84127-06-0

Basic information

• Product Name: bis[4-(N,N-dimethylaminephenyl)]phosphine oxide
• Synonyms: bis[4-(N,N-dimethylaminephenyl)]phosphine oxide
• CAS NO: 84127-06-0
• Molecular Weight: 288.329
• Mol File: 84127-06-0.mol

Chemical Properties

• CAS DataBase Reference: bis[4-(N,N-dimethylaminephenyl)]phosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: bis[4-(N,N-dimethylaminephenyl)]phosphine oxide(84127-06-0)
• EPA Substance Registry System: bis[4-(N,N-dimethylaminephenyl)]phosphine oxide(84127-06-0)

Safety Data

• Hazardous Substances Data: 84127-06-0(Hazardous Substances Data)

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 762-04-9 phosphonic acid diethyl ester 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 762-04-9 Diethyl phosphonate 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 698-69-1 4-chloro-N,N-dimethylaniline 

Downstream Products

• 7439-52-3 bis(p-(dimethylamino)phenyl)phosphonic acid 
• 35003-92-0 2-[Bis-(4-dimethylamino-phenyl)-phosphinoyl]-1,4-diphenyl-butane-1,4-dione 
• 35003-60-2 N-{[Bis-(4-dimethylamino-phenyl)-phosphinoyl]-phenyl-methyl}-benzenesulfonamide 
• 35003-93-1 C₂₉H₃₂N₃OP 
• 108142-53-6 [Bis-(4-dimethylamino-phenyl)-phosphinoyl]-methanol 
• 108142-52-5 bis-(p-dimethylaminophenyl)chloromethylphosphine oxide 
• 1769-51-3 bis-(4-dimethylaminophenyl)phosphine 
• 803-20-3 bis(4-(N,N'-dimethylamine)phenyl)phenylphosphine oxide 
• 84127-04-8 bis(4-methoxyphenyl)phosphine 
• 125518-43-6 tetrakisbisphosphine 
• 81542-31-6 bismethylphosphine oxide 
• 35003-61-3 N-{[Bis-(4-dimethylamino-phenyl)-phosphinoyl]-phenyl-methyl}-4-chloro-benzenesulfonamide 

Relevant articles and documents

Visible-light-driven metal-free aerobic synthesis of highly diastereoselective phosphinoylpyrroloindoles

A visible-light-driven metal-free phosphorus radical mediated construction of 2-phosphinoyl-3H-pyrrolo[1,2,a]indoles is described. This mild tandem phosphinoylation/cyclization protocol utilizes air as a green oxidant and proceeds in a short span of time at room temperature with high functional group tolerance, and excellent chemo- A nd diastereoselectivity.

Siladifluoromethylation and Deoxo-trifluoromethylation of PV-H Compounds with TMSCF3: Route to PV-CF2- Transfer Reagents and P-CF3 Compounds

A method for siladifluoromethylation of dialkyl phosphonates and secondary phosphine oxides with TMSCF3 to produce nucleophilic PV-CF2- transfer reagents is disclosed, with multigram scale reactions included. Condition-dependent divergent reactivity under the established conditions is demonstrated by the formation of trifluoromethylphosphines. Both one-pot transformations are operationally simple and employ inexpensive materials. Mechanistic investigations suggest the divergent reactivity originates from a common intermediate, with Li+ concentration directing the chemoselectivity.

Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides

A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.

Rapid Metal-Free Formation of Free Phosphines from Phosphine Oxides

A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH3?THF) and borane dimethyl sulfide complex (BH3?SMe2). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co-catalyst, but also with silane and aluminium based reagents. (Figure presented.).

Synthesis and Characterization of Manganese(I) Carbonyl Complexes of the Type [(OC)4Mn{μ-P(R)Aryl}]2

Metalation of secondary phosphanes HPRR′ [R = R′ = C6H4-4-Me, C6H3-3,5-Me2 (3), C6H4-4-NMe2 (4); R/R′ = Ph/cHex] with Mn2(CO)10 in boiling xylene

Selective dehydrocoupling of phosphines by lithium chloride carbenoids

The development of a simple, transition-metal-free approach for the formation of phosphorus-phosphorus bonds through dehydrocoupling of phosphines is presented. The reaction is mediated by electronically stabilized lithium chloride carbenoids and affords a variety of different diphosphines under mild reaction conditions. The developed protocol is simple and highly efficient and allows the isolation of novel functionalized diphosphines in high yields.

Selective formation of a polar incomplete coordination cage induced by remote ligand substituents

Instead of highly symmetrical T-symmetry cages common in self-assembly, the p-NMe2-substituted triphosphine CH3C{CH 2P(4-C6H4NMe2)3 gives open, polar C3 symmetry cages [Ag6(triphos) 4X3]3+ which lack one of the expected face-capping anions; despite its subtlety this difference occurs selectively in solution and two examples have been crystallographically characterised.

Process research on the asymmetric hydrogenation of a benzophenone for developing the manufacturing process of the squalene synthase inhibitor TAK-475

A practical synthetic method for the synthesis of the chiral benzhydrol 8, which is the key intermediate of the squalene synthase inhibitor TAK-475 (1), has been developed. The method, via asymmetric hydrogenation of the benzophenone 7, employed Noyori's ruthenium precatalyst of the type [RuCl 2(diphosphine)(diamine). We focused on tuning of the chiral diphosphine, and have discovered a novel ligand, DADMP-BINAP (18c), for the catalyst that has allowed reduction of the operating pressure in the asymmetric hydrogenation. The precatalyst containing 18c performed effectively at low hydrogen pressure (1 MPa) with sufficient enantioselectivity, and the result enabled us to successfully obtain enantiomerically pure 8 on a multikilogram scale.

DIPHOSPHINE LIGAND AND TRANSITION METAL COMPLEX USING THE SAME

The present invention provides a novel ligand represented by the following formula and a novel transition metal complex having the ligand, which shows superior enantioselectivity and catalytic efficiency, particularly high catalyst activity, in various asymmetric synthesis reactions. A transition metal complex having, as a ligand, a compound represented by the formula wherein R4 is a hydrogen atom or a C1-6 alkyl group optionally having substituent(s), and R5 and R6 are each a C1-6 alkyl group optionally having substituent(s), or the formula is a group represented by the formula wherein ring B is a 3- to 8-membered ring optionally having substituent (s).

A superior method for the reduction of secondary phosphine oxides

(Chemical Equation Presented) Diisobutylaluminum hydride (DIBAL-H) and triisobutylaluminum have been found to be outstanding reductants for secondary phosphine oxides (SPOs). All classes of SPOs can be readily reduced, including diaryl, arylalkyl, and dialkyl members. Many SPOs can now be reduced at cryogenic temperatures, and conditions for preservation of reducible functional groups have been found. Even the most electron-rich and sterically hindered phosphine oxides can be reduced in a few hours at 50-70°C. This new reduction has distinct advantages over existing technologies.