Amyl Thiocyanate

Isobutyl sulfide, b.p. 168°, is prepared in 71% yield from 106 g. (0.77 mole) of isobutyl bromide and 116.7 g. (0.49 mole) of sodium sulfide. 

A mixture of 340 ml. of ethanol and 147 g. (1.52 moles) of potassium thiocyanate is heated to reflux, and 157 g. (1.04 moles) of n-amyl bromide is added dropwise. Reflux is continued for 2 hours after completion of the addition of the bromide. Most of the ethanol is removed by distillation, and the residue is diluted with water and extracted with ether. The combined ethereal extracts are dried over calcium chloride, and the ether is removed by distillation. Fractional distillation of the residue at 16 mm. pressure gives an 85% yield of n-amyl thiocyanate, b.p. 90-91°. 

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Alkyl thiocyanates, R—S—C=N, of lower carbon numbers are highly toxic. These compounds liberate HCN as a result of metabolic processes and can cause death (Manahan 1989). Methyl thiocyanate [556-64-9] is highly toxic, with an intravenous LD50 value of 18 mg/kg in mice (NIOSH 1986). Ethyl thiocyanate [542-90-5], allyl thiocyanate [764-49-8], butyl thiocyanate [628-83-1], and amyl thiocyanate [32446-40-5] are all toxic compounds with an LD50 (subcutaneous) value of less than 100 mg/kg. The phenyl ester [5285-87-0] exhibits greater toxicity (intravenous LD50 value in mice 6.7 mg/kg) than that of the aliphatic esters of thiocyanic acid. 

Ammonium sulfide, 3, n Ammonium thiocyanate, 7, 48 Ammonolysis, 4, 3 7, 16 o-Amyl alcohol, 1, 4, 10 Amyl alcohol, active, 7, 77 mo-Amyl Bromide, 1,1, 2, 4, 10 w-Amyl Methyl Ketone, 7, do -Amyl propiolic acid, 7, 62 Analysis of Benzoylhydroperoxide, 8,32 Analysis of Benzoylperoxide, 8, 31 Anhydro-o-Hydroxymercoribenzoic Acid, 7, 3... 

I-A1ON0-2-NAPHIH0L-4-SULE0NIC acid, 11, 72 16, 91 17, 91 Aminonaphtholsulfonic acids, coupling to form azo dyes, 16,16 p-Aminophenol, 16, 39 Aminopiperole, 16, 6 /3-Ahinopropionic acid, 16, 1 4-Aminoveratrole, 16, 4 Ammonium dichromate, 16, 74 Ammonium formate, 17, 77 Ammonium thiocyanate, 16, 74 Ammonium vanadate, 13, 1 to w-Amyl alcohol, IS, 17 hri.-Amyl alcohol, 13, 68 -Amylbenzene, 10, 4 -Amyl borate, 13, 17 -Amyl bromide, 16, 41 iso-Amyl iodide, 13, 62 n-Amyl iodide, 13, 62 n-Amybnagnesium bromide, 16, 41... 

The theory of melting continues to be the subject of recent publications, including consideration of vacancy concentrations near the melting point [8,9], lattice vibrations and expansions [8,10—12], Meanwhile, the phenomenon also continues to be the subject of experimental investigations Coker et al. [13], from studies of the fusion of tetra-n-amyl ammonium thiocyanate, identify the greatest structural change as that which... 

Inorganic extractions seem to have come into practical use without any great notice. Although Peligot in 1842 reported that uranyl nitrate could be recrystalhzed from ether, he never mentioned extraction of this salt from aqueous solutions. In textbooks after 1870, however, it is stated briefly that ether can even withdraw sublimate (HgCy from aqueous solution. It was also reported, for example, that cobalt thiocyanate is weakly extracted by ether, better by amyl alcohol, and even better by a mixture of both. 

Compound Name Ammonium Oxalate Ammonium Oxalate Ammonium Pentaborate Ammonium Pentaborate Zinc Ammonium Chloride Ammonium Perchlorate Ammonium Persulfate Ammonium Persulfate Ammonium Phosphate Ammonium Phosphate Ammonium Thiocyanate Ammonium Thiocyanate Ammonium Silicofluoride Ammonium Stearate Ammonium Sulfamate Ammonium Sulfate Ammonium Sulfide Ammonium Sulfide Ammonium Sulfide Ammonium Sulfite Ammonium Thiocyanate Ammonium Thiocyanate Ammonium Tartrate Ammonium Thiocyanate Ammonium Thiosulfate Zinc Ammonium Chloride Phosphorus, Red Ammonium Sulfamate Amyl Acetate Amyl Acetate N-Amyl Alcohol N-Amyl Alcohol Valeraldehyde Hexanol... 

Treatment of cyanide poisoning includes rapid administration of activated charcoal (although charcoal binds cyanide poorly, it can reduce absorption) and general supportive care. The conventional antidote kit available in the USA includes two forms of nitrite (amyl nitrite and sodium nitrite) and sodium thiosulfate. The nitrites induce methemoglobinemia, which binds to free CI T creating the less toxic cyanomethemoglobin thiosulfate is a cofactor in the enzymatic conversion of CN to the much less toxic thiocyanate (SCINT). Recently, the FDA approved a concentrated form of hydroxocobalamin, which is now available as the Cyanokit (EMD Pharmaceuticals, Durham, North Carolina). Hydroxocobalamin (one form of vitamin B12) combines rapidly with CN to form cyanocobalamin (another form of vitamin B12). 

Silver, lead, copper(l). and thallium(I) thiocyanates are insoluble and mercuiy(II), bismuth, and tm(II) thiocyanates slightly soluble. All of these, are soluble in excess of soluble (e.g., ammonium) thiocyanate, forming complexes. Iron(III) thiocyanate gives a blood-red solution, used in detecting either Fe(lll) or thiocyanate in solution, and is extracted from water by amyl alcohol. It is not formed in the presence of fluoride, phosphate and other strongly complexing ions,... 

Potassium thiocyanate yields a blue colour with solutions of cobalt salts, a blue alcoholic layer being produced on addition of amyl alcohol or of alcohol and ether to the mixture (see p. 71) and shaking. 

Ammonium Standard Solution, 849 Ammonium Sulfanilate TS, 850 Ammonium Sulfate, 28 Ammonium Sulfide TS, 850 Ammonium Thiocyanate, 0.1 N, 856 Ammonium Thiocyanate TS, 850 Amyl Acetate, 510 1-Amyl Alcohol, 454, (S3)66 Amylase, 130, (S3)18 a-Amylase, 132, 786 P-Amylase, 132, 786 Amyl Butyrate, 454, 510, (S3)66 Amyl Caprylate, 454 Amylcinnamaldehyde, 454 a-Amylcinnamaldehyde, 454, 605,... 

The 10-mlnute Co82 produced by the Ni82(n,p) reaction has been extracted as the thiocyanate into an organic layer of amyl alcohol-ethyl ether (l l) from a weak hydrochloric acid solution saturated with ammonium thiocyanate and then back-extracted with 6 N ammonia solution (156,208). The 5-2-minute W17 produced by a Ta (p,3n) reaction has also been extracted as the thiocyanate of W(lV) Into ethyl acetate (268). 

This chargeless molecule can be extracted by ether or amyl alcohol. In addition to this a set of complex ions, such as [Fe(SCN)]2+, [Fe(SCN)2]+, [Fe(SCN)4]-, [Fe(SCN)5]2-, and [Fe(SCN)6]3 are also formed. The composition of the product in aqueous solution depends mainly on the relative amounts of iron and thiocyanate present. Phosphates, arsenates, borates, iodates, sulphates, acetates, oxalates, tartrates, citrates, and the corresponding free acid interfere due to the formation of stable complexes with iron(III) ions. 

The cyanide antidote kit contains amyl nitrate, sodium nitrate, and sodium thiosulfate. Nitrates convert hemoglobin to methemoglobin, which in turn competes for cyanide with the mitochondrial oxidase complex. Amyl nitrate pearls, administered by inhalation, can be utilized as a first aid measure when intravenous (IV) access is impossible or will be delayed. If IV access is available, IV sodium nitrate is preferred, followed by sodium thiosulfate. Sodium thiosulfate reacts with cyanide to form nontoxic thiocyanate, which is then excreted into the urine. 

Chromous Thiocyanate, Cr(SCN)-2, and Chromous Sodium Thiocyanate, SNaCNS.CrlCNSlj.llHaO, are known to exist. By passing nitric oxide into a moist amyl-alcoholic solution of chromous thiocyanate, the compound 0[Cr(SCN)2]2.J NH3 is obtained. Compounds with pyridine have also been described. 

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