Month: December 2022

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

Chen, Kai published the artcileEfficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions, HPLC of Formula: 214360-44-8, the publication is Chemical Science (2016), 7(6), 3676-3680, database is CAplus and MEDLINE.

A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.

Chemical Science 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, HPLC of Formula: 214360-44-8.

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

Cai, Shunyou published the artcileNew Approach to Oximes through Reduction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis, Formula: C9H6N2O2, the publication is Organic Letters (2013), 15(11), 2660-2663, database is CAplus and MEDLINE.

A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)₃Cl₂ photocatalyst, Huenig’s base, Mg(ClO₄)₂ activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.

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, Formula: C9H6N2O2.

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

Leowanawat, Pawaret published the artcileNi(COD)₂/PCy₃ catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature, Computed Properties of 214360-44-8, the publication is Journal of Organic Chemistry (2011), 76(24), 9946-9955, database is CAplus and MEDLINE.

Reaction conditions for the Ni(COD)₂/PCy₃ catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)₂/PCy₃ was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.

Journal of Organic Chemistry 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, Computed Properties of 214360-44-8.

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