Author: Jessica.F

Genokhova, N. S. published the artcileSynthesis of metallic complexes of 1,19-dimethyloctadehydrocorrins with electron acceptor β-substituents, SDS of cas: 26187-28-0, the publication is Zhurnal Obshchei Khimii (1977), 47(1), 121-9, database is CAplus.

I (M = Co, Ni, R = Me, CH2CO2H, R’ = CH2CH2CO2H; R = CO2Et, CN, R’ = Me) were prepared by the oxidative cyclization of hexamethylbiline derivatives in the presence of Ni and Co ions. The hexamethylbiline derivatives were also prepared The complexes and the ligands were characterized by electronic and NMR spectra.

Zhurnal Obshchei Khimii published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, SDS of cas: 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Henze, Henry R. published the artcileHydantoins containing a tetrahydropyranyl substituent, Computed Properties of 30431-99-3, the publication is Journal of the American Chemical Society (1942), 1672-4, database is CAplus.

Refluxing a mixture of 155 g. NCCH₂CO₂Et and 97 g. (ClCH₂CH₂)₂O with 31.5 g. of Na in 450 cc. EtOH for 3 h. gives 31% of the Et ester, b₁₆ 135°, n_D²⁰ 1.4539, d₄²⁰ 1.1109, γ²⁰ 37.4, of 4-cyanotetrahydro-4-pyrancarboxylic acid; heating the acid at 180-200° gives 90% of tetrahydro-4-pyrancarbonitrile (I), b₁₀ 82-3°, n_D²⁰ 1.4521, d₄²⁰ 1.0343, γ²⁰ 40.7. 4-Acyltetrahydropyrans, RCOCH(CH₂.CH₂)₂O, were prepared by addition of a mol. proportion of I in absolute ether to 1.2-2 M proportions of the Grignard reagent (R is given): Me, b₁₄₄ 205-7°, n_D²⁰ 1.4530, d₄²⁰ 1.0243, γ²⁰ 35.8, MR 33.98, 53% yield (semicarbazone, m. 178° (all m. ps. corrected)); Et, b₂₀ 101°, n 1.4541, d. 1.0016, γ 37.2, MR, 38.60, 72% (semicarbazone, m. 151°); Pr, b₅ 85-8°, n 1.4545, d. 0.9828, 57% (semicarbazone, m. 145-6°); Bu, b₅ 100°, n 1.4551, d. 0.9700, 67% (semicarbazone, m. 180°; 2,4-dinitrophenylhydrazone, m. 99°); iso-Bu, b₆ 90-2°, n 1.4545, d. 0.9648, γ 33.2, MR 47.83, 69% (semicarbazone, m. 187-8°; 2,4-dinitrophenylhydrazone, m. 122°); Am, b₅ 106-7°, n 1.4573, d. 0.9589, γ 33.3, MR 52.45, 64% (semicarbazone, m. 117°; 2,4-dinitrophenylhydrazone, m. 89-90°); iso-Am, b₇ 116-17°, n 1.4567, d. 0.9562, γ 32.9, MR 52.45, 65% (semicarbazone, m. 158-9°; 2,4-dinitrophenylhydrazone, m. 134-5°); hexyl, b₆ 134-5°, n 1.4569, d. 0.9446, MR 57.07, 61% (semicarbazone, m. 161°); cyclohexyl, b₅ 142°, n 1.4839, d. 1.0262, MR 54.87, 46% (semicarbazone, m. 213-14°); Ph, m. 57-8°, 67%. The ketone with 1.8 molar equivalents of KCN and 3.6 molar equivalents of (NH₄)₂CO₃ in about 150 cc. 50% EtOH heated 12 h. at 58-60° gives 5-substituted 5-(tetrahydro-4-pyranyl)hydantoins, HN.CO.NH.CO.CRCH(CH₂.CH₂)₂O (R given): Me, m. 250°, 51%; Et, m. 246°, 70%; Pr, m. 223°, 66%; Bu, m. 195°, 49%; iso-Bu, m. 222°, 53%; Am, m. 171-2°, 79%; iso-Am, m. 195-6°, 68%; hexyl, m. 169°, 48%; cyclohexyl, m. 304-6°, 65%; Ph, m. 253°, 72%. The iso-Am and Ph derivatives exhibit mild anticonvulsant activity and are devoid of any hypnotic action.

Journal of the American Chemical Society published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Computed Properties of 30431-99-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Campbell, Neil published the artcilePreparation of the halophenylacetic acids, Quality Control of 13312-84-0, the publication is Journal of the Chemical Society (1948), 1251-5, database is CAplus.

Gränacher’s synthesis (C.A. 16, 3898; 17, 2424) has been applied to the preparation of XC₆H₄CH₂CO₂H; the method depends on a satisfactory preparation of rhodanine (I), which is discussed. The yield of I depends upon the yield of H₂NCSSNH₄ (II) in the 1st stage of the reaction; the yield of II, as compared with that of CS(SNH₄)₂ (III), is a function of the NH₃ concentration which, in turn, is dependent on the temperature The more concentrated the NH₃ solution, the greater is the yield of III; the best yield of II is obtained at 10-15°; the yield of I from II is 44%. When the temperature is kept below 0%, III is the main product. Methods of distinguishing between II and III are given. Mol. quantities of aldehyde and I in AcOH (5 cc. per g. aldehyde), refluxed 0.5 h. with fused AcONa (twice the weight of I), give the following benzylidenerhodanines (IV): ο-Cl, pale yellow, m. 192°, 97% (Andreasch, C.A. 22, 3410, gives 169°); m-Cl, pale yellow, m. 233°, 93%; p-Cl, yellow, m. 231-2°, 93%; ο-Br, orange, m. 183.5°, 80%; m-Br, yellow, m. 238°, 90%; p-Br, yellow, m. 237-8°, 84%. IV were transformed into β-phenyl-α-thiopyruvic acids (V) by heating with 8 cc. 8% NaOH (per g. IV) at 50-5° until a clear or nearly clear solution resulted, cooling in an ice-salt bath, and acidifying rapidly with 3 N HCl; the crude acid in cold EtOH is precipitated with 1-2 volumes cold H₂O and recrystallized from MeOH, petr. ether, etc.; however, the crude acids were used in the next step. ο-Cl, m. 134-5°, 72% (A. gives 119-20°); m-Cl, straw-colored, m. 134°, 84%; p-Cl, yellow, m. 169-71°, 84% [a byproduct is probably α,α’-dithiobis(m-chlorocinnamic acid), yellow, m. 221-2°]; ο-Br, lemon-yellow, m. 142-3°, 70%; m-Br, pale yellow, m. 133-4°, 81%; p-Br, m. 165-80°, 75% (could not be purified further). α-Isonitroso-β-(halophenyl)propionic acids (VI) were prepared from V by refluxing (about 0.5 h.) in alc. containing 3 mols. NH₂OH (until H₂S evolution ceases); the crude acid is precipitated from dilute NaOH solution with concentrated HCl. ο-Cl, m. 156°, 83%; m-Cl, m. 149° (decomposition), 100%; p-Cl, m. 170° (decomposition) (1 sample m. 182°), 100%; ο-Br, m. 150° (decomposition), 100%; m-Br, m. 151°, 93%; p-Br, m. 173°, 85% (yields are of crude products). VI, refluxed 10 min. with Ac₂O (4 cc. per g. VI), the Ac₂O removed in vacuo, and the residue extracted with ether, give the (halophenyl)acetonitriles (VII): ο-Cl, b₁₁ 123-5°, 64%; m-Cl, b₁₀ 134-6°, 55%; p-Cl, b₁₂ 137-9°, m. 31-2°, 80%; ο-Br, b₁₃, 140-1°, 88%; m-Br, b₁₀ 145-7°, m. 27-8°, 70%; p-Br, b_10-12 152-6°, m. 48°, 72%. The over-all yields of the VII from the aldehydes were: ο-, m-, and p-Cl, 57, 47, 62%; ο-, m-, and p-Br, 49, 44, 38%; further losses, sometimes considerable, occur in the next step. VII were hydrolyzed by boiling with 60% H₂SO₄ or, preferably, with 20% EtOH-KOH, giving RC₆H₄CH₂CO₂H (R given): ο-Cl, m. 93-5° (p-nitrobenzyl ester, m. 70-1°); m-Cl, m. 77° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 138°); p-Cl, m. 104-6° (p-nitrobenzyl ester, m. 117°); ο-Br, m. 104-5° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 183-4°; anilide, m. 153-4°); m-Br, m. 102-3° (p-nitrobenzyl ester, m. 75-6°; p-toluidide, m. 135°); p-Br, m. 113-15° (p-nitrobenzyl ester, m. 128-9°; anilide, m. 174-6°; p-toluidide, m. 203°). The results show that this method leaves much to be desired. The crystalline compound from 20 g. p-BrC₆H₄CHO, 80 cc. NaHSO₃, and 5 cc. EtOH, stirred 2 h. with 10 g. KCN in 20 cc. H₂O, gives 12.5 g. p-bromomandelonitrile, m. 78-9°; 11 g. and 46 cc. HI (d. 1.94), refluxed 1 h. give 1.5 g. p-BrC₆H₄CH₂CO₂H; an unknown compound, m. 126-7°, is a byproduct. ο-ClC₆H₄CHO, through ο-ClC₆H₄CH(OH)CN, yields the benzoate (no properties given); refluxing with Pt black in tetralin did not give ο-ClC₆H₄CH₂CN. p-MeOC₆H₄CH₂CN was obtained in 39% yield (yield of intermediate benzoate 74 and 92% in 2 experiments). Other methods were tried without much success. A mixture of ο- and p-BrC₆H₄CH₂CO₂H could not be separated by fractional distillation of the acid chlorides or Et esters; chromatog. separation of the anilides, p-toluidides, and 2-naphthalides was only partially successful (they fluoresce in C₆H₆ but not on the Al₂O₃ column). α-(ο-Bromophenyl)aceto-2-naphthalide, m. 188-9°; p-isomer, m. 203-4°. α-Phenylaceto-2-naphthalide m. 162-3°. In the preparation of the naphthalides by heating the acids with 2-C₁₀H₇NH₂, (2-C₁₀H₇)₂NH is obtained, the catalyst presumably being the halo acid. 2-C₁₀H₇NH₂ and PhNH₂ give 2-C₁₀H₇NHPh, and p-MeC₆H₄NH₂ gives 2-C₁₀H₇NHC₆H₄Me-p, but ο- or m-ClC₆H₄NH₂ gives only (2-C₁₀H₇)₂NH. 2-C₁₀H₇NH₂ and its derivatives are more strongly adsorbed than the corresponding 1-derivatives

Journal of the Chemical Society published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Quality Control of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Smyth, Lynette A. published the artcileSynthesis and reactivity of 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones: development of a novel kinase-focussed library, HPLC of Formula: 57663-05-5, the publication is Tetrahedron (2010), 66(15), 2843-2854, database is CAplus.

3-Amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones represent a potentially attractive heteroaromatic scaffold for drug-discovery chem. In particular, the arrangement of hydrogen bond donor and acceptor groups in the bicyclic core can fulfil the requirements for ATP competitive binding to kinase enzymes. Efficient and regioselective routes from simple starting materials to novel functionalized 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones and related 3-amino-2H-pyrazolo[4,3-c]pyridines were explored and adapted for parallel synthesis, resulting in a library of compounds suitable for screening against kinases and other cancer drug targets. Methods for substituent variation at five distinct positions around the bicyclic core were devised to generate sets of compounds containing two- or three-point diversity.

Tetrahedron published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C14H31NO2, HPLC of Formula: 57663-05-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Frias, Maria published the artcileAsymmetric Synthesis of Rauhut-Currier type Products by a Regioselective Mukaiyama Reaction under Bifunctional Catalysis, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Journal of the American Chemical Society (2017), 139(2), 672-679, database is CAplus and MEDLINE.

The reactivity and the regioselective functionalization of silyl-diene enol ethers under a bifunctional organocatalyst provokes a dramatic change in the regioselectivity, from the 1,5- to the 1,3-functionalization. This variation makes possible the 1,3-addition of silyl-dienol ethers to nitroalkenes, giving access to the synthesis of tri- and tetrasubstituted double bonds in Rauhut-Currier type products. The process takes place under smooth conditions, nonanionic conditions, and with a high enantiomeric excess. A rational mechanistic pathway is presented based on DFT and mechanistic experiments

Journal of the American Chemical Society published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kai, Shumpei published the artcileQuantitative Analysis of Self-Assembly Process of a Pd₂L₄ Cage Consisting of Rigid Ditopic Ligands, Product Details of C10H12F6N4O6PdS2, the publication is Chemistry – A European Journal (2018), 24(3), 663-671, database is CAplus and MEDLINE.

The self-assembly process of a Pd₂L₄ cage complex consisting of rigid ditopic ligands, in which two 3-pyridyl groups are connected to a benzene ring through acetylene bonds and Pd^II ions was revealed by a recently developed quant. anal. of self-assembly process (QASAP), with which the self-assembly process of coordination assemblies can be investigated by monitoring the evolution with time of the average composition of all the intermediates. QASAP revealed that the rate-determining steps of the cage formation are the intramol. ligand exchanges in the final stage of the self-assembly: [Pd₂L₄Py*₂]⁴⁺→[Pd₂L₄Py*₁]⁴⁺+Py* and [Pd₂L₄Py*₁]⁴⁺→[Pd₂L₄]⁴⁺+Py* (Py*: 3-chloropyridine, which was used as a leaving ligand on the metal source). The energy barriers for the two reactions were determined to be 22.3 and 21.9 kcal mol^-1, resp. DFT calculations of the transition-state (TS) structures for the two steps indicated that the distortion of the trigonal-bipyramidal Pd^II center at the TS geometries increases the activation free energy of the two steps.

Chemistry – A European Journal published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Product Details of C10H12F6N4O6PdS2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Motiyenko, Roman A. published the artcileHigh-Resolution Millimeter Wave Spectroscopy and Ab Initio Calculations of Aminomalononitrile, Application In Synthesis of 5098-14-6, the publication is Journal of Physical Chemistry A (2015), 119(6), 1048-1054, database is CAplus and MEDLINE.

The HCN trimer aminomalononitrile (H₂NCH(CN)₂, AMN) is considered as a key compound in prebiotic chem. and a potential candidate for detection in the interstellar medium. In this view, we studied the rotational spectrum of AMN in the 120-245 GHz frequency range. The spectroscopic work was augmented by high-level ab initio calculations The calculations showed that between two existing rotamers, sym. and asym., the most stable is the asym. conformation, and it is the only conformation observed in the recorded spectra. The sym. conformation is 6.7 kJ/mol higher in energy and thus has a very low Boltzmann factor. The anal. of the rotational spectra of the A conformation has shown that the observed lines exhibit a doublet or quartet structure owing to two large-amplitude motions, C-N torsion and amino group inversion. To study the large-amplitude motions in detail, we calculated a two-dimensional potential energy surface and determined the barrier heights for the torsion and inversion, V_t = 12.5 kJ/mol and V_i = 19.1 kJ/mol. About 2500 assigned rotational transitions in the ground vibrational state were fitted within exptl. accuracy using the reduced axes system Hamiltonian. The set of obtained spectroscopic parameters allows accurate calculation of transition frequencies and intensities for an astrophys. search of AMN.

Journal of Physical Chemistry A published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Application In Synthesis of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Makida, Yusuke published the artcileNickel-catalysed carboxylation of organoboronates, Related Products of nitriles-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(59), 8010-8013, database is CAplus and MEDLINE.

A nickel/N-heterocyclic carbene (NHC) catalyzed carboxylation of aryl-, heteroaryl- and alkenylboronates, affording the corresponding carboxylic acids, has been developed. This transformation proceeds under one atm. of CO₂ with a broad range of substrates and exhibits good functional group compatibility.

Chemical Communications (Cambridge, United Kingdom) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wu, Ao-rong published the artcileSynthesis of aromatic acyl cyanides catalyzed by Sm(OTf)₃, COA of Formula: C8H6ClN, the publication is Nongyao (2013), 52(4), 241-243, 246, database is CAplus.

The paper aimed to study a new synthetic method of aromatic acyl cyanides. Catalyzed by samarium triflate [Sm(OTf)₃] aromatic acyl chlorides was reacted with sodium cyanide to give aromatic acyl cyanides. Under the optimal reaction conditions, the yields and purities of aromatic acyl products reached about 90% and above 98% resp. It was a novel practical method to prepare aromatic acyl cyanides, with mild reaction conditions and high selectivity, and without the use of phase transfer catalyst.

Nongyao published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C23H23ClN2O4, COA of Formula: C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Maity, Soham published the artcileEfficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO₂ and TEMPO, Quality Control of 5153-73-1, the publication is Journal of the American Chemical Society (2013), 135(9), 3355-3358, database is CAplus and MEDLINE.

Nitroolefins are common and versatile reagents. Their synthesis from olefins is generally limited by the formation of mixtures of cis and trans compounds Here the authors report that silver nitrite (AgNO₂) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein, starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.

Journal of the American Chemical Society published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts