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482625

Sigma-Aldrich

(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol

98%

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About This Item

Linear Formula:
[BrC10H5(OH)]2
CAS Number:
80655-81-8
Molecular Weight:
444.12
MDL number:
MFCD00798290
UNSPSC Code:
12352005
PubChem Substance ID:
24871837
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +49°, c = 1.8 in THF

mp

195-199 °C (lit.)

InChI

1S/C20H12Br2O2/c21-13-3-5-15-11(9-13)1-7-17(23)19(15)20-16-6-4-14(22)10-12(16)2-8-18(20)24/h1-10,23-24H

InChI key

OORIFUHRGQKYEV-UHFFFAOYSA-N

General description

(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol is an aromatic chiral Bronsted acid.

Application

(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol may be used in the synthesis of (2R,3S)-3-phenylisoserine hydrochloride. It may also be used in the synthesis of BINOL-derived chiral ligands with aryl substituents in the 6,6-positions. [BINOL=1,1′-bi-2-naphthol]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

482625-VAR:
482625-250MG:
482625-BULK:
482625-500MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chiral bis-trifluoromethanesulfonylamide as a chiral Br?nsted acid catalyst for the asymmetric hetero Diels-Alder reaction with Danishefsky's diene.
Tonoi T and Mikami K.
Tetrahedron Letters, 46(37), 6355-6358 (2005)
Asymmetric epoxidation of a, ?-unsaturated ketones catalyzed by chiral ytterbium complexes.
Chen R, et al.
Tetrahedron Letters, 42(39), 6919-6921 (2001)
Catalytic asymmetric synthesis of both syn-and anti-?-amino alcohols.
Kobayashi S, et al.
Journal of the American Chemical Society, 120(2), 431-432 (1998)

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