April, 1947
COMMUNICATIONS TO TRE EDITOR
981
Anal. Calcd. for C4HISiCls: Si, 14.6; C1, 55.6; mol. wt., 191. Found: Si, 14.7; CI, 55.7; cryoscopic mol. wt. in benzene, 189. t-Butyltrichlorosilane is unusual. It is a white waxy solid which becomes granular on standing I I1 (36) and sublimes readily at room temperature, giving The synthesis of I1 was accomplished by con- well-defined fern-like crystals (Fig. 1). It is less easily hydrolyzed than other alkyltrichlorosilanes. densing the previously d e ~ c r i b e dN,N-dimethyl~.~ N ' (a-pyridy1)-ethylenediamine with ol-thienyl cho1ride.l The product, h. p. 173-175O at 3 mm., n Z 5 1.5835 ~ was obtained in a 64% yield. Anal. Calcd. for CI~HIQNIS:N, 16.09. Found: N, 1G.12. The monohydrochloride melted at 161-1U2". Anal. Calcd. for ClrHrnN8SCI: N. 14.12. Found: N, 14.16. The methiodide had m. p. 156-157'' (dec.). Anal. Calcd. for ClaHnN,SI: N. 10.42. Found: N, 10:39. Preliminary pharmacological data7 indicate that, experimentally in animals, I1 exhibits the same order of antihistaminic activity as I. The toxicity of both compounds is approximately equal. Additional information concerning 11 and other homologs will be published at some future date. I'ig. l.-Phutograpli o i ci yslsl. o i subliincd l ~ i u t y l t r i ( 5 ) Whitmore. Mostier, Gs>Id.imith and Rytina. i b i d . . 6T, 393 (1945). chlorosilane by Dr. M. L. Willard. H. Francis. G. KauB( 6 ) BlleLesodLeonarcl, i b i d . , 6 8 , 1 ! W (l94G).
(7) Rofh.RiehnrdllandShepperd, Fcdrroliun P r o c . . i n
I ~ S (1947). S
man, T Reissmann.
ORonmc RESEARCH DEPARTMENT With methylmagnesium bromide the above ABBOIT LABORATORIES ARTHURW. WESTON compound gives a 61% yield of t-butyltrimethylNORTHCHICAGO, ILLINOIS silane, m.p. 75-77", b. p. 103" at 740 mm. RECEIVED MARCH18. 1947 f-BUTYL.SIL.ICON COMPOUNDS
Sir: From t-butyllithiuml and silicon tetrachloride we have synthesized in 55'r, yield the first tertiary alkyl silicon compound, 1-butyltrichlorosilane, m. p. 9&99O, b. p. 133' at 740 mm. (1) Ormadithiurn compound2 hawe brco used t o mnkc o~mnosilicon compounds: Fleming and Laureas. U. S. Patent 2,386,452. (1845); C. A , . (40. 603 (1946): Gilmea and Clarke. Tels J O U ~ I L , 08. 1675 (1946).
Anal. Calcd. for CIHlsSi: Si, 21.6; mol. wt., 130. Found: Si, 21.7; mol. wt., 132. I t is a white waxy solid with faint camphoric odor. I t sublimes readily to crystals resembling those in Fig. 1. Distillation of t-hutyltrimethylsilane from hot concd. sulfuric acid gave a product with unchanged m. p., thus indicating a high degree of inertness of the C-Si bond.
RECBIVED MARCH7.1947
