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246956

Sigma-Aldrich

(S)-(−)-1,1′-Bi(2-naphthol)

99%

Synonym(s):

(−)-2,2′-Dihydroxy-1,1′-dinaphthyl, (S)-(−)-1,1′-Binaphthalene-2,2′-diol, (S)-BINOL

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10 MG
CN¥532.96
50 MG
CN¥1,783.43
100 MG
CN¥2,154.06

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10 MG
CN¥532.96
50 MG
CN¥1,783.43
100 MG
CN¥2,154.06

About This Item

Linear Formula:
HOC10H6C10H6OH
CAS Number:
Molecular Weight:
286.32
Beilstein:
4296068
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

CN¥532.96


In StockDetails


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Quality Level

Assay

99%

optical activity

[α]22/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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1 of 4

This Item
I8260I8265I9140
conjugate

unconjugated

conjugate

unconjugated

conjugate

unconjugated

conjugate

unconjugated

form

buffered aqueous solution

form

buffered aqueous solution

form

buffered aqueous solution

form

buffered aqueous solution

shipped in

dry ice

shipped in

wet ice

shipped in

dry ice

shipped in

dry ice

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

grade

technical grade

grade

reagent grade

grade

technical grade

grade

technical grade

assay

≥80% (SDS-PAGE)

assay

~95% (HPLC)

assay

≥80% (SDS-PAGE)

assay

≥80% (SDS-PAGE)

Application

(S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:
  • asymmetric addition of alkynylzinc to unactivated ketones[1]
  • enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines[2]
  • asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones[3]
It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.[4]
Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.[5]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Gerlândia Neres Pontes et al.
FEMS immunology and medical microbiology, 47(3), 405-413 (2006-07-29)
We evaluated the ability of human maternal and cord serum antibodies to protect mice challenged with live Escherichia coli serotype O6:K2ac (E. coli O6). Mice received paired maternal or cord serum pools before a challenge with E. coli O6 to
Simone F A Wouters et al.
Bioconjugate chemistry, 31(3), 656-662 (2020-01-08)
Bioluminescent antibodies represent attractive detection agents in both bioanalytical assays and imaging. Currently, their preparation relies on genetic fusion of luciferases to antibodies or nonspecific chemical conjugation strategies. Here, we report a generic method to generate well-defined covalent antibody-luciferase conjugates
Chuan Chiang-Ni et al.
Frontiers in microbiology, 9, 2592-2592 (2018-11-15)
Group A streptococci (GAS) with spontaneous mutations in the CovR/CovS regulatory system are more invasive and related to severe manifestations. GAS can replicate inside phagocytic cells; therefore, phagocytic cells could serve as the niche to select invasive covS mutants. Nonetheless
K M Dziegielewska et al.
The Histochemical journal, 33(8), 443-451 (2002-04-05)
Fetuin, a foetal protein of unknown function, has been shown to be expressed in both the immune and nervous systems, especially during development. Here, we show for the first time, that fetuin is abundantly present in many cells of the
Ruben Godoy-Silva et al.
Biotechnology and bioengineering, 102(4), 1119-1130 (2008-10-30)
The effect of hydrodynamic forces on animal cell cultures, while extensively studied, still lacks significant, fundamental understanding. A previous manuscript reported on the acute exposure of CHO cells to hydrodynamic forces in a second generation convergent-divergent microfluidic device (Mollet et

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