(S)-(-)-1,1'-Bi-2-naphthol Chemical Properties

Melting point:

215-218 °C

alpha 

-35.5 º (c=1, THF)

Boiling point:

388.69°C (rough estimate)

Density 

1 g/cm³

refractive index 

-36.0 ° (C=1, THF)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

dioxane: 50 mg/mL, clear

pka

8.29±0.50(Predicted)

form 

Crystals or Crystalline Powder

color 

White to light gray

optical activity

[α]22/D 34°, c = 1 in THF

Merck 

14,1226

BRN 

3592999

CAS DataBase Reference

18531-99-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25-36-36/37/38

Safety Statements 

26-45-24/25-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DU3106100

F 

10

TSCA 

No

HazardClass 

6.1

PackingGroup 

III

HS Code 

29072990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-(-)-1,1'-Bi-2-naphthol Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:

• asymmetric addition of alkynylzinc to unactivated ketones
• enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines
• asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones

It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.

Uses

Chiral ligand.

Definition

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

Purification Methods

Dissolve it in cold 2.5N NaOH, extract with CH2Cl2, and acidify with 5% HCl. Collect the white precipitate and recrystallise it from aqueous EtOH and dry it in a vacuum [Akimoto & Yamada Tetrahedron 27 5999 1971]. It is optically stable in dioxane-water (100o/24hours). Racemisation: 72% in 1.2N HCl at 100o/24hours and 68% in 0.67M KOH in BuOH at 118o/23hours [Kyba et al. J Am Chem Soc 95 2693 1973]. It has also been crystallised from *C6H6 (solubility is 1%) using Norite or aqueous EtOH after chromatography through silica gel, eluting with Me2CO/*C6H6. [Kyba et al. J Org Chem 42 4173 1977; see also Brussee & Jansen Tetrahedron Lett 24 3261 1983, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 6 IV 7020.]

(S)-(-)-1,1'-Bi-2-naphthol(18531-99-2)Related Product Information

• ALPHA-NAPHTHOLBENZEIN
• p-Naphtholbenzein
• Solvent Red 43
• (n)-1,1'-bi(2-naphthol),(+/-)-1,1A-Bi-2-naphthol,(±)-1,1'-Bi(2-naphthol),99%,(+/-)-1,1'-BI(2-NAPHTHOL),1,1'-BI-2-NAPHTHOL
• 1-Naphthol
• Terbinafine Hydrochloride
• 2-Naphthol
• Phenmedipham
• (S)-(-)-1,1''-BI-2-NAPHTHOL 99 E.E+%
• (R)-(+)-1,1'-Bi-2-naphthol
• 5,5',6,6',7,7',8,8'-Octahydro-bi-2-naphthol,(R)-(+)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthol,99%
• (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol
• (R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol
• (-1,1'-Bi-2-Naphthol Deacetate
• (S)-1,1μ-Binaphthalene-2,2μ-diyl bis(trifluoromethanesulfonate), (S)-1,1μ-Bi(2-naphthol) bis(trifluoromethanesulfonate)
• (S)-(-)-3,3&#39-Dibromo-1,1&#39-bi-2-naphthol,(S)-(-)-3,3'-Dibromo-1,1'-bi-2-naphthol,99%
• (S)-(-)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthol,99%
• (S)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL,6,6'-Dimethyl-1,1'-bi-2-naphthol