1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate, CAS No. 35193-63-6

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35193-63-6

Catalog No. EBD15247

CAS 35193-63-6

Name 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

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Basic Information

Synonyms: 4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin4-oxide 1,1'-Binaphthyl-2,2'-diylhydrogenphosphate 1,1'-binaphthyl-2,2'-diylhydrogen-phosphate 1,1-Binaphthyl-2,2-diylhydrogenphosphate (+/-)-1,1A-Binaphthyl-2,2A-diylhydrogenphosphate dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ol4-oxide 2'-[(hydroxyphosphinato)oxy]-1,1'-binaphthalen-2-ylphosphate 1,1'-Binaphthalene-2,2'-diylhydrogenphosphate (R)-(-)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate (-)-1,1 (r)-1,1 (r)-bnppa (r)-(-)-1,1 (r)-(-)-bndhp -binaphthyl-2,2 -dinaphthyl-2,2 dinaphtho[2,1-d:1 -bi-2-naphthol-2,2 (r)-(-)-binaphthyl-2,2 -diylhydrogenphosphate (-)-4-hydroxydinaphtho[2,1-d:1 -f][1,3,2]dioxaphosphepin4-oxide BNDHP

Molecular Formula: C20H13O4P

Molecular Weight: 348.29

MDL Number: MFCD00010045

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

Product Description:

1,1'-Bi-2-naphthol (BINOL) phosphoric acid derivatives, such as the compound represented by CAS 35193-63-6, are a class of chiral Brønsted acid catalysts. They are typically synthesized from enantiomerically pure BINOL via phosphorylation. These compounds feature a rigid, axially chiral 1,1'-binaphthyl backbone coupled with a strongly acidic phosphoric acid moiety. Their primary and most significant application is in asymmetric organocatalysis. They act as powerful chiral Brønsted acids to activate substrates like imines, carbonyl compounds, and alkenes, facilitating a wide range of enantioselective transformations, including Mannich reactions, Friedel-Crafts alkylations, transfer hydrogenations, and cycloadditions. The steric and electronic properties of the substituents on the 3,3'-positions of the naphthyl rings are crucial for tuning catalytic activity and enantioselectivity. Due to their efficiency and broad utility in constructing chiral molecules, these catalysts are indispensable tools in academic research and the pharmaceutical industry for the synthesis of enantiomerically pure intermediates and active pharmaceutical ingredients (APIs). They represent a landmark advancement in the field of asymmetric synthesis.

Physical Properties

Melting Point: ≥300 °C

Boiling Point: 619.5 °C at 760 mmHg

Flash Point: 328.5 °C

Density: 1.493 g/cm3