144868-15-5

Basic information

• Product Name: (S)-(-)-Diphenylphosphino-2"-hydroxy-1,1"-binaphthyl
• Synonyms: (R)-(+)-2-DIPHENYLPHOSPHINO-2'-HYDROXY-1,1'-BINAPHTHYL;(S)-(-)-DIPHENYLPHOSPHINO-2'-HYDROXY-1,1'-BINAPHTHYL;(R)-(+)-DIPHENYLPHOSPHINO-2'-HYDROXY-1,1'-BINAPHTHYL;(S)-2'-(Diphenylphosphino)-(1,1'-Binaphthalen)-2-ol;(S)-2-Diphenyphosphino-2'-hydroxyl-1,1'-binaphthyl;(S)-2'-(Diphenylphosphino)-[1,1'-binaphthalen]-2-ol,99%e.e.
• CAS NO: 144868-15-5
• Molecular Formula: C₃₂H₂₃OP
• Molecular Weight: 454.5
• Mol File: 144868-15-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 602.3 °C at 760 mmHg
• Flash Point: 318.1 °C
• Appearance: /
• PKA: 8.93±0.50(Predicted)
• CAS DataBase Reference: (S)-(-)-Diphenylphosphino-2"-hydroxy-1,1"-binaphthyl(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Diphenylphosphino-2"-hydroxy-1,1"-binaphthyl(144868-15-5)
• EPA Substance Registry System: (S)-(-)-Diphenylphosphino-2"-hydroxy-1,1"-binaphthyl(144868-15-5)

Safety Data

• Hazardous Substances Data: 144868-15-5(Hazardous Substances Data)

Usage

General Description

"(S)-(-)-Diphenylphosphino-2"-hydroxy-1,1"-binaphthyl", also known as (S)-(-)-BINAPOH, is a type of chiral biaryl phosphine that is used as a ligand in catalytic reactions. This organic compound is primarily used in the field of chemistry, specifically in the field of asymmetric synthesis. It is a white to off-white crystalline powder which frequently serves a crucial role in catalyzing some significant organic reactions due to its ability to form chiral metal complexes. As a versatile chiral ligand, it facilitates many forms of stereoselective synthesis, contributing to the production of new materials, natural products, and pharmaceuticals.

Upstream product

• 13922-41-3 1-Naphthylboronic acid 
• 1589518-11-5 (1-bromonaphthalen-2-yl)diphenylphosphine oxide 
• 132532-04-8 (R)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 199681-29-3 Diphenyl-(2'-trimethylsilanyloxy-[1,1']binaphthalenyl-2-yl)-phosphane 
• 1079-66-9 chloro-diphenylphosphine 
• 132548-91-5 (S)-(+)-2-hydroxy-2'-diphenylphosphinoyl-1,1'-binaphthyl 
• 4559-70-0 Diphenylphosphine oxide 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 

Downstream Products

• 639464-83-8 Pd(acac)((R)-2-(diphenylphosphino)-2'-hydroxy-1,1'-binaphthyl) 
• 1290543-32-6 Λ-[Ru(2,2'-bipyridine)2((R)-2-diphenylphosphino-2'-hydroxy-1,1'-binaphthyl(-1H))]Cl 
• 639464-85-0 Pd(acac)((R)-2-(diphenylphosphino)-2'-hydroxy-1,1'-binaphthyl)*dichloromethane 
• 835655-21-5 [RuH((+/-)-2'-(diphenylphosphino)-2-oxy-1,1'-binaphthyl)(PPh₃)] 
• 132548-91-5 (S)-(+)-2-hydroxy-2'-diphenylphosphinoyl-1,1'-binaphthyl 
• 149917-85-1 (R,S)-binaphos 

Relevant articles and documents

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.

Optically active phosphine derivative having at least two vinyl groups, polymer produced using the same as monomer, and transition metal complexes of these

A 2′-diarylphosphino-1,1′-biphenylen-2-yloxy(6,6′-divinyl-1,1′-binaphthalene-2,2′-diyloxy)phosphine derivative is disclosed, which is represented by general formula (I): wherein Ar is an optionally substituted phenyl or naphthyl; R1and R2

Phosphine compound, complex containing the phosphine compound as ligand, process for producing optically active aldehyde using the phosphine compound or the complex, and 4-[(R)-1'-formylethyl]azetidin-2-one derivatives

A phosphine compound represented by one of the formulas: STR1 wherein R1 and R2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R3 and R4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R6 and R6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R5, R5', R11 and R11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R5 and R6 or a pair of R5' and R6' may form a ring; R7 and R8, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a lower alkyl group, a halogen atom or a lower alkoxy group; and R9 and R10, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a lower alkyl group, a lower alkoxy group or a halogen atom; or R9 and R10 may be taken together to form a divalent hydrocarbon group.