Category: 4435-14-7

Pyrolysis of esters. XVIII. Synthesis of nitriles by pyrolysis of cyanoacetic esters was written by Bailey, William J.;Daly, John J. Jr.. And the article was included in Journal of the American Chemical Society in 1959.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

The pyrolysis of cyanoacetic esters was investigated as a convenient method of synthesis for the corresponding nitriles. NCCH₂CO₂Et (169.5 g.), 118.8 g. EtAc, 11.7 g. NH₄OAc, 18 g. AcOH, 300 cc. 95% EtOH, and 3 g. Pd-C hydrogenated 36 hrs. at room temperature yielded 223.5 g. EtMeCHCH(CN)CO₂Et (I), b₉ 103-4.5鎺? n²⁵_D 1.4268. I (153 g.) added dropwise during 3.75 hrs. to a Vycor tube packed with glass helices at 520鎺?and the resulting pyrolyzate distilled yielded 63.7 g. EtMeCHCH₂CN, b₉₂ 88鎺?n²⁶_D 1.4051. Et cyclohexylidenecyanoacetate (93 g.), b₉ 148-9鎺? n²⁵_D 1.4938, obtained in 83% yield by the condensation of cyclohexanone and NCCH₂CO₂Et, hydrogenated catalytically gave 86 g. Et cyclohexylcyanoacetate (II), b₁₂ 146-8鎺? n²⁵_D 1.4580. II (80 g.) pyrolyzed during 2 hrs. at 520鎺?gave 38.8 g. cyclohexylacetonitrile, b₁₂ 86鎺? n²⁵_D 1.4548. Na (46 g.) in 500 cc. absolute EtOH treated with 226 g. NCCH₂CO₂Et, stirred 15 min., treated rapidly with 254 g. (CH₂CH₂Cl)₂, refluxed 48 hrs., treated with 46 g. Na in 500 cc. absolute EtOH, refluxed 72 hrs., and evaporated, the residue dissolved in H₂O, the solution extracted with Et₂O, and the extract distilled gave 200 g. 1-cyano-1-carbethoxycyclopentane (III), b₁₈ 118鎺? n²⁵_D 1.4452. III (101 g.), pyrolyzed during 2.8 hrs. at 510鎺?in the usual manner and the pyrolyzate fractionated gave 47.3 g. cyclopentanecarbonitrile, b₂₀ 67-8鎺? n²⁵_D 1.4403, and 11 g. unchanged III. Et₂C(CN)CO₂Et (57 g.), b₁₀ 92鎺? n²⁷_D 1.4200, pyrolyzed in the usual manner during 1.7 hrs. at 510鎺?and fractionated gave 20.5 g. Et₂CHCN, b₃₈ 60-2鎺? n²⁶_D 1.3995, and 9.5 g. unchanged starting material. Na (18 g.) in 400 cc. absolute EtOH and 202 g. Br(CH₂)₃Br added simultaneously with stirring to 27.6 g. Na in 600 cc. absolute EtOH and 135.6 g. NCCH₂CO₂Et during 1 hr., heated 1.5 hrs., the EtOH distilled, the residue extracted with H₂O, the extract re姣泋td. with C₆H₆, and the combined extract and original organic layer distilled yielded 110 g. 1-cyano-1-carbethoxycyclobutane (IV), b₁₀ 94.5-7.5鎺? n²⁴_D 1.4395. IV (39.5 g.) pyrolyzed during 1 hr. at 520鎺?and the product fractionated gave 7.5 g. crude CH₂:CHCN, b. 76-7鎺?(BrCH₂CHBrCN m. 131-2鎺?. EtMeC:C(CN)CO₂Et (167 g.), b₉ 111-12鎺? n²⁵_D 1.4648, pyrolyzed during 3.75 hrs. at 510鎺?and the pyrolyzate fractionated gave 62.3 g. mixture of 80-5% EtMeC:CHCN and 15-20% MeCH:CMeCH₂CN, b_80-4 90-1鎺? n²⁵_D 1.4386, and 42 g. starting ester. Et cyclohexylidenecyanoacetate (158 g.) pyrolyzed during 3.2 hrs. at 510鎺?and the product fractionated gave 65.7 g. mixture of 85-90% 1-cyclohexenylacetonitrile and 5-10% cyclohexylideneacetonitrile, b₁₀ 89.5-90鎺? n²⁵_D 1.4832. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Recommanded Product: 2-Cyclohexylacetonitrile

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Light-mediated cyanomethylation of cycloalkenes with acetonitrile was written by Sonawane, Harikisan R.;Bellur, Nanjundiah S.;Shah, Virendra G.. And the article was included in Journal of the Chemical Society, Chemical Communications in 1990.SDS of cas: 4435-14-7 This article mentions the following:

The addition of cyanomethyl radicals, generated from MeCN via photoinduced decomposition of H₂O₂, to cycloalkenes gave cycloalkylmethyl nitriles and cycloalkanols. The homolytic cyanomethylation of 3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane gave endo-2-(2-cyanoethyl)- and endo-2-(hydroxymethyl)-3,3-dimethylbicyclo[2.2.1]heptane in 76% overall yield in a 49:51 product ratio. The homolytic cyanomethylation of norbornene gave exo-2-(cyanomethyl)bicyclo[2.2.1]heptane and exo-norborneol in 72% overall yield in a 80:20 product ratio. The reaction mechanism was discussed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7SDS of cas: 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閳ユ弲 bond formation or by dehydration of primary carboxamides. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 4435-14-7

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Direct cyanomethylation of aliphatic and aromatic hydrocarbons with acetonitrile over a metal loaded titanium oxide photocatalyst was written by Wada, Emiko;Takeuchi, Tomoaki;Fujimura, Yuki;Tyagi, Akanksha;Kato, Tatsuhisa;Yoshida, Hisao. And the article was included in Catalysis Science & Technology in 2017.Recommanded Product: 4435-14-7 This article mentions the following:

A platinum-loaded TiO₂ (Pt/TiO₂) photocatalyst promoted cyanomethylation of aliphatic hydrocarbons, namely cyclohexane and cyclohexene, with acetonitrile, where the photogenerated hole oxidatively dissociates the C-H bond of both the acetonitrile and the aliphatic hydrocarbons to form each corresponding radical species before their radical cross-coupling. The Pt/TiO₂ photocatalyst was more active than the Pd/TiO₂ photocatalyst in these reactions. In contrast, the cyanomethylation of benzene was promoted by the Pd/TiO₂ photocatalyst or a phys. mixture of the Pt/TiO₂ photocatalyst and a Pd catalyst supported by Al₂O₃, while it was hardly promoted by the Pt/TiO₂ photocatalyst alone. The temperature dependence of the reaction rate proved that the Pd nanoparticles on the TiO₂ thermally function as a metal catalyst. However, in the cyanomethylation of aliphatic hydrocarbons, the catalytic effect of the metal particles was not observed, meaning that the radical coupling takes place without the metal catalysis. Thus, it is concluded that in the case of the benzene cyanomethylation the Pd nanoparticles play dual roles, as a catalyst to catalyze the substitution reaction of benzene with the cyanomethyl radical, and as an electron receiver to reduce the recombination of the photoexcited electrons and holes in the TiO₂ photocatalyst, although they could not contribute as a catalyst to the cyanomethylation of aliphatic hydrocarbons. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180鎺?which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two 锜? bond in the triple bond. 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: 4435-14-7

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Direct cyanomethylation of aliphatic and aromatic hydrocarbons with acetonitrile over a metal loaded titanium oxide photocatalyst was written by Wada, Emiko;Takeuchi, Tomoaki;Fujimura, Yuki;Tyagi, Akanksha;Kato, Tatsuhisa;Yoshida, Hisao. And the article was included in Catalysis Science & Technology in 2017.Recommanded Product: 4435-14-7 This article mentions the following:

A platinum-loaded TiO₂ (Pt/TiO₂) photocatalyst promoted cyanomethylation of aliphatic hydrocarbons, namely cyclohexane and cyclohexene, with acetonitrile, where the photogenerated hole oxidatively dissociates the C-H bond of both the acetonitrile and the aliphatic hydrocarbons to form each corresponding radical species before their radical cross-coupling. The Pt/TiO₂ photocatalyst was more active than the Pd/TiO₂ photocatalyst in these reactions. In contrast, the cyanomethylation of benzene was promoted by the Pd/TiO₂ photocatalyst or a phys. mixture of the Pt/TiO₂ photocatalyst and a Pd catalyst supported by Al₂O₃, while it was hardly promoted by the Pt/TiO₂ photocatalyst alone. The temperature dependence of the reaction rate proved that the Pd nanoparticles on the TiO₂ thermally function as a metal catalyst. However, in the cyanomethylation of aliphatic hydrocarbons, the catalytic effect of the metal particles was not observed, meaning that the radical coupling takes place without the metal catalysis. Thus, it is concluded that in the case of the benzene cyanomethylation the Pd nanoparticles play dual roles, as a catalyst to catalyze the substitution reaction of benzene with the cyanomethyl radical, and as an electron receiver to reduce the recombination of the photoexcited electrons and holes in the TiO₂ photocatalyst, although they could not contribute as a catalyst to the cyanomethylation of aliphatic hydrocarbons. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. 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: 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines was written by Desikan, Vasumathi;Liu, Yonglin;Toscano, John P.;Jenks, William S.. And the article was included in Journal of Organic Chemistry in 2008.Reference of 4435-14-7 This article mentions the following:

Time-resolved IR (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene precursor, i.e., that the ground-state multiplicity is singlet. In contrast, product studies clearly indicate triplet reactivity for trifluoroacetylnitrene, though TRIR experiments were more ambiguous. Product studies suggest that these sulfilimines are superior sources for sulfonylnitrenes, which have triplet grounds states, to the corresponding azides, and computational studies shed light on the electronic structure of the nitrenes. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Reference of 4435-14-7

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Iridium-Catalyzed Enantioselective C(sp³)-H Borylation of Aminocyclopropanes was written by Shi, Yongjia;Yang, Yuhuan;Xu, Senmiao. And the article was included in Angewandte Chemie, International Edition in 2022.Formula: C8H13N This article mentions the following:

Transition-metal-catalyzed regio- and stereo-controllable C-H functionalization remains a formidable challenge in asym. catalysis. Herein, we disclose the first example of iridium-catalyzed C(sp³)-H borylation of aminocyclopropanes by using simple imides as weakly coordinating directing groups under mild reaction conditions. The reaction proceeded via a six-membered iridacycle, affording a vast range of chiral aminocyclopropyl boronates. The current method features a broad spectrum of functional groups (36 examples) and high enantioselectivities (up to 99%). We also demonstrated the synthetic utility by a preparative scale C-H borylation, C-B bond transformations, and conversion of the directing group. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Formula: C8H13N

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Action of stilbene on tetrachloro-ο-benzoquinone was written by Schonberg, Alexander;Latif, Nazih. And the article was included in Journal of the American Chemical Society in 1950.COA of Formula: C8H13N This article mentions the following:

Tetrachloro-ο-quinone (I) (1 g.) and (PhCH:)₂ (II) in 30 cc. C₆H₆, exposed 13 days to sunlight, give 2,3-diphenyl-5,6,7,8-tetrachloro-1,4-benzodioxan (III), m. about 172°; III results in 70% yield on boiling 1.2 g. I and 0.9 g. II in C₆H₆ 15 hrs. in the dark. I (0.6 g.) and 0.5 g. (p-MeC₆H₄CH:)₂, exposed 10 days to sunlight, give 2-phenyl-3-(p-tolyl)-5,6,7,8-tetrachloro-1,4-benzodioxan, m. 132°. III, heated 15 min. in a C₆H₄(CO₂Et)₂ bath (oil-pump vacuum), gives II. III does not react with ο-C₆H₄(NH₂)₂ (refluxed 2 hrs. in 90% AcOH). In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7COA of Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.COA of Formula: C8H13N

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Selective reduction of α,β-unsaturated nitriles with combined reducing agent bismuth chloride/sodium borohydride was written by Ren, Ping-Da;Shao, Dong;Dong, Ting-Wei. And the article was included in Youji Huaxue in 1997.Quality Control of 2-Cyclohexylacetonitrile This article mentions the following:

Bismuth chloride/sodium borohydride reacts chemoselectively with α,β-unsaturated nitriles in 95% ethanol to give the corresponding saturated nitriles with good yields. E.g., reduction of PhCH:CHCN with NaHBH₄/BiCl₃ in 95% EtOH at room temperature for 3 h gave 90% PhCH₂CH₂CN. The reduction mechanism was discussed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Quality Control of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Quality Control of 2-Cyclohexylacetonitrile

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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

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Nitrile – Wikipedia,
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Tellurium tetrachloride-olefin addition compounds was written by Arpe, Hans J.;Kuckertz, Herbert. And the article was included in Angewandte Chemie, International Edition in English in 1971.Formula: C8H13N This article mentions the following:

Propylene and butadiene react with TeCl4 to give Cl2Te(C3H6Cl)2 and Cl2Te(CH2CH:CHCH2Cl)2. The reaction of TeCl4 with ethylene is slower, the (2-chloroethyl)tellurium chlorides, Cl2Te(CH2CH2Cl)2 and Cl3TeCH2CH2Cl, are obtained. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. 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.Formula: C8H13N

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts