CAS 18531-99-2|CAS 602-09-5|CAS 18531-94-7|2,2'-Dihydroxy-[1,1']-binaphthyl|1,1'-Binaphthalene-2,2'-diol|1,1'-bi-2-naphthol|1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol|(S)-BINOL|(1S)-1,1'-Binaphthal...

General Information

Structure

Molecular Formula

C₂₀H₁₄O₂

Molecular Mass

286.32396

Exact Mass

286.09937969

Charge

InChI

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

InChIKey

PPTXVXKCQZKFBN-UHFFFAOYSA-N

Canonic Smiles

Oc1ccc2c(c1c1c(O)ccc3c1cccc3)cccc2

Isomeric Smiles

c1(c(ccc2ccccc12)O)c1c(ccc2ccccc12)O

Calculated Properties

JChem

Acid pKa

8.967017

H Acceptors

H Donor

LogD (pH = 5.5)

4.992147

LogD (pH = 7.4)

4.9807143

Log P

4.992294

Molar Refractivity

88.0564

Polarizability

37.822727

Polar Surface Area

40.46

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

2,2'-Dihydroxy-[1,1']-binaphthyl1,1'-Binaphthalene-2,2'-diol(S)-BINOL(1S)-1,1'-Binaphthalene-2,2'-diol(1S)-2,2'-Dihydroxy-[1,1']-binaphthyl(S)-(-)-1,1'-Bi-2-naphthol(R)-(+)-BINOL(R)-(+)-1,1'-Binaphthalene-2,2'-diol(R)-(+)-1,1'-联(2-萘酚)(R)-(+)-1,1'-Bi(2-naphthol)R(+)-1,1'-BI-2-NAPHTHOL(R)-BINOL2,2'-DIHYDROXY-1,1'-DINAPHTHYL(1R)-2,2'-Dihydroxy-[1,1']-binaphthyl(1R)-1,1'-Binaphthalene-2,2'-diol(S)-(-)-1,1′-Bi(2-naphthol)(S)-(-)-1,1′-联(2-萘酚)(-)-2,2′-二羟基-1,1′-联萘(-)-2,2′-Dihydroxy-1,1′-dinaphthyl(S)-(-)-1,1′-Binaphthalene-2,2′-diol(S)-(-)-1,1′-联萘-2,2′-二醇1,1'-Bi-2-naphthol1,1-Binaphthol1,1'-Bi-2,2'-naphtholBINOL(R)-(+)-1,1′-Binaphthalene-2,2′-diol(±)-2,2′-Dihydroxy-1,1′-dinaphthyl1,1′-联-2-萘酚(R)-(+)-1,1′-联萘-2,2′-二醇(±)-1,1′-联萘-2,2′-二醇(R)-(+)-1,1′-联(2-萘酚)2,2′-Dihydroxydinaphthyl2,2′-Dinaphthol(±)-2,2′-二羟基-1,1′-联萘(±)-1,1′-Bi(2-naphthol)(±)-1,1′-Binaphthalene-2,2′-diol(+)-2,2′-二羟基-1,1′-联萘2,2′-Dihydroxybinaphthalene1,1′-Bi-2-naphthol(+)-2,2′-Dihydroxy-1,1′-dinaphthyl(R)-(+)-1,1′-Bi(2-naphthol)(±)-1,1′-联(2-萘酚)(+/-)-BINOL(±)-1,1'-Bi(2-naphthol)[1,1'-Binaphthalene]-2,2'-diol(+/-)-Binaphthalene-2,2'-diol(R)-[1,1'-Binaphthalene]-2,2'-diol(S)-[1,1'-Binaphthalene]-2,2'-diol(+/-)-1,1'-联(2-萘酚)(R)-(+)-1,1'-Bi-2-naphthol

IUPAC Traditional name

1,1'-bi-2-naphthol

IUPAC name

1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol

Names and Identifiers

Registration numbers

MDL Number

MFCD00004068

CAS Number

18531-99-2602-09-518531-94-7

Beilstein Number

36168374296068997518

PubChem SID

248548372484861424846670162036066248486152485483824848612

EC Number

PubChem CID

Merck Index

CHEMBL

Wikipedia Title

Chemspider ID

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02199547

Off white powder.
Optical Purity: >99%
Chemical Purity: >99%

05202016

MP Biomedicals Rare Chemical collection

Wikipedia

1,1'-Bi-2-naphthol

Sigma Aldrich

246956

Application
Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.1
Packaging
1, 5, 10, 25 g in glass bottle

246948

Packaging
1, 5 g in glass bottle
10 g in poly bottle
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 rearrangements4 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.

104655

Application
Chiral ligand and auxiliary for asymmetric Michael addition reaction; enantioselective Diels-Alder reaction; alkynylation.
Packaging
25 g in poly bottle
5 g in glass bottle

14383

Other Notes
Atropisomeric diol with many applications: auxiliary in the enantioselective reduction of ketones;1,2 ligand in chiral titanium catalysts, used for enantioselective reactions, e.g.: glyoxylate ene reactions;3 Diels-Alder CA.4

14382

Other Notes
Zum Weinsäurenachweis1

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

1,1'-bi-2-naphthol

IUPAC name

1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol

Registration numbers

MDL Number

MFCD00004068

CAS Number

18531-99-2602-09-518531-94-7

Beilstein Number

36168374296068997518

PubChem SID

248548372484861424846670162036066248486152485483824848612

EC Number

PubChem CID

Merck Index

CHEMBL

Wikipedia Title

Chemspider ID

Molecule Details

Off white powder.
Optical Purity: >99%
Chemical Purity: >99%

05202016

MP Biomedicals Rare Chemical collection

Wikipedia

1,1'-Bi-2-naphthol

Sigma Aldrich

246956

Application
Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.1
Packaging
1, 5, 10, 25 g in glass bottle

246948

104655

Application
Chiral ligand and auxiliary for asymmetric Michael addition reaction; enantioselective Diels-Alder reaction; alkynylation.
Packaging
25 g in poly bottle
5 g in glass bottle

14383

14382

Other Notes
Zum Weinsäurenachweis1

References

PubChem Literature

No Data Available

Click here to submit data

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:70346