1,1'-BINAPHTHALENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H14
Molecular Weight	254.3252
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CC2=CC=CC(=C2C=C1)C3=C4C=CC=CC4=CC=C3

InChI

InChIKey=ZDZHCHYQNPQSGG-UHFFFAOYSA-N

InChI=1S/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/h1-14H

HIDE SMILES / InChI

Molecular Formula	C20H14
Molecular Weight	254.3252
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Efficient synthesis of chiral 1,1'-binaphthalenes by the asymmetric suzuki-miyaura reaction: dramatic synthetic improvement by simple purification of naphthylboronic acids.	2006-12-13	17004292
Electrophoretic analysis of proteins and enantiomers using capillaries modified by a successive multiple ionic-polymer layer (SMIL) coating technique.	2006-10	16703385
Self-assembly of multinuclear complexes with enantiomerically pure chiral binaphthoxy imine ligands: effect of the alkyl spacer connecting two binaphthyl units on the metal binding.	2006-09	16823815
Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: a novel ship's wheel-like interlocked structure.	2006-07-17	16548022
Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py.	2006-07-12	16819850
Effect of racemic and (+)- and (-)-gossypol on the survival and development of Helicoverpa zea larvae.	2006-05	16739016
Three-dimensional description of the spontaneous onset of homochirality on the surface of a conglomerate crystal phase.	2006-04-27	16623535
1,1'-Binaphthyl-2,2'-diyl phosphoroselenoyl chloride as a chiral molecular tool for the preparation of enantiomerically pure alcohols and amines.	2006-04-12	16594690
A novel supported Katsuki-type (salen)Mn complex for asymmetric epoxidation.	2006-03-07	16493476
Binaphthalene molecules with tetrathiafulvalene units: CD spectrum modulation and new chiral molecular switches by reversible oxidation and reduction of tetrathiafulvalene units.	2006-03-03	16497001
Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes.	2006-02-08	16448108
First optically active molecular electronic wires.	2006-02-02	16435833
Enhancement of a pentacyclic tyrosine kinase inhibitor production in Cladosporium cf. cladosporioides by Cladosporol.	2006-02	15986220
Solid film versus solution-phase charge-recombination dynamics of exTTF-bridge-C60 dyads.	2005-12-09	16254937
Topological effects of a rigid chiral spacer on the electronic interactions in donor-acceptor ensembles.	2005-12-09	16163762
Enantiopure 1,1'-binaphthyl-based polyoxometalate-containing molecular hybrids.	2005-10-31	16241119
Synthesis of helical polyacetylene in chiral nematic liquid crystals using crown ether type binaphthyl derivatives as chiral dopants.	2005-10-26	16231917
Chiral symmetry breaking and polymorphism in 1,1'-binaphthyl melt crystallization.	2005-10-13	16853413
Probing stereoselective inhibition of the acyl binding site of cholesterol esterase with four diastereomers of 2'-N-alpha-methylbenzylcarbamyl-1, 1'-bi-2-naphthol.	2005-09-22	16176589
Chromophoric binaphthyl derivatives.	2005-08-18	16092844
Tuning the CD spectrum and optical rotation value of a new binaphthalene molecule with two spiropyran units: mimicking the function of a molecular "AND" logic gate and a new chiral molecular switch.	2005-08-05	16050673
Highly enantioselective synthesis of (2S)-alpha-(hydroxymethyl)-glutamic acid by the catalytic Michael addition of 2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester.	2005-07-21	16018622
Applications of 4,4'-(Me3Si)2-BINAP in transition-metal-catalyzed asymmetric carbon-carbon bond-forming reactions.	2005-07-07	15987160
Design of an axially chiral amino acid with a binaphthyl backbone as an organocatalyst for a direct asymmetric aldol reaction.	2005-05-13	15828036
Bis(cyclopentadienyl)titanium complexes of naphthalene-1,8-dithiolates, biphenyl 2,2'-dithiolates, and related ligands.	2005-04-18	15819557
Cohaerins A and B, azaphilones from the fungus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect. Annulata.	2005-04	15797606
[Application of binaphthyl derivatives as chiral stationary phases in high performance liquid chromatography].	2005-03	16013557
Development of 4,4'-substituted-XylBINAP ligands for highly enantioselective hydrogenation of ketones.	2005-02-18	15704949
A binaphthyl-containing Eu(III) complex and its interaction with human serum albumin: a luminescence study.	2005-02-07	15672168
Kinetic model for the chiral symmetry breaking transition in the growth front of a conglomerate crystal phase.	2005-02-03	16851129
Chiral separations using a polypeptide and polymeric dipeptide surfactant polyelectrolyte multilayer coating in open-tubular capillary electrochromatography.	2004-11-15	15538792
Synthesis and luminescence studies of mono- and C3-symmetric, tris(ligand) complexes of Sm(III), Y(III) and Eu(III) with sulfur-bridged binaphtholate ligands.	2004-11-07	15510302
The control of the cholesteric pitch by some azo photochemical chiral switches.	2004-11-05	15470693
Chiral molecular squares based on angular bipyridines: self-assembly, characterization, and photophysical properties.	2004-10-18	15476354
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s.	2004-10-01	15387580
Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands for Rh-catalyzed asymmetric hydrogenation.	2004-09-30	15387554
Macrocyclic bisbinaphthyl fluorophores and their acyclic analogues: signal amplification and chiral recognition.	2004-09-17	15357587
Metal-assisted assembly of pyridine-containing arylene ethynylene strands to enantiopure double helicates.	2004-08-25	15315454
Chiral separations in microemulsion electrokinetic chromatography. Use of micelle polymers and microemulsion polymers.	2004-07-23	15330104
Models for biological trinuclear copper clusters. Characterization and enantioselective catalytic oxidation of catechols by the copper(II) complexes of a chiral ligand derived from (S)-(-)-1,1'-binaphthyl-2,2'-diamine.	2004-07-21	15249957
A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives.	2004-06-11	15176851
Asymmetric benzoin condensation catalyzed by chiral rotaxanes tethering a thiazolium salt moiety via the cooperation of the component: can rotaxane be an effective reaction field?	2004-03-24	15025467
Absorption, fluorescence, and cd spectroscopic study of chiral recognition by a binaphthyl-derived chromogenic calixcrown host.	2004-03	14770414
Novel anionic copolymerized surfactants of mixed achiral and chiral surfactants as pseudostationary phases for micellar electrokinetic chromatography.	2004-02	14981705
Chiral recognition of binaphthyl derivatives using electrokinetic chromatography and steady-state fluorescence anisotropy: effect of temperature.	2004-02	14981704
Combination of cyclodextrins and polymeric surfactants for chiral separations.	2004-02	14981703
Polymeric alkenoxy amino acid surfactants: III. Chiral separations of binaphthyl derivatives.	2004-02	14981700
Chiral symmetry-breaking transition in growth front of crystal phase of 1,1'-binaphthyl in its supercooled melt.	2004-02	14712477
Evaluation of newly synthesized and commercially available charged cyclomaltooligosaccharides (cyclodextrins) for capillary electrokinetic chromatography.	2004-01-22	14698882
A unique binaphthyl strapped iron-porphyrin catalyst for the enantioselective epoxidation of terminal olefins.	2004-01-05	14695567

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:26:00 GMT 2025` Edited by `admin` on `Mon Mar 31 19:26:00 GMT 2025`
Record UNII	T87T28S609
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,1'-BINAPHTHALENE

Systematic Name

English

NSC-15230

Preferred Name

English

.ALPHA.,.ALPHA.'-BINAPHTHYL

Systematic Name

English

NSC-662279

Code

English

DI-.ALPHA.-NAPHTHOL

Common Name

English

(±)-BINAPHTHYL

Systematic Name

English

1,1'-BINAPHTHYL

Systematic Name

English

Code System Code Type Description

PUBCHEM

11789