Molbank

Open AccessShort Note

2-Oxo-2H-chromen-7-yl 4-chlorobenzoate

by

Diana Becerra

,

Jaime Portilla

and

Juan-Carlos Castillo

Molbank 2021, 2021(3), M1279; https://doi.org/10.3390/M1279 - 14 Sep 2021

Abstract

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester [...] Read more.

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester 3 was completely characterized by mass spectrometry, IR, UV–Vis, 1D, and 2D NMR spectroscopy. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

► Show Figures

Figure 1

Open AccessShort Note

4,6-Bis((E)-2-(4′-N,N-diphenylamino-[1,1′-biphenyl]-4-yl)vinyl)-2-phenylpyrimidine

by

Lacina Diarra

,

Françoise Robin-le Guen

and

Sylvain Achelle

Molbank 2021, 2021(3), M1278; https://doi.org/10.3390/M1278 - 10 Sep 2021

Abstract

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with [...] Read more.

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with 4-(N,N-diphenylamino)phenylboronic acid. This compound exhibits intense emission in moderately polar solvents as well as in solid state. This compound is characterized by an intense emission solvatochromism with emission ranging from blue in non polar n-heptane to orange in dichloromethane. This chromophore is also sensible to the presence of acid with a bathochromic shift of the charge transfer absorption band and emission quenching. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

Open AccessArticle

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

by

Otávio Augusto Chaves

,

Vitor Sueth-Santiago

,

Douglas Chaves de Alcântara Pinto

,

José Carlos Netto-Ferreira

,

Debora Decote-Ricardo

and

Marco Edilson Freire de Lima

Molbank 2021, 2021(3), M1276; https://doi.org/10.3390/M1276 - 07 Sep 2021

Abstract

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization [...] Read more.

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7 was performed by ¹H and ¹³C nuclear magnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfect match between them. UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log ε = 4.57) and fluorescence quantum yield (ϕ = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

► Show Figures

Graphical abstract

Open AccessShort Note

2,6-Dimethoxybenzyl Bromide

by

R. Alan Aitken

,

Elizabeth A. Saab

and

Alexandra M. Z. Slawin

Molbank 2021, 2021(3), M1277; https://doi.org/10.3390/M1277 - 07 Sep 2021

Abstract

The unstable title compound has been characterized for the first time. Its melting point, UV, IR, ¹H and ¹³C-NMR and high-resolution mass spectra are presented. The X-ray structure has also been determined and shows a rather long C–Br bond perpendicular to [...] Read more.

The unstable title compound has been characterized for the first time. Its melting point, UV, IR, ¹H and ¹³C-NMR and high-resolution mass spectra are presented. The X-ray structure has also been determined and shows a rather long C–Br bond perpendicular to the otherwise planar molecule. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

Open AccessCommunication

Practical and Asymmetric Synthesis of Apremilast Using Ellman’s Sulfinamide as a Chiral Auxiliary

by

Bofei Wang

and

Fangrui Zhong

Molbank 2021, 2021(3), M1275; https://doi.org/10.3390/M1275 - 02 Sep 2021

Abstract

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and [...] Read more.

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and with 95.5% ee. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

Open AccessCommunication

4-(((4-Methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-Methoxy-5-((phenylamino)methyl)phenol

by

Peter A. Ajibade

and

Fartisincha P. Andrew

Molbank 2021, 2021(3), M1274; https://doi.org/10.3390/M1274 - 31 Aug 2021

Abstract

Molecular structures of 4-(((4-methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-methoxy-5-((phenylamino)methyl)phenol synthesized via Schiff bases reduction route are reported. The compounds consist of asymmetric units of C₁₆H₂₀N₂O (1) and C₁₄H₁₅NO₂ ( [...] Read more.

Molecular structures of 4-(((4-methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-methoxy-5-((phenylamino)methyl)phenol synthesized via Schiff bases reduction route are reported. The compounds consist of asymmetric units of C₁₆H₂₀N₂O (1) and C₁₄H₁₅NO₂ (2) in orthorhombic and monoclinic crystal systems, respectively. Compound 1 consist of intermolecular C11—H11···N2 hydrogen bonding with C11···N21 = 3.463(4) Å. The hydroxyl group in 2 is also involved in intermolecular O2—H2···O2 and O2—H2···O21 hydrogen bonding with O2···O11 = 2.8885(15) Å and O1···O21 = 2.9277(5) Å. The molecular structures of the compounds are stabilized by secondary intermolecular interactions of C1—H1B···O11 and C5—H···(C41, C51, C61, C71) for 1 and H···C, C—H···O and N—H···C for 2. The reported compounds are important starting material for the synthesis of many compounds such as azo dyes and dithiocarbamate. Full article

► Show Figures

Figure 1

Open AccessCommunication

Synthesis of 4-[(1H-Benzimidazol-2-yl)sulfanyl]benzaldehyde and 2-({4-[(1H-Benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide

by

Mustafa Turki Ubeid

,

Hamdy Khamees Thabet

and

Mohamed Yousef Abu Shuheil

Molbank 2021, 2021(3), M1273; https://doi.org/10.3390/M1273 - 26 Aug 2021

Abstract

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux [...] Read more.

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux temperature yielded 2-({4-[(1H-benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide. The structure of the synthesized compounds was established by NMR spectroscopy (¹H, ¹³C), mass spectrometry, and infrared spectroscopy. Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

► Show Figures

Scheme 1

Open AccessShort Note

3-(3-Hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde Methyl Hemiacetal

by

Massimiliano Cordaro

Molbank 2021, 2021(3), M1272; https://doi.org/10.3390/M1272 - 20 Aug 2021

Abstract

The synthesis of 3-(3-hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde as a stable methyl hemiacetal through a convenient 3-step procedure is reported. The molecule is multifunctional as it contains a formyl group, a hydroxyl group and the imide moiety. Each of these groups can play a role in specific [...] Read more.

The synthesis of 3-(3-hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde as a stable methyl hemiacetal through a convenient 3-step procedure is reported. The molecule is multifunctional as it contains a formyl group, a hydroxyl group and the imide moiety. Each of these groups can play a role in specific transformations or uses. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

Open AccessShort Note

5-(2,6-Diacetamidopyridin-4-yl)-kryptoBODIPY

by

Massimiliano Cordaro

and

Mariachiara Trapani

Molbank 2021, 2021(3), M1271; https://doi.org/10.3390/M1271 - 13 Aug 2021

Abstract

The development of new dyes for various fields of application is of primary interest for the scientific community, among these BODIPY are widely studied for their versatility. This communication describes the synthesis of a BODIPY dye on which a diacetoamidopyridine moiety is connected [...] Read more.

The development of new dyes for various fields of application is of primary interest for the scientific community, among these BODIPY are widely studied for their versatility. This communication describes the synthesis of a BODIPY dye on which a diacetoamidopyridine moiety is connected in meso position. The synthesis procedure requires a one-pot step and the dye is obtained with a yield of 20%. The diacetoamido portion contains chemical functionalities able to favor the interaction of BODIPY with complementary molecules, such as uracil or thymine, offering potential applications for the design of new functional materials or sensors. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

Open AccessShort Note

2-((E)-2-((E)-4-Chloro-5-(2-((E)-5-methoxy-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene) ethylidene)-1,1-dimethyl-1,2,5,6-tetrahydropyridin-1-ium-3-yl)vinyl)-5-methoxy-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium

by

Emmanuel Ramsey Buabeng

and

Maged Henary

Molbank 2021, 2021(3), M1270; https://doi.org/10.3390/M1270 - 11 Aug 2021

Abstract

A heptamethine fluorophore, ERB-60, has been synthesized efficiently in four steps in a good yield. The structure of this fluorophore consists of an electron-donating group (methoxy), a hydrophobic moiety (phenylpropyl) with a rotatable bond, a quaternary ammonium fragment, and indolium rings at [...] Read more.

A heptamethine fluorophore, ERB-60, has been synthesized efficiently in four steps in a good yield. The structure of this fluorophore consists of an electron-donating group (methoxy), a hydrophobic moiety (phenylpropyl) with a rotatable bond, a quaternary ammonium fragment, and indolium rings at the terminal ends connected via polymethine chain. All these inherent chemical features fine-tuned the optical properties of the fluorophore. This compound was characterized by both ¹H NMR, ¹³C NMR and mass spectra. The optical properties, including molar absorptivity, fluorescence, Stokes’s shift, and quantum yield, were measured in different solvents such as DMSO, DMF, MeCN, i-PrOH, MeOH, and H₂O. The wavelengths of maximum absorbance of ERB-60 were found to be in the range of 745–770 nm based on the solvents used. In decreasing order, the maximum wavelength of absorbance of ERB-60 in the tested solvents was DMSO > DMF > i-PrOH > MeOH > MeCN > H₂O while the decreasing order of the extinction coefficient was found to be MeCN > MeOH > DMSO > i-PrOH > H₂O > DMF. ERB-60 was found to be more photostable than IR-786 iodide, a commercially available dye, and brighter than the FDA-approved dye, indocyanine green (ICG). Full article

► Show Figures

Figure 1

Open AccessShort Note

(E)-3-[4-(1H-Imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one

by

Nicholas Bailey

and

Bradley O. Ashburn

Molbank 2021, 2021(3), M1269; https://doi.org/10.3390/M1269 - 10 Aug 2021

Abstract

Imidazole-containing chalcones have been shown to be strongly effective against Aspergillusfumigatus, the causative agent for the disease pulmonary aspergillosis. Claisen–Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 4′-methylacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H [...] Read more.

Imidazole-containing chalcones have been shown to be strongly effective against Aspergillusfumigatus, the causative agent for the disease pulmonary aspergillosis. Claisen–Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 4′-methylacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one in good yield and purity after recrystallization from hot methanol. With the known antifungal properties of these combined pharmacophores, this novel compound is suitable for anti-aspergillus activity study. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

Open AccessShort Note

(±)-2-{[4-(4-Bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol

by

Milenca Mariana Vorga

and

Valentin Badea

Molbank 2021, 2021(3), M1268; https://doi.org/10.3390/M1268 - 06 Aug 2021

Abstract

The novel racemic secondary alcohol (±)-2-{[4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol (12) has been successfully synthesized through S-alkylation of 4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazole-3-thiol (10) in alkaline medium with 2-bromo-1-phenylethanone followed by reduction of the corresponding ketone 11. All the synthesized compounds [...] Read more.

The novel racemic secondary alcohol (±)-2-{[4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol (12) has been successfully synthesized through S-alkylation of 4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazole-3-thiol (10) in alkaline medium with 2-bromo-1-phenylethanone followed by reduction of the corresponding ketone 11. All the synthesized compounds were characterized by IR, 1D (¹H, ¹³C, DEPT135) and 2D (¹H-¹H, ¹H-¹³C and ¹H-¹⁵N) NMR spectroscopy, elemental analysis and HRMS spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Scheme 1

Open AccessCommunication

4-Aminoalkyl Quinolin-2-one Derivatives via Knorr Cyclisation of ω-Amino-β-Keto Anilides

by

Plamen Angelov

,

Stilyana Velichkova

and

Pavel Yanev

Molbank 2021, 2021(3), M1266; https://doi.org/10.3390/M1266 - 05 Aug 2021

Abstract

In a high-yielding and solvent-free procedure N-ethoxycarbonyl protected ω-amino-β-keto anilides undergo Knorr cyclisation in neat polyphosphoric acid to provide straightforward route to 4-aminoalkyl quinolin-2-one derivatives with variable length of the alkyl chain. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Scheme 1

Open AccessShort Note

2-Diphenylphosphinomethyl-3-methylpyrazine

by

Tiziana Boccuzzi

,

Luciana Cicco

,

Andrea Francesca Quivelli

,

Paola Vitale

,

Filippo Maria Perna

,

Konstantin Karaghiosoff

and

Vito Capriati

Molbank 2021, 2021(3), M1267; https://doi.org/10.3390/M1267 - 05 Aug 2021

Abstract

The lateral metalation-electrophilic trapping reaction of alkyl-substituted pyrazines has always been challenging and poorly regioselective, with the corresponding derivatives often being isolated in moderate yield. In this contribution, we first report on the preparation of an unsymmetrically-substituted pyrazine, that is 2-diphenylphosphinomethyl-3-methylpyrazine, by subjecting [...] Read more.

The lateral metalation-electrophilic trapping reaction of alkyl-substituted pyrazines has always been challenging and poorly regioselective, with the corresponding derivatives often being isolated in moderate yield. In this contribution, we first report on the preparation of an unsymmetrically-substituted pyrazine, that is 2-diphenylphosphinomethyl-3-methylpyrazine, by subjecting to metalation with n-BuLi the commercially available 2,3-dimethylpyrazine, followed by interception of the putative lithiated benzyl-type intermediate with Ph₂PCl. Such a functionalization has been successfully carried out in the absence of additional ligands, working either in THF at −78 °C or in a more environmentally friendly solvent like cyclopentyl methyl ether at 0 °C, with the desired phosphine derivative being isolated in 70–85% yield. The newly synthesized adduct has been fully characterized by means of multinuclear magnetic resonance spectroscopic techniques, and also by preparing a selenium derivative, which furnished single crystals that were suitable for X-ray analysis. Full article

► Show Figures

Figure 1

Open AccessShort Note

4-Chlorobenzyl Chloride

by

R. Alan Aitken

and

Alexandra M. Z. Slawin

Molbank 2021, 2021(3), M1265; https://doi.org/10.3390/M1265 - 04 Aug 2021

Abstract

The X-ray structure of the title compound has been determined for the first time. Its molecular structure is in good agreement with those previously determined for similar benzyl halides and the angles between the ring–Cl bonds in adjacent molecules show values in good [...] Read more.

The X-ray structure of the title compound has been determined for the first time. Its molecular structure is in good agreement with those previously determined for similar benzyl halides and the angles between the ring–Cl bonds in adjacent molecules show values in good agreement with an early Zeeman quadrupole spectroscopy study. Full article

(This article belongs to the Section Structure Determination)

► Show Figures

Figure 1

Open AccessShort Note

2-Hydroxy-3-octyloxybenzaldehyde

by

Julia V. Novoselova

,

Anatoliy A. Vereshchagin

,

Arseniy Y. Kalnin

,

Daniil A. Lukyanov

and

Oleg V. Levin

Molbank 2021, 2021(3), M1264; https://doi.org/10.3390/M1264 - 03 Aug 2021

Abstract

Herein, we report the chromatography-free synthesis of 2-hydroxy-3-octyloxybenzaldehyde by the alkylation of 2,3-dihydroxybenzaldehyde as a promising precursor for new SalEn-type complexes with transition metals. The structure of the product is elucidated by means of ¹H and ¹³C-NMR spectra, high-resolution mass spectrometry [...] Read more.

Herein, we report the chromatography-free synthesis of 2-hydroxy-3-octyloxybenzaldehyde by the alkylation of 2,3-dihydroxybenzaldehyde as a promising precursor for new SalEn-type complexes with transition metals. The structure of the product is elucidated by means of ¹H and ¹³C-NMR spectra, high-resolution mass spectrometry with electrospray ionization (ESI-HRMS) and Fourier-transform infrared spectroscopy (FTIR). Full article

► Show Figures

Graphical abstract

Open AccessShort Note

1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo [d] imidazole-2-amine

by

Fiach B. Meany

,

Sarah O’Rourke

and

Paul V. Murphy

Molbank 2021, 2021(3), M1262; https://doi.org/10.3390/M1262 - 31 Jul 2021

Abstract

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to [...] Read more.

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by ¹H-NMR and ¹³C-NMR spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

Open AccessShort Note

4′,4′′′,4′′′′′-Nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde)

by

Anatoliy A. Vereshchagin

,

,

,

and

Molbank 2021, 2021(3), M1263; https://doi.org/10.3390/M1263 - 31 Jul 2021

Abstract

Multipodal salicylaldehydes have attracted much scientific interest as scaffolds for the construction of multinuclear complexes, as well as metal and covalent organic frameworks. Herein, we report a preparation of 4′,4′′′,4′′′′′-nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde), a direct precursor for the tripodal salicylaldehyde with triphenylamine core. The structure of [...] Read more.

Multipodal salicylaldehydes have attracted much scientific interest as scaffolds for the construction of multinuclear complexes, as well as metal and covalent organic frameworks. Herein, we report a preparation of 4′,4′′′,4′′′′′-nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde), a direct precursor for the tripodal salicylaldehyde with triphenylamine core. The structure of the product was confirmed by molecular spectroscopy. The reported approach may be broadened over a variety of multipodal salicylaldehydes. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

Open AccessShort Note

4,4′-Di-tert-butyl-2,2′-bipyridinium Trifluoromethanesulfonate

by

,

,

and

Molbank 2021, 2021(3), M1261; https://doi.org/10.3390/M1261 - 28 Jul 2021

Abstract

4,4′-Di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-Di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, ¹H, ¹³C{¹H} and ¹⁹F{¹H} [...] Read more.

4,4′-Di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-Di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, ¹H, ¹³C{¹H} and ¹⁹F{¹H} NMR spectroscopy and CHN elemental analysis. This is a safe and simple method to obtain mono-protonated bipyridinium trifluoromethanesulfonate without the direct use of trifluoromethanesulfonic acid. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

Journal Description

Molbank

Latest Articles

Journal Menu

Journal Browser

Highly Accessed Articles

Latest Books

E-Mail Alert

News

Conferences

Special Issues

Topical Collections

Jobs in Research

Further Information

Guidelines

MDPI Initiatives

Follow MDPI