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246948

Sigma-Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

Synonyme(s) :

(+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL

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1 G
62.00 CHF
5 G
126.00 CHF
10 G
238.00 CHF

About This Item

Formule linéaire :
HOC10H6C10H6OH
Numéro CAS:
18531-94-7
Poids moléculaire :
286.32
Beilstein:
3616837
Numéro MDL:
MFCD00004068
Code UNSPSC :
12352104
ID de substance PubChem :
24854837
Numéro de classement CE :
606-048-4
Nomenclature NACRES :
NA.22

62.00 CHF

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Devis pour commande en gros

Essai

99%

Forme

solid

Activité optique

[α]21/D +34°, c = 1 in THF

Pureté optique

ee: 99% (HPLC)

Pf

208-210 °C (lit.)

Chaîne SMILES 

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

Clé InChI

PPTXVXKCQZKFBN-UHFFFAOYSA-N

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Catégories apparentées

Application

A chiral auxiliary used in the catalytic asymmetric oxidation of sulfides to sulfoxides.[1] Chiral lanthanide triflates formed from binaphthol serve as catalysts for asymmetric Diels-Alder reactions.[2][3] Derivatives of binaphthol have recently found use in asymmetric Claisen rearrangements[4] and asymmetric epoxidations.[5] The lithium aluminum hydride derivative of these diols (BINAP-H) has been used extensively for the reduction of ketones.[6]
Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.[7]

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
MKCW3516
MKCT1737
MKCR8797
MKCQ1892
MKCQ2475

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

Sigma-Aldrich

382434

(S)-(−)-1,1′-Binaphthyl-2,2′-diamine

Noyori, R. et al.
Journal of the American Chemical Society, 106(22), 6709-6709 (1984)
Molecular design of a chiral Lewis acid for the asymmetric Claisen rearrangement.
Maruoka, K. et al.
Journal of the American Chemical Society, 117(3), 1165-1165 (1995)
Asymmetric Diels-Alder reactions catalyzed by chiral lanthanide (III) trifluoromethanesulfonates. Unique structure of the triflate and stereoselective synthesis of both enantiomers using a single chiral source and a choice of achiral ligands.
S. Kobayashi et al.
Tetrahedron, 50(40), 11623-11623 (1994)
Asymmetric aza-Diels-Alder reaction catalyzed by boron reagent: Effect of biphenol and binaphthol ligand.
Hattori, K. Yamamoto, H.
Synlett, 1993(02), 129-129 (1993)
Philip C Bulman Page et al.
The Journal of organic chemistry, 72(12), 4424-4430 (2007-05-18)
A series of binaphthalene-fused azepinium salts has been generated and used as organocatalysts in the asymmetric epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.
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Articles

BINOL and Derivatives

We present an article concerning BINOL and Derivatives.

Questions

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  1. 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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  2. How can I determine the shelf life / expiration / retest date of this product?

    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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