Category: nitriles-buliding-blocks

Design, characterisation and anticonvulsant evaluation of thienopyrimidinone derivatives synthesised by green chemistry was written by Raju, Gollapalli Naga;Sucharitha, Nallamothu;Navya, Nagandla;Nadendla, Rama Rao. And the article was included in Journal of Chemical and Pharmaceutical Research in 2017.COA of Formula: C8H8N2S This article mentions the following:

The synthesis and biol. evaluation of some novel thieno[2,3-d]pyrimidin-4(3H)one derivatives was aimed at creating a new scaffold. Considering the previous articles activity profile of thienopyrimidinone derivatives, fifteen new substituted thieno[2,3-d]pyrimidin-4(3H)one derivatives were synthesized by reacting different 2-amino-4,5-substituted thiophene-3-carbonitriles with appropriate aliphatic carboxylic acids in presence of phosphoryl trihloride and alumina by conventional synthesis as well as microwave assisted route. Structural characterizations of all the synthesized compounds were performed by using spectral and elemental anal. All the synthesized compounds were evaluated for their antimicrobial and anticonvulsant activities by using disk diffusion method and maximal electroshock induced seizures (MES) method. It was found that the compounds possessed potent antimicrobial and anticonvulsant activities. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.COA of Formula: C8H8N2S

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Nitrile – Wikipedia,
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2-Substituted 8,9-cycloalkathieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones was written by Chernyuk, O. M.;Tolmachova, V. S.;Vovk, M. V.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 2009.Recommanded Product: 70291-62-2 This article mentions the following:

A series of cycloalkane-fused thieno[3.2-e][1,2,4]triazolo[1,5-c]pyrimidinones I [R¹R² = (CH₂)₃, (CH₂)₄, CH₂CHMeCH₂CH₂, (CH₂)₅; R³ = Ph, 4-FC₆H₄, 2-furyl, 3-pyridyl, etc.] was synthesized by condensation of N-(cyanothienyl) carbamates II with carboxylic acids hydrazides R³CONHNH₂. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.Recommanded Product: 70291-62-2

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Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N-O Bond Redox Fragmentation was written by Jelier, Benson J.;Tripet, Pascal F.;Pietrasiak, Ewa;Franzoni, Ivan;Jeschke, Gunnar;Togni, Antonio. And the article was included in Angewandte Chemie, International Edition in 2018.Application of 63968-85-4 This article mentions the following:

A simple trifluoromethoxylation method enables non-directed functionalization of C-H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF₃ radical mechanism mediated by a photoredox catalyst, which triggers an N-O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Application of 63968-85-4).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application of 63968-85-4

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Synthesis of intermediate of strontium ranelate by using ionic liquid as phase transfer catalyst was written by Li, Cen;Jiang, Yi;Jiang, Ye;Liu, Feng-hua. And the article was included in Huaxi Yaoxue Zazhi in 2009.Application of 58168-20-0 This article mentions the following:

OBJECTIVE: To study a new catalytic way using ionic liquid as phase transfer catalyst for the synthesis of intermediate of strontium ranelate. METHODS: Tetra-Et ester of 5-aminothiophene was synthesized from 5-aminothiophene using Et bromoacetate as alkylating reagent and ionic liquid as phase transfer catalyst. RESULTS and CONCLUSION: The proposed method was not only suitable for industrial manufacture with high yield of 81%, but also could cut down the discharging of pollutants. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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. 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.Application of 58168-20-0

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Optimization of 5-(2,6-dichlorophenyl)-3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase was written by Labadie, Sharada;Dragovich, Peter S.;Chen, Jinhua;Fauber, Benjamin P.;Boggs, Jason;Corson, Laura B.;Ding, Charles Z.;Eigenbrot, Charles;Ge, HongXiu;Ho, Qunh;Lai, Kwong Wah;Ma, Shuguang;Malek, Shiva;Peterson, David;Purkey, Hans E.;Robarge, Kirk;Salphati, Laurent;Sideris, Steven;Ultsch, Mark;VanderPorten, Erica;Wei, BinQing;Xu, Qing;Yen, Ivana;Yue, Qin;Zhang, Huihui;Zhang, Xuying;Zhou, Aihe. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Quality Control of 2-Bromo-4-hydroxybenzonitrile This article mentions the following:

Optimization of 5-(2,6-dichlorophenyl)-3-hydroxy-2-mercaptocyclohex-2-enone using structure-based design strategies resulted in inhibitors with considerable improvement in biochem. potency against human lactate dehydrogenase A (LDHA). These potent inhibitors were typically selective for LDHA over LDHB isoform (4-10 fold) and other structurally related malate dehydrogenases, MDH1 and MDH2 (>500 fold). An X-ray crystal structure of enzymically most potent mol. bound to LDHA revealed two addnl. interactions associated with enhanced biochem. potency. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Quality Control of 2-Bromo-4-hydroxybenzonitrile).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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.Quality Control of 2-Bromo-4-hydroxybenzonitrile

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Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines was written by Desikan, Vasumathi;Liu, Yonglin;Toscano, John P.;Jenks, William S.. And the article was included in Journal of Organic Chemistry in 2008.Reference of 4435-14-7 This article mentions the following:

Time-resolved IR (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene precursor, i.e., that the ground-state multiplicity is singlet. In contrast, product studies clearly indicate triplet reactivity for trifluoroacetylnitrene, though TRIR experiments were more ambiguous. Product studies suggest that these sulfilimines are superior sources for sulfonylnitrenes, which have triplet grounds states, to the corresponding azides, and computational studies shed light on the electronic structure of the nitrenes. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Reference of 4435-14-7

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Nitrile – Wikipedia,
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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

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Nitrile – Wikipedia,
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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

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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

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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