113567-21-8

Basic information

• Product Name: [1,1'-Binaphthalene]-2,2'-dicarboxylic acid, dimethyl ester, (R)-
• CAS NO: 113567-21-8
• Molecular Formula: C24H18O4
• Molecular Weight: 370.405
• Mol File: 113567-21-8.mol

Chemical Properties

• CAS DataBase Reference: [1,1'-Binaphthalene]-2,2'-dicarboxylic acid, dimethyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Binaphthalene]-2,2'-dicarboxylic acid, dimethyl ester, (R)-(113567-21-8)
• EPA Substance Registry System: [1,1'-Binaphthalene]-2,2'-dicarboxylic acid, dimethyl ester, (R)-(113567-21-8)

Safety Data

• Hazardous Substances Data: 113567-21-8(Hazardous Substances Data)

Upstream product

• 89555-39-5 methyl 1-bromo-2-naphthalenecarboxylate 
• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 74-88-4 methyl iodide 
• 76635-70-6 (1-bromo-2-naphthyl)methanol 
• 91-57-6 2-Methylnaphthalene 
• 3378-82-3 1-bromo-2-naphthaldehyde 
• 76373-11-0 1-bromo-2-naphthoyl chloride 
• 37763-43-2 1-bromo-2-(bromomethyl)naphthalene 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 138488-70-7 Methyl 1-chloro-2-naphthoate 

Downstream Products

• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 

Relevant articles and documents

A Novel Clathrate Design: Selective Inclusion of Uncharged Molecules via the Binaphthyl Hinge and Appended Coordinating Groups. X-ray Crystal Structures and Binding Modes of 1,1'-Binaphthyl-2,2'-dicarboxylic Acid Host/Hydroxylic Guest Inclusions

1,1'-Binaphthyl-2,2'-dicarboxylic acid (1) is demonstrated as a novel type of clathrate host whose main mode of action is derived from a combination of the steric barrier and the coordinative interaction principle which constitutes the new "coordinatoclathrate" strategy.Inclusion properties of the crystal lattice of 1 are revealed for a variety of uncharged organic guest molecules (30 examples), ranging from OH-, to NH-, to CH-acidic compounds such as alcohols, carboxylic acids, amides, and nitriles to rather unpolar compounds like bromobenzene and toluene.Marked discrimination selectivities in the clathrate formation from solvent mixtures are found in regard to the group functionality, the substitution pattern, and the molecular size of the guest species, making accessible a simple process for chemical compound separation.The stoichiometries and the increased-temperature as well as the reduced-pressure stabilities of the various clathrates are discussed.The principles of stucture of five different alcohol clathrates of 1 are determined with the aid of X-ray structure analysis at 273 K: 1*2MeOH (10) 1/n, a = 15.642 Angstroem, b = 14.532 Angstroem, c = 9.292 Angstroem, β = 95.14 deg, Z = 4>; 1*2EtOH (11) ; 1*2(2-PrOH) (13) ; 1*2-BuOH (15) 1/n, a = 12.009 Angstroem, b = 12.747 Angstroem, c = 14.982 Angstroem, β = 105.52 deg, Z = 4>; 1*ethylene glycol (24) 1/n, a = 14.276 Angstroem, b = 9.533 Angstroem, c = 15.556 Angstroem, β = 109.19 deg, Z = 4>.In all these cases, however, hydroxyl groups of the host molecules were found to be intercalated via large pseudo-ring formation between the carboxyl functions of at least two host units of opposite chirality with a different mode of hydrogen bridging.Depending on the host:guest stoichiometry (1:1 or 1:2) and on the nature of the guest molecules, these entities consist of three, four, or eight moieties (COOH, OH).The direction of the strong and cooperative bonds is always homodromic.The shape and the size of the cleft formed in the matrix of cooperating host moieties are shown to vary, matching the specific needs of coordinating interactions (hydrogen bonding) and topological requirements (branching, e.g.) of the guest species.

Red or near-infrared light operating negative photochromism of a binaphthyl-bridged imidazole dimer

The development of red or near-infrared light (NIR) switchable photochromic molecules is required for an efficient utilization of sunlight and regulation of biological activities. While the photosensitization of photochromic molecules to red or NIR light has been achieved by a two-photon absorption process, the development of a molecule itself having sensitivity to red or NIR light has been now a challenging study. Herein, we developed an efficient molecular design for realizing red or NIR-light-responsive negative photochromism based on binaphthyl-bridged imidazole dimers. The introduction of electron-donating substituents shows the red shift of the absorption band at the visible-light region because of the contribution of a charge-transfer transition. Especially, the introduction of a di(4-methoxyphenyl)amino group (TPAOMe) and a perylenyl group largely shifts the absorption edge of the stable colored form to 900 nm. In addition, because the absorption band of one of the derivatives substituted with TPAOMe covers the whole visible-light region, the colored form shows a neutral gray color. Upon red (660 nm) or NIR-light (790 nm) irradiation, we observed the negative photochromic reaction from the stable colored form to the metastable colorless form. Therefore, the substituted binaphthyl-bridged imidazole dimers constitute the attractive photoswitches within a biological window.

Synthesis method of axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid

The invention relates to the technical field of bromination, hydrolysis, oxidation and coupling reaction in organic synthesis, particularly a synthesis method of an axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method comprises the following steps: synthesizing a compound 1-bromo-2-methylnaphthalene from an initial raw material 2-bromomethylnaphthalene, carrying out bromination, hydrolysis and oxidation on the 1-bromo-2-methylnaphthalene to obtain 1-bromo-2-naphthoic acid, generating an ester under the actions of methanol and thionyl chloride, protecting the carboxyl group, carrying out Ullmann reaction under the action of copper powder to perform coupling, carrying out hydrolysis to obtain 2,2'-dinaphthyl-1,1'-dicarboxylic acid, and finally, resolving to obtain the (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method is simple to operate, and has the advantages of higher yield and favorable economical efficiency.

Design and synthesis of new stable fluorenyl-based radicals

Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.

Synthesis of axially chiral amino acid derivatives via the selective monoesterification of 1,1′-biaryl-2,2′-dicarboxylic acids

Axially chiral amino acid derivatives were synthesized via a selective single-step monoesterification of 1,1′-binaphthyl-2,2′-dicarboxylic acids. In the presence of Ag2CO3, the alkylative monoesterification of a 1,1′-binaphthyl-2,2′-dicarboxylic acid with an alkyl halide proceeded selectively in a single operation. Curtius rearrangement of the monomethyl ester and successive alcoholysis of the corresponding isocyanate afforded the N-protected binaphthyl amino acids. Georg Thieme Verlag Stuttgart, New York.

Reductive Ullmann coupling of aryl halides by palladium nanoparticles supported on cellulose, a recoverable heterogeneous catalyst

Palladium nanoparticles supported on cellulose were prepared without using any reducing agent and used as a highly efficient catalyst for the Ullmann reductive coupling of aryl halides in the presence of zinc, in a water-alcohol mixture as solvent in air. The obtained palladium nanoparticles were characterized by scanning electron microscopy (SEM), FTIR, thermogravimetric analysis (TGA) and ICP-AES analysis. The synthesis of biaryls from chloroarenes was performed by this catalyst with good yield. The catalyst remains stable up to 75 °C and can be recovered and reused several times without loss of activity.

Synthesis of (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin oxide and preliminary studies on its use in the oxidation of sulfides

The first synthesis (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]- selenepin oxide 1 has been achieved from (R)-(+)-1,1'-bi-2-naphthol, which in turn was obtained by resolution of rac-1,1'-bi-2-naphthol. Palladium catalyzed alkoxy-carbonylation of ditriflate 4 gave dimethyl ester 5 which was then reduced and the resultant diol converted to key intermediate chloride 8. Cyclization with sodium selenolate gave novel enantiomerically pure selenide 9, which upon oxidation yielded the desired selenoxide (R)-1. Preliminary studies on the oxidation of sulfides to sulfoxides using 1 and 2,2,2-trifluoroethane sulfonic acid are also described.

A practical synthesis of C2-symmetric chiral binaphthyl ketone catalyst

A practical synthesis of 11-membered C2-symmetric binaphthyl ketone (R)-1, a catalyst for asymmetric epoxidation, was developed. (±)-1,1'-Binaphthyl-2,2'-dicarboxylic acid [(±)-6] was efficiently resolved by (R)-(-)-1-cyclohexylethylamine to give (R)-6 in >99% ee and in 38% yield. Condensation of the acid chloride derived from (R)-6 with 1,3-dihydroxyacetone dimer at 60-70 °C provided the desired chiral ketone (R)-1 in 61-63% yield without need for high dilution techniques.

Enantioselective dihydroxylation of olefins by osmium tetroxide in the presence of an optically active 1,1'-binaphthyl diamine derivative

The chiral diamine (S)-1, introduced by Cram and Mazaleyrat, has been reprepared following a different sequence which involves the resolution of diacid (RS)-3. The e.e. (via HPLC and NMR), the absolute configuration (via CD) and the most stable conformation (via UV and molecular mechanics calculations) of (S)-1 have been determined. (S)-1 has been employed as a chiral auxiliary in the stoichiometric syn-dihydroxylation of olefins obtaining optically active 1,2-diols with e.e.s up to 98%.

A Convenient Synthesis of Optically Pure Dimethyl 1,1'-Binaphthalene-2,2'-dicarboxylate from 1,1'-Binaphthalene-2,2'-diol

Optically pure dimethyl 1,1'-binaphthalene-2,2'-dicarboxylate has been prepared by methoxycarbonylation of ditriflate of 1,1'-binaphthalene-2,2'-diol catalyzed by Pd(OAc)2-dppp-N,N-diisopropylethylamine in the presence of methanol under CO atmosphere in 83percent yield.