376355-58-7

Basic information

• Product Name: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][
• Synonyms: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][;BIPOL-A1(S), (S,S)-N-(5,7-Diox-6-phosphadibenzo[a,c]cyclohepten-6-yl)bis(1-phenylethyl)amine, O,Oμ-(2,2μ-Biphenyldiyl) N,N-bis[(S)-1-phenylethyl]phosphoramidite;N,N-Bis[(1S)-(-)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine;N,N-Bis[(1R)-(+)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine;1,1'-Biphenyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite;N,N-bis[(1R)-1-phenylethyl]-Dibenzo[d,f][1,3,2]dioxaphosphepin-6-aMine;Biphenyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite
• CAS NO: 376355-58-7
• Molecular Formula: C₂₈H₂₆NO₂P
• Molecular Weight: 439.492
• Product Categories: phosphine-amine ligand;Chiral Phosphine;CPN
• Mol File: 376355-58-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 99-102 °C
• Boiling Point: 578.426°C at 760 mmHg
• Flash Point: 303.621°C
• Appearance: white/Powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.31±0.20(Predicted)
• Sensitive: moisture sensitive
• CAS DataBase Reference: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(CAS DataBase Reference)
• NIST Chemistry Reference: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(376355-58-7)
• EPA Substance Registry System: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(376355-58-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 376355-58-7(Hazardous Substances Data)

Usage

Description

N,N-Bis-[(S)-1-PHENYLETHYL]DIBENZO[D F][1,3,2]DIOXAPHOSPHEPIN-6-AMINE is a complex organic compound with a unique structure that features a dibenzo[d,f][1,3,2]dioxaphosphepin core and phenylethyl substituents. This molecule is known for its potential applications in various chemical reactions and processes.

Uses

1. Used in Iridium-Catalyzed Allylic Arylation:
N,N-Bis-[(S)-1-PHENYLETHYL]DIBENZO[D F][1,3,2]DIOXAPHOSPHEPIN-6-AMINE is used as a ligand in the iridium-catalyzed allylic arylation. In this application, the compound plays a crucial role in enhancing the efficiency and selectivity of the reaction, leading to the formation of desired products with improved yields.
2. Used in Copper Complex Preparation for Asymmetric Addition Reactions:
N,N-Bis-[(S)-1-PHENYLETHYL]DIBENZO[D F][1,3,2]DIOXAPHOSPHEPIN-6-AMINE is also utilized in the preparation of a copper complex (Cu2X2L3). This complex is specifically designed to detect transmetalation intermediates in asymmetric addition reactions using ZnEt2. N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F]['s unique structure and properties make it an ideal candidate for this purpose, allowing for better understanding and control of the reaction mechanisms.

Reaction

Ligand for the copper catalyzed, highly regioselective substitution reactions of a wide variety of aromatic substituted allylic halides to form branched chiral products from diverse Grignard reagents. Ligand for the copper catalyzed, highly enantioselective conjugate addition of diethylzinc to eneones and nitro olefins. Ligand for the nickel catalyzed, highly enantioselective hydrovinylation of alkenes. Ligand for the rhodium catalyzed, highly enantioselective hydroformylation of vinylarenes. Ligand for gold catalyzed asymmetric Intramolecular hydroamination of allenes

InChI:InChI=1/C28H26NO2P/c1-21(23-13-5-3-6-14-23)29(22(2)24-15-7-4-8-16-24)32-30-27-19-11-9-17-25(27)26-18-10-12-20-28(26)31-32/h3-22H,1-2H3/t21-,22-/m0/s1

Upstream product

• 40648-92-8 hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine 
• 16611-68-0 6-chloro-dibenzo[d,f][1,3,2]-dioxaphosphepin 
• 21003-56-5 (1S,1'S)-bis(1-phenylethyl)amine 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 777067-25-1 [(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride 

Relevant articles and documents

On the use of phosphoramidite ligands in copper-catalyzed asymmetric transformations with trialkylaluminum reagents

Phosphoramidites based on BINOL readily react with trimethylaluminum in "noncoordinating" solvents, leading to the corresponding aminophosphine which is the real ligand in copper-catalyzed asymmetric transformations. This artifact explains the experimenta

(R)-2,2’-Binaphthoyl-(S,S)-di(1-phenylethyl) aminophosphine. Scalable protocols for the syntheses of phosphoramidite (feringa) ligands

-

Rh-catalyzed enantioselective conjugate addition of arylboronic acids with a dynamic library of chiral tropos phosphorus ligands

A library of 19 chiral tropos phosphorus ligands, based on a free-to-rotate (tropos) biphenol unit and a chiral P-bonded alcohol (11 phosphites, 1-P(O)2O to 11-P(O)2O) or secondary amine (8 phosphoramidites, 12-P(O)2N to 19-P(O)2N). were screened, individually and in combinations of two, in the rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to enones and enoates. High enantioselectivities (up to 99% ee) and excellent yields were obtained in the addition to either cyclic or acyclic substrates. The flexible biphenolic P ligands outperformed the analogous rigid binaphtholic P ligands. Variable-temperature 31P NMR studies revealed that the biphenolic ligands are tropos even at low temperature. Only below 190 K was a coalescence observed: upon further cooling, two atropisomers were detected. The Rh homocomplexes ([Rh(La)2]+) were also studied: in general, a single doublet (P-Rh coupling) was observed in the case of the biphenolic phosphite ligands, over the temperature range 380-230 K, demonstrating their tropos nature in the rhodium complexes even at low temperatures. On the other hand, the phosphoramidites showed different behaviors depending on the structure of the ligand and on the nature of the rhodium source. The spectrum at 230 K of the mixture of [Rh(acac)(eth)2] (eth = C2H4) with phosphite 6-P(O)2O and phosphoramidite 19-P(O)2N (the most enantioselective ligand combination in the conjugate addition reaction) revealed the presence of four homocomplexes (total approximately 40%: [Rh(6-P(O)2}2], [Rh{(aR)-19-P(O)2N}2], [Rh((aS)-19-P(O)2N) 2], [Rh((aR)-19-P(O)2N}((aS)-19-P(O)2N}]) and one heterocomplex, [Rh{6-P(O)2O){(aR)-19-P(O)2NJ] (approximately 60%) In the heterocomplex, the biphenol-derived phosphite is free to rotate (tropos) while the biphenol-derived phosphoramidite shows a temperature-dependent tropos/atropos behavior (coalescence temperature = 310 K).