Nitriles-buliding-blocks

A Bis(phosphaethenyl)pyridine Complex of Iridium(I): Synthesis and Catalytic Application to N-Alkylation of Amines with Alcohols was written by Chang, Yung-Hung;Nakajima, Yumiko;Ozawa, Fumiyuki. And the article was included in Organometallics in 2013.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The Ir(I) complex [IrCl(BPEP-H)] (1), coordinated with 2,6-bis[2-(2,4,6-tri-tert-butylphenyl)-2-phosphaethenyl]pyridine (BPEP-H) as a PNP-pincer-type phosphaalkene ligand, was synthesized and fully characterized by elemental anal., NMR spectroscopy, and x-ray diffraction anal. Complex 1 (1 mol %) catalyzes N-alkylation of primary and secondary amines with alcs., leading to the selective formation of secondary and tertiary amines, resp. Primary amines are smoothly alkylated with a variety of benzylic and aliphatic alcs. (1 or 3 equiv) at 100° under basic conditions (CsOH, 10 mol %) to give the corresponding secondary amines in good to high yields. However, N-alkylation of secondary amines with benzyl alc. (3 equiv) proceeds in the presence of KH₂PO₄ (5 mol %) at 140° to afford tertiary amines in high yields. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Name: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A highly efficient Co-based catalyst fabricated by coordination-assisted impregnation strategy towards tandem catalytic functionalization of nitroarenes with various alcohols was written by Wang, Jing;She, Wei;Li, Xuewei;Li, Zhibin;Li, Jingfang;Mao, Guijie;Li, Weizuo;Li, Guangming. And the article was included in Journal of Catalysis in 2021.SDS of cas: 4714-63-0 This article mentions the following:

A well-defined hexamethylenetetramine (abbreviated as HMTA) based two-dimensional (2D) MOFs metalloligand (termed Zn-HMTA), with free uncoordinated tertiary amine groups, has been synthesized via solution diffusion method for the first time. The crystal structure of 2D Zn-HMTA metalloligand was determined by the single crystal X-ray diffraction (SCXRD). The SCXRD and XPS analyses have revealed that the 2D Zn-HMTA metalloligand is rich in- free tertiary amine groups, which are of strong coordination ability to transition metal ions (e.g. Ni²⁺, Co²⁺, Zn²⁺, Cu²⁺). As a result, a 2D bimetallic Co@Zn-HMTA MOFs was synthesized via coordination-assisted impregnation (CAI) strategy attributed to the unique feature of strong coordinated ability of free tertiary amine groups. Furthermore, a series of self-supported Co-ZnO-CN nanocatalysts were afforded upon the as-synthesized Co@Zn-HMTA MOFs served as a self-sacrificial template for pyrolysis at different temperatures The optimized catalyst (termed as Co-ZnO@CN-CAI) demonstrated the excellent catalytic performance for hydrogenation-alkylation tandem reaction in comparison with the classic ZnO@CN composite (derived from Zn-HMTA MOFs) supported metallic Co catalyst (Co-ZnO@CN-IWI) prepared by incipient wetness impregnation method. Moreover, the kinetic study was also performed to confirm that the alkylation is the rate-determining step in the hydrogenation-alkylation tandem reaction. The origin of enhanced catalytic performance of Co-ZnO@CN-CAI and the role of Co@Zn-HMTA MOFs precursor have been explored by way of various characterizations, e.g. HADDF-STEM-EDS, SEM-EDS, ¹³C MAS NMR, XRD, Raman and XPS, etc. It is anticipated that the prepared low-cost and easily prepared 2D Zn-HMTA metalloligand will become a general template for synthesis of highly self-supported catalysts with coordination-assisted impregnation strategy (CAI) for various catalytic reactions. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0SDS of cas: 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.SDS of cas: 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A novel three-component reaction of triphenylphosphine, DMAD, and electron-deficient styrenes: facile synthesis of cyclopentenyl phosphoranes was written by Nair, Vijay;Deepthi, Ani;Beneesh, P. B.;Eringathodi, Suresh. And the article was included in Synthesis in 2006.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

The zwitterion formed from triphenylphosphine and DMAD (di-Me acetylenedicarboxylate) adds to electron-deficient styrenes to form stable cyclopentenyl phosphoranes in 23% to 80% yield. This is the first example of such a zwitterion in which the phosphine is incorporated into the addition product. A mechanism for the reaction is proposed. The mol. structure of the formed cyclopentenyl phosphorane (I) was determined by x-ray crystallog. This cyclopentenyl phosphorane did not undergo Wittig reaction with 4-nitrobenzaldehyde. The cyclopentenyl phosphoranes thus formed can be oxidized to cyclopentene 1,2-diones. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Aromatic Nitriles via the Temporary Complexation of Nitroarenes to the Cationic Cyclopentadienyliron Moiety was written by Abd-El-Aziz, Alaa S.;Boraie, Waleed;Gavel, Nicole T.. And the article was included in Organometallics in 1999.Name: 5-Methyl-2-nitrobenzonitrile This article mentions the following:

Cyanide addition to cationic cyclopentadienyliron complexes of substituted nitroarenes (I; R = 4-Me, -Et, -CHMe₂, -n-Bu, -tert-Bu, -sec-Bu, -(CH)₄CH₃; 2-CHMe₂; 2,3-, 2,4-, 3,4-, 3,5-Me₂) produced nitrile adducts (II, R = same as above) where the cyano group added regioselectively in the ortho position with respect to the nitro group. Cleavage of the cyclopentadienyliron moiety via oxidative demetalation with DDQ gave functionalized benzonitriles (III, R = same as above) in good yields. Thus, I (R = 4-Me) reacted with a 7-fold excess of NaCN in DMF under mild exptl. conditions to give 72% II (R = 4-Me) which subsequently underwent oxidative demetalation with DDQ to give 83% III (R = 4-Me). In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Name: 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Name: 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Observation of hyperpositive non-linear effect in catalytic asymmetric organozinc additions to aldehydes was written by Geiger, Yannick;Achard, Thierry;Maisse-Francois, Aline;Bellemin-Laponnaz, Stephane. And the article was included in Chirality in 2020.SDS of cas: 101219-69-6 This article mentions the following:

Asym. amplification is a phenomenon that is believed to play a key role in the emergence of homochirality in life. In asym. catalysis, theor. and exptl. models have been investigated to provide an understanding of how chiral amplification is possible, in particular based on non-linear effects. Interestingly, it has been proposed a quarter century ago that chiral catalysts, when not enantiopure might even be more enantioselective than their enantiopure counterparts. We show here that such hyperpos. non-linear effect in asym. catalysis is indeed possible. An in-depth study into the underlying mechanism was carried out, and the scheme we derive differs from the previous proposed models. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6SDS of cas: 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. SDS of cas: 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Shedding Light on the Lewis Acid Catalysis in Organic Transformations Using a Zn-MOF Microflower and Its ZnO Nanorod was written by Gandhi, Shradha;Sharma, Vandana;Koul, Ishfaq S.;Mandal, Sanjay K.. And the article was included in Catalysis Letters.Application of 55490-87-4 This article mentions the following:

The Lewis acidic nature of both {[Zn₄(μ₃-OH)₂(D-2,4-cbs)₂(H₂O)₄]^.5H₂O}_n(Zn-CBS) and its ZnO nanostructures (ZnO_1, 3D microflower; ZnO_2, 3D polyhedron; and ZnO_3, 1D nanorod) was explored for the comparative study of the C-C and C-N bond forming reactions, such as Knoevenagel condensation, Friedel-Crafts alkylation and Strecker reaction, with various substrates. Notably, the nanorod (ZnO_3) is found to be an exceptionally efficient heterogeneous catalyst in comparison to its parent Zn-CBS for the Knoevenagel condensation reaction showing 100% conversion in 15 min with only 2 mol% catalyst in methanol at 25 °C. Similar catalytic results were obtained in the multicomponent Strecker reaction where ZnO_3 showed an enhanced catalytic activity in water as compared to Zn-CBS. However, for the Friedel-Crafts alkylation reaction, Zn-CBS was better than ZnO_3. These highly efficient catalysts are recyclable for three consecutive runs without any notable change in the catalytic activity. Their mechanism of action for all three reactions is also explained. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. 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.Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Organophosphorus compounds with β-cyanoethyl-type structural components. I. Synthesis of β-cyanoethylated amidophosphites and phosphoramides was written by Petrov, Pavel;Vlad, Florin-Iosif;Muresan, Sorel;Valceanu, Radu. And the article was included in Revista de Chimie (Bucharest) in 1995.Electric Literature of C9H12N4 This article mentions the following:

This paper presents three types of phosphorylation reactions for mixtures of NH(CH₂CH₂CN)₂ with N(CH₂CH₂CN)₃, obtained by nucleophilic addition reaction of NH₃ to acrylonitrile. Thus, reaction of 10 equiv (MeO)₂P(O)H with a 10:1 mixture of the above amines in PhMe containing CCl₄ and Et₃N gave (MeO)₂P(O)N(CH₂CH₂CN)₂. Reaction of 4 equiv PCl₃ or P(O)Cl₃ with a 21:3 mixture of the amines in dichloroethane gave P[N(CH₂CH₂CN)₂]₃ or P(O)[N(CH₂CH₂CN)₂]₃, resp. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Electric Literature of C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Electric Literature of C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Substituted benzocarbocycles by palladium-catalyzed cascade reactions featuring a C(sp³)-H activation step was written by Hitce, Julien;Baudoin, Olivier. And the article was included in Advanced Synthesis & Catalysis in 2007.Electric Literature of C8H5Br2N This article mentions the following:

Valuable 4- and 5-membered benzocarbocycles were synthesized via selective Pd-catalyzed cascade reactions which combined C(sp³)-H activation, Heck cyclization, Heck arylation or olefin hydrogenation. In all cases, all mechanistically independent steps were catalyzed by a single multi-functional catalyst, e.g. Pd(OAc)₂/(5-F-2-MeC₆H₃)₃P. One product, (E)-1-ethyl-2-[(3,4,5-trimethoxyphenyl)methylene]benzocyclobutane-1-carbonitrile, showed promising antimicrotubule activity. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Electric Literature of C8H5Br2N).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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.Electric Literature of C8H5Br2N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

One-Pot Synthesis of Quinazolines via Elemental Sulfur-Mediated Oxidative Condensation of Nitriles and 2-(Aminomethyl)anilines was written by Tan, Yuxing;Jiang, Wujiu;Ni, Penghui;Fu, Yang;Ding, Qiuping. And the article was included in Advanced Synthesis & Catalysis in 2022.Recommanded Product: 2-Amino-3-chlorobenzonitrile This article mentions the following:

A strategy for the synthesis of quinazolines I [R = H, 6-Me, 8-Br, etc.; Ar = Ph, 4-MeC₆H₄, 2-ClC₆H₄, etc.] via elemental sulfur-mediated oxidative condensation of nitriles and 2-(aminomethyl)anilines was developed. The reaction was carried out under metal-/solvent-free conditions, tolerated a wide range of functional groups to provide the corresponding products in 56%-91% yield, and was performed on a gram-scale. The UV/Vis absorption and fluorescence spectra of several product derivatives were measured to study their photophys. properties. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Recommanded Product: 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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.Recommanded Product: 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Utilization of tetraethylammonium cyanide for preparation of cyclopentadienyl iron cyanocyclohexadienyl complexes. Study of their electrochemical and chemical oxidation. was written by Guennec, N.;Moinet, C.. And the article was included in Journal of Organometallic Chemistry in 1995.Product Details of 64113-86-6 This article mentions the following:

Addition of Et₄NCN to a solution of (η⁵-cyclopentadienyl)(η⁶-arene)iron(1+), in MeCN was studied by voltammetry. With electron-withdrawing groups such as nitro, keto, sulfone, azo and azoxy bonded to the arene, the reaction occurs immediately and a wave resulting from oxidation of hexadienyl species is observed in the range 0-1V vs. SCE. Preparation of various hexadienyl compounds, e.g. I (X = NO₂, COPh, SO₂Ph) was achieved with good yields. To obtain ortho-substituted benzonitriles, electrochem. and chem. oxidations of hexadienyl complexes were compared. The best results were obtained with N-bromosuccinimide (NBS) and a demetalation generally occurs. A 1-pot synthesis of benzonitrile compounds can be achieved after addition of cyanide ion and then NBS to a solution of (η⁵-cyclopentadienyl)(η⁶-arene)iron(1+) in MeCN. [CpFe{η⁶-C₆H₅N(O):NC₆H₄CN-2}]⁺ is directly obtained from the azoxy dicationic compound [(CpFe)₂(PhN(O)NPh)]²⁺. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Product Details of 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. 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.Product Details of 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts