133545-16-1

Basic information

• Product Name: R(+)-2 2'-BIS-(DIPHENYLPHOSPHINO)-6 6'-&
• Synonyms: R(+)-2 2'-BIS-(DIPHENYLPHOSPHINO)-6 6'-&;(R)-(+)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine);(R)-(+)-2,2'-Bis(diphenylphosphino)-6,6'-dimethoxy-1,1'-biphenyl,min.97%(R)-MeO-BIPHEP;(R)-(+)-MeO-BIPHEP, SL-A101-1, (R)-(+)-2,2μ-Bis(diphenylphosphino)-6,6μ-dimethoxy-1,1μ-biphenyl;97% (R)-MeO-BIPHEP;(R)-(+)-2,2'-Bis(diphenylphosphino)-6,6'-diMethoxy-1,1'-biphenyl,(R)-MeO-BIPHEP;(R)-(+)-2,2'-Bis(diphenylphosphino)-6,6'-dimethoxy-1,1'-biphenyl,97% (R)-MeO-BIPHEP;(R)-(+)-MeO-BIPHEP
• CAS NO: 133545-16-1
• Molecular Formula: C₃₈H₃₂O₂P₂
• Molecular Weight: 582.607002
• Product Categories: Chiral Phosphine;MeOBIPHEP Series
• Mol File: 133545-16-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 213-216 °C
• Boiling Point: 651.1ºC at 760 mmHg
• Flash Point: 438.5ºC
• Appearance: off-white/crystal
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: R(+)-2 2'-BIS-(DIPHENYLPHOSPHINO)-6 6'-&(CAS DataBase Reference)
• NIST Chemistry Reference: R(+)-2 2'-BIS-(DIPHENYLPHOSPHINO)-6 6'-&(133545-16-1)
• EPA Substance Registry System: R(+)-2 2'-BIS-(DIPHENYLPHOSPHINO)-6 6'-&(133545-16-1)

Safety Data

• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 133545-16-1(Hazardous Substances Data)

Usage

Description

R(+)-2,2'-Bis-(diphenylphosphino)-6,6'-& is a white powder that serves as a greener alternative product, adhering to the 12 Principles of Greener Chemistry. It has been enhanced for catalytic efficiency and is used as a ligand in various chemical reactions.

Uses

Used in Greener Chemistry:
R(+)-2,2'-Bis-(diphenylphosphino)-6,6'-& is used as a ligand for ruthenium-catalyzed greener amine synthesis by enamine reduction with hydrogen gas. This process adheres to the principles of greener chemistry, promoting environmentally friendly and sustainable practices in chemical synthesis.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, R(+)-2,2'-Bis-(diphenylphosphino)-6,6'-& is used as a ligand for the synthesis of (S)-3-Amino-4-methoxy-butan-1-ol through reductive amination. This application highlights its versatility in facilitating the production of enantiomerically pure compounds, which are crucial in various industries such as pharmaceuticals and agrochemicals.

Reactions

In many respects the catalytic profile of the MeOBIPHEP ligands is similar to that of other atropisomeric diphosphines such as binap and its many analogs. The nature of the PR2 group strongly influences the catalytic performance of the metal complexes. The rhodium and ruthenium MeO-BIPHEP catalysts are highly effective for the hydrogenation of various C=O, C=C and C=N bonds and several synthetically useful C-C coupling reactions. Ru and Ir catalyzed dynamic kinetic resolution for the synthesis of hydroxy, amino acid derivatives. 1.Ru-catalyzed asymmetric hydrogenation of ketones and alkenes. Ir catalyzed enantioselective hydrogenation of heteroaromatic compounds. Conjugate addition using 2-heteroaryl titanates and zinc reagents. Enantio- and regioselective heck-type reaction of aryl boronic acids with 2,3-dihydrofuran Rhodium-catalyzed carbonyl Z-dienylation. Rhodium-catalyzed asymmetric 1,4 addition of arylboronic acids to maleimides and enones.

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 133545-15-0 (RS)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) 
• 133545-14-9 (2-iodo-3-methoxyphenyl)diphenylphosphine oxide 
• 134435-27-1 (2-bromo-3-methoxyphenyl)diphenylphosphine oxide 
• 95278-09-4 (3-methoxylphenyl)diphenylphosphine oxide 
• 13145-84-1 (3-methoxyphenyl)(diphenyl)phosphane 
• 2398-37-0 3-methoxyphenyl bromide 
• 133545-15-0 (Sa)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) 
• 133545-15-0 (Ra)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) 
• 3335-35-1 4-methyl-1-(trichloromethyl)benzene 
• 7732-18-5 water 

Downstream Products

• 299197-81-2 ((Z,Z)-cycloocta-1,5-diene){(R)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine)}rhodium(I) tetrafluoroborate 
• 221155-04-0 Pd(cyclopent-4-ene-1,3-dione)((S)-MeO-biphep) 
• 181955-02-2 Pt(CH₃)(Cl)((CH₃OC₆H₃P(C₆H₅)2)2) 
• 767323-65-9 [Rh(CO)Cl((C₆H₃(OCH₃)P(C₆H₅)2)2)] 
• 1134789-66-4 [((S)-2,2'-bis(diphenylphosphino)-6,6'-dimethoxy-1,1'-biphenyl)(AuCl)2] 
• 1147564-30-4 [RuH(1,2-bis(dimethylphosphino)ethane)((R)-MeO-BiPHEP)][tetraphenylborate] 
• 960051-00-7 [RuCl₂((C₆H₃OCH₃P(C₆H₅)2)2)(C₅H₄NCH(C₆H₅)NH₂)] 
• 853997-16-7 [(p-cymene)Ru(MeO-BIPHEP)Cl][SbF₆] 
• 199541-16-7 [RuCl(S-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine))(benzene)]Cl 
• 373388-98-8 PdBr(C₆F₅)((S)-MeO-biphep) 
• 221154-87-6 Pd(dibenzylidene acetone)((S)-MeO-biphep) 

Relevant articles and documents

Process for producing optically active gamma-butyrolactone

This invention provides a novel process for producing optically active 3-hydroxy-γ-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-γ-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

Process for preparing oprtically active trimethyllactic acid and its ester

The invention relates to a novel process for preparing optically active trimethyllactic acid and/or its esters by catalytic hydrogenation of trimethylpyruvic acid and/or its esters in the presence of noble metal complex catalysts containing phosphorus ligands.

Chiral phosphorus compounds

Novel chiral phosphorus compounds of the formula STR1 wherein R signifies lower alkyl, R1 signifies phenyl and R2 and R3 signify hydrogen or lower alkoxy, which are suitable in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.