Category: 319016-04-1

Air- and moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions was written by Takahashi, Rina;Kubota, Koji;Ito, Hajime. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Product Details of 319016-04-1 The following contents are mentioned in the article:

In this report, a Xantphos-ligated palladium dialkyl complex that acts as a powerful precatalyst for C-N, C-S, and C-C cross-coupling reactions is described. This precatalyst is air- and moisture stable but can be thermally activated in the absence of external reagents. Addnl., potential catalyst inhibitors are not generated during the precatalyst activation. This complex thus represents a convenient alternative to previously reported classes of Xantphos-ligated precatalysts. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Product Details of 319016-04-1).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) 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.Product Details of 319016-04-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some derivatives of 4′-hydroxydiphenylamine-4-carboxylic acid was written by Burger, Alfred;Darby, Robert A.. And the article was included in Journal of the American Chemical Society in 1955.Category: nitriles-buliding-blocks The following contents are mentioned in the article:

p-HOC₆H₄NHPh (260 g.), 375 g. Bz₂O, and 250 cc. dry pyridine heated 6 h. on the steam bath, the cooled mixture acidified with cold 50% H₂SO₄ and filtered, the brownish residue washed with 2% aqueous NaOH and H₂O, treated with EtOH and diluted with H₂O, and the precipitate crystallized from aqueous EtOH gave 330 g. p-BzOC₆H₄NHPh, pale yellow leaflets, m. 112-14°. p-BzOC₆H₄NHC₆H₄Br-p (40 g.) and 16 g. CuCN in 240 cc. dry quinoline refluxed 6 h., the red solution cooled and poured with stirring into 200 cc. 37% HCl, and the precipitate filtered, washed, and recrystallized from C₆H₆-ligroine gave 17.5 g. p-BzOC₆H₄NHC₆H₄CN-p (I), almost colorless needles, m. 178.5-80.5° (all m.ps. are corrected). I treated 0.5 h. with hot KOH in EtOH gave 71% p-HOC₆H₄NHC₆H₄CN-p (II), m. 193-4.5° (from aqueous EtOH). II treated with CH₂N₂ gave the Me ether (III), m. 99-100° (from aqueous Me₂CO). III refluxed 20 h. with 15% alc. KOH yielded 43% p-MeOC₆H₄NHC₆H₄CO₂H-p (IV), m. 165-7° (from MeOH). II (5 g.) in 40 cc. (CH₂OH)₂ containing 6 g. KOH refluxed 3 h., cooled, acidified, and filtered, and the brown crystalline filter residue recrystallized with Darco from MeOH yielded 3.56 g. p-HOC₆H₄NHC₆H₄CO₂H-p, colorless crystals, m. 229-30° (decomposition) (it turned pink in air), which treated with CH₂N₂ gave the Me ester of IV, m. 91.5-3.5° (from Et₂O-ligroine). II (0.1 mol) treated with 0.4 mol ICl and the resulting pink powder (which turned blue in air) recrystallized repeatedly from Et₂O-ligroine gave 30% 3,5,4-Cl₂(HO)C₆H₂NHC₆H₄CN-p, almost transparent colorless needles, m. 215-16° (from Et₂O-ligroine). This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Category: nitriles-buliding-blocks).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Large Electro-optic Activity and Enhanced Thermal Stability from Diarylaminophenyl-Containing High-β Nonlinear Optical Chromophores was written by Cheng, Yen-Ju;Luo, Jingdong;Hau, Steven;Bale, Denise H.;Kim, Tae-Dong;Shi, Zhengwei;Lao, David B.;Tucker, Neil M.;Tian, Yanqing;Dalton, Larry R.;Reid, Philip J.;Jen, Alex K.-Y.. And the article was included in Chemistry of Materials in 2007.Category: nitriles-buliding-blocks The following contents are mentioned in the article:

Two series of highly efficient and thermally stable nonlinear optical chromophores based on the (4-diarylamino)phenyl electron donors have been synthesized and systematically investigated. A modular approach has been employed to synthesize these electron donors with tunable size, shape, and electron-donating abilities. Efficient conjugated bridges were extended from these donors and coupled with very strong CF₃-TCF electron acceptors to afford chromophores with very high β values (up to 7077 × 10^-30 esu at 1.907 μm). These chromophores possess much higher thermal stability (with their onset decomposition temperatures all above 220 °C) than those substituted with (4-dialkylamino)phenyl donors. Most importantly, the high mol. hyperpolarizability of these chromophores can be effectively translated into very large electro-optic (E-O) coefficients (r₃₃) in poled polymers through suitable shape engineering. Exemplified by the chromophore B4, which has a fluorinated aromatic substituent anchored at its donor end, it showed a very large r₃₃ (169 pm/V) at 1.31 μm. This value is almost 1 order higher than the E-O activities usually reported for (4-diarylamino)phenyl-substituted NLO chromophores. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Category: nitriles-buliding-blocks).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amination with Pd-NHC Complexes: Rate and Computational Studies Involving Substituted Aniline Substrates was written by Hoi, Ka Hou;Calimsiz, Selcuk;Froese, Robert D. J.;Hopkinson, Alan C.;Organ, Michael G.. And the article was included in Chemistry – A European Journal in 2012.Application of 319016-04-1 The following contents are mentioned in the article:

The amination of aryl chlorides with various aniline derivatives using the N-heterocyclic carbene-based Pd complexes Pd-PEPPSI-IPr and Pd-PEPPSI-IPent (PEPPSI=pyridine, enhanced precatalyst, preparation, stabilization, and initiation; IPr=diisopropylphenylimidazolium derivative; IPent= diisopentylphenylimidazolium derivative) has been studied. Rate studies have shown a reliance on the aryl chloride to be electron poor, although oxidative addition is not rate limiting. Anilines couple best when they are electron rich, which would seem to discount deprotonation of the intermediate metal ammonium complex as being rate limiting in favor of reductive elimination. In previous studies with secondary amines using PEPPSI complexes, deprotonation was proposed to be the slow step in the cycle. These exptl. findings relating to mechanism were corroborated by computation. Pd-PEPPSI-IPr and the more hindered Pd-PEPPSI-IPent catalysts were used to couple deactivated aryl chlorides with electron poor anilines; while the IPr catalysis was sluggish, the IPent catalyst performed extremely well, again showing the high reactivity of this broadly useful catalyst. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Application of 319016-04-1).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) 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. 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 319016-04-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A group of diphosphine-thiosemicarbazone complexes of palladium: Efficient precursors for catalytic C-C and C-N coupling reactions was written by Thapa, Kiran;Paul, Piyali;Bhattacharya, Samaresh. And the article was included in Inorganica Chimica Acta in 2019.Application of 319016-04-1 The following contents are mentioned in the article:

Reaction of 4-R-benzaldehyde thiosemicarbazone (denoted in general as HL-R; where H stands for the dissociable acidic proton and R (R = OCH₃, CH₃, H, Cl and NO₂) for the substituent) with [Pd(dppe)(EtOH)₂]²⁺, generated in situ via interaction of [Pd(dppe)Cl₂] (dppe = 1,2-bis(diphenylphosphino)ethane) with AgNO₃ in hot ethanol, in the presence of triethylamine affords a group of orange complexes of the type [Pd(dppe)(L-R)]NO₃. Structures of [Pd(dppe)Cl₂] and [Pd(dppe)(L-OCH₃)]NO₃ have been determined by X-ray crystallog. In the [Pd(dppe)(L-R)]NO₃ complexes, the thiosemicarbazone ligands are coordinated to the metal center as monoanionic bidentate N,S-donors forming five-membered chelate rings. The [Pd(dppe)(L-R)]NO₃ complexes show intense absorptions in the visible and UV regions, which have been analyzed by TDDFT calculations All the [Pd(dppe)(L-R)]NO₃ complexes are found to efficiently catalyze Suzuki-type C-C and Buchwald-type C-N coupling reactions. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Application of 319016-04-1).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application of 319016-04-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Comparison of the effect of N-methyl and N-aryl groups on the hydrolytic stability and electronic properties of betalain dyes was written by Pioli, Renan Moraes;Mattioli, Renan Rodini;Esteves, Larissa Cerrato;Dochev, Stefan;Bastos, Erick Leite. And the article was included in Dyes and Pigments in 2020.Quality Control of 4-((4-Methoxyphenyl)amino)benzonitrile The following contents are mentioned in the article:

Betalains are antioxidant secondary metabolites that emerged as safe color additives for food and cosmetics, fluorescent dyes, and redox mediators. Herein, we describe the semisynthesis of N-Me phenylbetalain (mepBeets) and N-aryl phenylbetalain (dipBeets) dyes and compare the effect of the structure on their hydrolytic stability and electronic properties. Eight model compounds were semisynthesized by coupling betalamic acid with either N-Me anilines or N-aryl anilines in Et acetate using p-toluenesulfonic acid as catalyst. The presence of electron-withdrawing substituents in the aryl moiety of mepBeets and dipBeets results in faster hydrolysis, lower anodic potentials and increased fluorescence quantum yields compared to the corresponding unsubstituted parent compounds The results are rationalized by considering the charge distribution in the 1,7-diazaheptamethinium chromophore and are useful for the development of new hydrolytically stable betalain dyes with tunable redox and optical properties. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Quality Control of 4-((4-Methoxyphenyl)amino)benzonitrile).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) 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. 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.Quality Control of 4-((4-Methoxyphenyl)amino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts