137156-22-0

Basic information

• Product Name: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE
• Synonyms: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE;(S)-(+)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE;(S)-(+)-Chlorodinaphthol[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,min.97%;(S)-(+)-4-CHLORODINAPHTHOL[2,1-D:1'',2''-F][1,3,2]DIOXAPHOSPHEPIN, MIN. 97%;(R)-(-)-4-Chlorodinaphthol[2,1-d:1',2'-f][1,3,2]dioxaphosphepin;S-4-chloro-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin;(11bS)-4-Chlorodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin;(S)-(+)-4-Chlorodinaphthol[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
• CAS NO: 137156-22-0
• Molecular Formula: C₂₀H₁₂ClO₂P
• Molecular Weight: 350.73
• Product Categories: Chiral Phosphine;P-Cl
• Mol File: 137156-22-0.mol

Chemical Properties

• Boiling Point: 518.5±19.0 °C(Predicted)
• Appearance: white/Powder
• Sensitive: moisture sensitive
• CAS DataBase Reference: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE(137156-22-0)
• EPA Substance Registry System: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE(137156-22-0)

Safety Data

• Hazardous Substances Data: 137156-22-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE is used as a chiral ligand for [application reason] in the development of enantioselective catalysts, which are crucial for the synthesis of pharmaceutical compounds with high purity and selectivity. The ability to create enantioselective reactions ensures that the desired enantiomer of a drug is produced, avoiding potential side effects and improving the therapeutic efficacy of the medication.
Used in Chemical Synthesis:
In the field of chemical synthesis, (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE is used as a catalyst in [application type] for facilitating asymmetric reactions. This is essential for the production of chiral compounds with specific stereochemistry, which is vital in creating molecules with desired biological activities and properties.
Used in Research and Development:
(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE is utilized as a research tool in [application type] for studying the mechanisms of asymmetric catalysis and developing new catalytic systems. Its unique properties make it a valuable asset in academic and industrial research settings, where it contributes to the advancement of enantioselective synthetic methods and the discovery of novel chemical compounds.

Upstream product

• 602-09-5 1,1'-bi-2-naphthol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 137156-23-1 4-(4-Methoxy-phenoxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 150646-49-4 4-Triphenylsilanyloxy-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 182181-52-8 (+/-)-2-(1,3-bis(diphenylphosphino)-2-propoxy)dinaphtho[2,1-d:4,3-f]-1,3-dioxa-2-phosphepin 
• 180581-29-7 4-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 1228672-54-5 1,1-dibenzyl-3-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)urea 

Relevant articles and documents

Diastereoselective formation of 18-membered ring BINOL-hydrogen phosphonate dimers - Quasicovalent hydrogen bonds?

Diastereoselective syntheses of the unusual dimers, 4-heptyl-2-(2′- hydroxy-binaphthyl)hydrogen phosphonate (5) and the cyclohexyl analogue (7), are achieved by hydrolysis of 4-(3,5-dioxa-4-phosphacyclohepta[2,1-α;3,4- α′]dinaphthalene-4-yloxy)heptane (4)

Asymmetric hydrocyanation of olefins catalyzed by chiral diphosphite-nickel complexes

Chiral aryl diphosphite ligands derived from binaphthol were found to be effective in the nickel-catalyzed hydrocyanation of a variety of olefins. Enantioselective hydrocyanations of styrene, 4-substituted styrenes and norbornene were achieved with excell

On the use of seven-membered phosphorous heterocycles based on 2,2′-dihydroxy-1,1′-binaphthalene and 1,4:3,6-dianhydro-D-mannitol in the 31P NMR analysis of the enantiomeric composition of chiral alcohols

Some aspects of phosphorylation of 2,2′-dihydroxy-1,1′-binaphthalene (BINOL) and 1,4:3,6-dianhydro-D-mannitol (isomannide) were investigated. The possibility of using the corresponding cyclic chloro-and amidophosphites for the analysis of enantiomeric com

New catalysts for the asymmetric hydrosilylation of ketones discovered by mass spectrometry screening

A method for determining enantiomeric excess by mass spectrometry was employed to screen a family of chiral phosphite P,N-ligands for activity in the rhodium-catalyzed asymmetric hydrosilylation of ketones. The identification of an effective set of ligand

Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization

The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.

Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks

A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole-terpenoid framewo

P-chirogenic diphosphazanes with axially chiral substituents and their use in rh-catalyzed asymmetric hydrogenation

A convenient synthesis of enantiopure P-chirogenic diphosphazanes incorporating bulky bisphenol and 1,1′-bi-2-naphtholderived substituents via the functionalization of a readily accessible enantiopure lithium phosphinoamide with chlorophosphoridites was developed. Since the product requires no subsequent deprotection, the protocol provides an easy, convenient synthesis of P-chirogenic ligands on the gram scale. The ligands were applied in the Rh-catalyzed asymmetric hydrogenation of benchmark substrates furnishing enantiomeric excess values up to 96%.

Rh(i)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates

An asymmetric intermolecular [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates, which was catalyzed by a rhodium(i)-chiral phosphoramidite complex, was developed. This protocol provided a highly enantioselective access to prepare carbonyl substituted cyclohexa-1,4-dienes with up to 96% yield and >99% ee. Notably, a cycloaddition on the 10 g scale gave the product in 92% yield and with 99% ee, which showed great potential for the scale-up synthesis of carbonyl substituted cyclohexa-1,4-dienes. In addition, oxidative aromatizations and hydrolysis of the products were also investigated.

ORGANOPHOSPHORUS COMPOUNDS, CATALYTIC SYSTEMS COMPRISING SAID COMPOUNDS AND METHOD OF HYDROCYANATION USING SAID CATALYTIC SYSTEMS

The present invention relates to organophosphorus compounds belonging to the phosphinite-phosphite family, catalytic systems comprising a metallic element forming a complex with said phosphinite-phosphite compounds and methods of hydrocyanation employed in the presence of said catalytic systems.

Palladium-catalyzed enantioselective allylic alkylations through C-H activation

A new ligand class: The title reaction was made possible by the discovery of a new class of phosphoramidite ligands. A variety of sterically and electronically diverse allylarenes undergo reaction with 2-acetyl-1-tetralones to form quaternary carbon stereocenters. This is a conceptually and mechanistically distinct strategy from traditional methods for the synthesis of enantioenriched allylic substitution products. 2,6-DMBQ=2,6- dimethylbenzoquinone. Copyright