Month: February 2023

Direct and Practical Synthesis of Primary Anilines through Iron-Catalyzed C-H Bond Amination was written by Legnani, Luca;Prina Cerai, Gabriele;Morandi, Bill. And the article was included in ACS Catalysis in 2016.Electric Literature of C8H8N2O This article mentions the following:

The direct C-H amination of arenes is an important strategy to streamline the discovery and preparation of functional mols. Herein, we report an operationally simple arene C-H amination reaction that, in contrast to most literature precedence, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II) sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional mols. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Electric Literature of C8H8N2O).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C8H8N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mixed-Linker Isoreticular Zn(II) Metal-Organic Frameworks as Bronsted Acid-Base Bifunctional Catalysts for Knoevenagel Condensation Reactions was written by Huang, Guo-Quan;Chen, Jun;Huang, Yong-Liang;Wu, Kun;Luo, Dong;Jin, Ji-Kang;Zheng, Ji;Xu, Shi-Hai;Lu, Weigang. And the article was included in Inorganic Chemistry in 2022.Application of 55490-87-4 This article mentions the following:

Multicomponent metal-organic frameworks (MOFs) have received an increasing amount of attention due to their potential to produce new topologies, pore metrics, and functionalities compared to MOFs with a single metal cluster and one organic linker. Herein, five isoreticular Zn MOFs were obtained by mixing two types of linear ditopic linkers in a one-pot solvothermal synthesis. Interestingly, in the resulting Zn MOFs a six-connected cyclic trinuclear Zn(II) cluster and an eight-connected linear trinuclear Zn(II) cluster coexist, leading to an uncommon (6,8)-connected network. Catalytic activities toward the solvent-free Knoevenagel reactions were observed for all of these MOFs. Further exptl. and computational studies suggest that they are Bronsted acid-base bifunctional catalysts. Through chem. modifications of dicarboxylate ligands, including their aromatic backbones and substituents, we have successfully implemented reticular chem. for the modulations of pore sizes, surface areas, and catalytic performances in a series of four-component isoreticular MOFs. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Development and characterization of 3-(arylsulfamoyl)benzamides as potent and selective SIRT2 inhibitors was written by Khanfar, Mohammad A.;Quinti, Luisa;Wang, Hua;Choi, Soo Hyuk;Kazantsev, Aleksey G.;Silverman, Richard B.. And the article was included in European Journal of Medicinal Chemistry in 2014.HPLC of Formula: 1753-48-6 This article mentions the following:

Inhibitors of sirtuin-2 deacetylase (SIRT2) have been shown to be protective in various models of Huntington’s disease (HD) by decreasing polyglutamine aggregation, a hallmark of HD pathol. The present study was directed at optimizing the potency of SIRT2 inhibitors containing the neuroprotective sulfobenzoic acid scaffold and improving their pharmacol. To achieve that goal, 176 analogs were designed, synthesized, and tested in deacetylation assays against the activities of major human sirtuins SIRT1-3. This screen yielded 15 compounds with enhanced potency for SIRT2 inhibition and 11 compounds having SIRT2 inhibition equal to reference compound AK-1. The newly synthesized compounds also demonstrated higher SIRT2 selectivity over SIRT1 and SIRT3. These candidates were subjected to a dose-response bioactivity assay, measuring an increase in α-tubulin K40 acetylation in two neuronal cell lines, which yielded five compounds bioactive in both cell lines and eight compounds bioactive in at least one of the cell lines tested. These bioactive compounds were subsequently tested in a tertiary polyglutamine aggregation assay, which identified five inhibitors. ADME properties of the bioactive SIRT2 inhibitors (e.g., I) were assessed, which revealed a significant improvement of the pharmacol. properties of the new entities, reaching closer to the goal of a clin.-viable candidate. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6HPLC of Formula: 1753-48-6).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 1753-48-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Direct cyanomethylation of aliphatic and aromatic hydrocarbons with acetonitrile over a metal loaded titanium oxide photocatalyst was written by Wada, Emiko;Takeuchi, Tomoaki;Fujimura, Yuki;Tyagi, Akanksha;Kato, Tatsuhisa;Yoshida, Hisao. And the article was included in Catalysis Science & Technology in 2017.Recommanded Product: 4435-14-7 This article mentions the following:

A platinum-loaded TiO₂ (Pt/TiO₂) photocatalyst promoted cyanomethylation of aliphatic hydrocarbons, namely cyclohexane and cyclohexene, with acetonitrile, where the photogenerated hole oxidatively dissociates the C-H bond of both the acetonitrile and the aliphatic hydrocarbons to form each corresponding radical species before their radical cross-coupling. The Pt/TiO₂ photocatalyst was more active than the Pd/TiO₂ photocatalyst in these reactions. In contrast, the cyanomethylation of benzene was promoted by the Pd/TiO₂ photocatalyst or a phys. mixture of the Pt/TiO₂ photocatalyst and a Pd catalyst supported by Al₂O₃, while it was hardly promoted by the Pt/TiO₂ photocatalyst alone. The temperature dependence of the reaction rate proved that the Pd nanoparticles on the TiO₂ thermally function as a metal catalyst. However, in the cyanomethylation of aliphatic hydrocarbons, the catalytic effect of the metal particles was not observed, meaning that the radical coupling takes place without the metal catalysis. Thus, it is concluded that in the case of the benzene cyanomethylation the Pd nanoparticles play dual roles, as a catalyst to catalyze the substitution reaction of benzene with the cyanomethyl radical, and as an electron receiver to reduce the recombination of the photoexcited electrons and holes in the TiO₂ photocatalyst, although they could not contribute as a catalyst to the cyanomethylation of aliphatic hydrocarbons. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Recommanded Product: 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ethylene diamine grafted nanoporous UiO-66 as an efficient basic catalyst in the multi-component synthesis of 2-aminothiophenes was written by Erfaninia, N.;Tayebee, R.;Dusek, M.;Amini, M. M.. And the article was included in Applied Organometallic Chemistry in 2018.Application of 70291-62-2 This article mentions the following:

This study demonstrates ED-UiO-66 as a novel and effective solid nanoporous basic catalyst prepared through the amine grafting onto the pores of UiO-66. The manufactured nanoparticles were identified by FT-IR, XRD, TGA, FESEM, TEM, CHN and BET and the characterization results certified formation of a single phase nanoporous substance with the medium grain size less than 90 nm. The synthesized material was employed as an efficient catalyst for the preparation of 2-aminothiophenes I [R = 4,5-(-CH₂-)₅, 5-CH₃, 5-C₆H₅] through the Gewald method. This thermochem. stable nanocatalyst was environmentally safe, reusable and economic. Therefore, this methodol. can be simply extended for industrial goals. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Application of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mechanistic investigation of the iridium-catalysed alkylation of amines with alcohols was written by Fristrup, Peter;Tursky, Matyas;Madsen, Robert. And the article was included in Organic & Biomolecular Chemistry in 2012.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

The [Cp*IrCl₂]₂-catalyzed alkylation of amines with alcs. was investigated using a combination of exptl. and theor. methods. A Hammett study involving a series of para-substituted benzyl alcs. resulted in a line with a neg. slope. This clearly documents that a pos. charge is built up in the transition state, which in combination with the measurement of a significant kinetic isotope effect determines hydride abstraction as being the selectivity-determining step under these conditions. A complementary Hammett study using para-substituted anilines was also carried out. Again, a line with a neg. slope was obtained suggesting that nucleophilic attack on the aldehyde is selectivity-determining A computational investigation of the entire catalytic cycle with full-sized ligands and substrates was performed using d. functional theory. The results suggest a catalytic cycle where the intermediate aldehyde stays coordinated to the iridium catalyst and reacts with the amine to give a hemiaminal which is also bound to the catalyst. Dehydration to the imine and reduction to the product amine also takes place without breaking the coordination to the catalyst. The fact that the entire catalytic cycle takes place with all the intermediates bound to the catalyst is important for the further development of this synthetic transformation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt(III) complex-promoted hydrolysis of phosphate diesters: comparison in reactivity of rigid cis-diaquo(tetraaza)cobalt(III) complexes was written by Chin, Jik;Banaszczyk, Mariusz;Jubian, Vrej;Zou, Xiang. And the article was included in Journal of the American Chemical Society in 1989.Name: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The efficiencies of three rigidly held cis-aquohydroxotetraazacobalt(III) complexes [(cyclen)Co(OH)(OH₂)]²⁺ (cyclen = 1,4,7,10-tetraazacyclododecane), [(tren)Co(OH)(OH₂)]²⁺ [tren = N(CH₂CH₂NH₂)₃], and [(trpn)Co(OH)(OH₂)]²⁺ [trpn = N(CH₂CH₂CH₂NH₂)₃] in promoting the hydrolysis of bis(p-nitrophenyl) phosphate (BNPP) have been compared. In neutral water at 50°, the rate constant for hydrolysis of the phosphate diester bond in [(cyclen)Co(OH)(BNPP)]⁺, [(tren)Co(OH)(BNPP)]⁺, [(trpn)Co(OH)(BNPP)]⁺ are 4.6 × 10^-1, 8.1 × 10^-3, and 2.5 s^-1, resp. [(Trpn)Co(OH)(BNPP)]⁺ is hydrolyzed at about the same rate as BNPP bound to a real enzyme from Enterobacter aerogenes and about 10¹⁰ times more rapidly than free BNPP. The dramatic increase in the activity of the Co(III) complex with change in the tetraamine ligand structure can be explained in terms of a detailed mechanism of the reaction. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Name: 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Name: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Base- and Metal-free Protocol for the Synthesis of 2-Aryl/heteroaryl Thiazolines was written by Chaudhary, Shweta;Milton, Marilyn D.;Garg, Parul. And the article was included in ChemistrySelect in 2017.Formula: C12H14N2O This article mentions the following:

A simple and efficient base- and metal-free protocol for the synthesis of 2-aryl/heteroarylthiazolines I [Ar = 4-BrC₆H₄, 4-n-BuHNCH₂C₆H₄, 2-pyridyl, etc.; R = H, CO₂Et] from aryl/heteroaryl nitriles and cysteamine hydrochloride was reported. This method was applicable to a series of aryl/heteroaryl nitriles containing different substituents such as halides, amines, substituted azoles, etc. and furnishing the corresponding thiazolines in up to 99% yields. A selective synthesis of mono- or bis-thiazoline in more than 90% yield was also observed by modifying the duration of the reaction. A probable reaction mechanism involving the formation of highly activated arylimino chloride was also given. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C12H14N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photoelectrochemical and thermal characterization of aromatic hydrocarbons substituted with a dicyanovinyl unit was written by Kotowicz, Sonia;Sek, Danuta;Kula, Slawomir;Fabianczyk, Aleksandra;Malecki, Jan Grzegorz;Gnida, Pawel;Mackowski, Sebastian;Siwy, Mariola;Schab-Balcerzak, Ewa. And the article was included in Dyes and Pigments in 2020.Safety of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

Seven aromatic hydrocarbons bearing a dicyanovinyl unit were prepared to determine the relation between both the number of aromatic rings and location of acceptor substituent on their thermal and optoelectronic properties. Addnl., the d. functional theory calculations were performed. The obtained compounds showed temperatures of the beginning of thermal decomposition in the range of 137-289°, being above their resp. m.ps. found between 88 and 248°. They were electrochem. active and showed quasi-reversible reduction process, except for 2-(phen-1-yl)methylene malononitrile. Electrochem. estimated energy band gaps were below 3.0 eV, in the range of 2.10-2.50 eV. The absorption and emission spectra were recorded in CHCl₃ and NMP and in solid state. All compounds strongly absorbed radiation with absorption maximum ranging from 307 to 454 nm ascribed to the intramol. charge transfer between the donor and acceptor units. The aromatic hydrocarbons were luminescent in all investigated media and exhibited higher photoluminescence quantum yields in the solid state due to the aggregation induced emission phenomena. Electroluminescence ability of selected compounds was tested in a diode with guest-host configuration. Addnl., the selected compound together with a com. N719 was applied in the dye-sensitized solar cell. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Safety of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-taste relationship of perillartine and nitro- and cyanoaniline derivatives was written by Iwamura, Hajime. And the article was included in Journal of Medicinal Chemistry in 1980.SDS of cas: 60979-25-1 This article mentions the following:

The relation between structure and taste potency of perillartine (I) and its analogs was investigated quant. by physicochem. parameters and regression anal. The results indicated that the hydrophobicity estimated from the octanol/water partition coefficient and the mol. widths from the bond axis connecting the oxime C atom and alicyclic ring are important, regardless of whether the taste is sweet or bitter, so far as taste potency is concerned. The structure-activity relation for the sweet/bitter ratio was not established quant., but the mol. width and thickness and the position-specific electronic effect appeared to delineate the ratio qual.; i.e., in principle, the wider and(or) the thicker the mol., the more bitter the taste. The quant. structure-activity relation of 5-nitro- and 5-cyanoaniline sweetener was formulated to show the nonsignificance of hydrophobicity within the compounds investigated but the importance of steric dimensions in determining the activity. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1SDS of cas: 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.SDS of cas: 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts