1,1'-Bi-2-naphthol

1,1′-Bi-2-naphthol is a white to yellowish gray crystalline powder. It is known to be soluble in methanol. Store in a cool and dark place at ambient temperatures for best keeping.

(+/-)-1,1'-Bi(2-naphthol) acts as chiral separation agents. It is widely used in chiral liquid crystal,medicines,spices etc,.

Chiral ligand and auxiliary for asymmetric Michael addition reaction; enantioselective Diels-Alder reaction; alkynylation.

1,1'-Bi-2-naphthol is used as a chiral ligand in alkynylation, Diels-Alder and assymmetric Michael addition reactions.

ChEBI: (S)-(-)-1,1'-Bi-2-naphthol is a member of naphthols.

Tetrahedron, 48, p. 9483, 1992 DOI: 10.1016/S0040-4020(01)88316-2
Tetrahedron Letters, 24, p. 3261, 1983 DOI: 10.1016/S0040-4039(00)88151-4

reagent type: ligand

1,1'-Bi-2-naphthol is incompatible with oxidizing agents and should not be stored or handled near them. Poison by ingestion and causes skin irritation along with serious eye irritation. When heated to decomposition it emits acrid smoke and irritatingvapors.

A process for coupling 2-naphthols which comprises contacting a 2-naphthol dissolved in a polar acidic organic solvent in the presence of a catalytic amount of a catalyst which comprises a readily reducible form of a Group IB, Group VIII or manganese metal in the further presence of oxygen or a source of oxygen at a temperature between 0° and 200° C. under conditions such that a 1,1'-bi-2-naphthol is prepared wherein the product contains less than about 1 mole percent of binaphthenoquinones.

Crystallise the binaphthol from toluene or *benzene (10mL/g). When crystallised from chlorobenzene it has m 238o. Its solubility in dioxane is 5%. [Beilstein 6 IV 7020.]