MilliporeSigma
All Photos(3)

246948

Sigma-Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

All Photos(3)
Synonym(s):
(+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL
Linear Formula:
HOC10H6C10H6OH
CAS Number:
18531-94-7
Molecular Weight:
286.32
Beilstein:
3616837
MDL number:
MFCD00004068
PubChem Substance ID:
24854837
EC Index Number:
606-048-4
NACRES:
NA.22

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(S)-(−)-1,1′-Bi(2-naphthol)

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1,1′-Bi-2-naphthol

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(R)-(+)-3,3′-Dibromo-1,1′-bi-2-naphthol 97%

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(R)-(+)-3,3′-Dibromo-1,1′-bi-2-naphthol

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(R)-(+)-1,1′-Binaphthyl-2,2′-diamine 99%

Sigma-Aldrich

382426

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

99%

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate ≥98%

Sigma-Aldrich

248932

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

≥98%

(R)-(+)-1,1′-Binaphthyl-2,2′-diol for synthesis

Sigma-Aldrich

8.14774

(R)-(+)-1,1′-Binaphthyl-2,2′-diol

for synthesis

(S)-(−)-1,1′-Binaphthyl-2,2′-diamine 99%

Sigma-Aldrich

382434

(S)-(−)-1,1′-Binaphthyl-2,2′-diamine

99%

(R)-BINAP

Sigma-Aldrich

693065

(R)-BINAP

(R)-(+)-2,2′-Bis(methoxymethoxy)-1,1′-binaphthalene 97%

Sigma-Aldrich

631582

(R)-(+)-2,2′-Bis(methoxymethoxy)-1,1′-binaphthalene

97%

(S)-(−)-3,3′-Dibromo-1,1′-bi-2-naphthol 96%

Sigma-Aldrich

595837

(S)-(−)-3,3′-Dibromo-1,1′-bi-2-naphthol

96%

Quality Level

100

assay

99%

form

solid

optical activity

[α]21/D +34°, c = 1 in THF

optical purity

ee: 99% (HPLC)

mp

208-210 °C (lit.)

SMILES string

Oc1ccc2ccccc2c1-c3c(O)ccc4ccccc34

InChI

1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H

InChI key

PPTXVXKCQZKFBN-UHFFFAOYSA-N

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Related Categories

Application

A chiral auxiliary used in the catalytic asymmetric oxidation of sulfides to sulfoxides. Chiral lanthanide triflates formed from binaphthol serve as catalysts for asymmetric Diels-Alder reactions. Derivatives of binaphthol have recently found use in asymmetric Claisen rearrangements and asymmetric epoxidations. The lithium aluminum hydride derivative of these diols (BINAP-H) has been used extensively for the reduction of ketones.
Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

Packaging

250 mg
1, 5 g in glass bottle
10 g in poly bottle

Pictograms

Skull and crossbonesExclamation mark
GHS06,GHS07

Signal Word

DangerWarning

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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