| Identification | Back Directory | [Name]
CHLOROTRIBENZYLSILANE | [CAS]
18740-59-5 | [Synonyms]
CHLOROTRIBENZYLSILANE
TRIBENZYL CHLOROSILANE
TRIBENZYLSILYL CHLORIDE
tribenzylchlorosilicane
Tribenzylchlorosilane 97%
Chlorotris(phenylmethyl)silane
chlorotris(phenylmethyl)-silan
Tribenzylchlorosilane, Tribenzylsilyl chloride | [EINECS(EC#)]
242-549-0 | [Molecular Formula]
C21H21ClSi | [MDL Number]
MFCD00004768 | [MOL File]
18740-59-5.mol | [Molecular Weight]
336.93 |
| Hazard Information | Back Directory | [Physical properties]
mp 141–142 °C;1,2 a somewhat higher value
(143–145 °C) is cited in the Aldrich catalog. | [Uses]
Tribenzylchlorosilane is widely used as reagent for alcohol protection. | [Preparation]
It is prepared by reaction of benzylmagnesium
chloride with SiCl4 in ether; separation from mono- and
dibenzylated chlorosilane byproducts is then accomplished by
fractional distillation (boiling range 300–360 °C/100 mmHg).
Other preparations involve the chlorination of tribenzylsilane
using Cl2
or an acyl chloride. No yields are reported for any
of the above preparative procedures. | [Purification Methods]
It is recrystallised three times from pet ether (in slender colourless needles, m 141o). It is sparingly soluble in pet ether but is soluble in Et2O. It does not fume in moist air but is decomposed by H2O to give tribenzyl silanol m 106o (from pet ether). [Robinson & Kipping J Chem Soc 93 439 1908, Jenkins & Post J Org Chem 15 556 1950, Beilstein 16 H 906, 16 IV 1498.] |
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