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(R)-(+)-1,1'-Bi-2-naphthol

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(R)-(+)-1,1'-Bi-2-naphthol Basic information

Product Name:
(R)-(+)-1,1'-Bi-2-naphthol
Synonyms:
  • (R)-(+)-BI-2-NAPHTHOL
  • (R)-[1,1']-Binaphth-2-ol, (R)-BINOL
  • (+)-2,2μ-Dihydroxy-1,1μ-dinaphthyl, (R)-(+)-1,1μ-Binaphthalene-2,2μ-diol, (R)-BINOL
  • (R)-(+)-1,1'-Bi-2-naphthol 99%
  • [aR,(+)]-1,1'-Binaphthalene-2,2'-diol
  • [aR,(+)]-Dinaphthol
  • R-(+)-1_Bi-2-naphthol
  • (R)-(+)-1,1'-Bi-2-na
CAS:
18531-94-7
MF:
C20H14O2
MW:
286.32
EINECS:
606-048-4
Product Categories:
  • BINOL Series
  • Chiral Oxygen
  • Intermediates of Dyes and Pigments
  • Alcohols and Derivatives
  • chiral
  • Chiral Reagent
  • CHIRAL COMPOUNDS
  • Asymmetric Synthesis
  • Synthetic Organic Chemistry
  • Chiral Compound
  • Peptide
Mol File:
18531-94-7.mol
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(R)-(+)-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 
1.301
refractive index 
36.0 ° (C=1, THF)
storage temp. 
Store below +30°C.
solubility 
dioxane: 50 mg/mL, clear
form 
Powder
pka
8.29±0.50(Predicted)
color 
white to off-white
optical activity
[α]21/D +34°, c = 1 in THF
Water Solubility 
Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
Merck 
14,1226
BRN 
3616837
CAS DataBase Reference
18531-94-7(CAS DataBase Reference)
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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
10
TSCA 
No
HazardClass 
6.1
PackingGroup 
III
HS Code 
29071590
Toxicity
LD50 orally in Rabbit: 113 mg/kg

MSDS

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

Chemical Properties

white to light yellow crystal powde

Uses

Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

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.]

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