1,1'-Bi-2-naphthol

Synonym(s):BINOL;(±)-1,1′-Binaphthalene-2,2′-diol;(±)-2,2′-Dihydroxy-1,1′-dinaphthyl;2,2′-Dihydroxybinaphthalene;2,2′-Dihydroxydinaphthyl

CAS NO.：602-09-5
Empirical Formula: C20H14O2
Molecular Weight: 286.32
MDL number: MFCD00004068
EINECS: 210-014-0
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 13:37:16

What is 1,1'-Bi-2-naphthol?

Chemical properties

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.

The Uses of 1,1'-Bi-2-naphthol

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

The Uses of 1,1'-Bi-2-naphthol

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

The Uses of 1,1'-Bi-2-naphthol

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

Definition

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

Synthesis Reference(s)

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

Safety Profile

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.

Purification Methods

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.]

Properties of 1,1'-Bi-2-naphthol

Melting point:	215-218 °C
Boiling point:	388.69°C (rough estimate)
Density	1g/cm
refractive index	1.7580 (estimate)
storage temp.	Inert atmosphere,Room Temperature
solubility	Soluble in dioxane (50 mg/mL).
solubility	dioxane: 50 mg/mL, clear
pka	8.29±0.50(Predicted)
form	Powder
color	White to beige
Water Solubility	insoluble
Merck	14,1226
BRN	997518
CAS DataBase Reference	602-09-5(CAS DataBase Reference)
NIST Chemistry Reference	1,1'-Bi-2-naphthol(602-09-5)
EPA Substance Registry System	[1,1'-Binaphthalene]-2,2'-diol (602-09-5)

Safety information for 1,1'-Bi-2-naphthol

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06
GHS Hazard Statements	H301:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.