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246948

Sigma-Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

Synonym(s):

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

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1 G
CLP 73,700
5 G
CLP 171,000
10 G
CLP 251,000

CLP 73,700

Estimated to ship onMay 17, 2025

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1 G
CLP 73,700
5 G
CLP 171,000
10 G
CLP 251,000

About This Item

Linear Formula:
HOC10H6C10H6OH
CAS Number:
18531-94-7
Molecular Weight:
286.32
Beilstein:
3616837
MDL number:
MFCD00004068
UNSPSC Code:
12352104
PubChem Substance ID:
24854837
EC Index Number:
606-048-4
NACRES:
NA.22

CLP 73,700

Estimated to ship onMay 17, 2025

Request a Bulk Order

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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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]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (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

Catalytic asymmetric oxidation of sulfides to sulfoxides with tert-butyl hydroperoxide using binaphthol as a chiral auxiliary.
Komatsu N, et al.
The Journal of Organic Chemistry, 58, 4529-4529 (1993)
Catalytic asymmetric epoxidation with (Salen) manganese (III) complex bearing binaphthyl groups of axial chirality.
Sasaki, H. et al.
Synlett, 1993(04), 300-300 (1993)
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%.
View All Related Papers

Articles

BINOL and Derivatives

We present an article concerning BINOL and Derivatives.

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    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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    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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