1,1′-Bi-2-naphthol

CAS 602-09-5HOC10H6C10H6OHCatalysis & Inorganic

1,1′-Bi-2-naphthol (CAS: 602-09-5) is a chiral organic compound with the molecular formula HOC₁₀H₆C₁₀H₆OH and a molecular weight of 286.32 g/mol. This white to off-white crystalline solid serves as a crucial chiral ligand and auxiliary in various asymmetric synthesis reactions, including Michael addition and Diels-Alder reactions. Its enantioselective properties make it invaluable for creating specific stereoisomers in complex chemical syntheses.

IUPAC: (±)-1,1′-Binaphthalene-2,2′-diol,(±)-2,2′-Dihydroxy-1,1′-dinaphthyl,2,2′-Dihydroxybinaphthalene,2,2′-Dihydroxydinaphthyl,2,2′-Dinaphthol,BINOL
Synonyms: HOC10H6C10H6OH(±)-1,1′-Binaphthalene-2,2′-diol(±)-2,2′-Dihydroxy-1,1′-dinaphthyl2,2′-Dihydroxybinaphthalene2,2′-Dihydroxydinaphthyl2,2′-DinaphtholBINOL

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1,1′-Bi-2-naphthol (HOC10H6C10H6OH) — chemical structure, CAS 602-09-5; Chemistry, fine chemical supplied by Tech Serve Solutions

Chemical SynthesisOther Ligands

01 /Applications

Asymmetric Michael Addition

1,1′-Bi-2-naphthol acts as a chiral ligand and auxiliary, facilitating enantioselective Michael addition reactions. This application is vital for the stereoselective formation of carbon-carbon bonds in organic synthesis.

Enantioselective Diels-Alder Reactions

It is employed as a chiral auxiliary in asymmetric Diels-Alder cycloadditions. This enables the synthesis of complex cyclic structures with high stereocontrol, which is significant in the development of pharmaceuticals and natural products.

Alkynylation Reactions

The compound finds use in enantioselective alkynylation processes, contributing to the stereoselective introduction of alkyne functionalities into organic molecules.

02 /Properties

Molecular weight	286.32
Linear formula	HOC10H6C10H6OH
Assay	99%
Solubility	dioxane: soluble0.5 g/10 mL, clear, colorless to slightly yellow
Application	Chiral ligand and auxiliary for asymmetric Michael addition reaction; enantioselective Diels-Alder reaction; alkynylation.
Melting point	214-217 °C(lit.)

03 /Safety & handling

GHS hazard pictogram: Toxic (GHS06) — Toxic

Danger

Hazard statements

H301Toxic if swallowed
H319Causes serious eye irritation

Precautionary statements

P301IF SWALLOWED
P305IF IN EYES

Protective equipment	Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Transport (UN / ADR)	UN 2811 6.1 / PGIII
Water hazard class (WGK, DE)	3
Hazard codes (EU)	T
Risk statements (R)	25-36
Safety statements (S)	26-45

Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.

04 /Identifiers & registry

CAS number

602-09-5

MDL number

MFCD00004068

PubChem substance

24846670

Beilstein registry

997518

05 /Quality & supply

Documentation

Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.

Supply & logistics

Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.

06 /Frequently asked questions

What is 1,1′-Bi-2-naphthol used for?

1,1′-Bi-2-naphthol is primarily used as a chiral ligand and auxiliary in asymmetric synthesis, including Michael addition reactions, enantioselective Diels-Alder reactions, and alkynylation reactions.

What are the CAS number and formula for 1,1′-Bi-2-naphthol?

The CAS number for 1,1′-Bi-2-naphthol is 602-09-5, and its linear formula is HOC₁₀H₆C₁₀H₆OH.

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies 1,1′-Bi-2-naphthol with an assay of 99%. This product is supplied for research and chemical synthesis purposes and is not intended for USP, BP, EP, or other pharmacopoeia applications unless explicitly stated.

What are the main hazards associated with 1,1′-Bi-2-naphthol?

1,1′-Bi-2-naphthol is classified as acutely toxic if swallowed (H301) and causes serious eye irritation (H319). Appropriate personal protective equipment, including eyeshields, face shields, gloves, and P2 respirator cartridges, must be used during handling. Refer to the Safety Data Sheet for comprehensive information.

How is 1,1′-Bi-2-naphthol shipped and exported?

As a hazardous substance (UN 2811, Class 6.1, PGIII), 1,1′-Bi-2-naphthol is carefully packaged and exported in compliance with international shipping regulations for toxic materials.