76189-56-5 Usage
Description
(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, commonly known as BINAP, is a chiral ligand that plays a crucial role in various chemical reactions due to its unique structure. It is a white to light yellow crystalline powder and is widely used in the field of asymmetric catalysis.
Uses
Used in Enantioselective and Diasteroselective Reactions:
BINAP is used as a ligand in enantioselective and diastereoselective unpoled carbonyl allylation reactions. Its chiral structure allows for the selective formation of desired enantiomers or diastereomers, which is essential in the synthesis of complex organic molecules.
Used in the Synthesis of Organophosphine Oxides:
BINAP is utilized as a ligand in the synthesis of organophosphine oxides, which are potential antitumor agents. Its unique structure contributes to the selectivity and efficiency of the reaction, leading to the production of the desired organophosphine oxides.
Used in SN2 Halogenation of Hydroxy Groups:
BINAP serves as a ligand in the SN2 halogenation of hydroxy groups, a reaction that is important in the synthesis of various organic compounds. Its presence enhances the selectivity and efficiency of the reaction, resulting in the desired halogenated products.
Used in the Synthesis of BINAP Complexes:
BINAP is used in the synthesis of its own metal complexes, such as rhodium and ruthenium derivatives. These complexes are highly selective homogeneous catalysts for various reactions, including the reduction of aryl ketones, β-keto esters, and α-amino ketones.
Used in Asymmetric Hydrogenation and Hydroformylation of Olefins:
BINAP and its metal complexes are employed as catalysts in asymmetric hydrogenation and hydroformylation of olefins. These reactions are crucial in the production of chiral compounds, which are essential in the pharmaceutical and agrochemical industries.
Used in Asymmetric Heck Reactions:
BINAP is used as a ligand in asymmetric Heck reactions, which are important in the synthesis of complex organic molecules with high enantioselectivity. Its chiral structure allows for the selective formation of desired products, making it a valuable tool in organic synthesis.
Used in Asymmetric Isomerizations of Allyls:
BINAP is utilized as a ligand in asymmetric isomerizations of allyl compounds. These reactions are essential in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Palladium-Catalyzed, Asymmetric, Tandem Heck Reaction-Carbanion Capture Process:
BINAP is used as a ligand in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process, which leads to the synthesis of a tricyclic sesquiterpene. This process is important in the production of complex organic molecules with high enantioselectivity.
Used in Ruthenium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Acids:
BINAP is employed as a ligand in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids. This reaction is crucial in the synthesis of chiral compounds, which are essential in various industries, including pharmaceuticals and agrochemicals.
Used in Studies of Conformational Flexibility of BINAP Chelates:
BINAP is used in research to study the conformational flexibility of its metal chelates. Understanding the conformational behavior of these chelates is essential for optimizing their performance in various catalytic reactions.
Reaction
(R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
Useful ligand in asymmetric Heck processes.
Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
Ligand employed in rhodium-catalyzed 1,4-additions to enones.
Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
Ligand employed in palladium-catalyzed synthesis of chiral allenes.
Check Digit Verification of cas no
The CAS Registry Mumber 76189-56-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,1,8 and 9 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 76189-56:
(7*7)+(6*6)+(5*1)+(4*8)+(3*9)+(2*5)+(1*6)=165
165 % 10 = 5
So 76189-56-5 is a valid CAS Registry Number.
76189-56-5Relevant articles and documents
One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP
Ye, Jing-Jing,Zhang, Jian-Qiu,Shimada, Shigeru,Han, Li-Biao
supporting information, (2021/11/18)
Herein reported is the convenient and efficient strategy for the preparation of binaphthyl-based phosphines through direct modification to the commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) with sodium. In the absence of 15-crown-5-ether, a cyclic sodium dinapthylphospholide intermediate is mainly generated. With 15-crown-5-ether, P-Ph bonds are selectively cleft by Na to produce binaphthyl-based disodium phosphides. The mechanism of selective formation of sodium dinapthylphospholide or binaphthyl-based disodium phosphides is proposed.
Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene
-
, (2020/09/12)
The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.
Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst
Chardon, Aurélien,Maubert, Orianne,Rouden, Jacques,Blanchet, Jér?me
, p. 4460 - 4464 (2017/11/22)
The general reduction of phosphine oxides, sulfoxides, and amine N-oxides was achieved by combining bis(2-chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2-chlorophenyl)borinic acid as a precatalyst.
