Trimethylsilyl cyanide
Trimethylsilyl cyanide structure
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Common Name | Trimethylsilyl cyanide | ||
|---|---|---|---|---|
| CAS Number | 7677-24-9 | Molecular Weight | 99.206 | |
| Density | 0.8±0.1 g/cm3 | Boiling Point | 118.5±0.0 °C at 760 mmHg | |
| Molecular Formula | C4H9NSi | Melting Point | 8-11 °C(lit.) | |
| MSDS | Chinese USA | Flash Point | 1.1±0.0 °C | |
| Symbol |
GHS02, GHS06 |
Signal Word | Danger | |
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Asymmetric activation of tropos 2,2'-biphenol with cinchonine generates an effective catalyst for the asymmetric strecker reaction of N-tosyl-protected aldimines and ketoimines.
Angew. Chem. Int. Ed. Engl. 46(44) , 8468-70, (2007)
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A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity.
Org. Biomol. Chem. 10(46) , 9271-7, (2012) KF-mediated nucleophilic activation of TMSCN as a functional isonitrile equivalent establishes an efficient and chemoselective Ugi-type multicomponent reaction of a heterocyclic amidine and aldehyde with TMSCN in water. In this approach, the use of isocyanide... |
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Sc₂(pydc)₂ unit based 1D, 2D and 3D metal-organic frameworks as heterogeneous Lewis acid catalysts for cyanosilylation.
Dalton Trans. 44(4) , 1942-7, (2014) Three scandium metal-organic frameworks (Sc-MOFs), [Sc(pydc)(Hpydc)(H2O)]·H2O (1), [Sc2(pydc)3(H2O)4]·5H2O (2) and [Sc(pydc)(H2O)(NO3)] (3) with similar Sc2(pydc)2 building unit were prepared by using 2,3-pyridinedicarboxylic acid (H2pydc) ligand under hydrot... |
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Facile and efficient enantioselective Strecker reaction of ketimines by chiral sodium phosphate.
Chemistry 15(24) , 6008-14, (2009) A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol % BNPNa (BNP = 1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol % para-tert-butyl-ortho-adamantylphen... |
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Synthesis of homo-N-nucleoside with 1,2,4-triazole-3-carboxamide.
Nucleosides Nucleotides Nucleic Acids 24(5-7) , 979-81, (2005) On the basis of potent biological activities of ribavirin and homo-N-nucleosides, a novel homo-N-1,2,4-triazole-3-carboxamide derivative 1 was synthesized starting from 2,3,5-tri-O-benzoylribofuranosyl-1-acetate as a potential antiviral agent. |
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Brønsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide.
Org. Biomol. Chem. 8(6) , 1399-405, (2010) A general method for the one-pot, three-component Strecker reaction of ketones was developed using Brønsted acids as organocatalysts. A series of alpha-aminonitriles were obtained in good to excellent yields (79-99%). A preliminary extension to a catalytic en... |
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Difluoro(trimethylsilyl)acetonitrile: synthesis and fluoroalkylation reactions.
J. Org. Chem. 77(13) , 5850-5, (2012) A new silicon reagent, difluoro(trimethylsilyl)acetonitrile, was prepared by insertion of difluorocarbene into silyl cyanide. The obtained silane served as a good cyanodifluoromethylating reagent toward aldehydes, N-tosylimines, N-alkylimines, and enamines un... |
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Enantioselective synthesis of tertiary α-hydroxy phosphonates catalyzed by carbohydrate/cinchona alkaloid thiourea organocatalysts.
Angew. Chem. Int. Ed. Engl. 51(35) , 8864-7, (2012)
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Effect of carbonates/phosphates as nucleophilic catalysts in dimethylformamide for efficient cyanosilylation of aldehydes and ketones.
Proc. Natl. Acad. Sci. U. S. A. 104(9) , 3026-30, (2007) Cyanosilylation of aldehydes and aliphatic ketones can be carried out in dimethylformamide even without the use of any catalyst. In the presence of nucleophilic catalysts such as carbonate and phosphate salts, the reaction rate is significantly enhanced. |
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Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control.
J. Am. Chem. Soc. 128(26) , 8671-7, (2006) The limitations of stereoelectronic models in assessing the stereoselective nucleophilic substitution reactions of cyclic oxocarbenium ions at high reaction rates are discussed. Evidence is provided suggesting that the diastereoselectivity of nucleophilic sub... |