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

• ChemBase ID: 70346
• Molecular Formular: C20H14O2
• Molecular Mass: 286.32396
• Monoisotopic Mass: 286.09937969
• SMILES: c1(c(ccc2ccccc12)O)c1c(ccc2ccccc12)O
• Canonical SMILES: Oc1ccc2c(c1c1c(O)ccc3c1cccc3)cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol
• IUPAC Traditional name: 1,1'-bi-2-naphthol
• Synonyms: (S)-(-)-1,1'-Bi-2-naphthol; 1,1'-Binaphthalene-2,2'-diol; 2,2'-Dihydroxy-[1,1']-binaphthyl; (1S)-1,1'-Binaphthalene-2,2'-diol; (S)-BINOL; (1S)-2,2'-Dihydroxy-[1,1']-binaphthyl; (1R)-1,1'-Binaphthalene-2,2'-diol; (R)-BINOL; (1R)-2,2'-Dihydroxy-[1,1']-binaphthyl; (R)-(+)-1,1'-Binaphthalene-2,2'-diol; (R)-(+)-BINOL; (R)-(+)-1,1'-Bi(2-naphthol); (+)-2,2′-Dihydroxy-1,1′-dinaphthyl; (R)-(+)-1,1′-Binaphthalene-2,2′-diol; (R)-(+)-1,1′-Bi(2-naphthol); 2,2′-Dihydroxybinaphthalene; 2,2′-Dihydroxydinaphthyl; 2,2′-Dinaphthol; (±)-1,1′-Binaphthalene-2,2′-diol; (±)-2,2′-Dihydroxy-1,1′-dinaphthyl; 1,1′-Bi-2-naphthol; 1,1'-Bi-2,2'-naphthol; 1,1-Binaphthol; BINOL; 1,1'-Bi-2-naphthol; 2,2'-DIHYDROXY-1,1'-DINAPHTHYL; (+/-)-Binaphthalene-2,2'-diol; (+/-)-BINOL; (±)-1,1'-Bi(2-naphthol); (R)-[1,1'-Binaphthalene]-2,2'-diol; (S)-[1,1'-Binaphthalene]-2,2'-diol; R(+)-1,1'-BI-2-NAPHTHOL; (±)-1,1′-Bi(2-naphthol); (-)-2,2′-Dihydroxy-1,1′-dinaphthyl; (S)-(-)-1,1′-Binaphthalene-2,2′-diol; (S)-(-)-1,1′-Bi(2-naphthol); (R)-(+)-1,1'-Bi-2-naphthol; [1,1'-Binaphthalene]-2,2'-diol; (R)-(+)-1,1'-联(2-萘酚); (+)-2,2′-二羟基-1,1′-联萘; (R)-(+)-1,1′-联萘-2,2′-二醇; (R)-(+)-1,1′-联(2-萘酚); (±)-1,1′-联萘-2,2′-二醇; (±)-2,2′-二羟基-1,1′-联萘; 1,1′-联-2-萘酚; (+/-)-1,1'-联(2-萘酚); (±)-1,1′-联(2-萘酚); (-)-2,2′-二羟基-1,1′-联萘; (S)-(-)-1,1′-联萘-2,2′-二醇; (S)-(-)-1,1′-联(2-萘酚)

Database IDs

• CAS Number: 18531-94-7; 602-09-5; 18531-99-2
• EC Number: 210-014-0
• MDL Number: MFCD00004068
• Beilstein Number: 3616837; 4296068; 997518
• Merck Index: 141226
• PubChem SID: 24848614; 162036066; 24854838; 24848612; 24854837; 24846670; 24848615
• PubChem CID: 11762
• CHEMBL: 138718
• Chemspider ID: 11269
• Wikipedia Title: 1,1'-Bi-2-naphthol

CALCULATED PROPERTIES

• Acid pKa: 8.967017
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.992147
• LogD (pH = 7.4): 4.9807143
• Log P: 4.992294
• Molar Refractivity: 88.0564 cm^3
• Polarizability: 37.822727 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dioxane: soluble50 mg/mL, clear
• Melting Point: 205-211 °C; 206-211°C; 207-210°C; 208-210 °C(lit.); 208-211°C; 214-217 °C(lit.); 215-218 °C; 215-218°C
• Density: 1.301
• Optical Rotation: [α]20/D +35.5±2°, c = 1% in THF; [α]20/D -36.0±2.0°, c = 1% in THF; [α]21/D +34°, c = 1 in THF; [α]22/D -34°, c = 1 in THF; +34.5 (c=1 in THF)

Safety Information

• Storage Warning: IRRITANT; Toxic
• RTECS: DU3106000; DU3106100
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 25-36; 25-36/37/38
• Safety Statements: 26-36/37-45; 26-45
• TSCA Listed: false; 否; 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H301-H319
• GHS Precautionary statements: P280H-P305+P351+P338-P309-P310; P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: >99%; ≥99.0% (NT); ≥99.0% (sum of enantiomers, HPLC); 95+%; 97%; 98%; 99%
• Grade: puriss.
• Optical Purity: ee: 99% (HPLC); enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: HOC10H6C10H6OH
• Empirical Formula (Hill Notation): C20H14O2

DETAILS

MP Biomedicals - 05202016

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02199547

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

Sigma Aldrich - 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

Sigma Aldrich - 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.

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

Sigma Aldrich - 14382

Other Notes
Zum Weinsäurenachweis1

Sigma Aldrich - 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