244261-66-3

Basic information

• Product Name: (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS
• Synonyms: (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS;(R)-(+)-5,5μ-Bis(diphenylphosphino)-4,4μ-bi-1,3-benzodioxole, [4(R)-(4,4μ-bi-1,3-benzodioxole)-5,5μ-diyl]bis[diphenylphosphine];(R)-SEGPHOS(R);(R)-(+)-SEGPHOS;Phosphine,1,1'-[(4R)-[4,4'-bi-1,3-benzodioxole]-5,5'-diyl]bis[1,1-diphenyl-;[(4R)-[4,4'-Bi-1,3-benzodioxole]-5,5'-diyl]bis[diphenylphosphine];(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,(R)-(+)-SEGPHOS;(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole
• CAS NO: 244261-66-3
• Molecular Formula: C₃₈H₂₈O₄P₂
• Molecular Weight: 610.574042
• Product Categories: Chiral Phosphine;Segphos Series
• Mol File: 244261-66-3.mol

Chemical Properties

• Melting Point: 168-172 °C
• Boiling Point: 715.4±60.0 °C(Predicted)
• Appearance: off-white/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS(244261-66-3)
• EPA Substance Registry System: (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS(244261-66-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 244261-66-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS is used as a chelating ligand for the preparation of coordination complex catalysts, specifically in Pd catalysts. These catalysts are essential for the enantioselective addition of diesters to 3,3-difluoropropenes, a crucial reaction in the synthesis of various pharmaceutical compounds. The high enantioselectivity provided by (R)-SEGPHOS ensures the production of desired chiral molecules with high purity, which is vital for the development of effective and safe drugs.
Used in Chemical Industry:
In the chemical industry, (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS is used as a component in the development of Ni-based catalysts for the asymmetric propargylic amination of propargylic carbonates with an internal alkyne group. This reaction is significant in the synthesis of complex organic molecules, including those with potential applications in materials science, agrochemistry, and other specialized fields. The use of (R)-SEGPHOS in these catalysts enhances the selectivity and efficiency of the reaction, leading to improved product yields and reduced waste generation.
Overall, (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS is a versatile and valuable chelating ligand with applications in various industries, particularly in the development of catalysts for enantioselective reactions. Its unique structure and high purity make it an essential component in the synthesis of complex molecules and the production of high-quality pharmaceutical compounds.

Reactions

Biaryl bisphosphine ligand with narrow dihedral angle. The SEGPHOS? ligand has been applied to a variety of metal catalyzed reactions. In many cases, yields and enantioselectivities, exceed results obtained earlier using BINAP. As ruthenium complex, SEGPHOS? generally gives higher levels of chiral induction in asymmetric hydrogenations of α,β,and γ-functionalized ketones.? Used in Rh-catalyzed transformations such as: (a) 1,4-addition of boronic acids to coumarins, (b) addition of titanium reagents to imines,(c) cotrimerization of alkenes and acetylenes,10 (d)double [2+2+2] cycloaddition,11 (e) indanone formation. Used in Pd-catalyzed transformations such as: (a) cycloaddition of 1,6-enyne,(b) arylative cyclization of allenyl aldehydes with boronic acids,13 (c) synthesis of chromans. Used in Cu-catalyzed transformations such as: (a) nitroso Diels-Alder,(b) reductive aldol condensation,(c) conjugate reduction of unsaturated sulfones,and phophonates. Iridium-catalyzed asymmetric hydrogenation of quinolines activated by chloroformates. Iridium-catalyzed asymmetric transfer hydrogenation used in polyketide construction. Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines. Palladium-catalyzed regio- and enantioselective dearomatization.

Downstream Products

• 1158398-82-3 Ir(allyl)((S)-SEGPHOS)(m-nitrobenzoate(-H)-kappa.C,O) 
• 1208092-27-6 [(S)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato] [1,2,3-eta-2-propenyl Ir(III)] 
• 670256-87-8 [Rh(CO)Cl((C₆H₂OCH₂OP(C₆H₅)2)2)] 
• 1005350-79-7 [((R)-segphos)Ni(C₆H₄-4-CN)(Br)] 

Relevant articles and documents

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.

Chiral diphosphine compound intermediate for preparing the same transition metal complex having the same diphosphine compound as ligand and asymmetric hydrogenation catalyst

A novel diphosphine compound of the formula (I): STR1 where R1 and R2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.