Page last updated: 2024-12-05

(s)-binol

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Description

A chiral, non-racemic compound with two hydroxyl groups, (s)-binol is widely used in asymmetric synthesis as a ligand for a variety of transition metal catalysts. Its synthesis typically involves a multi-step process starting from commercially available reagents. (s)-binol has been found to be a highly effective chiral catalyst for a wide range of enantioselective reactions, including Diels-Alder, aldol, and Michael reactions. Its enantioselectivity, ease of use, and broad applicability make it a valuable tool for synthetic chemists and researchers. (s)-binol has been shown to have various pharmacological effects, including anti-inflammatory and antioxidant properties. It is also studied for its potential applications in materials science, particularly in the development of chiral sensors and liquid crystals. The unique properties of (s)-binol, such as its chirality and its ability to form stable complexes with metal ions, make it a highly valuable research subject.'

(1,1'-binaphthalene)-2,2'-diol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11762
CHEMBL ID138718
CHEBI ID189881
SCHEMBL ID29027
MeSH IDM0361199

Synonyms (178)

Synonym
AC-6133
[1,1'-binaphthalene]-2,2'-diol
2,1'-binaphthyl
2,2'-dihydroxydinaphthyl
602-09-5
nsc-27049
.alpha.-binaphthyl-2,2'-diol
1,1'-bi-2-naphthol ,
1,1'-bis-2-naphthol
nsc27049
2,1'-binaphthalene
2,2'-dihydroxybinaphthalene
.beta.-binaphthol
2,2'-dinaphthol
bis-.beta.-naphthol
(r)-(+)-1,1'-bi-2-naphthol
inchi=1/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/h1-12,21-22
2,2'-dihydroxy-1,1'-dinaphthyl
2,2'-dihydroxy-1,1'-binaphthalene
(1,1'-binaphthalene)-2,2'-diol
einecs 210-014-0
chiral binaphthol
1,1'-binaphthyl-2,2'-diol
brn 0997518
ai3-19388
beta-binaphthol
nsc 27049
alpha-binaphthyl-2,2'-diol
2,2'-dihydroxy-1,1'-binaphthyl
bis-beta-naphthol
1,1'-bi-2-naphthol, 99%
(s)-(-)-1,1'-bi(2-naphthol), 99%
(r)-(+)-1,1'-bi(2-naphthol), 99%
(r)-(+)-2,2'-dihydroxy-1,1'-binaphthyl
(r)-(+)-binol
(s)-(-)-binol
18531-94-7
B0461
B1142
(s)-(-)-1,1'-bi-2-naphthol
18531-99-2
(s)-(-)-2,2'-dihydroxy-1,1'-binaphthyl
B1100 ,
CHEMBL138718
AKOS000280003
(r)-(+)-1,1'-bi(2-naphthol)
CHEBI:189881
1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol
A832643
binol
(r)-1,1'-bi-2-naphthol
(+/-)-1,1'-binaphthalene-2,2'-diol
(+/-)-2,2'-dihydroxy-1,1'-dinaphthyl
A812947
1-(2-oxidanylnaphthalen-1-yl)naphthalen-2-ol
1-(2-hydroxy-1-naphthalenyl)-2-naphthalenol
(r)-(+)-bi-2-naphthol
s-(-)-2,2'-dihydroxy-1,1'-dinaphthyl
AKOS015950732
AKOS015950645
AM62789
(+)-2,2'-dihydroxy-1,1'-dinaphthyl
(r)-binol
r-(+)-1,1'-bi-2-naphthol
(s)-binol
(r)-[1,1'-binaphthalene]-2,2'-diol
(+)-1,1'-bi-2-naphthol
(+)-2,2'-dihydroxy-1,1'-binaphthyl
(s)-2,2'-dihydroxy-1,1'-binaphthalene
(r)-bi-2-naphthol
binol, (+)-
(+)-1,1'-bis(2-naphthol)
(-)-2,2'-binaphthol
(+)-(r)-2,2'-dihydroxy-1,1'-binaphthyl
binol (r)-(+)-form [mi]
(s)-binaphthol
(+)-bi-beta-naphthol
binol (s)-(-)-form [mi]
(-)-(1s)-(1,1'-binaphthalene)-2,2'-diol
(-)-1,1'-bi-2-naphthol
(+)-2,2'-binaphthol
(1,1'-binaphthalene)-2,2'-diol, (r)-(+)-
(+)-(1r)-(1,1'-binaphthalene)-2,2'-diol
(+)-2,2'-dihydroxy-1,1'-binaphthalene
unii-m6idz128wt
(-)-1,1'-bis(2-naphthol)
(s)-(-)-2,2'-dihydroxy-1,1'-binaphthalene
m6idz128wt ,
(s)-2,2'-dihydroxy-1,1'-binaphthyl
binol, (-)-
(+)-bi-2-naphthol
(r)-binaphthol
unii-54ot5rrv4c
(1,1'-binaphthalene)-2,2'-diol, (s)-(-)-
(-)-bi-beta-naphthol
(-)-binol
54ot5rrv4c ,
(r)-(1,1'-binaphthalene)-2,2'-diol
ec 606-050-5
(s)-[1,1'-binaphthalene]-2,2'-diol
unii-25ab254328
25ab254328 ,
4-06-00-07020 (beilstein handbook reference)
FT-0602420
FT-0605200
FT-0604444
s-(-)-1,1'-bi-2-naphthol
[1,1']binaphthalenyl-2,2'-diol
BP-21310
(r)-2,2'-dihydroxy-[1,1']-binaphthyl
SCHEMBL29027
(-)-bi-.beta.-naphthol
binol, (s)-
J-503719
2,2'-dihydroxyl-1,1'-binaphthyl
[1,1']-binaphthalenyl-2,2'-diol
(5)-1,1'-bi-2-naphthol
(s)-(-)-1,1'-bi-2-naphtol
(s)-1,1'-bi-2-naphthol
DTXSID9060526
Q-103560
Q-200048
Q-103561
(r)-1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol
(s)-(-)-1,1'-bi(2-naphthol)
(r)-(+)-1,1-bi-2-naphthol
(+/-)-1,1'-bi(2-naphthol)
(s)-(-)-1,1-bi-2-naphthol
(+)-bi-.beta.-naphthol
binol, (r)-
mfcd00004068
r-(+)-2,2'-dihydroxy-1,1'-dinaphthyl
GS-3437
(s)-1,1'-binaphthalene-2,2'-diol
AC-2795
1,1a(2)-bi-2-naphthol
(+/-)-1,1'-bi(2-naphthol), puriss., >=99.0% (nt)
(r)-(+)-1,1'-bi(2-naphthol), puriss., >=99.0% (sum of enantiomers, hplc)
CS-W018498
(rs)-1,1'-bi-2,2'-naphthol
(1s)-[1,1'-binaphthalene]-2,2'-diol
J-011889
CS-D1439
F0001-0669
BCP23136
BCP23230
(+/-)-1,1'-bi-2-naphthol
(r,s)-binol
Q161292
benzamide,n-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)-2-[2-(dimethylamino)ethoxy]-
BCP30910
(r)-(+)-1
rac-[1,1'-binaphthalene]-2,2'-diol
(r)-(+)-1,1`-bi-2-naphthol
(s)-(+)-1,1`-bi-2-naphthol
(s)-(-)-1,1`-bi-2-naphthol
(1r)-[1,1'-binaphthalene]-2,2'-diol
2,2'-dihydroxy-[1,1']-binaphthyl
(r)-2,2'-dihydroxy-1,1'-binaphthalene
(s)-2,2'-binaphthol
(s)-1,1'-binaphthyl-2,2'-diol
(r)-1,1'-binaphthalene-2,2'-diol
(r)-1,1'-binaphthyl-2,2'-diol
(-)-1,1'-binaphthyl-2,2'-diol
(+)-1,1'-binaphthyl-2,2'-diol
(r)-(+)-2,2'-dihydroxy-1,1'-binaphthalene
(r)-2,2'-binaphthol
(+/-)-2,2'-dihydroxy-1,1'-binaphthyl
(+/-)-1,1'-binaphthyl-2,2'-diol
(rs)-1,1'-bi-2-naphthol
(+/-)-binol
rac-2,2'-dihydroxy-1,1'-binaphthyl
(+/-)-1,1'-bis(2-naphthol)
racemic 2,2'-dihydroxy-1,1'-binaphthyl
binol [mi]
(+/-)-2,2'-dihydroxy-1,1'-binaphthalene
(+/-)-bi-.beta.-naphthol
EN300-67379
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
naphtholsAny hydroxynaphthalene derivative that has a single hydroxy substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID46670Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 10 uM in COS-7 cells1998Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22
Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (54)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (3.70)18.2507
2000's30 (55.56)29.6817
2010's20 (37.04)24.3611
2020's2 (3.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.07

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.07 (24.57)
Research Supply Index4.03 (2.92)
Research Growth Index5.43 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.82%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other54 (98.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]