155613-52-8

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;(R)-(-)-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, MIN. 97%;(R)-1,1′-Binaphthyl-2,2′-diyl phosphorochloridate;R-4-chloro-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin;(11bR)-4-Chlorodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin;(R)-(1,1'-Binaphthalene-2,2'-dioxy)chlorophosphine
• CAS NO: 155613-52-8
• Molecular Formula: C₂₀H₁₂ClO₂P
• Molecular Weight: 350.73
• Product Categories: Chiral Phosphine;P-Cl
• Mol File: 155613-52-8.mol
• Article Data: 27

Chemical Properties

• Melting Point: 92-94℃
• Boiling Point: 518.5±19.0 °C(Predicted)
• Appearance: white/Powder
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• 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(155613-52-8)
• EPA Substance Registry System: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE(155613-52-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 155613-52-8(Hazardous Substances Data)

Usage

General Description

(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE is a chemical compound that is commonly used as a chiral ligand in asymmetric synthesis and catalysis. It belongs to the family of binaphthyl-based ligands, which are widely used in various organic reactions to control the stereochemistry of the products. (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE has a chiral phosphorus center and two biaryl groups, which provide high enantioselectivity in a range of transformations. It is known for its utility in the synthesis of pharmaceuticals, natural products, and other fine chemicals, making it an important tool for organic chemists in the development of new and efficient synthetic methods.

Upstream product

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

Downstream Products

• 150646-49-4 4-Triphenylsilanyloxy-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 479253-09-3 (1'S,2'R)-2-(1'-benzyl-3'-dimethylamino-2'-methyl-1'-phenyl-propoxy)dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine 
• 137156-23-1 4-(4-Methoxy-phenoxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 149917-85-1 (R,S)-binaphos 
• 1110685-33-0 rac-(1,1'-binaphthyl-2,2'-diyl)(2,4-di-tert-butylphenyl)phosphite 

Relevant articles and documents

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.

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%.

Iridium-catalyzed enantioselective allylic vinylation with potassium alkenyltrifluoroborates

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