137219-86-4

Basic information

• Product Name: (R)-DM-BINAP
• Synonyms: (R)-(+)-2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]-1,1'-BINAPHTHYL;(R)-(+)-2,2'-BIS[BIS(3,5-DIMETHYLPHENYL)PHOSPHINO]-1,1'-BINAPHTHYL;RACEMIC-2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]-1,1'-BINAPHTHYL;RAC-XYLYL-BINAP;(R)-3,5-XYLYL-BINAP;2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]-1,1'-BINAPHTHYL;2,2'-BIS[BIS(3,5-DIMETHYLPHENYL)PHOSPHINO]-1,1'-BINAPHTHYL;(R)-(+)-2,2'-Bis(di-(3,5-dimethylphenyl)phosphino)-1,1'-binaphthyl, ((R)-Xylyl-B
• CAS NO: 137219-86-4
• Molecular Formula: C₅₂H₄₈P₂
• Molecular Weight: 734.89
• EINECS: 1312995-182-4
• Product Categories: BINAP Series;Chiral Phosphine
• Mol File: 137219-86-4.mol

Chemical Properties

• Melting Point: 203-206°C
• Boiling Point: 825.3±65.0 °C(Predicted)
• Appearance: white to pale yellow/crystal
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water
• CAS DataBase Reference: (R)-DM-BINAP(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-DM-BINAP(137219-86-4)
• EPA Substance Registry System: (R)-DM-BINAP(137219-86-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 137219-86-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-DM-BINAP is used as a chiral ligand for the synthesis of various pharmaceutical compounds. Its high enantioselectivity allows for the production of enantiomerically pure compounds, which is crucial in the development of effective and safe drugs. The ligand plays a vital role in asymmetric catalysis, enabling the selective formation of desired enantiomers in chemical reactions.
Used in Chemical Industry:
(R)-DM-BINAP is used as a catalyst in the preparation of various chemical compounds, such as chiral intermediates and specialty chemicals. Its high stability and enantioselectivity make it an ideal choice for industrial applications where the production of high-quality, enantiomerically pure products is required.
Used in Research and Development:
(R)-DM-BINAP is used as a research tool in the development of new asymmetric catalytic reactions and the study of reaction mechanisms. Its unique structure and properties allow chemists to explore new reaction pathways and improve the efficiency of existing processes.

Upstream product

• 126613-06-7 (S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 
• 556-96-7 5-bromo-1,3-xylene 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 187344-92-9 bis(3,5-dimethylphenyl)phosphine oxide 
• 137219-86-4 2,2'-bis[di(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 137219-83-1 (3-(chloro(3,5-dimethylphenyl)phosphoryl)-5-methylphenyl)methylium 
• 1342819-37-7 bis(3,5-dimethylphenyl)bromophosphine 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 74289-57-9 bis-(3,5-dimethylphenyl)chlorophosphine 
• 194149-25-2 [bis-(3,5-dimethylphenyl)](diethylamino)phosphine 
• 137219-84-2 2,2'-bis[di-(3,5-dimethylphenyl)phosphoryl]-1,1'-binaphthyl 

Downstream Products

• 135139-00-3 (S)-2,2'-bis-1,1'-binaphthyl 
• 137268-63-4 {RuI((S)-2,2'-bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthyl)(p-cymene)}I 
• 1207107-24-1 [Cl2Ru((R)-2,2'-bis(3,5-xylylphosphino)-1,1'-binaphthyl)(κN3-1-methylbenzimidazole)2] 
• 1345887-44-6 [RuCl(p-cymene)((S)-xylbinap)]Cl 

Relevant articles and documents

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).

A 2,2 the [...] -bis [(3,5- xylyl ) phosphorus] dinaphthalene method for the preparation of

The invention relates to the field of organic synthesis, and in particular relates to a method for preparing 2, 2'-bis [(3, 5-xylyl) phosphorus) dinaphthalene. The method comprises the following steps: preparing N-methyl piperazine phosphorus dichloride h

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.

Improved syntheses of phosphine ligands by direct coupling of diarylbromophosphine with organometallic reagents

Br versus Cl: It is found that the use of diarylbromophosphines instead of diarylchlorophosphines is crucial for their direct coupling with binaphthylmagnesium bromide or BINOL triflate. This finding has led to an improved preparation of both electron-deficient BINAP-type phosphine ligands and several important Buchwald's ligands. Copyright

Process research on the asymmetric hydrogenation of a benzophenone for developing the manufacturing process of the squalene synthase inhibitor TAK-475

A practical synthetic method for the synthesis of the chiral benzhydrol 8, which is the key intermediate of the squalene synthase inhibitor TAK-475 (1), has been developed. The method, via asymmetric hydrogenation of the benzophenone 7, employed Noyori's ruthenium precatalyst of the type [RuCl 2(diphosphine)(diamine). We focused on tuning of the chiral diphosphine, and have discovered a novel ligand, DADMP-BINAP (18c), for the catalyst that has allowed reduction of the operating pressure in the asymmetric hydrogenation. The precatalyst containing 18c performed effectively at low hydrogen pressure (1 MPa) with sufficient enantioselectivity, and the result enabled us to successfully obtain enantiomerically pure 8 on a multikilogram scale.

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.

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.

Process for preparing optically active 4-methyl-2-oxetanone

A process for preparing optically active 4-methyl-2-oxetanone which comprises asymmetrically hydrogenating 4-methylene-2-oxetanone in the presence of a ruthenium-optically active phosphine complex. Optically active 4-methyl-2-oxetanone can easily and economically be obtained at high optical purity.