Month: January 2023

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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