganden V. Pentacarbonylhalogenaminophosphinkomplexe (CO)5MPRXNR'2 durch Umsetzung von (CO)5MPR(NR'2)2 mit Halogenwasserstoff

Aminophosphines RP(NR'2)2 (R = Ph, cyclo-Hex, (-)-Men, t-Bu; R' = Me, Et) as ligands L in complexes (CO)5ML (M = Cr, Mo, W) have been found to react with HX (X = Cl, Br) mainly under substitution of only one of the two dialkylamino groups by halogen.Under similar conditions the free phosphines are converted into the dihalogenphosphines.The halogenamino complexes (CO)5MPRXNR'2 are readily accessible by this reaction, the mechanism of which is discussed.The preparation of several new compounds RP(NR'2)2 is reported.

SYNTHESE UND SPEKTROSKOPISCHE CHARAKTERISIERUNG VON CYCLOPENTADIENYLEISEN-KOMPLEXEN MIT P-N-LIGANDEN DES TYPS (C6H5)3-nP(NR2)N (n = 0-3; R = CH3, C2H5)

The complex cations BF4 (L = (C6H5)3-nP(NR2)n; n = 0-3; R = CH3, C2H5) have been obtained from the reaction of BF4 (I) with L.The reaction of I with E(NR2)3 (E = As, Sb; R = CH3) is also described.Spectroscopic investigations (IR, 1H, 13C and 31P NMR) indicate an increase in electron density on the iron center through increase of the number of P-bound NR2 groups.

ZUR KENNTNIS DER ORGANOPHOSPHORVERBINDUNGEN XX. Bifunktionelle Aminophosphane (Et2N)2P-n-P(NEt2)2 und Et2N(R)P-n-P(R)NEt2

Bifunctional aminophosphanes (Et2N)2P-n-P(NEt2)2 (n = 1-10) (1) and Et2NP(R)-n-P(R)NEt2 (n = 2-4, R = Alkyl, Ph) (2), which are valuable intermediates in organophosphorus synthesis, are obtained by two methods.Because of the marked nucleophility of phosphorus in 1 and 2, reactions with Lewis acids take place very smoothly as is shown by preparation of (Et2N)2P(X)-4-(X)P(NEt2)2 (X = O, S, Se, Te, BH3, BBr3) and 4-(CH3)P(NEt2)2>2+2I-.Fission of P-N bonds by PCl3, MeOH, H2S and CS2 affords Cl2P-4-PCl2, (MeO)2P-4-P(OMe)2, (MeO)Et2NP-4-PNEt2(OMe), the dithiophosphinate 4-(H)PS2>2-2 Et2NH2+, and the dithiocarbaminate 2P-4-P2.The 31P/1H/NMR-Spectra are discussed especially with regard to steric aspects in the synthesis of the chiral compounds 2 and their derivatives.