Tag: M.W=150-200

Manna, Srimanta published the artcileSynthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO, SDS of cas: 5153-73-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(46), 5286-5288, database is CAplus and MEDLINE.

Nitroolefins are usually synthesized using the Henry reaction. Here, the authors report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using tert-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

Chemical Communications (Cambridge, United Kingdom) 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, SDS of cas: 5153-73-1.

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

Zhang, Kun published the artcileSynthetic Diversity from a Versatile and Radical Nitrating Reagent, Quality Control of 5153-73-1, the publication is Chemistry – A European Journal (2019), 25(56), 12929-12939, database is CAplus and MEDLINE.

A new methodol. was described for the activation of N-nitrosuccimide for the direct synthesis of β-nitroalkenes, β-nitrohydrins, β-nitroethers, isoxazolines I [R = Me, cyclopropyl; R¹ = n-heptyl, Bn, CH₂OPh; R² = H, R¹R² = (CH₂)₄, (CH₂)₉, (CH₂)₁₀C(O)(CH₂)₃; R³ = H, Me] and isoxazoles II [R⁴ = CO₂Et, CH₂CH₂Br, cyclohexyl, etc.]. Detailed mechanistic studies strongly suggested that a mesolytic N-N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, ESR spectroscopy, direct evidence of a nitryl radical in solution by nitrone spin-trapping was observed To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C-H partners to prepare isoxazolines I and isoxazoles II was presented. This approach allowed for the formation of an in situ nitrile oxide from a ketone partner, the presence of which was detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeded in a single-operational step using a mild, regioselective and general protocol with broad chemoselectivity.

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 C12H10N2O5, Quality Control of 5153-73-1.

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

Kuang, Dai-Zhi published the artcileSynthesis and crystal structure of tetra(o-cyanobenzyl)tin, Product Details of C8H6ClN, the publication is Chinese Journal of Structural Chemistry (2008), 27(1), 35-38, database is CAplus.

The tetra(o-cyanobenzyl)tin compound was synthesized by the reaction of cyanobenzyl chloride with tin, and its mol. structure was characterized by elemental anal., IR spectra, ¹H NMR and X-ray diffraction. Crystal data for this compound: monoclinic, space group C2/c, M_r = 583.24, a = 1.9629(2), b = 1.05967(13), c = 1.41249(18) nm, β = 118.180(2)°, V = 2.5898(5) nm³, Z = 4, D_c = 1.496 g/cm³, μ(MoKα) = 1.015 cm^-1, F(000) = 1176, R = 0.0189, wR = 0.0497 (observed reflections with I > 2σ(I)) and R = 0.0218, wR = 0.0513 (all reflections). The mol. structure adopts a distorted tetrahedral geometry around the tin atom. The Sn…N weak interaction between the Sn and N atoms of cyano forms an intermol. H-bonding, and the bond length is 0.3570 nm; the interaction between hydrogen of methylene and benzene ring of benzyl forms C-H…C with its bond length of 0.2817 nm; and the interaction among hydrogen of benzene ring and carbon of cyano forms Ph-H…C bond (0.2897 nm) of the σ…π interaction. A 3D chain structure is formed by the above weak intermol. interactions.

Chinese Journal of Structural 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, Product Details of C8H6ClN.

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

Xiao, Yuanyuan published the artcileEnantioselective Construction of Spiro Thiazol-4-one Derivatives with Multiple Stereocenters via an Organocatalyzed Multicomponent Cascade Reaction, Computed Properties of 5153-73-1, the publication is Advanced Synthesis & Catalysis (2018), 360(10), 1961-1966, database is CAplus.

An organocatalyzed asym. three-component reaction of thiazol-4-ones, acrolein and nitroolefins, which provides an efficient approach to access optically active spiro thiazol-4-ones I (R = C₆H₅, 4-FC₆H₄, 4-F₃CC₆H₄, etc.; R¹ = C₆H₅, 1-naphthyl, 2-thienyl, etc.) is developed. Under the catalysis of a bifunctional squaramide derived from L-tert-leucine, the reactions of a wide range of thiazol-4-ones, acrolein and nitroolefins took place smoothly to generate the corresponding spirothiazolone derivatives bearing four contiguous stereogenic centers in good yields with high levels of enantioselectivity. The title chiral spirothiazolones were obtained as a pair of separable epimers, which are formed through a double Michael addition followed by a Henry process.

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 C4H3Cl2N3, Computed Properties of 5153-73-1.

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

Liu, Chunsheng published the artcileGreen synthesis process of fluorescent brightener ER, Category: nitriles-buliding-blocks, the publication is Ranliao Yu Ranse (2010), 47(5), 41-43, database is CAplus.

2-Cyanobenzyl chloride directly reacted with a slight excess of tri-Et phosphite by esterification reaction without adding other organic solvents, so the solvent recovery process was avoided. Using recrystallization mother liquor as the condensation reaction solvent, the process of solvent recovery was avoided also. The solvent loss and energy consumption were reduced by this process, and the yield of fluorescent brightener ER was increased by 10%. The green synthesis of fluorescent brightener ER was realized authentically.

Ranliao Yu Ranse 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, Category: nitriles-buliding-blocks.

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

Gibson, Charles S. published the artcileSyntheses with β,β’-dichlorodiethyl ether. I. Derivatives of tetrahydropyran, Computed Properties of 30431-99-3, the publication is Journal of the Chemical Society (1930), 2525-30, database is CAplus.

(ClCH₂CH₂)₂O (I), m. -24.5°, b₁₂ 66°, b₁₅ 70°, b₇₄₄ 176°, with a large excess of NaI in Me₂CO, gives the β,β’-diiododiethyl ether (II), b₁₀ 123.5-4°. I, CH₂(CO₂Et)₂ and Na in EtOH, boiled 5 hrs., give Et tetrahydropyran-4,4-dicarboxylate, b₁₂ 134-5°; hydrolysis with EtOH-KOH gives 81% of the acid, which loses CO₂ at 175-85°, giving 94.5% of tetrahydropyran-4-carboxylic acid (III), b₁₅ 146-7°; acid chloride, b₁₆ 85-6°; Me ester, b₁₆ 80.5-1°; Et ester, b₁₂ 82.5°; amide, m. 179°; anilide, m. 163°. I and NCCHNaCO₂Et in EtOH, heated 3 hrs. and kept 12 hrs., give 33% of Et 4-cyanotetrahydropyran-4-carboxylate, b₁₆ 125°; free acid, m. 160-2°; amide, in. 158°; heating at 180-200° for 1 hr. gives 66% of 4-cyanotetrahydropyran, b₁₀ 82-3°; this could not be reduced to the amine by Na in AmOH. I and AcCHNaCO₂Et gave only a small amount of high-boiling material. II gives a product b₉ 122.5-3.5°, which, on hydrolysis, gives III, AcOH and a trace of a ketone. No results were obtained in the Friedel-Crafts reaction with I and C₆H₆ or between I and KCN. I, As₂O₃ and NaOH gave no condensation product.

Journal of the 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

Ozawa, Jun published the artcileSilver-Catalyzed C(sp³)-H Chlorination, Name: 2-(Chloromethyl)benzonitrile, the publication is Organic Letters (2017), 19(6), 1430-1433, database is CAplus and MEDLINE.

A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp³)-H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atm. with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver species cannot be ruled out.

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, Name: 2-(Chloromethyl)benzonitrile.

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

Fang, Zengjun published the artcileSynthesis and Biological Evaluation of a Series of 2-((1-substituted-1H-1,2,3-triazol-4-yl)methylthio)-6-(naphthalen-1-ylmethyl)pyrimidin-4(3H)-one As Potential HIV-1 Inhibitors, Computed Properties of 612-13-5, the publication is Chemical Biology & Drug Design (2015), 86(4), 614-618, database is CAplus and MEDLINE.

A series of (arylmethyl)(arylmethyltriazolylmethylthio)dihydropyrimidinones I (R = 1-naphthalenyl, 2,6-dichlorophenyl; R¹ = H, I, Me; R² = Ph, 4-FC₆H₄, 4-MeOC₆H₄, 4-H₂NCOC₆H₄, 2-NCC₆H₄, 2-MeC₆H₄, 4-H₂NSO₂C₆H₄) were synthesized using copper-catalyzed azide-alkyne cycloadditions and evaluated as inhibitors of HIV-1. Among them, the most active HIV-1 inhibitor was compound I (R = 2,6-dichlorophenyl; R¹ = Me; R² = 4-H₂NSO₂C₆H₄), which exhibited similar HIV-1 inhibitory potency (EC₅₀ = 3.22 U+03BCM) compared with 3TC (EC₅₀ = 2.24 U+03BCM). None of these compounds demonstrated inhibition against HIV-2 replication. The preliminary structure-activity relationship (SAR) of these new derivatives was discussed briefly.

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 C8H6ClN, Computed Properties of 612-13-5.

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

Li, Hui published the artcileSynthesis and evaluation of the anticonvulsant activity of 9-alkyl-2,9-dihydro-3H-1,2,4-triazolo[4,3-a]benzimidazole-3-one derivatives, Category: nitriles-buliding-blocks, the publication is Latin American Journal of Pharmacy (2015), 34(1), 5-12, database is CAplus.

A series of novel benzimidazole derivatives I [R = Pr, Bu, benzyl, etc.] were synthesized via reaction of 2-chloro-N-substituted-benzimidazole II with Me hydrazinocarboxylate. The synthesized compounds were screened for their in vivo anticonvulsant activity and neurotoxicity(NT) by maximal electroshock test(MES) and rotarod test. Among the synthesized compounds, I [R = 2,6-Cl₂C₆H₃CH₂] was the most active compound with a median ED (ED₅₀) of 31.69 mg/kg, a median toxicity dose (TD₅₀) > 350 mg/kg, and the protective index (PI) > 11.04 by i.p. administration in the mice. Meanwhile, compound I [R = 2,6-Cl₂C₆H₃CH₂] exhibited ED₅₀ values of 44.01 mg/kg and the PI values of 31.6 by oral administration.

Latin American Journal of Pharmacy 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, Category: nitriles-buliding-blocks.

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

Mlynarski, Scott N. published the artcileDirect Stereospecific Amination of Alkyl and Aryl Pinacol Boronates, HPLC of Formula: 238088-16-9, the publication is Journal of the American Chemical Society (2012), 134(40), 16449-16451, database is CAplus and MEDLINE.

The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.

Journal of the American Chemical Society published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C10H18BNO2, HPLC of Formula: 238088-16-9.

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