Cyanides butyronitrile

Synonyms Butanenitrile Butyric acid nitrile Cyanopropane Propyl cyanide -Butyronitrile 1-Butyronitrile 1-Cyanopropane... 

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. 

Vesey et al. 1976) and a series of commercially important, simple, aliphatic nitriles (e.g., acetonitrile, propionitrile, acrylonitrile, n-butyronitrile, maleonitrile, succinonitrile) (Willhite and Smith 1981) release cyanide upon metabolism. These drugs and industrial chemicals have been associated with human exposure to cyanide and have caused serious poisoning and, in some cases, death. 

To a hot solution of potassium cyanide (80 gms.) dissolved in 125 gms. of water, hot 96 per cent, alcohol is added (500 c.c,), and to this clear, hot mixture, trimethylene chlorobromide (200 gms.) is added the whole is then boiled for 1 hours on the water-bath under a reflux condenser, The alcohol is next distilled off, and carries with it most of the unchanged trimethylene chlorobromide, Water is then added to the residue in the flask to dissolve potassium salts, and the oily layer is distilled after drying over calcium chloride. After two or three fractionations the portion boiling at 192°—205° is taken as y-chloro-butyronitrile. B.p. 195°—197°. Yield, 50 per cent. 

Nitriles are cyanogenic substances — substances that produce cyanide when metabolized. It is likely that nitriles are teratogens because of maternal production of cyanide in pregnant females. A study of the teratogenic effects on rats of saturated nitriles, including acetonitrile, propionitrile, and n-butyronitrile, and of unsaturated nitriles, including acrylonitrile, methacrylonitrile, allylnitrile, m-2-pcntenenitrile, and 2-chloroacrylonitrile, has shown a pattern of abnormal embryos similar to those observed from administration of inorganic cyanide.6... 

The solution of 16.0 g of bromine in 10 ml of petroleum ether is slowly added to the solution of 6.7 g of allyl cyanide in 30 ml of the same solvent, while stirring and keeping the temperature at about -15°C. After removal of the solvent the oily 3,4-dibromo-butyronitrile is obtained [J.A. C.S. 67, 400 (1945)]. 

To a solution of 6.7 g of sodium amide in 100 ml of anhydrous diethyl ether was added dropwise 26 g of 4-isobutylbenzene cyanide while the mixture was stirred and heated under gentle reflux. After all of the 4-isobutylbenzene cyanide had been added, the mixture was heated under gentle reflux for 15 min, after which 23.4 g of ethyl iodide was slowly added dropwise thereto from the dropping funnel. After completion of the addition of the ethyl iodide, the mixture was heated under gentle reflux for an initial period of 15 min, after which it was diluted with an equal volume of water and shaken. The two layers that formed were separated and the aqueous layer was then extracted with two 50 ml portions of diethyl ether. The ether extracts were combined and then washed with two 80 ml portions of water and dried over anhydrous magnesium sulfate. The dried ether extract was then distilled at a subatmospheric pressure. In this manner, 25 g of a clear transparent uncolored liquid having a boiling point of 118-122°C at a pressure of 1mm of mercury, which consisted of 2-(4-isobutylphenyl)butyronitrile, was collected. This yield was equivalent to 83% of the theoretical. 

SYNS BUTANENITRILE n-BUTANENITRILE BUTYRIC ACID NITRILE BUTYRONITRILE (DOT) 1-CYANOPROPANE PROPYL CYANIDE... 

The acute toxicity of butyronitriles is thought to be due to release of cyanide through metabolism of the parent compound. Signs of acute butyronitrile intoxication including dyspnea, ataxia, and convulsions are similar to those noted with acute cyanide intoxication. The onset and duration suggests that these nitriles require metabolism to elicit toxicity. Cyanide and thiocyanate have both been found in urine and... 

BUTYRONITRILE (109-74-0) Forms explosive mixture with air (flash point 79°F/26°C oc). Contact with steam or hot surfaces forms hydrogen cyanide gas. Exothermic reaction with strong acids (liberating hydrogen cyanide gas) or strong oxidizers. May accumulate static electrical charges may cause ignition of its vapors. 

Butyronitrile. Butaaenitrile propyl cyanide butyric acid nilriie. C4H7N mol wt 69.10. C 69.52%, H 10.21%, N 20.27%. CHjCH2CH2CN Prepd from I -butanol by controlled cyanation with NH, at 300° in the presence of Ni—AI2Oj catalysts Popov, Shuikin, Izvest. Akad. Nauk... 

Synonyms/Trade Names Butanenitrile, Butyronitrile, 1-Cyanopropane, Propyl cyanide, n-Propyl cyanide... 

Propyl cyanide n-Propyl cyanide. See Butyronitrile Propylcyclohexane CAS 1678-92-8... 

C4HVN 109-74-0 Butanenitrile syn. 1-Cyanopropane Butanonitiile Butyronitrile 1-Propanecarbonitiile nPropyl cyanide... 

Organic cyanides are commonly named after the corresponding acid, by changing the -ic or -ok suffix to -onitrile (hence, butyronitrile in eq. 10.16). In the lUPAC system, the suffix -nitrile is added to the name of the hydrocarbon with the same number of carbon atoms (hence butanenitrile in eq. 10.16). 

Using your roadmap as a guide, show how to convert propane into butyronitrile.You must use propane and sodium cyanide as the source of all of the carbon atoms in the butyronitrile product. Show all reagents and all molecules synthesized along the way. 

Vinylpyridine, benzyl cyanide, and methanol treated with 100 drops of aq. 58%-TritonB soln., and refluxed 3 hrs. -> a-phenyl-y-(2-pyridyl) butyronitrile. Y 87.9%. E. Profft and W. Steinke, B. 94, 2267 (1961) formulas s. Synth. Meth. 9, 764. 

In the presence of EtgAlCl or AICI3 catalysts, trimethylsilyl cyanide reacts with oxetanes and epoxides to yield 4-(trimethylsilyloxy)butyronitriles and 3-(trimethylsilyloxy)propiononitriles respectively (Scheme 25). However, in... 

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