(R)-SEGPHOS CAS 244261-66-3

Introduction：Basic information about (R)-SEGPHOS CAS 244261-66-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(R)-SEGPHOS Basic information

• Product Name: (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-;(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,(R)-(+)-SEGPHOS;(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole;[(4R)-[4,4'-Bi-1,3-benzodioxole]-5,5'-diyl]bis[diphenylphosphine]
• CAS: 244261-66-3
• MF: C38H28O4P2
• MW: 610.59
• Product Categories: Chiral Phosphine;Segphos Series
• Mol File: 244261-66-3.mol

(R)-SEGPHOS Chemical Properties

• Melting point: 168-172 °C
• Boiling point: 715.4±60.0 °C(Predicted)
• storage temp.: Inert atmosphere,Room Temperature
• form: Powder
• color: off-white
• Optical Rotation: [α]20/D +11°, c = 0.5 in chloroform
• InChIKey: RZZDRSHFIVOQAF-UHFFFAOYSA-N
• SMILES: P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC2OCOC=2C=1C1C2OCOC=2C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1

Safety Information

• WGK Germany: 3
• HS Code: 2932.99.7000

(R)-SEGPHOS Usage And Synthesis

Reactions

1. 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.
2. As ruthenium complex, SEGPHOS® generally gives higher levels of chiral induction in asymmetric hydrogenations of α,β,and γ-functionalized ketones. 
3. 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.
4. 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.
5. Used in Cu-catalyzed transformations such as: (a) nitroso Diels-Alder,(b) reductive aldol condensation,(c) conjugate reduction of unsaturated sulfones,and phophonates.
6. Iridium-catalyzed asymmetric hydrogenation of quinolines activated by chloroformates.
7. Iridium-catalyzed asymmetric transfer hydrogenation used in polyketide construction.
8. Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines.
9. Palladium-catalyzed regio- and enantioselective dearomatization.

Uses

(R)-(+)-SEGPHOS? is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective addition of diesters to 3,3-difluoropropenes, and in the Ni-based catalyst for the asymmetric propargylic amination of propargylic carbonates with an internal alkyne group.