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Trimethylsilyl cyanide

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Trimethylsilyl cyanide Basic information
Trimethylsilyl cyanide Chemical Properties
  • Melting point:8-11 °C(lit.)
  • Boiling point:114-117 °C(lit.)
  • Density 0.793 g/mL at 20 °C(lit.)
  • refractive index n20/D 1.392(lit.)
  • Flash point:34 °F
  • storage temp.  0-6°C
  • solubility Miscible with organic solvents.
  • form liquid
  • color Yellow
  • Specific Gravity0.744
  • Water Solubility reacts
  • Sensitive Moisture Sensitive
  • Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
  • BRN 1737612
  • CAS DataBase Reference7677-24-9(CAS DataBase Reference)
  • EPA Substance Registry SystemSilanecarbonitrile, trimethyl- (7677-24-9)
Safety Information
Trimethylsilyl cyanide Usage And Synthesis
  • Chemical Propertiesclear colorless to yellow liquid
  • UsesReacts with aldehydes and ketones to give cyanohydrin-TMS ethers which can be reduced to β-aminoethyl alcohols.
  • UsesTrimethylsilyl Cyanide is used as a reagent in the synthesis of optically active cyanohydrins. Used in the preparation of Reissert compounds, which represent reactive polyamides. Toxic to humans.
  • Purification MethodsThe material should have only one sharp signal in the 1H NMR (in CCl4 with CHCl3 as internal standard) : 0.4ppm and IR with max at 2210cm1 [McBride & Beachall J Am Chem Soc 74 5247 1952, Prober J Am Chem Soc 77 3224 1955]; otherwise purify it by fractionating through an 18 x 1/4inch column. [Evers et al. J Am Chem Soc 81 4493 1959.] It has also been carefully distilled using a 60cm vacuum jacketed column. If the volume of sample is small, the cyanide can be chased (in the distillation) with xylene that had been previously distilled over P2O5. It is HIGHLY TOXIC and FLAMMABLE. [Evans et al. J Org Chem 39 914 1974, Beilstein 4 IV 3893.]
Trimethylsilyl cyanide Preparation Products And Raw materials
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