Month: January 2023

Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles was written by Lambert, Kyle M.;Bobbitt, James M.;Eldirany, Sherif A.;Kissane, Liam E.;Sheridan, Rose K.;Stempel, Zachary D.;Sternberg, Francis H.;Bailey, William F.. And the article was included in Chemistry – A European Journal in 2016.Computed Properties of C8H4F3NO This article mentions the following:

Synergism among several intertwined catalytic cycles allowed for selective, room temperature oxidation of primary amines to the corresponding nitriles in 85-98 % isolated yield. This metal-free, scalable, operationally simple method employed a catalytic quantity of 4-acetamido-TEMPO (ACT; TEMPO = 2,2,6,6-tetramethylpiperidine N-oxide) radical and the inexpensive, environmentally benign triple salt oxone as the terminal oxidant under mild conditions. Simple filtration of the reaction mixture through silica gel afforded pure nitrile products. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Computed Properties of C8H4F3NO).

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.Computed Properties of C8H4F3NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode was written by Abazid, Ayham H.;Clamor, Nils;Nachtsheim, Boris J.. And the article was included in ACS Catalysis in 2020.Reference of 101219-69-6 This article mentions the following:

The application of a triazole-substituted chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes was reported. This method allows the rapid synthesis of chiral benzyl alcs. in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C-H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It initiates the radical bromination in its oxidized state through an in-situ-formed bromoiodane and in the second, Cu-catalyzed step, it acts as a chiral ligand. This work demonstrates the ability of a chiral aryl iodide catalyst acting both as an oxidant and as a chiral ligand in a highly enantioselective C-H-activating transformation. Furthermore, this concept presents an enantioconvergent hydroxylation with high selectivity using a synthetic catalyst. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Reference of 101219-69-6).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

X-ray crystal structure of a 2-amino-3,4-dihydroquinazoline 5-HT₃ serotonin receptor antagonist and related analogs was written by Abdelkhalek, Ahmed S.;Musayev, Faik N.;Iyer, Kavita A.;Hemanth, Prithvi;Safo, Martin K.;Dukat, Malgorzata. And the article was included in Journal of Molecular Structure in 2020.Electric Literature of C7H5ClN2 This article mentions the following:

Certain 2-amino-3,4-dihydroquinazolines bind at 5-HT₃ serotonin receptors and act as antagonists (e.g. 6-chloro) whereas others bind with little to no affinity and lack functional activity (e.g. 8-chloro). The purpose of this investigation was to gain insight as to why this might be the case. X-Ray crystallog. studies revealed that the N-C-N distances in the examined analogs are nearly identical (1.31-1.34 Å), suggesting that differences in N-C-N delocalization does not account for differences in affinity/action. Homol. modeling hydrophatic interactions (HINT) anal. revealed that the 6-chloro analog formed a greater number, and more favorable, interactions with the receptor, whereas the 8-chloro analog formed fewer, and unfavorable, interactions. The affinity and activity of the 6-chloro quinazoline relative to its 8-chloro counterpart are unrelated to the N-C-N delocalization pattern but might be related to specific (favorable and unfavorable) interactions of quinazoline substituents with certain receptor features as determined by HINT anal. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Electric Literature of C7H5ClN2).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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. 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. Electric Literature of C7H5ClN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An efficient Ir(III) catalyst for the asymmetric transfer hydrogenation of ketones in neat water was written by Li, Xiaohong;Blacker, John;Houson, Ian;Wu, Xiaofeng;Xiao, Jianliang. And the article was included in Synlett in 2006.Related Products of 101219-69-6 This article mentions the following:

The chiral M-CsDPEN [M = Ru, Rh, Ir; CsDPEN = (R,R,R)- or (S,S,S)-N-camphorsulfonyl-1,2-diphenylethylenediamine] catalysts were shown to be efficient for the asym. transfer hydrogenation (ATH) of aryl ketones by formate in neat water. Of particular note is the Ir-(R,R,R)-CsDPEN catalyst, which catalyzes the ATH of a wide range of ketones and delivers almost full conversions within a few hours at a S/C ratio of 1000 at 40° in most cases, with enantioselectivities ≤98% ee. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 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. 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.Related Products of 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2-Azidobenzonitrile Derivatives was written by Nakhai, Azadeh;Stensland, Birgitta;Svensson, Per H.;Bergman, Jan. And the article was included in European Journal of Organic Chemistry in 2010.Name: 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

3-Substituted 3,4-dihydro-4-imino-1,2,3-benzotriazine derivatives 7 (e. g. I) were formed from 2-azidobenzonitriles as starting materials on treatment with Grignard or lithium organic reagents. In some cases these procedures gave aryltriazenes, e. g. II and III, as products. All compounds were identified by NMR spectroscopy and the structures of three products, namely I, II and III, were corroborated by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Name: 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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: 2-Amino-3,5-dibromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rhodium-Catalyzed Anti-Markovnikov Hydrohydrazination of Terminal Alkynes with N-Alkyl- and N,N-Dialkylhydrazines was written by Fukumoto, Yoshiya;Ohmae, Akihiro;Hirano, Masaya;Chatani, Naoto. And the article was included in Asian Journal of Organic Chemistry in 2013.Product Details of 4435-14-7 This article mentions the following:

The anti-Markovnikov addition of hydrazines to terminal alkynes in the presence of [TpRh(C₂H₄)₂]/P(2-furyl)₃ (Tp=trispyrazolylborate) as a catalyst system has been developed. N-alkyl- and N,N-dialkyl-substituted hydrazines are applicable to this highly regioselective hydrohydrazination, which affords aldimine-type hydrazine derivatives In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Product Details of 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. Product Details of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C-N Cross-Coupling Reactions was written by Kampmann, Sven S.;Skelton, Brian W.;Wild, Duncan A.;Koutsantonis, George A.;Stewart, Scott G.. And the article was included in European Journal of Organic Chemistry in 2015.Synthetic Route of C14H12N2 This article mentions the following:

In this report we describe the design and preparation of a new air-stable nickel phosphite based catalyst for unique C-N bond forming processes. Specifically, (BINAP)Ni[P(OPh)₃]₂, is presented as an effective catalyst for a range of amination reactions between aryl halides and primary alkylamines. The results are supported by relevant kinetic studies, DFT calculations and a catalytic cycle indicating possible reaction intermediates. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Synthetic Route of C14H12N2).

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. 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.Synthetic Route of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Imidazolium-based phosphinite ionic liquid (IL-OPPh₂) as reusable catalyst and solvent for the Knoevenagel condensation reaction was written by Valizadeh, Hassan;Gholipour, Hamid. And the article was included in Synthetic Communications in 2010.Electric Literature of C14H14N2O2 This article mentions the following:

A task-specific ionic liquid (IL), which bears a weak Lewis base (OPPh₂) in an imidazolium cation, efficiently catalyzed the Knoevenagel condensation of aryl aldehydes with H₂C(CN)₂, H₂C(CO₂Me)₂, H₂C(CO₂Et)₂, and NCCH₂CO₂Et. This IL played a dual role as both the reaction medium and also catalyst, and it could be easily recovered and reused in several runs. Satisfactory results were obtained with good yields, short reaction time, and simplicity in the exptl. procedure. A variety of coumarin derivatives were synthesized in this procedure. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Electric Literature of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and properties of several nitrile analogs of bis(2-chloroethyl)amine was written by Rodionov, P. V.;Rapp, L. B.;Nikolaeva, S. V.. And the article was included in Fiziologicheski Aktivnye Veshchestva (1966-1992) in 1973.Recommanded Product: 7528-78-1 This article mentions the following:

Reaction of RN(CH2CH2Cl)2 (R = NCCH2CH2, m-BrC6H4CH2, p-FC6H4CH2, m-, p-, and o-MeC6H4CH2) with NaCN-EtOH gave a mixture of RN(CH2CH2CN)2 and RN(CH2CH2CN)CH2CH2OEt. The LD50 of (NCCH2CH2)3N in mice (s.c.) was 880 mg/kg; the maximum transfer dose was 300 mg/kg. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Recommanded Product: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of antipodagra febuxostat was written by Liu, Xiao-zu;Liu, Pei-jun;Yuan, Ze-li;Hu, Qing-hong. And the article was included in Jingxi Huagong in 2014.Recommanded Product: 5203-15-6 This article mentions the following:

Febuxostat was synthesized from 4-hydroxybenzonitrile via alkylation, bromination, thioformylation, cyclization, cyanation, and hydrolysis. In the improved process, a LiCl-promoted thioformylation needed less time as well as avoided the use of strong acidic conditions. With the catalysis of trace Pd (OAc)₂, a cyano group was smoothly installed in the presence of K₄ [Fe (CN)₆] without anhydrous anaerobic operation. Non-toxic K₄ [Fe (CN)₆] was used advantageously compared to toxic cyanide sources. The total yield was as high as 64.3%. The structure was confirmed by m.p., ¹H-NMR, ¹³C-NMR and ESI-MS. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Recommanded Product: 5203-15-6).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) 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.Recommanded Product: 5203-15-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts