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104655

Sigma-Aldrich

1,1′-Bi-2-naphthol

99%

Synonym(s):

(±)-1,1′-Binaphthalene-2,2′-diol, (±)-2,2′-Dihydroxy-1,1′-dinaphthyl, 2,2′-Dihydroxybinaphthalene, 2,2′-Dihydroxydinaphthyl, 2,2′-Dinaphthol, BINOL

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5 G
HUF 12,200.00
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HUF 31,600.00

About This Item

Linear Formula:
HOC10H6C10H6OH
CAS Number:
602-09-5
Molecular Weight:
286.32
Beilstein:
997518
EC Number:
210-014-0
MDL number:
MFCD00004068
UNSPSC Code:
12161600
PubChem Substance ID:
24846670
NACRES:
NA.22

HUF 12,200.00

Please contact Customer Service for Availability
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Assay

99%

reaction suitability

reagent type: ligand

mp

214-217 °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

Application

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2034V
WXBD4813V
WXBD3075V
WXBD2396V
WXBC9636V

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2,2′-Dibromo-1,1′-binaphthyl 96%

Sigma-Aldrich

676438

2,2′-Dibromo-1,1′-binaphthyl

BINOL: a versatile chiral reagent.
Jean Michel Brunel
Chemical reviews, 105(3), 857-897 (2005-03-10)
Bixia Yao et al.
Journal of chromatography. A, 1216(28), 5429-5435 (2009-06-09)
In this work, the enantioseparations of 1,1'-bi-2-naphthol (BINOL) and its three derivatives were performed on an immobilized polysaccharide-based chiral stationary phase, Chiralpak IA, under normal-phase mode. The effects of the content of polar modifier in the mobile phase and the
Fengping Zhan et al.
Journal of chromatography. A, 1217(26), 4278-4284 (2010-05-15)
Enantioseparation of 1,1'-bi-2-naphthol (BINOL) was performed on a polysaccharide-based chiral stationary phase, Chiralcel OD-H, under normal-phase mode. The effects of polar modifier in the mobile phase on the retention, enantioseparation and elution order were investigated in detail. Solvent-induced reversal of
Na Ji et al.
Journal of the American Chemical Society, 128(27), 8845-8848 (2006-07-06)
Chiral sum-frequency (SF) spectroscopy that measures both the real and the imaginary components of the SF spectral response was demonstrated for the first time. It was based on interference of the SF signal with a dispersionless SF reference. Solutions of
Hai-Lei Cui et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(7), 1574-1577 (2009-01-10)
The first highly enantioselective allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates by dual catalysis of (DHQD)(2)AQN and (S)-BINOL has been investigated. Excellent stereoselectivities have been achieved for a broad spectrum of substrates (d.r. > 99:1, up to 99 % ee).
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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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