Butyronitriles

The propensity of nitriles to release cyanide subsequent to metaboHsm is the basis of their acute toxicity. Nitriles that form tertiary radicals at their alpha carbon atoms (eg, isobutyronitrile, 2-methylbutyronitrile) are substantially more acutely lethal than nitriles that form secondary radicals at their alpha carbons (eg, butyronitrile, propionitnle). Cyanohydrins are acutely toxic because they are unstable and release cyanide quickly. Alpha-aminonitriles are also acutely toxic, presumably by analogy with cyanohydrins. 

Va2o-64, Self-Reactive Solid Type C, Temperature Controlled (2,2 -a2odi(iso-butyronitrile)). 

HCl until the smell of the isonitrile had gone, then dried with K2CO3 and fractionally distd [Turner J Chem Soc 1681 1956]. Alternatively it was twice heated at 75° and stirred for several hours with a mixture of 7.7g Na2C03 and 11.5g KMn04 per L of butyronitrile. The mixture was cooled, then distd. The middle fraction was dried over activated alumina. [Schoeller and Wiemann 7 Am Chem Soc 108 22 1986.]... 

C4H7N BUTYRONITRILE 32.613 2.4673E-01 2.5125E-05 108.66 193 C5H8 1.4-PENTADIENE 104.148 2.1318E-01 2.5915E-05 170.25... 

A number of ingredients may be used from time to time in PVC formulations. For example, blowing agents such as azodicarbonamide and azodi-iso-butyronitrile are frequently used in the manufacture of cellular PVC. 

Three skeleton atoms of a hetero-l,3-diene are incorporated into a five-membered ring system on reaction with 1,2 [n,n] compounds (e.g., hydrazines, reaction type 4, equation 10). On further heating in the presence of azobisiso-butyronitrile (AIBN), the bis(trifluoromethyl)-substituted 1,2,4-triazolines are transformed into 5-tnfluoromethyl-l,2,4-triazoles in high yield [t02 (equation 22). 

Dimethylindole magnesium iodide reacts with chloroacetonitrile in ether to give 3-cyanomethyl-2,3-dimethylindolenine (234). Majima and Hoshino obtained 3-(2-cyanoethyl)lndole (235) by the action of -chloropropionitrile on indole magnesium iodide. The reaction was slower with -chloropropionitrilc than with chloro-aoetonitrile. 3-(3-Cyano-w-propyl)indole (236), required as an intermediate in the synthesis of 3-indolyl-y-w-butyric acid, was prepared, but not isolated, by the action of y-chloro-w-butyronitrile on indole magnesium iodide. ... 

Catalysts show remarkable product variation in hydrogenation of simple nitriles. Propionitrile, in neutral, nonreactive media, gives on hydrogenation over rhodium-on-carbon high yields of dipropylamine, whereas high yields of tripropylamine arise from palladium or platinum-catalyzed reductions (71). Parallel results were later found for butyronitrile (2S) and valeronitrile (74) but not for long-chain nitriles. Good yields of primary aliphatic amines can be obtained by use of cobalt, nickel, nickel boride, rhodium, or ruthenium in the presence of ammonia (4J 1,67,68,69). 

A mixture of 23 parts of the ethyl ester of 4 phenylisonipecotic acid and 15 parts of 2,2-diphenyl-4-bromobutyronitrile in 19 parts of xylene is heated for 24 hours at 100°-120°C and then cooled and filtered to remove the precipitate of the hydrobromide of the ethyl ester of 4-phenylisonipecotic acid. The filtrate is then extracted with dilute hydrochloric acid and the extract is rendered alkaline by addition of concentrated aqueous potassium hydroxide and extracted with ether. This ether extract is treated with gaseous hydrogen chloride. The resulting precipitate is collected on a filter. The hydrochloride of the ethyl ester of 2,2 diphenyl-4-(4 -carboxy-4 -phenyl-1 -piperidino) butyronitrile thus obtained melts at about 220.5-222°C. See Meperidine hydrochloride for synthesis of 4-phenyl-isonipecotic acid ethyl ester. 

A solution of 27.2 parts of 4-diisopropvlamino-2-phenvl-2-(2-pvridvl)butyronitrile in 200 parts of concentrated sulfuric acid is heated on a steam bath for 4 hours and then poured onto ice. The resultant mixture is alkalized with ION sodium hydroxide, and the pH is adjusted to 6 by the addition of acetic acid. The solution is washed once with benzene before it is alkalized again with ION sodium hydroxide solution. The resultant mixture is extracted with benzene, and the solvent is evaporated from the benzene extract. The resultant residue is dissolved in ethanol and the alcohol solution is treated with charcoal and filtered. Evaporation of the solvent leaves a residue which is recrystallized from hexane to give 4-diisopropvlamino-2-phenvl-2-(2-Pvridvl)butyramide melting at about 94.5°-95°C. 

Butanemtrile, 2-ethenyl 3 methyl 2 phenyl-[Butyronitrile, 3-methyl-2-phenyl-2-vinyl-], 55, 102... 

M TRAP /acetonitrile 0.1 M TRAP /propionitrile 0.1 MTBAP /butyronitrile 0.1 MTBAP /nitromethane 0.1 MTBAP /nitrobenzene 0.1 MTBAP/PC... 

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