Diethyltin dichloride

Diethyl stannic dichloride, AD32 Diethyl(2-th ioethyl) amine, A139 Diethyltin dichloride, AD32... 

SYNS DIAETHYLZINNDICHLORID (GERMAN) DICHLORODIETHYLTIN DIETHYLDICHLORO-STANNANE DIETHYLSTANNYL DICHLORIDE DIETHYLTIN CHLORIDE DIETHYLTIN DICHLORIDE... 

Under similar conditions, ethyl chloride gave only low yields of diethyltin dichloride, and attempts to alkylate tin, either in a sealed tube or under these flow conditions, with butyl chloride, butyl bromide, or bromobenzene were unsuccessful. 

Organic tin compounds Dialkyltin compounds - especially dimethyl-tin and diethyltin dichloride - are dermal irritants, but several of them (e.g., dibutyltin diacetate, dilaurate, maleate, oxide) do not cause such irritation (Lyle 1958). Tributyl and trimethyltin compounds are not allergic dermal and conjunctival irritants, but are responsible for the acute burns that appear several hours after the dermal contact. 

In an interesting extension of the above reactions, diorganotin dihydrides have been treated with amines to obtain cyclic polytin compounds 159,188, 192, 194a, 236, 236b, 236c). In one reported case 18S) a 94% yield of octadecaethylcyclononatin was obtained from diethyltin dihydride and a pyridine-diethyltin dichloride complex. It is apparently also possible to obtain straight-chain products with suitable reagents. 

Cleavage with formation of the halide is accomplished with a number of reagents other than the halogens. Treatment of hexamethylditin with hydrobromic (206) or hydrochloric (273) acid leads to the corresponding trimethyltin halide. In contrast, hexaethylditin has been found to react with 4 moles of hydrogen chloride to form diethyltin dichloride. 

Figure 12.12 Mossbauer spectrum of the product of diethyltin dichloride and ciprofloxacin...

Dermal Effects. Dialkyltin compounds, especially dimethyltin and diethyltin dichloride, are dermal irritants but several of them, like dibutyltin diacetate, dilaurate, maleate, and oxide, are not [42], Tributyl- and trimethyltin compounds are not allergic dermal and conjunctival irritants but are responsible for acute bums appearing several hours after the dermal contact [42]. The lesions last several days, and consist of follicular inflammarion, pruritis, and minute pustules that dry after 2 or 3 days. Recovery takes a week. The hair doesn t seem to be affected. Subacute contacts are responsible for pruritis and scratching lesions, reddening of the skin, and sticky skin. Lesions affect the lower abdomen, thighs, groin, and perineum. Tetraalkyltin compounds applied on the skin have never produced any effect [42]. 

The following chemicals are utilized without further purification (from Ventron-Alfa Inorganics unless noted otherwise), dibutyltin dichloride (Fisher), diethyltin dichloride, dimethyl-tin dichloride, dioctyltin dichloride, dilauryltin dichloride (Metallcxner Labs.), triphenyltin chloride, tri-n-butyltin chloride (Aldrich), tribenzyltin chloride, tricyclohexyltin bromide, tri-n-propyltin chloride, dibutyltin dibromde, diphenyltin dichloride (Metallomer Labs.), dextran (molecular weight 200,000-300,000 United States Biochemical Corp.), triethylenediamine (Eastman), triethylamine (Eastanan), piperdine (Matheson, Coleman and Bell), N,N-dimethylaniline (Fisher), Aniline (Baker), 4-dimethylamino-pyridine (gift from Reilly Tar and Chemical Corp.), 3,5-lutidine (Aldrich) and pyridine (Baker). 

C4H1oBr3NOSn, Tribromomethyl(dimethylformamide)tin(IV), 44B, 668 C4H,oCl2Sn, Diethyltin dichloride, 43B, 9l9 CijH,ol2Sn, Diethyltin diiodide, 43B, 919... 

The following chemicals were used without further ourifi-cation dibutyltin dichloride (Fisher Scientific Co., Fairlawn, N.J.), diphenyltin dichloride (Metallomer Laboratories, Maynard, Mass.), dibutyltin dibromide, dilauryltin dichloride, tri-n-propyltin chloride, diethyltin dichloride, dimethyltln dichloride, dioctyltin dichloride, tricyclohexyltin bromide, triphenyltin dichloride and tribenzyltin chloride (all from Ventron-Alfa Inorganics, Danvers, Mass.), tri-n-butyltin chloride (Aldrich Chemical Co., Milwaukee, Wis.) and dextran (molecular weight - 200,000 - 300,000 United States Biochemical Corp., Cleveland, Ohio). 

It is interesting that as soon as some of the organic part of the molecule is replaced, as in diethyltin dichloride, the compound is a solid... 

In 1980 Crowe et al " published the first report on the anticancer activity of a series of diorganotin dihalides and complexed products of the general formula R2SnX22L, where 2L (bidentate) = phenanthroUne, bipyridyl, 2-aminomethylpyri-dine L (monodentate) = dimethylsrrlfoxide, pyridine X = halides and R = methyl, ethyl, propyl, butyl, or phenyl. They postulated that a somewhat stable organotin complex is needed for good activity. The diethyltin dichloride compounds were found to be the most active. 

This study focused on the diethyltin derivative since this was most active against bacteria. The polymer showed equal or better ability to inhibit cell growth in comparison to diethyltin dichloride with decent inhibition at 5 pg/mL. 

Chemicals were used as received. Acyclovir [CA (chem. Abstracts) 59277-89-3], and dimethyltin dichloride (CA 753-73-1) were purchased from die Aldrich Chemical Company, Milwaukee, WS. Diethyltin dichloride (CA 866-55-7) and... 

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