Tetramethylammonium Iodid

Ammonium Compounds. Salts and hydroxides containing quadricovalent nitrogen are named as a substituted ammonium salt or hydroxide. The names of the substituting radicals precede the word ammonium, and then the name of the anion is added as a separate word. For example, (CH3)4N+I is tetramethylammonium iodide. 

Tetramethylammonium iodide [75-58-1] M 201.1, m >230°(dec). Crystd from water or 50% EtOH, EtOH/diethyl ether, ethyl acetate, or from acetone/MeOH (4 1) by adding an equal volume of acetone. Dried in a vacuum desiccator. 

Gramine forms flat needles or leaflets, m.p. 138-9°, [a]p 0°, and yields a pierate, m.p. 144-5°, perehlorate, m.p. 150-1° platiniehloride, red needles, m.p. 180-1° dec.) and a methiodide, m.p. 176-7°. Aeeording to Madinaveitia, gramine on treatment with methyl iodide in methyl aleohol yields trimethylamine, tetramethylammonium iodide and a substanee presumed to be 3-hydroxymethylindole. With ethyl iodide in acetone a normal ethiodide, CiaH gNjI, m.p. 176°, is formed. 

Experiments using a series of methylated 2-amino-1,2,4-thiadia-zoles of unequivocal structure (351-353) show that thiadiazoles (e.g. 351) are not reducible in methanolic lithium chloride solution, while thiadiazolines (e.g. 352-353) are uniformly reduced at E0 = — 1.6 + 0.02V. In aqueous alcoholic tetramethylammonium iodide,... 

C103 mw 157.59 N 8.89% wh crysts, mp explodes at 230° sol in ale or w was prepd by double decompn of tetramethylammonium iodide AgC103 and evapg the soln on a w bath to crystn. This compd suddenly flashes in contact with a flame or in contact with coned H2S04(Refs 1 2)... 

Therefore we may expect the reaction of ammonia with methyl iodide to give four possible alkylation products, mono-, di-, and trimethylamines, as well as tetramethylammonium iodide ... 

H. E. Armstrong emphasized the inadequacy of the ammonium theory to account for the extraordinary stability of tetramethylammonium iodide, (CH3)4NI, towards the strongest caustic alkali, and showed that the halogen compound behaves more like an alkyl iodide than ammonium iodide. Hence, it was inferred that the halogen is not simply associated with the nitrogen, but is rather retained and protected or masked by combination with a hydrocarbon radicle. The idea can be illustrated graphically ... 

Tetramethy(ammonium Chlorate. (CH N. CIOJ mw 157.62 N 8.89% OB to C02 -60.91% white cryst. V sol in ethanol and w. Prepn is by double decompn between tetramethylammonium-iodide and Ag chlorate followed by evapn of the resulting soln on a w bath to crystn. The chlorate explds at 230°... 

An attempt to repeat a reported preparation of the salt (228) from trimethylamine and 6-chlorophenanthridine failed after metathesis only tetramethylammonium iodide could be isolated. A similar... 

Magadiite apart from pentasil phases can be found in zeolites synthesized with mono-n-methy1-, -ethyl-, -propyl- or -butylamine, with di-n-methyl-, -ethyl- or -propylamine, with tri-n-methyl- or -ethylamine and with tetramethylammonium iodide. Table IV shows that the zeolite content increases with the number of carbon atoms per group and with the number of alkyl groups. 

Introduction, Amines are organic derivatives of ammonia, with one, two, or three hydrogen atoms replaced by an organic radical. The three types of amines, primary (RNHj), secondary (RjNH), and tertiary (R3N), may be prepared by the reaction of mono-halides with ammonia. In the case of reactive halides, like methyl iodide, the reaction proceeds to the formation of the quaternary salt— tetramethylammonium iodide ... 

When one mole of methyl iodide and four moles of ammonia are used, the formation of primary, secondary, and tertiary amines proceeds rapidly, so that within two minutes the formation of tetramethylammonium iodide assumes the dominant role of the reaction. About seventy-five per cent of the methyl iodide is converted to the quaternary salt, while the remainder forms a mixture of the three amines. The formation of the quaternary salt can be inhibited to a large extent by the addition of an ammonium salt, such as ammonium nitrate, which reacts with the free amino group of the amine to form the ion ... 

B) Quaternary Base. Dissolve 0.1 g of tetramethylammonium iodide in 10 ml of water. Use 2 ml to test the pH. To another 2-ml portion add a drop of silver nitrate solution. To the remainder add 2 ml of sodium hydroxide solution and heat. Note whether there is any odor of ammonia or amine, and hold moistened litmus over the tube. 

Onium salt Formed when a Lewis base expands its valence, e g. tetramethylammonium iodide,... 

During an attempt to prepare the tetramethylammonium radical, Thompson and Cundall 143) reported that the reaction of tetramethylammonium iodide with potassium in liquid ammonia gave trimethyl-amine, ethane, and potassium iodide, but no methane. 

Disproportion tes to tetramethylammonium iodide and the compound Me NIi upon recrystallization. 

Dissolve iodine and iodine monochloride in hot ethanol and add to hot solution of tetramethylammonium iodide. 

---