Author: Jessica.F

Xu, Jian-Xing published the artcileRuthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond, Quality Control of 214360-44-8, the publication is Organic Letters (2020), 22(7), 2756-2760, database is CAplus and MEDLINE.

Herein, the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines I (R¹ = H; R² = Me, F, Cl, t-Bu, H; R³ = H, F; R¹R² = -CH=CH-CH=CH-) and N,N-dimethyl-2-(pyrimidin-2-yl)aniline via C(aryl)-N bond cleavage was reported. Without any ligand and base, diaryl ketones II (R⁴ = 3-bromophenyl, 2,4,6-trimethylphenyl, 2-naphthyl, etc.) and phenyl(2-(pyrimidin-2-yl)phenyl)methanone can be obtained in moderate to high yields by using Ru₃(CO)₁₂ as the catalyst and chelation assisted by pyridine. The pyridine ring has a significant effect on both high efficiency and high regioselectivity in the cleavage of the aryl C-N bond in anilines.

Organic Letters 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 C14H23N, Quality Control of 214360-44-8.

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

Zhang, Chen-Sheng published the artcileEfficient production of (R)-o-chloromandelic acid by deracemization of o-chloromandelonitrile with a new nitrilase mined from Labrenzia aggregata, Category: nitriles-buliding-blocks, the publication is Applied Microbiology and Biotechnology (2012), 95(1), 91-99, database is CAplus and MEDLINE.

(R)-o-Chloromandelic acid (I) is the key precursor for the synthesis of Clopidogrel, a best-selling cardiovascular drug. Although nitrilases are often used as an efficient tool in the production of α-hydroxy acids, there is no practical nitrilase specifically developed for I. Here, a new nitrilase from L. aggregata (II) was discovered for the 1st time by genomic data mining, which hydrolyzed o-chloromandelonitrile (III) with high enantioselectivity, yielding (R)-o-chloromandelic acid in 96.5% ee. II was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties were studied. When III was used as the substrate, the V_max and K_m values of II were 2.53 μmol min^-1 mg^-1 protein and 0.39 mM, resp., indicating its high catalytic efficiency. In addition, a study of the substrate spectrum showed that II preferred to hydrolyze arylacetonitriles. To relieve substrate inhibition and to improve the productivity of II, a biphasic system of toluene-water (1:9, volume/volume) was adopted, in which III at 300 mM (apparent concentration, based on total volume) could be transformed by II in 8 h, giving an isolated yield of 94.5%. Thus, the development of II makes it possible to produce I by deracemizing III with a good ee value and high substrate concentration

Applied Microbiology and Biotechnology 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 C2H4ClNO, Category: nitriles-buliding-blocks.

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

He, Yu-Cai published the artcileBiocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401, Synthetic Route of 13312-84-0, the publication is Journal of Industrial Microbiology & Biotechnology (2010), 37(7), 741-750, database is CAplus and MEDLINE.

The nitrilase from Alcaligenes faecalis ECU0401 belongs to the category of arylacetonitrilase, which could hydrolyze 2-chloromandelonitrile, 3,4-dimethoxyphenylacetonitrile, mandelonitrile, and phenylacetonitrile into the corresponding arylacetic acids. To overcome the permeability barrier and prepare whole cell biocatalysts with high activities, permeabilization of Alcaligenes faecalis ECU0401 in relation to nitrilase activity was optimized by using cetyltrimethylammonium bromide (CTAB) as permeabilizing agent. The nitrilase activity from Alcaligenes faecalis ECU0401 increased 4.5-fold when the cells were permeabilized with 0.3% (w/v) CTAB for 20 min at 25°C and pH 6.5. Consequently, almost all the mandelonitrile was consumed and converted to (R)-(-)-mandelic acid with greater than 99.9% enantiomeric excess (e.e.) by the CTAB-permeabilized cells. The permeability barrier has been significantly reduced in the hydrolysis of mandelonitrile by using CTAB-permeabilized cells and a dynamic resolution was successfully achieved, giving a 100% theor. yield of (R)-(-)-mandelic acid. Efficient biocatalyst recycling was achieved as a result of cell immobilization in calcium alginate, with a product-to-biocatalyst ratio of 3.82 g (R)-(-)-mandelic acid g^-1 dry cell weight (dcw) cell after 20 cycles of repeated use.

Journal of Industrial Microbiology & Biotechnology 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, Synthetic Route of 13312-84-0.

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

Yang, Chu-Ting published the artcileCopper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides, Category: nitriles-buliding-blocks, the publication is Angewandte Chemie, International Edition (2011), 50(17), 3904-3907, S3904/1-S3904/108, database is CAplus and MEDLINE.

A copper-catalyzed cross-coupling of non-activated alkyl electrophiles with organoboron compounds has been developed. The use of LiOtBu as a base was found to be crucial to the reaction. The reaction is applicable to alkyl iodides, bromides, tosylates, mesylates, and even chlorides, and tolerates many more functional groups than the previously described copper-catalyzed coupling of Grignard reagents. It provides practically useful reactivities and may thus compliment palladium and nickel-catalyzed Suzuki-Miyaura coupling reactions of alkyl halides.

Angewandte Chemie, International Edition 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 C4H7F3O2, Category: nitriles-buliding-blocks.

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

Li, Shuan published the artcileSynthesis of hydralazine hydrochloride with by products in manufacture of o-cyanobenzyl chloride, Related Products of nitriles-buliding-blocks, the publication is Jingxi Shiyou Huagong (2008), 25(2), 32-35, database is CAplus.

A method for the synthesis of the title compound [i.e., hydralazine hydrochloride, 1-hydrazinylphthalazine hydrochloride (1:1)] is reported here. Hydralazine hydrochloride was synthesized from the byproducts, containing o-cyanotoluene, o-cyanobenzyl chloride and o-cyanobenzal chloride with the mass percentage of 10%, 30% and 50%, resp., generated from the manufacture of o-cyanobenzyl chloride. Effects of reaction temperature and time and ratio of reactants on the yield of o-cyanobenzaldehyde and hydralazine hydrochloride were investigated. The procedures and optimized conditions were found as follows: the byproduct reacted with chlorine at 150-155° in the presence of initiator, to give o-cyanobenzal chloride with purity of above 85%. Secondly, o-cyanobenzal chloride and sodium methoxide, in molar ratio of 1:2.05, were refluxed for 20 h to produce a corresponding acetal. Thirdly, that acetal was hydrolyzed with HCl, in n(acetal):n(HCl) = 1:3.9, at 0° for 3 h to obtain o-cyanobenzaldehyde (90.5% yield). Finally, hydralazine hydrochloride was synthesized (75% yield) by refluxing o-cyanobenzaldehyde and hydrazine for 8 h at a molar ratio of 1:3.5 in the presence of HCl and methanol.

Jingxi Shiyou Huagong 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, Related Products of nitriles-buliding-blocks.

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

Chen, Zhen published the artcileTransition-Metal-Free [3 + 2] Cycloaddition of Nitroolefins and Diazoacetonitrile: A Facile Access to Multisubstituted Cyanopyrazoles, Synthetic Route of 5153-73-1, the publication is Organic Letters (2018), 20(7), 2120-2124, database is CAplus and MEDLINE.

Nitroalkenes such as β-nitrostyrenes (E)-RCH:CHNO₂ [R = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-Me₂NC₆H₄, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-F₃CC₆H₄, 4-NCC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 2-BrC₆H₄, 1-naphthyl, 2-naphthyl, 9-anthracenyl, 2-furyl, 2-thienyl, (E)-R¹CH:CH, PhCC, PhCH₂CH₂, Bu, i-Bu, cyclohexyl; R¹ = Ph, 4-MeOC₆H₄, 2-O₂NC₆H₄] underwent metal-free regioselective [3+2]-cycloaddition reactions with diazoacetonitrile N₂:CHCN either used sep. or generated in situ from aminoacetonitrile hydrochloride with Cs₂CO₃ in THF to give 3-pyrazolecarbonitriles such as I [R = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-Me₂NC₆H₄, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-F₃CC₆H₄, 4-NCC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 2-BrC₆H₄, 1-naphthyl, 2-naphthyl, 9-anthracenyl, 2-furyl, 2-thienyl, (E)-R¹CH:CH, PhCC, PhCH₂CH₂, Bu, i-Bu, cyclohexyl; R¹ = Ph, 4-MeOC₆H₄, 2-O₂NC₆H₄] in 55-93% yields. The cycloaddition reaction was also performed in tandem with regioselective N-alkylation reactions with MeI or PhCH₂Br to yield 1-methyl- or 1-benzyl-3-pyrazolecarbonitriles in 31-73% yields with 10-48% of the 2-alkyl-3-pyrazolecarbonitrile regioisomers (<25% yields in ten of twelve cases). Diazoacetonitrile is potentially explosive and should be handled with caution.

Organic 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, Synthetic Route of 5153-73-1.

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

Jiang, Huanfeng published the artcileA Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO₂, and Chloroalkanes, Synthetic Route of 612-13-5, the publication is Organic Letters (2019), 21(2), 345-349, database is CAplus and MEDLINE.

Chloroalkyl and benzylic o-chlorobenzoates such as I were prepared by three-phase, four-component coupling reactions of o-trimethylsilylaryl triflates, KCl, CO₂, and dichloroalkanes such as 1,2-dichloroethane or benzylic chlorides, incorporating both chloride and CO₂ simultaneously. I underwent nucleophilic substitution reactions at the alkyl chloride moiety and a Suzuki coupling reaction at its aryl chloride moiety.

Organic Letters 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, Synthetic Route of 612-13-5.

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

Lv, Zhiliang published the artcileDesign and synthesis of novel 2′-hydroxy group substituted 2-pyridone derivatives as anticancer agents, Computed Properties of 612-13-5, the publication is European Journal of Medicinal Chemistry (2013), 447-453, database is CAplus and MEDLINE.

The authors have synthesized a series of novel pyridones I [R = Ph, 2-BrC₆H₄, 4-ClC₆H₄, etc.] and evaluated their antitumor activities in vitro. The bioassays showed that the majority of the resultant compounds exerted inhibitory effects on six human cancer cell lines to various extents. Compound I [R = 4-ClC₆H₄] showed the best antitumor activities (IC₅₀ values of A549, HeLa and SW480 cancer cell lines were 0.86±0.17 μM, 0.54±0.23 μM and 0.21±0.13 μM, resp.).

European Journal of Medicinal Chemistry 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, Computed Properties of 612-13-5.

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

Li, Hua published the artcileModular Bifunctional Chiral Thioureas as Versatile Organocatalysts for Highly Enantioselective Aza-Henry Reaction and Michael Addition, HPLC of Formula: 5153-73-1, the publication is Advanced Synthesis & Catalysis (2012), 354(11-12), 2264-2274, S2264/1-S2264/57, database is CAplus.

A series of new modular bifunctional chiral thiourea organocatalysts were synthesized from natural Cinchona alkaloids and amino acids, and their performance in the aza-Henry reaction of nitroalkanes to imines, the Michael addition of acetylacetone to nitroolefins and the Michael addition of acetone to nitroolefins was investigated. Under the mild conditions, the important building blocks β-nitro amines and γ-nitro carbonyl compounds could be obtained in good yields (up to 95%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivity (up to 17:1).

Advanced Synthesis & Catalysis 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, HPLC of Formula: 5153-73-1.

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

Zhang, Xiao published the artcileSilver(I)-catalyzed carboxylation of arylboronic esters with CO₂, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2012), 48(50), 6292-6294, database is CAplus and MEDLINE.

A variety of arylboronic esters were efficiently carboxylated with CO₂ using a simple AgOAc/PPh₃ catalyst, affording the corresponding carboxylic acids in good yield. This simple and efficient silver(i) catalytic system showed wide 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 C10H12O5, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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