(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

• Catalog No.: 295825
• CAS Number: 76189-56-5
• M. F.: C44H32P2
• M. W.: 622.672402
• Purity: 97%

SYNONYMS

• Title: (S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘
• IUPAC name: {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane
• IUPAC Traditional name: binap
• Synonyms: (S)-(-)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine); (S)-(-)-1,1′-联萘-2,2'-双二苯膦; (S)-(-)-BINAP

DATABASE IDS

• Beilstein Number: 5321443
• MDL Number: MFCD00010805
• CAS Number: 76189-56-5
• PubChem SID: 24857815

PROPERTIES

• Linear Formula: [(C6H5)2PC10H6-]2
• Optical Purity: ee: 99% (HPLC)
• Purity: 97%
• Melting Point: 238-240 °C(lit.)
• Optical Rotation: [α]19/D -233°, c = 0.3 in toluene
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• German water hazard class: 3

DETAILS

Description (English)

Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Application
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,1 β-keto esters,2 and α-amino ketones.3 They have also been used for asymmetric hydrogenation4 and hydroformylation of olefins,5 asymmetric Heck reactions,6 and asymmetric isomerizations of allyls.7,8Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

Description (简体中文)

包装
1, 5 g in glass bottle
250 mg in glass bottle
Application
2,2′-双(二苯基膦)-1,1′-联萘及其铑和钌衍生物可作为高选择性均相催化剂，用于芳基酮、1β-酮酸酯2和 α-氨基酮的还原反应。3也可用于烯烃的不对称氢化4和氢甲酰化反应、5不对称 Heck 反应6和烯丙基的不对称异构化反应。7,8 用于钯催化不对称串联 Heck 反应的配体，这种碳负离子捕获过程可合成三环倍半萜烯。也可用于钌催化的 α,β-不饱和酸的不对称氢化反应。
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates