2,2-Bis(diphenylphosphino)-1,1-binaphthalene 2,2-双(二苯基膦)-1,1’-联萘

CAS 98327-87-8 MFCD00010805

化学结构图

98327-87-8
SMILES: c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1

化学属性

Melting Point283-286°C
TSCANo
Density1.422
Solubilityinsoluble
Refractive index235 ° (C=0.3, Toluene)
Mol. FormulaC44H32P2
Appearance white to light-yellow xtl.
Mol. Weight622.67
Boiling Point724.3°C at 760 mmHg
RedoxReduction

别名和识别编码

Chemical Name2,2-Bis(diphenylphosphino)-1,1-binaphthalene
Alfabeta NameBISDIPHENYLPHOSPHINOBINAPHTHYL 2211()---,,''
Synonym (Rac)-BINAP {LY} (Rac)-BINAP {} {LY} (Rac)-BINAP {} {} {LY} (Rac)-BINAP {} {} {} {LY} (Rac)-BINAP {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} (Rac)-BINAP {} {} {} {
Beilstein Registry Number5321443
PubChem Substance ID24871738
Reaxys-RN5321443
Merck Number1223
EC NumberNone
Chemical Name Translation2,2-双(二苯基膦)-1,1’-联萘
InChIKeyMUALRAIOVNYAIW-UHFFFAOYSA-N
LabNetwork Molecule IDLN00154548
MDL NumberMFCD00010805
CAS Number98327-87-8
Canonical SMILESC1(C=CC=C2)=C2C(C3=C(C=CC=C4)C4=CC=C3P(C5=CC=CC=C5)C6=CC=CC=C6)=C(P(C7=CC=CC=C7)C8=CC=CC=C8)C=C1
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分类

  • {SNA} Asymmetric Synthesis, BINAPs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes
  • {SNA} Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis, Development Quantities for Research, Phosphine Compounds, Polydentate Phosphine Ligands
  • {SNA} Buchwald Ligands and Complexes, Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling, Development Quantities for Research, Phosphine Compounds, Polydentate Phosphine Ligands, Related Palladacycles
  • {SNA} Related Palladacycles, Buchwald Ligands and Complexes, Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis,

产品应用

  • 用作非对称反应催化的过渡金属配体。

相关文献及参考

  • The combination with Tris(dibenzyl­ideneacetone)­dipalladium(0)­, 12760, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998).
  • For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999).
  • Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010),
  • {
  • Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).
  • Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral
  • Ito, H., et al.: Nat. Chem., 2, 972 (2010),
  • See also previous entry.
  • Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of ß-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996).
  • Merck: 14,1223

安全信息

Warnings IRRITANT
WGK Germany3
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S37 Wear suitable gloves 戴适当手套;
  • S22 Do not breathe dust 不要吸入粉尘;
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition 2-8°C, protect from light, stored under nitrogen {LY} 2-8°C, protect from light, stored under nitrogen Air Sensitive {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from lig
Signal word Warning
GHS Symbol
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
Hazard Codes Xi

其他信息

  • Acros Organics:双二苯基磷酰联萘/BINAP (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 99+%(76189-55-4)
  • 下游产品:3-码啉苯硼酸四甲基二酯 --> 3-吗啉基苯甲醛 --> 3-吗啉苯酚
  • MSDS 信息:2,2'-Bis(diphenylphosp
  • Alfa Aesar:(R)-(+)-2,2'-联(二苯基膦基)-1,1'-联萘,98% (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%(76189-55-4)
  • 1,1'-联萘-2,2'-双二苯膦价格(试剂级):更新日期 产品编号 产品名称 包装 价
  • 上游原料:乙醇 --> 乙酸乙酯 --> 甲醇 --> 二氯甲烷 --> N,N-二甲基甲酰胺 --> 吡啶 --> 三苯基膦 --> 三氟乙酸酐 --> 六水合氯化镍 --> 三乙烯二胺 --> 1,2-双(二苯基膦)乙烷 --> R-1,1'-联-2-萘酚 --> 二苯基膦
  • TCI Shanghai
  • R-(+)-1,1'-联萘-2,2'-双二苯膦价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 B1406 (R)-(+)-2,2'-双(二苯膦)-1,1'-联萘 (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 1G 1370元 2011/04/16 B1406 (R)-(+)-2,2'-双(二苯膦)-1,1'-联萘 (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 5G 4780元 2010/06/21 265530050 R-(+)-1,1'-联萘-2,2'-双二苯膦 (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 99+% 5 GR 4500元
  • This product and its derivatives, rhodium and ruthenium 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. Ligand 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.
  • 1,1'-联萘-2,2'-双二苯膦价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 B2383 (+/-)-2,2'-双(二苯基膦)-1
  • MOL 文件:76189-55-4.mol
  • TCI Shanghai:(R)-(+)-1,1'-联萘-2,2'-双苯基膦 (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,>;98.0%(GC)(76189-
  • Alfa Aesar:(±)-2,2'-双(二苯基膦基)-1,1'-联萘,98% (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%(98327-87-8)
  • 用途一:用于不对称氢化催化,羰基还原等。
  • 外消旋型

系列性分类


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