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
• Article Data: 27

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

General Description

(R)-(-)-1,1'-binaphthyl-2,2'-dioxychlorophosphine is a chiral phosphine ligand commonly used in asymmetric catalysis. It is a white to off-white solid and is commercially available. (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE is known for its ability to facilitate asymmetric catalysis and has been used in a variety of organic transformations, including asymmetric hydrogenation, allylic substitution, and other types of C-C and C-H bond activations. Its unique structure and stereochemistry makes it a valuable tool for creating enantioselective reactions in organic synthesis. The compound is often used in conjunction with metal catalysts to achieve high enantioselectivity in a variety of reactions.

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

• 479253-15-1 (2'S)-2-[(1'-benzyl-pyrrolidinyl-2')methoxy]dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine 
• 688764-75-2 (R)-(1,1'-binaphthyl-2,2'-diyl)(5-(phenyl-2-yl)-10,15,20-tris(phenyl) zinc(II) porphyrin)phosphite 
• 688764-15-0 (S)-(1,1'-binaphthyl-2,2'-diyl)(5-(phenyl-2-yl)-10,15,20-tris(phenyl) zinc(II) porphyrin)phosphite 
• 1272384-56-1 (Rax)-2-[N-(o-carboranylmethyl)-N-(4-fluorophenyl)amino]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepane 
• 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 
• 182181-52-8 (+/-)-2-(1,3-bis(diphenylphosphino)-2-propoxy)dinaphtho[2,1-d:4,3-f]-1,3-dioxa-2-phosphepin 
• 171878-46-9 (racemic)-(1,1'-binaphthyl-2,2'-dioxy)PN(CHMe₂)PPh₂ 

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)

Iridium-catalyzed enantioselective allylic vinylation with potassium alkenyltrifluoroborates

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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.

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.