(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene - ≥98% , CAS No.76189-55-4

CAS: 76189-55-4 Cat. No.: B106732 Molecular Weight: 622.67 EC Number: 616-304-7

GRADE & PURITY ≥98%

Synonyms

(R)-(+)-BINAP | 2,2'-bis(diphenylphosphino)-1,1'-binaphtyl | FT-0604001 | HY-Y0982 | MUALRAIOVNYAIW-UHFFFAOYSA- | OL10216 | Phosphine, 1,1'-(1,1'-binaphthalene)-2,2'-diylbis(1,1-diphenyl- | (R)-2,2'-Bis(diphenylphosphanyl)-1,1'-binaphthalene | (S)-(-)-2,2

Storage

Argon charged,Room temperature

Shipped In

Normal

Overview

Product Introduction

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions. 

Application

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.

Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds. 

Specifications

Synonyms

(R)-(+)-BINAP | 2, 2'-bis(diphenylphosphino)-1, 1'-binaphtyl | FT-0604001 | HY-Y0982 | MUALRAIOVNYAIW-UHFFFAOYSA- | OL10216 | Phosphine, 1, 1'-(1, 1'-binaphthalene)-2, 2'-diylbis(1, 1-diphenyl- | (R)-2, 2'-Bis(diphenylphosphanyl)-1, 1'-binaphthalene | (S)-(-)-2, 2

Specifications & Purity

≥98%

Storage

Argon charged, Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488190831
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488190831
• Canonical Smiles: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
• IUPAC Name: [1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
• InChIKey: MUALRAIOVNYAIW-UHFFFAOYSA-N
• INCHI: 1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H
• Isomeric SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
• WGK Germany: 3
• Molecular Weight: 622.67
• Reaxy-Rn: 4914062
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4914062&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Phenylphosphines and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Phenylphosphines and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylphosphines and derivatives
• Alternative Parents: Naphthalenes Organic phosphines and derivatives Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Triphenylphosphine - Naphthalene - Phenylphosphine - Phosphine - Organopnictogen compound - Hydrocarbon derivative - Organophosphorus compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylphosphines and derivatives. These are compounds containing a phenylphosphine, which consists of phosphine substituent bound to a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in water.
• Sensitivity: Air & moisture sensitive
• Specific Rotation[α]: 235 ° (C=0.3, Toluene)
• Melt Point(°C): 239-242°C
• Molecular Weight: 622.700 g/mol
• XLogP3: 11.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 622.198 Da
• Monoisotopic Mass: 622.198 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 797.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Minting Liang, Xiaofeng Xia, Xiang Liu, Hexing Li.  (2015)  Asymmetric Hydrosilylation of Aromatic Ketones Catalyzed by an Economical and Effective Copper-Diphosphine Catalytic System in Air.  CHINESE JOURNAL OF CHEMISTRY,  33  (5): (578-582).  [PMID:] [10.1002/cjoc.201500072]