100165-88-6

Basic information

• Product Name: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
• Synonyms: (S)-TOL-BINAP;(R)-TOL-BINAP;(S)-(-)-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;BisdiptolylphosphinobinaphthylSTolBI;(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, (S)-p-Tol-BINAP;(S)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-&
• CAS NO: 100165-88-6
• Molecular Formula: C₄₈H₄₀P₂
• Molecular Weight: 678.78
• EINECS: 1312995-182-4
• Product Categories: BINAP Series;Chiral Phosphine
• Mol File: 100165-88-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 252-256 °C
• Boiling Point: 754.4 °C at 760 mmHg
• Flash Point: 438.8 °C
• Appearance: White/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(100165-88-6)
• EPA Substance Registry System: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL(100165-88-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 100165-88-6(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 iridium-catalyzed enantioselective C-H bond activation of 2-(alkylamino)-pyridine with alkenes. Iridium-catalyzed regio-, diastereo-, and enantioselective tert-(hydroxyl)-prenylation of alcohols. Rhodium-catalyzed cross cyclotrimerization.

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 100165-88-6 differently. You can refer to the following data:
1. (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is chiral ligand widely used in asymmetric synthesis. It also used as excellent catalysts for asymmetric hydrogenation of alkenes and some cyclic anhydrides. BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium
2. (S)-T-BINAP reacts with silver nitrate to form (S)-Tol-BINAP·AgNO3, which can catalyze the enantioselective allylation reaction of aldehydes to form enantiopure secondary alcohols. It may be used as a chiral ligand in the palladium catalyzed asymmetric double carbohydroamination of iodoarenes to form α-aminoamides. It can also catalyze the asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate to form chiral N-allyl ortho-tert-butylanilides.

Upstream product

• 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 
• 100165-87-5 2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl dioxide 
• 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

• 100165-87-5 (R)-(+)-2,2'-bis(di-p-tolylphosphinyl)-1,1'-binaphthyl 
• 112065-78-8 Δ-Ru(OOCCH3)2((S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) 
• 352230-33-2 [Ag[C₂₀H₁₂(P(C₆H₅)2)2]CH₃COO] 
• 352230-34-3 [Ag[C₂₀H₁₂(P(C₆H₄CH₃)2)2]CH₃COO] 
• 352232-75-8 [Ag₂[C₂₀H₁₂(P(C₆H₄CH₃)2)2](CH₃COO)2] 
• 210693-89-3 [(S)-Tol-BINAP]Pd(o-C₆H₄CN)Br 
• 210693-81-5 [(R)-Tol-BINAP]Pd(p-C₆H₄NO₂)I 
• 730961-38-3 PdCl2[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl] 
• 888955-58-6 hydrido(acetato)[(S)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl]chloroiridium(III) 
• 891831-32-6 [PdBr(10,20-diphenylporphyrinatonickel(II))((R)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl)] 
• 1001400-11-8 [Pd(η(3)-C11H17)((R)-p-TolBINAP)]PF6 

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.

PROCESS FOR PREPARATION OF DIPHOSPHINE COMPOUNDS AND INTERMEDIATES FOR THE PROCESS

A production method of a_compound represented by the formula wherein R1a, R1b, R1c, R1d, R1e, R1f, R2a, R2b, R2c R2d, R2e and R2f are the same or different and each is a hydrogen atom and the like, and R3, R4, R5, R6, R7, R8, R9 and R10 are the same or different and each is a hydrogen atom and the like, or a salt thereof, which comprises reacting a compound represented by the formula wherein X is a leaving group and other symbols are as defined above, or a salt thereof, with a phosphine-borane complex represented by the formula wherein the symbols are as defined above, or a salt thereof, in a solvent in the presence of an amine and a nickel catalyst, is provided.

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.