2- propionitrile

EPA Classified Hazardous Waste, RCRA Waste Number PlOl DOT Label Flammable Liquid and Poison, UN 2404 Formula CH3CH2CN MW 55.09 CAS [107-12-0] 

Structure and functional group H3C—CH2 —C N, aliphatic mononitrile active site —C=N functional group Synonyms ethyl cyanide propionic nitrile propanenitrile cyanoethane 

Propionitrile is used as a chemical intermediate. It is formed as a by-product of the electrodimerization of acrylonitrile to adiponitrile. 

Colorless liquid with a sweet ether-like odor bp 9TC (206°F) mp -92 C (-133°F) density 0.782 at 20°C (68°F) soluble in water (12 g/dL at 40°C (104°F)), alcohol, ether, and most organic solvents. 

Propionitrile is a moderate to highly toxic compound, an eye irritant, and a teratomer. The toxic symptoms are similar to acetonitrile. However, the acute inhalation toxicity is greater than that associate with acetonitrile. Willhite (1981) reported a median lethal concentration of 163 ppm in male mice exposed for 60 minutes. By comparison, acetonitrile and butyronitrile exhibited median lethal concentrations of 2693 and 249 ppm, respectively. 

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A useful catalyst for asymmetric aldol additions is prepared in situ from mono-0> 2,6-diisopropoxybenzoyl)tartaric acid and BH3 -THF complex in propionitrile solution at 0 C. Aldol reactions of ketone enol silyl ethers with aldehydes were promoted by 20 mol % of this catalyst solution. The relative stereochemistry of the major adducts was assigned as Fischer- /ir o, and predominant /i -face attack of enol ethers at the aldehyde carbonyl carbon atom was found with the (/ ,/ ) nantiomer of the tartaric acid catalyst (K. Furuta, 1991). 

The oxidation of terminal alkenes with an EWG in alcohols or ethylene glycol affords acetals of aldehydes chemoselectively. Acrylonitrile is converted into l,3-dioxolan-2-ylacetonitrile (69) in ethylene glycol and to 3,3-dimetho.xy-propionitrile (70) in methanol[28j. 3,3-Dimethoxypropionitrile (70) is produced commercially in MeOH from acrylonitrile by use of methyl nitrite (71) as a unique leoxidant of Pd(0). Methyl nitrite (71) is regenerated by the oxidation of NO with oxygen in MeOH. Methyl nitrite is a gas, which can be separated easily from water formed in the oxidation[3]. 

Since the exocyclic sulfur is more reactive in the ambident anion than in A-4-thiazoIine-2-thione. greater nucleophilic reactivity is to be expected. Thus a large variety of thioethers were prepared in good yields starting from alkylhalides (e.g.. Scheme 38 (54, 91, 111, 166-179). lactones (54, 160), aryl halides (54, 152. 180, 181), acyl chlorides (54. 149, 182-184). halothiazoles (54, 185-190), a-haloesters (149. 152. 177. 191-194), cyanuric chloride (151). fV.N-dimethylthiocarbamoyl chloride (151, 152. 195. 196), /3-chloroethyl ester of acrylic acid (197), (3-dimethylaminoethyl chloride (152). l,4-dichloro-2-butyne (152), 1,4-dichloro-2-butene (152), and 2-chloro-propionitrile (152). A general... 

Small amounts of propionitrile and bis(cyanoethyl) ether are formed as by-products. The hydrogen ions are formed from water at the anode and pass to the cathode through a membrane. The catholyte that is continuously recirculated in the cell consists of a mixture of acrylonitrile, water, and a tetraalkylammonium salt the anolyte is recirculated aqueous sulfuric acid. A quantity of catholyte is continuously removed for recovery of adiponitrile and unreacted acrylonitrile the latter is fed back to the catholyte with fresh acrylonitrile. Oxygen that is produced at the anodes is vented and water is added to the circulating anolyte to replace the water that is lost through electrolysis. The operating temperature of the cell is ca 50—60°C. Current densities are 0.25-1.5 A/cm (see Electrochemical processing). 

Ethylbenzene Phenylethane 72 CsHio n-Propionitrile Ethyl cyanide 178 C4H5N... 

The formation of ethyl cyano(pentafluorophenyl)acetate illustrates the intermolecular nucleophilic displacement of fluoride ion from an aromatic ring by a stabilized carbanion. The reaction proceeds readily as a result of the activation imparted by the electron-withdrawing fluorine atoms. The selective hydrolysis of a cyano ester to a nitrile has been described. (Pentafluorophenyl)acetonitrile has also been prepared by cyanide displacement on (pentafluorophenyl)methyl halides. However, this direct displacement is always aecompanied by an undesirable side reaetion to yield 15-20% of 2,3-bis(pentafluoro-phenyl)propionitrile. 

C2H2CL2 1,1-DICHLORO- 1.994 7.6745E-02 5.2089E-06 25.40 96 C3H5N PROPIONITRILE 49.759 1.4902E-01 2.0199E-05 96.15... 

Dow Chemical Company. Aldrich Chemical Company. "2,2-Azobis(2-methy]propionitrile). 

The first synthesis and use of a chiral oxazoline was reported by Meyers in 1974. The chiral oxazoline 1 was prepared in two steps by condensation of (-i-)-l-phenyl-2-amino-1,3-propanediol (6) with the ethyl imidate of propionitrile followed by 0-methylation of the resulting alcohol 7 with NaH/Mel. Meyers demonstrated chiral oxazoline 1 could be... 

Zenitz obtained the analogous compounds 237 and 238 by the action of the corresponding a-cyano-w-bromo-w-alkanes on 2-methylindolyl magnesium bromide in ether. Eiter and Svierak prepared a-(3-indolyl)propionitrile (239) by the action of a-bromopropionitrile on indole magnesium iodide in anisole. ... 

The propionitrile (94) also yielded a pyrido[2,3-d]pyTimidine (96) when treated with ammonia or methylamine, the intermediate amidine (95) undergoing hydrolysis during the reaction.Amination was shown to be the rate-determining stage. 

Other 4-aminopyrimidyl-5-propionitriles, obtained by oyanoethyl-ation of the required pyrimidine, have also been conYerted into py r ido [2, S-dJpyrimidmes. ... 

Claisen condensation of propionitrile with ethyl acetate in the presence of sodium ethoxide gives the cyanobutanone, 119. 

Preparation of the analogue metioprim involves an alternate approach. Aldol condensation of aldehyde 59 with propionitrile gives the cinnamonitrile Reaction of... 

Phenyl-propionitrile, CgHj. CH.2. CH2. CN, is present in nssturtium oil. It is a powerfully smelling oil, boiling at 261°. On hydrolysis by alcoholic potash it yields phenyl-propionic acid, melting at 47°. 

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