1,1'-binaphthyl-2,2'-diol, CAS No. 602-09-5

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602-09-5

Catalog No. EBD2202659

CAS 602-09-5

Name 1,1'-binaphthyl-2,2'-diol

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Basic Information

Synonyms: 1,1'-bis-2-naphthol 1,1'-binaphthyl-2,2'-diol rac-(+/-)-1,1'-Bi-2-naphthol 1,1'-Bi-naphthol (±)-1,1'-Bi(2-naphthol) (±)-BINOL (±)-1,1'-Bi-2-naphthol

Molecular Formula: C20H14O2

Molecular Weight: 286.32

MDL Number: MFCD00004068

Categories: Synthetic Chemistry > Catalysts and Ligands > Oxygen Ligands

Product Description:

1,1'-Binaphthyl-2,2'-diol (BINOL) is a C2-symmetric chiral compound featuring two naphthol rings connected at the 1,1' positions, with a CAS number of 602-09-5. It exists as a racemic mixture and is a fundamental building block in asymmetric synthesis. Structurally, it belongs to the class of phenolic compounds and is widely recognized for its axial chirality. Its primary application is as a chiral ligand or precursor for chiral ligands (e.g., BINAP, phosphoramidites) in asymmetric catalysis, including hydrogenation, cross-coupling, and aldol reactions. BINOL is also used as a resolving agent for chiral compounds and as a scaffold for designing chiral catalysts. Additionally, it serves as a versatile synthetic building block for constructing functional materials and molecular recognition systems. The compound is stable under standard conditions but should be stored away from strong oxidizing agents. It is commercially available in both racemic and enantiopure forms, with the (R)- and (S)-enantiomers being critical for enantioselective transformations. Its high optical purity and structural rigidity make it indispensable in modern organic chemistry.

Physical Properties

Melting Point: 215-218 °C

Boiling Point: 462.104 °C at 760 mmHg

Flash Point: 218.932 °C

Density: 1.303 g/cm3

Solubility: dioxane: 50 mg/mL, clear

Storage: 2-8°C

Safety Information

Packing Level: III

Hazard Category: 6.1

Transport Codes: 2811

Analytical Data

Appearance: white to beige powder