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693049

Sigma-Aldrich

(R)-T-BINAP

Sinonimo/i:

(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl

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About This Item

Formula empirica (notazione di Hill):
C48H40P2
Numero CAS:
99646-28-3
Peso molecolare:
678.78
Numero MDL:
MFCD01311709
Codice UNSPSC:
12352005
ID PubChem:
329761557
NACRES:
NA.22

Stato

solid

Livello qualitativo

100

Attività ottica

[α]20/D +162°, c = 0.5 in benzene

Impiego in reazioni chimiche

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

Punto di fusione

254-258 °C

Gruppo funzionale

phosphine

Stringa SMILE

Cc1ccc(cc1)P(c2ccc(C)cc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccc(C)cc7)c8ccc(C)cc8

InChI

1S/C48H40P2/c1-33-13-23-39(24-14-33)49(40-25-15-34(2)16-26-40)45-31-21-37-9-5-7-11-43(37)47(45)48-44-12-8-6-10-38(44)22-32-46(48)50(41-27-17-35(3)18-28-41)42-29-19-36(4)20-30-42/h5-32H,1-4H3
IOPQYDKQISFMJI-UHFFFAOYSA-N

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Descrizione generale

BINAP is based on a bis naphthalene backbone with different phosphine derivatives. 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl (p-Tol-BINAP)·AgF complex catalyzed asymmetric Mukaiyama-type aldol reaction is reported.

Applicazioni

Takasago Ligands and Complexes for Asymmetric Reactions
(R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It may be employed as chiral catalyst for allylation of N-tosyl α-imino esters.
Catalyst involved in studies of the role of excess phosphine ligand in enantioselective conjugate addition of ethylmagnesium bromide and α,β-unsaturated ester

Reactant serving as a precursor for:
  • Catalysts used for reductive amination of ketones
  • Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives
  • Chiral platinum catalysts for asymmetric Baeyer-Villiger oxidation of cyclic ketones
  • CuI-Tol-BINAP catalysts for enantioselective Michael reactions of Grignard reagents to unsaturated esters
  • BINAP Pt Dications for cation trapping

Note legali

Sold in collaboration with Takasago for research purposes only.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
MKCN7499
MKCL6765
MKCG5530
MKCG3166
MKCD7148

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(S)-DTBM-SEGPHOS® ≥94%

Sigma-Aldrich

692980

(S)-DTBM-SEGPHOS®

(S)-SEGPHOS ≥94%

Sigma-Aldrich

693006

(S)-SEGPHOS

Xiangming Fang et al.
The Journal of organic chemistry, 64(13), 4844-4849 (2001-10-25)
A new catalytic enantioselective approach for the formation of allyl alpha-amino acid derivatives by reaction of N-tosyl alpha-imino esters with allyl stannanes and silanes catalyzed by chiral copper(I) complexes has been developed. A series of different BINAP and phosphine-oxazoline (P,N)
Catalytic Asymmetric Aldol Reaction of Trimethoxysilyl Enol Ethers Using 2, 2'-Bis (di-p-tolylphosphino)-1, 1'-binaphthyl AgF Complex.
Yanagisawa A, et al.
Bulletin of the Chemical Society of Japan, 74(8), 1477-1484 (2001)
Asymmetric hydroformylation of vinyl acetate with BINAP-rhodium (I) complexes.
Hoegaerts D and Jacobs PA.
Tetrahedron Asymmetry, 10(15), 3039-3043 (1999)

Articoli

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

BINAP/SEGPHOS® Ligands and Complexes

We presents an article concerning BINAP/SEGPHOS® Ligands and Complexes.

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

Il team dei nostri ricercatori vanta grande esperienza in tutte le aree della ricerca quali Life Science, scienza dei materiali, sintesi chimica, cromatografia, discipline analitiche, ecc..

Contatta l'Assistenza Tecnica.