Author: Jessica.F

A new synthesis of 4-amino-2-quinolinones was written by Bergman, Jan;Brynolf, Anna;Vuorinen, Eino. And the article was included in Tetrahedron in 1986.Recommanded Product: 68385-95-5 This article mentions the following:

Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles, e.g. N-(2-bromopropionyl)-N-methyl-2-cyanoaniline, induced anion formation followed by cyclization to 4-amino-2-quinolinones, e.g. 4-amino-1,3-dimethyl-2-quinolinone (I). Substrates lacking α-hydrogen atoms, such as N-(α-bromoisobutyryl)-2-cyanoaniline, also yielded 3,3-dimethylquinolinedione by cyclization. In these cases the initial step is a halogen-metal exchange reaction. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Recommanded Product: 68385-95-5).

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

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Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as New Potent Anticancer Agents was written by Romagnoli, Romeo;Baraldi, Pier Giovanni;Kimatrai Salvador, Maria;Preti, Delia;Aghazadeh Tabrizi, Mojgan;Bassetto, Marcella;Brancale, Andrea;Hamel, Ernest;Castagliuolo, Ignazio;Bortolozzi, Roberta;Basso, Giuseppe;Viola, Giampietro. And the article was included in Journal of Medicinal Chemistry in 2013.HPLC of Formula: 64113-86-6 This article mentions the following:

Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3′,4′,5′-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine mol. skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the Me group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the Me was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the Me group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds I and II did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound I significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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.HPLC of Formula: 64113-86-6

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Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes was written by Livesley, Sarah;Sterling, Alistair J.;Robertson, Craig M.;Goundry, William R. F.;Morris, James A.;Duarte, Fernanda;Aissa, Christophe. And the article was included in Angewandte Chemie, International Edition in 2022.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Herein, the electrophilic activation of [1.1.1]propellane in a halogen bond complex was reported, which enabled its reaction with electron-neutral nucleophiles such as anilines/azoles to give nitrogen-substituted bicyclo[1.1.1]pentanes (BCP)s such as I [R = H, Ph, Bn, etc.; Ar = Ph, 4-CNPh, 3,5-di-FPh, etc.] that were prominent motifs in drug discovery. A detailed computational anal. indicated that the key halogen bonding interaction promotes nucleophilic attack without sacrificing cage stabilization. Overall, this work rehabilitates electrophilic activation of [1.1.1]propellane as a valuable strategy for accessing functionalised BCPs. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Safety of 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.Safety of 4-(Benzylamino)benzonitrile

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Copper-Catalyzed Coupling of Alkylamines and Aryl Iodides: An Efficient System Even in an Air Atmosphere was written by Kwong, Fuk Yee;Klapars, Artis;Buchwald, Stephen L.. And the article was included in Organic Letters in 2002.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C-N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atm. with comparable yield. Preliminary results on the amination of aryl bromides are also described. 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. 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 4-(Benzylamino)benzonitrile

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Synthesis and mesomorphic properties of some 3-substituted-4-cyanophenyl esters, 4′-cyano-3-substituted-4-biphenyl esters of 4-(trans-4-alkylcyclohexyl) benzoic, 4-alkyl-1,3-substituted biphenyl-4′-carboxylic, trans-4-alkylcyclohexanecarboxylic and 4-alkylbenzoic acids and electrooptic parameters of liquid-crystalline mixtures containing these compounds was written by Bezborodov, V. S.;Lapanik, V. I.;Adomenas, P.;Sirutkaitis, R.. And the article was included in Liquid Crystals in 1992.Computed Properties of C7H4BrNO This article mentions the following:

The reaction of trans-4-alkylcyclohexanecarboxylic acid chlorides, 4-alkylbenzoic, 4-(trans-4-alkylcyclohexyl)-benzoic, 4-alkyl-3-substituted biphenyl-4′-carboxylic acids with 4-hydroxy-3′-substituted benzonitriles and 4-hydroxy-3′-substituted-4′-cyanobiphenyls produced the corresponding esters. The mesomorphic properties of the esters and electrooptic and dynamic parameters of the mixtures containing these compound were studied. The liquid-crystalline mixtures containing 4-cyano-3-substituted-4′-biphenyl esters of 4-alkylbenzoic and trans-4-alkyl-cyclohexanecarboxylic acids have higher threshold voltages and saturation voltages in comparison with the analogous mixtures containing 4-cyano-3-substituted Ph esters of 4-(trans-4-alkylcyclohexyl)benzoic acids. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Computed Properties of C7H4BrNO).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C7H4BrNO

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Synthesis of trifluoromethyl-substituted phenylene diisocyanates was written by Inukai, Kan;Maki, Yasuo. And the article was included in Kogyo Kagaku Zasshi in 1965.HPLC of Formula: 1483-54-1 This article mentions the following:

F₃CC₆H₃(NCO)₂ were synthesized from the corresponding F₃CC₆H₃Br₂ through F₃CC₆H₃(CN)₂ → F₃CC₆H₃(CO₂H)₂. Thus, a mixture of 30.4 g. 2,4-F₃CC₆H₃Br₂ and 19.8 g. CuCN in 30 ml. HCONMe₂ was heated at 150° 3 hrs., 60 g. FeCl₃, 15 ml. concentrated HCl, and 90 ml. H₂O added, the whole heated at 60-70° 2 hrs., filtered, the precipitates extracted with hot EtOH to give 2,4-F₃CC₆H₃(CN)₂, pale yellow crystals, m. 106-7° (80% EtOH), in 93% yield. Similarly, 2,5-F₃CC₆H₃(CN)₂, pale yellow crystals, m. 101-2° (90% EtOH) was obtained in 68% yield and 3,4-F₃CC₆H₃(CN)₂, prisms, m. 113-14° (sublimation), in 10% yield. F₃CC₆(CO₂H)₂ was prepared by heating 25.5 g. F₃CC₆H₃(CN)₂, 25 ml. concentrated HCl, and 17 ml. AcOH in a sealed tube at 135-40° 10-15 hrs. (compound % yield, and m.p. given): 2,4-F₃CC₆H₃(CO₂H)₂, 72, 240-1° (EtOH); 2,5-F₃CC₆H₃(CO₂H), 68, sublimed; 3,4-F₃CC₆H₃(CO₂H)₂, 74, 264-5° (EtOH). F₃CC₆H₃(COCl)₂ was prepared by heating 23.4 g. F₃CC₆H₃(CO₂H)₂ and 80 g. SOCl₂ 5 hrs. (compound, % yield, b₁₀, n²⁰_D, and d₂₀ given): 2,4-F₃CC₆H₃(COCl)₂, 68, 119-20°, 1.5136, 1.5154; 2,5-F₃CC₆H₃(COCl)₂, 92, 115-16°, 1.5137, 1.5087; 3,4-F₃CC₆H₃(COCl)₂, 69, 108-9°, 1.5174, 1.5002. F₃CC₆H₃(NCO)₂ was prepared by heating 27.0 g. F₃CC₆H₃(COCl)₂ and 15.0 g. NaN₃ in 60 ml. xylene under N atm. with stirring 12-13 hrs. (compound, % yield, b.p., m.p., n²⁰_D, and d₂₀ given): 2,4-F₃CC₆H₃(NCO)₂, 58, 104-5°/5 mm., 36-7°, –, –. 2,5-F₃CC₆H₃(NCO)₂, 32, 103-4°/5 mm., –, 1.5202, 1.4398; 3,4-F₃CC₆H₃(NCO)₂, 80, 111-12°/11 mm., –, 1.5298, 1.4491. 3,4-F₃CC₆H₃(NCO)₂ was synthesized from 3,4-F₃CC₆H₃(NH₂)Br through 3,4-F₃CC₆H₃(CN)Br → 3,4-F₃CC₆H₃(CO₂H)Br → 3,4-F₃CC₆H₃(CO₂H)CN → 3,4-F₃CC₆H₃(CO₂H)₂. 3,4-F₃CC₆H₃(NH₂)CN, yellow crystals, b₇ 108-10°, m. 24-5°, was prepared in 26% yield by heating 30.0 g. 3,4-F₃CC₆H₃(NH₂)Br and 13.4 g. CuCN in 18 ml. HCONMe₂ 4 hrs. 3,4-F₃CC₆H₃(CN)Br, m. 43-4° (petr. ether), was prepared in 40% yield by heating ZnCl₂-diazonium salt of 24.0 g. 3,4-F₃CC₆H₃(NH₂)Br with 6.3 g. NaCN, 0.5 g. CuCN, 10 g. NaHCO₃, 100 ml. H₂O, and 50 ml. petr. ether with stirring for 2 hrs. Similarly, 3,4-F₃CC₆H₃(CO₂H)Br, m. 116-17° (petr. ether), and 3,4-F₃CC₆H₃(CO₂H)CN, m. 169-70° (EtOH), were obtained in 49% and 89% yield, resp. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1HPLC of Formula: 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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.HPLC of Formula: 1483-54-1

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Solid phase synthesis of functionalized indazoles using triazenes – scope and limitations was written by Garcia, Ana Maria;Jung, Nicole;Gil, Carmen;Nieger, Martin;Braese, Stefan. And the article was included in RSC Advances in 2015.Safety of 2-Amino-3-chlorobenzonitrile This article mentions the following:

A modular synthesis of highly substituted indazoles via a strategy on solid supports was discussed. The heterocyclic nitrogen atoms originated from diazonium salts, being cleaved from triazene containing resins. The scope and limitations of this process was explored, considering especially the competitive occurrence of triazines and the cleavage of hydrolyzed and traceless side products. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Safety of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Safety of 2-Amino-3-chlorobenzonitrile

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Discovery of a Quinoline-4-carboxamide Derivative with a Novel Mechanism of Action, Multistage Antimalarial Activity, and Potent in Vivo Efficacy was written by Baragana, Beatriz;Norcross, Neil R.;Wilson, Caroline;Porzelle, Achim;Hallyburton, Irene;Grimaldi, Raffaella;Osuna-Cabello, Maria;Norval, Suzanne;Riley, Jennifer;Stojanovski, Laste;Simeons, Frederick R. C.;Wyatt, Paul G.;Delves, Michael J.;Meister, Stephan;Duffy, Sandra;Avery, Vicky M.;Winzeler, Elizabeth A.;Sinden, Robert E.;Wittlin, Sergio;Frearson, Julie A.;Gray, David W.;Fairlamb, Alan H.;Waterson, David;Campbell, Simon F.;Willis, Paul;Read, Kevin D.;Gilbert, Ian H.. And the article was included in Journal of Medicinal Chemistry in 2016.Recommanded Product: 37812-51-4 This article mentions the following:

The antiplasmodial activity, DMPK properties, and efficacy of a series of quinoline-4-carboxamides are described. This series was identified from a phenotypic screen against the blood stage of Plasmodium falciparum (3D7) and displayed moderate potency but with suboptimal physicochem. properties and poor microsomal stability. The screening hit (1, EC₅₀ = 120 nM) was optimized to lead mols. with low nanomolar in vitro potency. Improvement of the pharmacokinetic profile led to several compounds showing excellent oral efficacy in the P. berghei malaria mouse model with ED₉₀ values below 1 mg/kg when dosed orally for 4 days. The favorable potency, selectivity, DMPK properties, and efficacy coupled with a novel mechanism of action, inhibition of translation elongation factor 2 (PfEF2), led to progression of 2 (DDD107498) to preclin. development. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Recommanded Product: 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Recommanded Product: 37812-51-4

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Synthesis and Biological Evaluation of Quinoxaline Derivatives for PET Imaging of the NMDA Receptor was written by Milicevic Sephton, Selena;Vetterli, Peter T.;Pedani, Valentina;Cermak, Stjepko;Chiotellis, Aristeidis;Roscales, Sylvia;Mueller Herde, Adrienne;Schibli, Roger;Auberson, Yves P.;Ametamey, Simon M.. And the article was included in Helvetica Chimica Acta in 2017.Formula: C8H6N2O2 This article mentions the following:

Due to the biol. complexity of the N-methyl-D-aspartate receptor (NMDAR), the development of a positron emission tomog. radiotracer for the imaging of NMDAR has met with limited success. Recent studies have established the presence of GluN2A subunit of the NMDAR in the heart and its role in the regulation of intracellular calcium levels. In our efforts to develop an imaging agent for the GluN2A subunit, we designed three new compounds based on a quinoxaline scaffold. The synthesis of the analogs was based on a two-step Kabachnik-Fields reaction in sequence with Suzuki cross-coupling and acid hydrolysis. They exhibited comparable high binding affinity values below 5 nM. A two-step radiolabeling procedure was successfully developed for the synthesis of [¹⁸F]I. [¹⁸F]I was obtained in a modest overall radiochem. yield of 5.5 ± 4.2%, a good specific radioactivity of 254 ± 158 GBq/μmol, and a radiochem. purity > 99%. While two compounds showed comparable binding affinity towards NMDAR, sluggish radiolabeling, prevented their further evaluation. For [¹⁸F]I, in vitro autoradiog. on rat heart slices demonstrated heterogeneous but unspecific accumulation, whereas for the brain a high in vitro specificity towards NMDAR, could be demonstrated. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Formula: C8H6N2O2).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. 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.Formula: C8H6N2O2

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Benzopolymethylene compounds. IV. The two ar-aldehydes of tetralin was written by Braun, Julius V.;Moldaenke, K.;Dirlam, H.;Gruber, H.. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1922.HPLC of Formula: 29809-13-0 This article mentions the following:

When tetralin (A) is treated with CO and HCl in the presence of AlCl₃ it is impossible to prevent the greater part of the A from condensing with itself in the same way as it does with AlCl₃ alone (Schroeter, C. A. 15, 525); the small part that does react with the CO and HCl gives exclusively the ar-tetralin-β-aldehyde (B) (2 g. from 100 g. A). Both B and the α-isomer (C) can be obtained from the ar-tetralin-β- and α-methylamines (D and E, resp.) through the corresponding alcs. Bamberger and Lodter’s statement that α-C₁₀H₇CH₂NH₂ on reduction takes up the H in the substituted nucleus (Ber. 20, 1708(1887)) seemed to exclude this compound and the β-isomer as the starting points in the synthesis of B and C. Accordingly the NH₂ group in the α- and β-tetralylamines was replaced by CN, which was then reduced to CH₂NH₂, but the yields are poor. On repeating B.’s work, however, it was found that it is the unsubstituted nucleus which takes up the H on reduction and that the pure D and E can easily be obtained in this way. ar-α-Tetralyl cyanide, obtained in 22% yield from the amine by the Sandmeyer reaction, b₁₅ 153°, solidifies to a yellowish crystalline mass m. 48° (Bamberger and Bordt, Ber. 22, 625(1889), describe it as an oil b₁₂₁ 277-9°, which does not solidify), hydrolyzed by fuming HCl in a sealed tube at 120° to the acid, m. 150° (B. and H. give 123°); reduction of the nitrile with Na and alc. gives chiefly A and only about 1/3 is converted into E, oil of basic odor, b₁₁ 149-52°, eagerly absorbs CO₂ from the air, also obtained in almost 90% yield from α-C₁₀H₇CH₂NH₂ with 8 atoms of Na in AmOH (in EtOH there is very little reaction); hydrochloride, silvery needles from alc., m. 253°; picrate, golden yellow prisms from alc., m. 242°; acetyl derivative, m. 125°; benzoyl derivative, m. 144°; phenylurea, m. 199°; phenylthiourea, m. 153°. The corresponding ar-α-tetralylmethylamine (from α-C₁₀H₇CN with Na and alc.) forms a hydrochloride m. 230°, picrate m. 169-70°, phenylurea m. 126°, and benzoyl derivative m. 125°. ar-β-Tetralyl cyanide (obtained in 45-60% yield), liquid of a not unpleasant odor, b₁₁ 151-2°, m. 20-1°, gives with Na and EtOH 30% of D, b₁₁ 146-8°; hydrochloride, m. 248°; picrate, m. 215°; benzoyl derivative, long needles from alc., m. 165°, b₁₀ 260-5°; p-nitrobenzoyl derivative, m. 170°; phenylthiourea, m. 130°. D is also obtained in almost 90% yield from β-C₁₀H₇CH₂NH₂ with Na and AmOH. ar-α-Tetralylcarbinol, obtained in 80% yield from E diazotized in AcOH with the calculated amount of NaNO₂ and heated on the H₂O bath until the evolution of gas ceases, b₁₂ 154-5°, gives in H₂SO₄ with the calculated amount of K₂Cr₂O₇ 1/3 of its weight of C, b₁₂ 131-3°, as an almost odorless oil; semicarbazone, m. 187°. KMnO₄ smoothly oxidizes C to the acid. ar-β-Tetralylcarbinol (yield, 70%), faintly yellow liquid with a strong pleasant odor, b₁₄ 148-52°, gives on oxidation 25% of B, liquid of characteristic peppermint-like odor, b₁₄ 138°; semicarbazone, m. 219°. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0HPLC of Formula: 29809-13-0).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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. 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.HPLC of Formula: 29809-13-0

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Nitrile – Wikipedia,
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