99646-28-3

Basic information

• Product Name: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
• Synonyms: (S)-TOL-BINAP;(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL;(R)-TOL-BINAP;(R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL;(R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL;(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, (R)-p-Tol-BINAP;(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 95+%;(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl,98%(R)-Tol-BINAP
• CAS NO: 99646-28-3
• Molecular Formula: C₄₈H₄₀P₂
• Molecular Weight: 678.78
• EINECS: 1312995-182-4
• Product Categories: BINAP Series;Chiral Phosphine
• Mol File: 99646-28-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 255-257 °C
• Boiling Point: 754.4 °C at 760 mmHg
• Flash Point: 438.8 °C
• Appearance: White to cream/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL(99646-28-3)
• EPA Substance Registry System: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL(99646-28-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 99646-28-3(Hazardous Substances Data)

Usage

Reaction

Useful ligand for palladium-catalyzed carbon-oxygen bond formation. Ligand for palladium-catalyzed α-arylation of ketones. Ligand for Cu-catalyzed asymmetric conjugate reduction. Ligand for Cu-catalyzed asymmetric dienolate addition to aldehydes. Enantioselective conjugate reduction of lactones and lactams. Ligand used in the enantioselective cycloaddition of allenylsilanes with α-Imino esters. Catalytic Aldol reaction to ketones. Ligand with rhodium catalyses [2+2+2] cycloaddition reaction of alkenes and alkynes. Ligand used in the copper-catalyzed asymmetric conjugate addition of alkyl Grignard reagents on α,β-unsaturated esters. Ligand used in the copper-catalyzed asymmetric synthesis of cyclopropanes via tandem conjugate addition and intramolecular enolate trapping.

Chemical Properties

White to cream powder

Uses

Different sources of media describe the Uses of 99646-28-3 differently. You can refer to the following data:
1. (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is used as chiral catalyst ligand. (R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It is a catalysts used for reductive amination of ketones, Pt dications for cation trapping, Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives.
2. (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.

General Description

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.

Upstream product

• 100165-87-5 2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl dioxide 
• 1342819-36-6 bis(4-methylphenyl)bromophosphine 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 126613-06-7 (S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 
• 4129-40-2 di(p-tolyl)phosphinic chloride 
• 100165-87-5 (S)-[1,1'-binaphthalene]-2,2'-diylbis(di-p-tolylphosphine oxide) 
• 1019-71-2 chlorodi-p-tolylphosphane 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 100165-87-5 (R)-(+)-2,2'-bis(di-p-tolylphosphinyl)-1,1'-binaphthyl 

Downstream Products

• 577712-50-6 (4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester 
• 112065-78-8 Δ-Ru(OOCCH3)2((S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) 
• 157262-10-7 {RuCl(C₆H₆)((S)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl)}Cl 
• 228120-95-4 RuCl(cymene)(S-tol-binap)Cl 
• 210693-89-3 [(S)-Tol-BINAP]Pd(o-C₆H₄CN)Br 
• 1001400-11-8 [Pd(η(3)-C11H17)((R)-p-TolBINAP)]PF6 
• 910134-29-1 dichloroplatinum(II)((R)-p-tolyl-BINAP 
• 881407-10-9 Pt((S)-(p-tolyl)2PC₁₀H₆C₁₀H₆P(p-tolyl)2)(Ph)Cl 
• 255907-73-4 Pt((S)-(p-tolyl)2PC₁₀H₆C₁₀H₆P(p-tolyl)2)(Me)Cl 
• 1178903-51-9 (R)-tert-butyl 3-(p-tolylamino)piperidine-1-carboxylate 
• 1178903-19-9 (R)-tert-butyl 3-(1-(4-methoxybenzyl)-1H-indazol-5-ylamino)piperidine-1-carboxylate 
• 1207107-21-8 [Cl2Ru((R)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl)(κN3-1-methylbenzimidazole)2] 

Relevant articles and documents

NOVEL RUTHENIUM COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL COMPOUND USING SAME AS CATALYST

The present invention provides: a novel ruthenium complex which has excellent catalytic activity with respect to reactivity in the reduction of a multiple bond, in particular, in the asymmetric reduction of a carbonyl compound, enantioselectivity, etc.; a catalyst which comprises the ruthenium complex; and a process for producing optically active compound, in particular, an optically active alcohol compound, using the catalyst. The ruthenium complex has a ruthenacyclic structure. The catalyst is a catalyst for asymmetric reduction which comprises the ruthenium complex.

Stereospecific deoxygenation of phosphine oxides with retention of configuration using triphenylphosphine or triethyl phosphite as an oxygen acceptor

(Chemical Equation Presented) A new protocol for deoxygenation of various phosphine oxides with retention of configuration is described. The advantage of the new method includes milder conditions and considerably shortened reaction times. Mechanistic studies about the oxygen transfer between the starting phosphine oxide and the sacrificial triphenylphosphine are also presented.

Ruthenium-I0D0-optically active phosphine complex

This invention is concerned with a ruthenium-iodo-optically active bidentate phosphine complex of the formula (I):[Ru-(I)q-(T1)n(SOL)r(L)]m(T2)p(I)s(I)wherein T1 represents a carboxylic acid anion, SOL represents a polar solvent, L represents an optically active bidentate phosphine ligand, T2 represents an anion different from halogen atom anions and carboxylic acid anions, n denotes 0 or 1, r denotes 0, 3 or 4, m denotes 1 or 2, q denotes 0 or 1, or where m is 2, q may represent 1 or 1.5, p denotes 0 or 1, and s denotes 0, 1 or 2 is prepared. Said phosphine complex is usefull as an efficient catalyst for asymmetrically hydrogenating 4-methylene-2-oxetanone into optically active 4-methyl-2-oxetanone.