422509-53-3

Basic information

• Product Name: (S)-(+)-(3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)[(1R)-1-PHENYLETHYL]AMINE
• Synonyms: (S,R)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)-(1-phenylethyl)amine 96%;(11bS)-N-[(R)-1-Phenylethyl]-dinaphtho[2,1-d:1',2'-f][1,3, 2]dioxaphosphepin-4-amine,99%e.e.;(S)-(+)-(3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)[(1R)-1-PHENYLETHYL]AMINE;(S,R)-(+)-(DIOXA-4-PHOSPHA-CYLCOHEPTA(2,1-A,3,4-A')DINAPHTHALEN-4-YL)-(1-PHENYLETHYL)AMINE, 96%;(S)-(+)-(3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)[(1R)-1-phenylethyl]amine,min.95%;(+)-N-(1(R1-Phenylethyl)-dinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-amine,.(11b,S);(S,R)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-aμ]dinaphthalen-4-yl)-(1-phenylethyl)amine
• CAS NO: 422509-53-3
• Molecular Formula: C28H22NO2P
• Molecular Weight: 435.45
• Product Categories: Chiral Phosphine;CPN
• Mol File: 422509-53-3.mol

Chemical Properties

• Melting Point: 212-213°C
• Boiling Point: 634.3±48.0 °C(Predicted)
• Appearance: white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.97±0.20(Predicted)
• Sensitive: moisture sensitive
• CAS DataBase Reference: (S)-(+)-(3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)[(1R)-1-PHENYLETHYL]AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-(3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)[(1R)-1-PHENYLETHYL]AMINE(422509-53-3)
• EPA Substance Registry System: (S)-(+)-(3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)[(1R)-1-PHENYLETHYL]AMINE(422509-53-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 422509-53-3(Hazardous Substances Data)

Usage

Uses

DSM MonoPhos Family of Highly Efficient Privileged Ligands

Upstream product

• 618-36-0 rac-methylbenzylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Relevant articles and documents

An efficient chiral phosphorus derivatizing agent for the determination of the enantiomeric excess of chiral alcohols and amines by31P NMR spectroscopy

The chiral phosphorus derivatizing agent (CDA) 1 was prepared from optically pure (S)-1,1-bis-2-naphthol. It was first used in the determination of the enantiomeric excess of chiral alcohols and amines by means of 31P NMR spectroscopy. It showe

Influence of phosphoramidites in copper-catalyzed conjugate borylation reaction

Copper(I) has become the preferred metal to catalyze the β-boration of α,β-unsaturated carbonyl compounds, and now we demonstrate that easily accessible monodentate chiral ligands, such as phosphoramidites and phosphites, can be convenient alternative ligands to induce asymmetry in the enantioselective version of this reaction, particularly in the β-boration of α,β-unsaturated imines.

31P NMR assays for rapid determination of enantiomeric excess in catalytic hydrosilylations and transfer hydrogenations

Chiral chlorophosphine (S)-(1,1′-binaphthalen-2,2′-dioxy)chlorophosphine (S)-2 was tested for its performance as a chiral-derivatizing agent (CDA) using solutions of various alcohols, amines, and N-BOC amino acids. Based on 31P NMR spectroscopy, the enantiomeric excess was determined within less than 5 min per sample, reaching an accuracy of ±1%. One-pot procedures for a combination of the method with typical homogenous catalytic transformations of prochiral ketones were established. Hydrosilylation products may be analyzed after conversion into alcohols using HF bound to PS-vinyl pyridine co-polymer beads. Transfer hydrogenations simply require solvent evaporation prior to the use of the CDA.

The development of an asymmetric Nicholas reaction using chiral phosphoramidite ligands

An asymmetric version of the Nicholas reaction involving the use of chiral phosphoramidite ligands has been developed. Treatment of a cobalt carbonyl complexed propargylic alcohol with two equivalents of the chiral ligand, followed by reaction with a sily

Asymmetric IrI-catalysed allylic alkylation of monosubstituted allylic acetates with phosphorus amidites as ligands

Monodentate phosphorus amidites derived from 2,2′-binaphthol and a variety of chiral amines were employed as ligands in IrI-catalysed allylic alkylations of unsymmetrically substituted allylic acetates. The enantio- and regioselectivities of these reactions were investigated. Phosphorus amidites of bulky secondary chiral amines induced enantioselectivities of up to 94% ee in reactions of linear substrates. Phosphorus amidites derived from chiral primary amines, which have not been previously employed in asymmetric catalysis, furnished improved regioselectivities. The use of LiCl as additive led to improved regio- and enantioselectivities. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Mono- versus bidentate ligands in rhodium-catalyzed asymmetric hydrogenation. A comparative rate study

(Matrix presented) Bidentate chiral phosphines are no longer essential for achieving a fast and highly enantioselective hydrogenation of α- or β-dehydroamino acid derivatives. In particular, a readily accessible and stable monodentate phosphoramidite can

Highly enantioselective rhodium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites

New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-β-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems were established for (E)-β-(acylamino)acrylates (98-99% ee) and (Z)-β-(acylamino)acrylates (92-95% ee) based on phosphoramidites 2 and 3, respectively. Copyright