Tag: M.W=150-200

Ooi, T. published the artcileZr(OBu^t)₄ as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes: development of a new asymmetric cyanohydrin synthesis, COA of Formula: C8H6ClNO, the publication is Tetrahedron (2001), 57(5), 867-873, database is CAplus.

Zr(OBu^t)₄ can serve as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation of aldehydes and also facilitate MPV type cyanide transfer to aldehyde carbonyls with com. available acetone cyanohydrin under mild conditions. Based on this finding, a new procedure for asym. cyanohydrin synthesis has been developed employing (4R,5R)-2,2-dimethyl-α,α,α’,α’-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL, I) as a chiral ligand. For instance, sequential treatment of a CH₂Cl₂ solution of I (1 equiv) with Zr(OBu^t)₄ (1 equiv) and acetone cyanohydrin (2 equiv) at room temperature for 1 h, and subsequent reaction with 3-phenylpropanal at -40° for 7.5 h resulted in formation of the corresponding cyanohydrin in 63% isolated yield with 85% ee. The scope and limitations of this method have been clarified with various aldehydes as substrates.

Tetrahedron 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, COA of Formula: C8H6ClNO.

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

Griffiths, M. H. published the artcileThe comparative metabolism of 2,6-dichlorothiobenzamide (Preflx) and 2,6-dichlorobenzonitrile in the dog and rat, Related Products of nitriles-buliding-blocks, the publication is Biochemical Journal (1966), 98(3), 770-81, database is CAplus and MEDLINE.

A single oral dose of either 2,6-dichlorothiobenzamide-¹⁴C (I) or 2,6-dichlorobenzonitrile-¹⁴C (II) fed to rats is almost entirely eliminated in 4 days; 84.8-100.5% of ¹⁴C from I is excreted 67.3-79.7% in the urine; 85.8-97.2% of ¹⁴C from II is excreted, 72.3-80.7% in the urine. Only 0.37% of the I dose and 0.25 ± 0.03% of the II dose are present in the carcass plus viscera after gut removal. Rats do not show sex differences in the pattern of elimination of the resp. metabolites of the two herbicides. The rates of elimination of ¹⁴C from the two compounds in the 24-hr. and 48-hr. urines are not different from one another. After oral administration to dogs, 85.9-106.1% of ¹⁴C from I is excreted, 66.6-80.9% in the urine, and 86.8-92.5% of ¹⁴C from II is excreted, 60.0-70.1% in the urine. Dogs do not show sex differences in the pattern of eliminating the metabolites of either I or II. Dogs and rats do not show species differences in the patterns of elimination of the two herbicides. I and II are completely metabolized; unchanged I and II are absent from the urine and feces, and from the carcasses when elimination is complete. In the hydrolyzed urine of rats dosed with either I or II, 2,6-dichloro-3-hydroxybenzonitrile accounts for approx. 42% of the ¹⁴C, a further 10-11% is accounted for by 2,6-dichlorobenzamide, 2,6-dichlorobenzoic acid, 2,6-dichloro-3- and -4-hydroxybenzoic acid and 2,6-dichloro-4-hydroxybenzonitrile collectively, and 25-30% by six polar constituents, of which two are S-containing amino acids. In the unhydrolyzed urines of rats dosed with either I or II, there are present free 2,6-dichloro-3- and -4-hydroxybenzonitrile, their glucuronide conjugates, ester glucuronides of the principal aromatic acids that are present in the hydrolyzed urines, and two S-containing metabolites analogous to mercapturic acids or premercapturic acids.

Biochemical Journal published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Related Products of nitriles-buliding-blocks.

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

Kashanna, Jajula published the artcilePalladium catalyzed carboannulation of nitrostyrenes with internal alkynes: a new synthetic strategy for cross coupling/C-H annulation and facile access to indenones, Application In Synthesis of 5153-73-1, the publication is Tetrahedron Letters (2016), 57(14), 1576-1581, database is CAplus.

Palladium(II) catalyzed carboannulation reaction of internal alkynes with nitrostyrenes to afford 2,3-disubstituted indenones is reported. The annulation reaction proceeds through transmetalation of Pd(II) with aldehydes generated from the nitrostyrene (C-H activation) and insertion of the alkynes, followed by cyclization via intramol. nucleophilic addition of intermediate organopalladium(II) species. This reaction proceeded in moderate to good yields and with high regioselectivity. Electron-rich nitrostyrenes were transformed to the corresponding aldehydes in high yields without addition of any peroxide reagent.

Tetrahedron Letters 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, Application In Synthesis of 5153-73-1.

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

Kiyokawa, Kensuke published the artcileStraightforward Synthesis of 1,2-Dicyanoalkanes from Nitroalkenes and Silyl Cyanide Mediated by Tetrabutylammonium Fluoride, Computed Properties of 5153-73-1, the publication is Chemistry – A European Journal (2015), 21(3), 1280-1285, database is CAplus and MEDLINE.

A straightforward synthesis of 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN [R = 4-OCH₃C₆H₄, thiophen-2-yl, pyridin-3-yl, etc.; R¹ = H; RR¹ = (CH₂)₄] by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride was described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride was essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol was applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN.

Chemistry – A European Journal 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, Computed Properties of 5153-73-1.

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

Xia, Dao-Cheng published the artcileCrystal structure of bis([3,2-c]isoquinolin-5-amine)benzofuro[6,5-b]furancadmium(II) dichloride, Cd(C₂₄H₁₄N₄O₂)Cl₂, COA of Formula: C8H6ClN, the publication is Zeitschrift fuer Kristallographie – New Crystal Structures (2010), 225(3), 563-564, database is CAplus.

Crystal data: monoclinic, C2/c, a = 15.9926(9), b = 10.2755(4), c = 12.5031(5) Å, β = 94.725(4)°, Z = 4, 1500 observed reflections with I > 2(I), 150 refined parameters, R_gt(F) = 0.030, wR_ref(F²) = 0.055. At. coordinates are given. The structure is discussed.

Zeitschrift fuer Kristallographie – New Crystal Structures 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 C24H26ClNO4, COA of Formula: C8H6ClN.

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

Li, Pengyu published the artcileCopper(II)-Schiff Base Complex-Functionalized Polyacrylonitrile Fiber as a Green Efficient Heterogeneous Catalyst for One-Pot Multicomponent Syntheses of 1,2,3-Triazoles and Propargylamines, Name: 2-(Chloromethyl)benzonitrile, the publication is Advanced Synthesis & Catalysis (2018), 360(8), 1673-1684, database is CAplus.

A series of copper(II)-Schiff bases-functionalized polyacrylonitrile fiber catalysts was successfully prepared using copper acetate as copper source and characterized by elemental anal., Fourier-transfer IR spectroscopy, UV-visible spectroscopy, XPS and inductively coupled plasma anal. Excellent phys. strength and thermal stability of the fiber catalysts were demonstrated by SEM, X-ray diffraction, thermogravimetric/differential scanning calorimetry anal. and mech. strength measurements. Furthermore, these catalysts were successfully applied to one-pot multicomponent copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and aldehyde, alkyne, amine (A3) coupling reaction in which the influence of different substituent groups on the catalytic activities of fiber catalysts were investigated in detail. Among them, the bis[N-ethyl-3,5-di-tert-butyl-salicylideneiminato]copper(II)-functionalized polyacrylonitrile fiber (PANS₂F-Cu) as a green, efficient catalyst exhibited the best catalytic activity as its high hydrophobic micro-environment could aggregate the reactants to the catalytic sites and accelerate the reaction. In addition, the PAN_S2F-Cu performed well in scaled-up experiment and showed excellent recyclability (at least ten times), and these characteristics enabled it to have great potential for further applications.

Advanced Synthesis & Catalysis 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 C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

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

Li, Feng published the artcileSynthesis of ethyl 4-cyanotetrahydropyran-4-carboxylate via solid-liquid phase transfer catalysis, Application of Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, the publication is Jingxi Huagong (2008), 25(6), 614-617, database is CAplus.

Eethyl 4-cyanotetrahydropyran-4-carboxylate was synthesized from di-(β-chloroethyl) ether, Et cyanoacetate and K₂CO₃ via solid-liquid phase transfer catalysis, using DMF as solvent and dodecyltrimethylammonium bromide (DTMAB) as catalyst [n(DTMAB):n(Et cyanoacetate) = 0.05:1]. The water produced was separated, sp. surface area of potassium carbonate was 6.72 × 10⁴ m^-1 and reaction temperature was 153°, the yield was 90.6%, the reaction time was 2 h. The mechanism and kinetics of the reaction were also studied. The reaction could be described by the pseudo-second-order kinetics. With DTMAB, CTMAB, TBAB and BETAC as catalysts, K_app were 0.01336, 0.01158, 0.00343. and 0.001738 L/(mol/min) respctively. The activation energy of di-(β-chloroethyl) ether and Et cyanoacetate was 58.94 kJ/mol.

Jingxi Huagong 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, Application of Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate.

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

Kwiatkowski, Jacek published the artcileHighly Enantioselective Michael Addition of 2-Fluoro-1,3-diketones to Nitroalkenes, Formula: C9H6N2O2, the publication is European Journal of Organic Chemistry (2015), 2015(2), 320-324, database is CAplus.

The highly enantioselective Michael addition of 2-fluoro-1,3-diketones R¹C(O)CHFC(O)R² (R¹ = Ph, phenanthren-3-yl, furan-2-yl, 4-BrC₆H₄; R² = Me, i-Pr) to nitroalkenes R³CH:CHNO₂ (R³ = i-Pr, Ph, 2-FC₆H₄, etc.) was developed, and the desired adducts I were obtained in good chem. yields with good diastereoselectivities and excellent enantioselectivities. Subsequent stereoselective reduction of the carbonyl groups led to the preparation of a functionalized fluoro isostere of glycerol that contains four continuous stereogenic centers.

European Journal of Organic Chemistry 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, Formula: C9H6N2O2.

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

Sikka, Harish C. published the artcileUptake and metabolism of dichlobenil by emersed aquatic plants, HPLC of Formula: 3336-34-3, the publication is Journal of Agricultural and Food Chemistry (1974), 22(2), 230-4, database is CAplus and MEDLINE.

14C-nitrile-labeled dichlobenil (2,6-dichlorobenzonitrile)(I) [1194-65-6] was readily absorbed and translocated by roots of the immersed aquatic plants, alligator weed (Alternanthera philoxeroides) and parrot feather (Myriophyllum brasiliense). Parrot feather metabolized I principally to 3-hydroxy-2,6-dichlorobenzonitrile [3336-34-3], 2,6-dichlorobenzamide [2008-58-4], and 2,6-dichlorobenzoic acid [50-30-6], whereas alligator weed did not metabolize I.

Journal of Agricultural and Food Chemistry published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C15H10O2, HPLC of Formula: 3336-34-3.

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

Wang, Lei published the artcileSynthesis, herbicidal activities and comparative molecular field analysis study of some novel triazolinone derivatives, SDS of cas: 612-13-5, the publication is Chemical Biology & Drug Design (2009), 73(6), 674-681, database is CAplus and MEDLINE.

A series of novel triazolinones were synthesized and their structures were characterized by ¹H NMR, elemental anal. and single-crystal X-ray diffraction anal. The herbicidal activities were evaluated against Echinochloa crusgalli (L.) Beauv., Digitaria adscendens, Brassica napus and Amaranthus retroflexus. The herbicidal activity data indicated that the title compounds had higher activities with substituted benzyl group moieties than with other groups such as sulfonyl, alkyl, etc. To further investigate the structure-activity relationship, comparative mol. field anal. was performed on the basis of herbicidal activity data. Both the steric and electronic field distributions of comparative mol. field anal. are in good agreement in this work. The results showed that a bulky and electroneg. group around the ortho- or para-positions of the benzene ring would possibly lead to higher activity. Based on the comparative mol. field anal., compound 2-[(1-(2,4-Dichlorophenyl)-3-methyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)methyl]benzonitrile was designed and synthesized, which displays as good herbicidal activities as the com. herbicide, carfentrazone-Et. The activity against Digitaria adscendens is 66.1% under preemergence at 300 g of a.i./ha.

Chemical Biology & Drug Design 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 C14H28O5S, SDS of cas: 612-13-5.

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