Category: nitriles-buliding-blocks

Microwave-accelerated Gewald reaction. Synthesis of 2-aminothiophenes was written by Sridhar, Madabhushi;Rao, Rayankula Mallikarjuna;Baba, Nanduri H. K.;Kumbhare, Ravindra M.. And the article was included in Tetrahedron Letters in 2007.Recommanded Product: 70291-62-2 This article mentions the following:

Microwave-promoted synthesis of 2-aminothiophenes by multicomponent reactions of a ketone with an active nitrile and elemental sulfur under KF-alumina catalysis is described. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 70291-62-2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Facile and efficient cyclization of anthranilonitrile to 2,4-dichloroquinazoline by bis(trichloromethyl) carbonate and catalytic amount triphenylphosphine oxide was written by Li, Zhenhua;Wu, Danli;Zhong, Weihui. And the article was included in Heterocycles in 2012.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

2,4-Dichloroquinazolines were synthesized by the cyclization of anthranilonitrile using bis(trichloromethyl)carbonate with the aid of catalytic amount of Ph₃PO at 120 °C. This method was also applied to the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidine. The plausible mechanism was presented. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Application In Synthesis of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Application In Synthesis of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Studies on aromatic nitro compounds. V. A simple one-pot preparation of o-aminoaroylnitriles from some aromatic nitro compounds was written by Tomioka, Yukihiko;Ohkubo, Kimiko;Yamazaki, Motoyoshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Synthetic Route of C8H5F3N2 This article mentions the following:

The reactions of aromatic nitro compounds I, II (R = H, R¹ = NO₂), and III (R, R¹ = same, R² = CF₃, MeCO, PhCO, R³ = H ; R² = R³ = CF₃) with Et cyanoacetate and KOH in DMF followed by hydrolysis of the reaction mixture with HCl or NaOH gave the corresponding o-aminoaroylnitriles I–III (R = CN, R¹ = NH₂). Acetylation-cyclization reactions of the products were carried out. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Synthetic Route of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Synthetic Route of C8H5F3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Facile synthesis of nitriles from primary nitro compounds via nitrolic acids and their esters was written by Chang, Rae Kyu;Kim, Kyongtae. And the article was included in Tetrahedron Letters in 1996.Application of 4435-14-7 This article mentions the following:

The reactions of alkane- and arylalkanenitrolic acids esters with Bu₃SnH in the presence of a catalytic amount of AIBN in refluxing benzene afforded the corresponding nitriles in excellent yields. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Application of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Inverse gas chromatography for identification of poly(ethylene glycol adipate) and tripropionitrilamine on the surface of polymeric sorbent was written by Kudasheva, F. Kh.;Guskov, V. Yu.;Ganieva, A. G.. And the article was included in Protection of Metals and Physical Chemistry of Surfaces in 2014.Recommanded Product: 7528-78-1 This article mentions the following:

Identification of the adsorption of poly(ethylene glycol adipate) (PEGA) and tris(2-cyanoethyl)amine (TPA) on styrene-divinylbenzene porous polymer was performed with the use of the inverse gas-chromatog. method in finite concentration PEGA and TPA were applied in quantities ω = 10-6-10-3 mass fractions. As test sorbates n-propanol, n-butanol, and n-hexane used. The adsorption isotherm and the values of specific retention volumes were calculated via the Glueckauf method. It was found that the dependence of the retention volumes on the sorbate concentration in gas phase of the studied samples is well approximated by a power function corresponding to the Freundlich isotherm. The possibility of detecting PEGA and TPA on the surface of sorbent through the A coefficients of a power function was shown, and a linear dependence between the A values and neg. logarithm of ω was also found, making it possible to quant. determine TPA and PEGA on the surface of a sorbent. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Recommanded Product: 7528-78-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Assembly of Furazan-Fused Quinolines via an Expeditious Metal-Free [2+2+1] Radical Tandem Cyclization Process was written by Deng, Guobo;Zhong, Ronglin;Song, Jianxin;Choy, Pui Ying;Kwong, Fuk Yee. And the article was included in Organic Letters in 2021.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

A [2+2+1]-NO-segment-incorporating heteroannulative cascade is described. This versatile method, particularly using modular cyanoarylated ketimine substrates 2-CN-3-R-4-R¹-5-R²C₆HN=C(Me)Ar (Ar = 3-methylphenyl, 4-bromophenyl, thiophen-2-yl, etc.; R = H, Br; R¹ = H, Br; R² = H, Me, F, Cl, Br, MeO, CF₃), allows efficient access to structurally diversified quinolines embedded with an oxadiazole core I. This metal-free protocol proceeds smoothly at 30°C, offers easy manipulation of substituents on the quinoline moiety, and tolerates a spectrum of functional groups. D. functional theory calculation revealed that the cyano moiety is crucial to facilitate the early cyclization step in this heteroannulation process and is different from the previously established late cyclization mechanistic interpretation. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature was written by Cao, Xian-Ting;Qiao, Li;Zheng, Hui;Yang, Hui-Yong;Zhang, Peng-Fei. And the article was included in RSC Advances in 2018.HPLC of Formula: 63968-85-4 This article mentions the following:

A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na₂S·9H₂O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed. In this reaction, readily available inorganic salt (Na₂S·9H₂O) served as the sulfur source and various functional groups of aryl nitriles were well tolerated at room temperature In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4HPLC of Formula: 63968-85-4).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.HPLC of Formula: 63968-85-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

P(RNCH₂CH₂)₃N: an efficient promoter for the synthesis of 3-substituted coumarins was written by Kisanga, Philip;Fei, Xiangshu;Verkade, John. And the article was included in Synthetic Communications in 2002.Synthetic Route of C14H14N2O2 This article mentions the following:

The title compounds wherein R = Me or i-Pr function as efficient promoters for the formation of coumarins in good to excellent yields (80-95%) from salicylaldehydes and di-activated methylene compounds of the type R’CH₂CO₂Et (R’ = CO₂Et, COMe, CN). Although the yields are not generally superior to those reported in the literature, the methodol. applied here is more convenient in that milder conditions and shorter reaction times are facilitated by the use of the aforementioned com. available catalysts. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Synthetic Route of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C14H14N2O2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly Enantioselective Iridium-Catalyzed Hydrogenation of o-Amidophenyl Ketones Enabled by 1,2-Diphenylethylenediamine-Derived P,N,N-Ligands with Tertiary Amine Terminus was written by Wan, Yin-Bo;Hu, Xiang-Ping. And the article was included in Organic Letters in 2022.SDS of cas: 53312-77-9 This article mentions the following:

A readily available and highly modular class of chiral P,N,N-ligands based on a structurally flexible nonchiral phosphine-amine framework with an optically active 1,2-diphenylethylenediamine unit bearing a tertiary amine terminus as the chiral source were developed and successfully applied in the Ir-catalyzed asym. hydrogenation of o-amidophenyl ketones. These tridentate P,N,N-ligands exhibited excellent activity, enantioselectivity, and substrate tolerance, thus furnishing various optically active o-amidobenzhydrols in up to 99% yields and with >99% ee. The utility of this protocol was proven by synthetically diverse product transformation and highly enantioselective production of a rice plant growth regulator, (S)-inabenfide. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9SDS of cas: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.SDS of cas: 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Alkylation of amines with alcohols over nanosized zeolite beta was written by Reddy, Marri Mahender;Kumar, Macharla Arun;Swamy, Peraka;Naresh, Mameda;Srujana, Kodumuri;Satyanarayana, Lanka;Venugopal, Akula;Narender, Nama. And the article was included in Green Chemistry in 2013.Formula: C14H12N2 This article mentions the following:

Direct N-alkylation of amines with alcs. was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcs. using nanosized zeolite beta. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts