5994-87-6

Usage

Uses

Used in Pharmaceutical Industry:
Diphenylphosphinamide is used as a key intermediate for the synthesis of chiral molecules with specific biological activities. Its ability to provide 5H-oxazol-4-ones with high diastereoselectivity and enantioselectivity makes it a valuable tool in the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
Diphenylphosphinamide is also used in the synthesis of chiral agrochemicals, where its ability to provide 5H-oxazol-4-ones with high diastereoselectivity and enantioselectivity can lead to the development of more effective and selective pesticides and other agrochemicals.

InChI:InChI=1/C12H12NOP/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,13,14)

Upstream product

• 24630-80-6 diphenylphosphine oxide 
• 67-56-1 methanol 
• 75-18-3 dimethylsulfide 
• 4129-17-3 diphenylphosphoranyl azide 
• 60066-32-2 trimethylammonio-P,P-diphenylphosphinamidate 
• 104-87-0 4-methyl-benzaldehyde 
• 82944-84-1 N-[(1E)-1-phenylethylidene]-P,P-diphenylphosphinic amide 
• 104-88-1 4-chlorobenzaldehyde 
• 89-98-5 2-chloro-benzaldehyde 
• 124730-93-4 triethylammonio-N-diphenylphosphinoylimide 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 67-68-5 dimethyl sulfoxide 
• 73452-22-9 N-(Diphenylphosphinyl)-hydroxylamin-methylsulfonat 

Downstream Products

• 610-15-1 2-nitrobenzamide 
• 619-56-7 4-chlorobenzamide 
• 645-09-0 3-nitrobenzamide 
• 619-80-7 4-nitrobenzamide 
• 6779-62-0 isocyanatodiphenylphosphine oxide 
• 56372-47-5 N,N-diethyl P,P-diphenylphosphinamide 
• 1110-78-7 hexaphenyl-cyclotriphosphazene 
• 27127-08-8 N-benzyl-P,P-diphenylphosphinic amide 
• 27127-09-9 N,N-dibenzyl-P,P-diphenylphosphinic amide 
• 6779-25-5 N-(diphenylphosphinyl)-N'-phenylurea 
• 6778-80-9 1-Diphenylphosphinyl-3-n-butyl-harnstoff 
• 6778-81-0 N-Isopropyl-N'-diphenylphosphinyl-harnstoff 
• 6230-69-9 N-propyl-P,P-diphenylphosphinic amide 
• 84718-88-7 n-diphenylphosphinyldimethylsulphilimine 

Relevant academic research and scientific papers

Electrooxidation of chlorodiphenylphosphine under ammonia atmosphere. Synthesis of 2,2,4,4,6,6-hexaphenylcyclotriphosphazene and iminobis(Aminodiphenylphosphorus) chloride

Electrooxidation of MeCN solution of chlorodiphenylphosphine in the presence of Cl? under NH3 atmosphere gave a mixture of 2,2,4,4,6,6-hexaphenylcyclotriphosphazene and iminobis(aminodiphenylphosphorus) chloride.

A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation

This manuscript describes a modular method for preparing N-alkyl phosphinic amides from primary or secondary alcohols and primary phosphinic amide (R1R2P = ONH2) nucleophiles via transfer hydrogenation. The transformation typically proceeds in excellent yields, employs conveniently available reagents, and produces water as the only byproduct.

Efficient asymmetric synthesis of structurally diverse p-stereogenic phosphinamides for catalyst design

The use of chiral phosphinamides is relatively unexplored because of the lack of a general method for the synthesis. Reported herein is the development of a general, efficient, and highly enantioselective method for the synthesis of structurally diverse P-stereogenic phosphinamides. The method relies on nucleophilic substitution of a chiral phosphinate derived from the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide. These chiral phosphinamides were utilized for the first synthesis of readily tunable P-stereogenic Lewis base organocatalysts, which were used successfully for highly enantioselective catalysis.

Nucleophilic addition of TMSCCl3 to N-phosphinoyl benzaldimines: A route to N-phosphinoyl-α-(trichloromethyl)benzylamines

Nucleophilic addition of readily available TMSCCl3 to N-phosphinoyl benzaldimines allows preparation of N-phosphinoyl-α-(trichloromethyl)benzylamines. Typically, the reaction in THF at room temperature using tetrabutylammonium difluorotriphenylsilicate (TBAT) as a catalytic promoter, afforded very good yields (65-95% range) for most derivatives within 1 h at room temperature.

Discovery and synthetic value of a novel, highly crowded cyclopentadienylphosphane Ph2P-CpH and its ferrocenyl-bisphosphane dppf

Base-catalysed condensation of Ph2P-C5H5 (1) with an excess of acetone leads to a fulvene-like diphenyl(4,4,6-trimethyl- 4,5-dihydropentalen-2-yl)phosphane Ph2P-C11H13 (3) as a product of double condensation. Carbometallation of 3 with MeLi, followed by aqueous work-up, results in formation of a new cyclopentadienylphosphane bearing a highly sterically demanding, anellated 1,1,3,3-tetramethylcyclopentane moiety (4, Ph2P-CpH). It reacts with chalcogene oxidants (H2O2, S8, Se) to form the corresponding phosphane chalcogenides Ph2P(=X)CpH, X = O (5), S (6), Se (7) in high yields. Quatemization of 4 with MeI gives the phosphonium salt 8 as a single isomer in high yield. Dehydrohalogenation of 8 by reaction with nBuLi gives Cp-phosphonium ylide Ph2P(Cp )Me (9). An alternative protocol towards 9 that includes deprotonation of 8 with benzylpotassium followed by P-alkylation is superior and gives 9 in more than 95% yield. Staudinger reaction of 4 with tBuN3 gives only P-arnino-cyclopentadienylidenephosphorane Ph2P(Cp)-NHtBu (10), whereas with Me3SiN3 only the tautomeric P-imino-cyclopentadienylphosphane Ph2P(NSiMe3)CpH (11) was isolated. Hydrolysis of 11 with wet MeCN leads to the new parent P-arnino-cyclopentadienyhdenephosphorane Ph2P-(Cp)NH 2 (12). Treatment of 4 with benzylpotassium followed by transmetallation with FeCl2 leads to the sterically most crowded ferrocenyl-bisphosphane [{Ph2P-Cp}2Fe] (13, dppf) in high yield. Its X-ray diffraction analysis reveals an anti-orientation of phosphane functionalities at both cyclopentadienyl rings. However, upon reaction of dppf with [PdCl2(MeCN)2], a constrained syn-orientation is achieved in the product [[dppf] PdCl2] (14). Halogen exchange by reaction of 14 with NaI leads to the corresponding [{dppf}PdI2] (15). Molecular structures of 4, 9, 13 and 15 have been confirmed by XRD studies.

Reaction prospecting by 31P NMR: enantioselective rhodium-DuPhos catalysed addition of ZnMe2 to diphenylphosphinoylimines

Chiral shift 31P NMR spectroscopy allows the identification of ligand leads in asymmetric catalyst systems for ZnMe2 addition to ArCH{double bond, long}NP(O)Ph2. Subsequent GC-based optimisation shows [RhCl(CH2{double bond, long}CH2)2]2 and (R,R)-MeDuPhos to be the optimal pre-catalyst combination (product in 78-93% ee). Transmetallation of [(MeDuPhos)Rh{N(P(O)Ph2-CHMeAr}] with ZnMe2 appears to be the rate limiting step of the catalytic cycle as competing coordination by the imine starting material leads to Ph2P(O)NHCH2Ar via MVP hydrogen-transfer. This limitation can largely be overcome by the slow addition of the imine.

Multicomponent one-pot procedure for the synthesis of free α-chiral amines from aldehydes

The synthesis of free a-chiral amines by a one-pot multi-component procedure from commercially available starting materials is described. This enantioselective reaction involves a catalytic asymmetric addition of dialkylzinc reagents to N-diphenylphosphin

Olefination reactions through phosphazenes

The first synthesis of di-, tri- and tetrasubstituted alkenes through reaction of lithium P-diphenyl(alkyl)(N-carboxymethyl)phosphazenes with aldehydes and ketones is reported.

Rearrangement of O-benzoyl-N-(diphenylphosphinothioyl) hydroxylamine: An 18O-labelling investigation of oxygen-sulfur transposition

When Ph2P(S)NHOCOPh labelled with 18O in the C=O group (43% isotopic enrichment) reacts with NaOMe in MeOH, the products are unlabelled Ph2P(O)NH2 and labelled PhCO2Me (43% isotopic enrichment). By implication, the intermediate Ph2P(O)NHSCOPh that results from rearrange- meat (translation of O and S atoms) has all the label in the C=O group and none in the P=O group.