Compounds > 1,1'-binaphthyl
Page last updated: 2024-12-05

1,1'-binaphthyl

Description

1,1'-Binaphthyl is a chiral molecule with a rigid structure and a large dihedral angle between the two naphthyl units. Its unique properties have made it a versatile building block in organic synthesis and a powerful chiral catalyst. The synthesis of 1,1'-binaphthyl typically involves the dimerization of naphthalene or the coupling of two naphthyl units. Notably, 1,1'-binaphthyl derivatives are known for their diverse applications, including:

- Chiral ligands in asymmetric catalysis: Many chiral ligands based on 1,1'-binaphthyl, such as BINAP and its derivatives, are highly effective in promoting enantioselective reactions. Their rigid structure and the presence of multiple chiral centers contribute to their high enantioselectivity.
- Chiral recognition: 1,1'-binaphthyl derivatives can be used as chiral selectors in chromatography and other analytical techniques for separating enantiomers.
- Liquid crystals: Some derivatives of 1,1'-binaphthyl exhibit liquid crystal properties, making them suitable for use in displays and other optoelectronic devices.
- Organic materials: The planar structure of 1,1'-binaphthyl enables it to form stable pi-stacked structures, which are important in organic electronics.
- Pharmaceuticals: Several 1,1'-binaphthyl derivatives have been investigated as potential drug candidates for treating various diseases.

Research on 1,1'-binaphthyl and its derivatives is driven by its versatile applications and the ongoing effort to develop novel chiral catalysts, materials, and drugs with improved properties.

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

Cross-References

ID SourceID
PubMed CID11789
MeSH IDM0368402

Synonyms (49)

Synonym
1-(1-naphthyl)naphthalene
AC-4950
nsc 15230
t87t28s609 ,
ai3-18146
einecs 210-070-6
di-alpha-naphthol
unii-t87t28s609
nsc-662279
nsc662279
nsc15230
1,1'-dinaphthyl
604-53-5
nsc-15230
1,1'-binaphthyl
1,1'-binaphthalene
di-.alpha.-naphthol
inchi=1/c20h14/c1-3-11-17-15(7-1)9-5-13-19(17)20-14-6-10-16-8-2-4-12-18(16)20/h1-14
B0805
AKOS000352081
1-naphthalen-1-ylnaphthalene
11068-27-2
binaphthalene
1-naphthalen-1-ylnaphthalin
1-(naphthalen-1-yl)naphthalene
binaphthyl
FT-0606058
(+/-)-binaphthyl
.alpha.,.alpha.'-binaphthyl
1,1'-binaphtyl
.alpha.,.alpha.'-dinaphthylene
mfcd00041740
1,1'-binaphthyl, 98%
1,1pr-binaphthyl
(+/-)-1,1'-binaphthyl
DTXSID70870671
SY037129
1,1 inverted exclamation mark -binaphthyl
AS-14353
AMY13703
OL10142
Q27289804
1,1/'-binaphthyl
i+/-,.i+/-'-binaphthyl
1,1-binaphthyl
1-(naphthalen-1-yl)naphthalene;1,1'-binaphthalene
A851185
PB47311
CS-W014087
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's8 (17.78)29.6817
2010's30 (66.67)24.3611
2020's7 (15.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.49

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 Index33.49 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.63 (4.65)
Search Engine Demand Index39.93 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.49)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (4.44%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other43 (95.56%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
imidazole
imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.		2.0610imidazole
naphthalene
[no description available]		2.0710naphthalenes;
ortho-fused bicyclic arene		apoptosis inhibitor;
carcinogenic agent;
environmental contaminant;
mouse metabolite;
plant metabolite;
volatile oil component
nickel
Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.		2.0810metal allergen;
nickel group element atom		epitope;
micronutrient
phosphoric acid
phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.		2.0610phosphoric acidsalgal metabolite;
fertilizer;
human metabolite;
NMR chemical shift reference compound;
solvent
camphor, (+-)-isomer
[no description available]		2.0710bornane monoterpenoid;
cyclic monoterpene ketone		plant metabolite
ethylenediamine
ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.		2.0610alkane-alpha,omega-diamineGABA agonist
cyanides
Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.		2.0610pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor
tert-butylhydroperoxide
tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.		2.0410alkyl hydroperoxideantibacterial agent;
oxidising agent
fluorene
[no description available]		2.0710ortho-fused polycyclic arene;
ortho-fused tricyclic hydrocarbon
2-naphthylamine
2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.		2.0510naphthylaminecarcinogenic agent
diphenyl
diphenyl: RN given refers to unlabeled cpd; structure		2.0810aromatic fungicide;
benzenes;
biphenyls		antifungal agrochemical;
antimicrobial food preservative
styrene
Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.		2.0510styrenes;
vinylarene;
volatile organic compound		mouse metabolite;
mutagen;
plant metabolite
vinyl acetate
[no description available]		2.0510acetate ester
allyl cyanide
TL 350: structure given in first source. allyl cyanide : An aliphatic nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an allyl group.		2.0510aliphatic nitrile;
olefinic compound		antifeedant;
neurotoxin;
plant metabolite
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		2.7330naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.11101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
thiazoles
[no description available]		2.11101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
(s)-binol
(1,1'-binaphthalene)-2,2'-diol: structure in first source		2.0510naphthols
2,2'-diamino-1,1'-dinaphthyl
2,2'-diamino-1,1'-dinaphthyl: structure in first source		2.0510
iridium
Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.		7.5520cobalt group element atom;
platinum group metal atom
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0610metal allergen;
nickel group element atom;
platinum group metal atom
rhodium
Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.		7.4720cobalt group element atom
titanium
Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.		2.0710titanium group element atom
europium
Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.		2.0610f-block element atom;
lanthanoid atom
phosphine
phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.		7.4720mononuclear parent hydride;
phosphanes;
phosphine		carcinogenic agent;
fumigant insecticide
salen
disalicylaldehyde ethylenediamine: reagents for determination of iron		2.0710
alkenes
[no description available]		2.0710
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.2510glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.07101,2,3-triazole
homocysteine
Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.		2.1310amino acid zwitterion;
homocysteine;
serine family amino acid		fundamental metabolite;
mouse metabolite
fullerene c60
Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.		2.0810fullerenegeroprotector
2-oxindole
2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.		2.0710gamma-lactam;
indolinone
tartaric acid
tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.		3.2310tartaric acidEscherichia coli metabolite
maleic acid
maleic acid: RN given refers to parent cpd(Z)-isomer which is maleic acid; all RR's given refer to (Z)-isomer; (E)-isomer is fumaric acid. maleic acid : A butenedioic acid in which the double bond has cis- (Z)-configuration.		2.0610butenedioic acidalgal metabolite;
mouse metabolite;
plant metabolite
fumaric acid
fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.		7.0610butenedioic acidfood acidity regulator;
fundamental metabolite;
geroprotector
gallium
Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.		2.1310boron group element atom
fumarates
Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)		2.0610butenedioate;
C4-dicarboxylate		human metabolite;
metabolite;
Saccharomyces cerevisiae metabolite
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		2.1310cysteiniumfundamental metabolite
phosphoramidite
phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.		2.0510
piperidines
Piperidines: A family of hexahydropyridines.		2.0810
smectite
smecta: used therapeutically in chronic gastritis. montmorillonite : An aluminosilicate mineral consisting of aluminosilicate layers approximately 1 nm thick which are surface-substituted with metal cations and stacked in ca. 10 mum-sized multilayer stacks. Its approximate formula is R(+)0.33(Al,Mg)2Si4O10(OH)2.nH2O where R(+) includes one or more of the cations Na(+), K(+), Mg(2+), and Ca(2+).		2.0410
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		2.0810
ConditionIndicatedRelationship StrengthStudiesTrials
Bacterial Disease
[description not available]		02.1110
Bacterial Infections
Infections by bacteria, general or unspecified.		02.1110
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