18293-53-3 Usage
Description
(TRIMETHYLSILYL)ACETONITRILE, also known as TMSACN, is an organic compound that serves as a versatile reagent in various chemical synthesis reactions. It is characterized by its physical properties, including a boiling point of 84-85°C at 54 mmHg, 66°C at 35 mmHg, and 65-70°C at 20 mmHg, and a density of 0.827 g/cm3.
Uses
Used in Chemical Synthesis:
(TRIMETHYLSILYL)ACETONITRILE is used as a reagent for various chemical synthesis reactions, including metalation, Peterson alkenation (cyanomethylenation), Michael addition, reactions with other electrophiles, cyanomethylation, and metal-catalyzed reactions. It is particularly useful as an alternative to LiCH2CN for nucleophilic cyanomethylation, providing a (Z)-selective outcome in Peterson alkenation.
Used in Catalytic Cyanomethylation:
(TRIMETHYLSILYL)ACETONITRILE is used as a catalyst in the cyanomethylation of various carbonyl compounds in the presence of Lewis bases. This application highlights its utility in organic chemistry for the synthesis of diverse chemical compounds.
Preparation
From chlorotrimethylsilane, zinc, and
XCH2CN, (X = Cl, 61% yield; X = Br, 81% yield).
Purification Methods
Check if NMR and IR spectra show impurities; if present dissolve it in *C6H6 (10volumes), wash it with buffer (AcOH/AcONa pH ca 7) several times, dry (CaCl2) it, evaporate and distil it. IR: (CCl4) 2215 (CN) cm-1, NMR (CCl4): 0.23 (s, 9H, SiMe3), and 1.53 (s, 2H, CH2CN). [Matsuda et al. J Chem Soc, Perkin Trans 1 26 1979, Beilstein 4 IV 3974.]
Check Digit Verification of cas no
The CAS Registry Mumber 18293-53-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,2,9 and 3 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 18293-53:
(7*1)+(6*8)+(5*2)+(4*9)+(3*3)+(2*5)+(1*3)=123
123 % 10 = 3
So 18293-53-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NSi/c1-7(2,3)5-4-6/h5H2,1-3H3
18293-53-3Relevant articles and documents
Reaction of organosilicon derivatives of 1,1-dimethylhydrazine with methyl iodide
Voronkov,Gostevskii,Shainyan,Rakhlin,Mirskov,Makarova
, p. 17 - 20 (2005)
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N-Methyl-N,N-bis(Silatranylmethyl)amine: Structure and reactivity
Albanov, Alexander,Gostevskii, Boris,Lazareva, Nataliya,Shagun, Vladimir,Vashchenko, Alexander
, (2020/05/18)
Trimethylsilylacetonitrile Me3SiCH2CN and N-methyl-N,N-bis(silatranylmethyl)amine hygrohalogenide were obtained by the interaction of N-methyl-N,N-bis(silatranylmethyl)amine MeN[CH2Si(OCH2CH2)3N]2 1 with MeCN/Me3SiX (X = Cl, I). The key stage of this reaction is the formation of the intermolecular complexes between amine 1 and Me3SiX. The alkylation of amine 1 by ICH2SiX3 (SiX3 = SiMe3, Si(OMe)3 and Si(OCH2CH2)3N) give rise to the generation of the corresponding ammonium salts {(X3SiCH2)MeN[CH2Si(OCH2CH2)3N]2}+I-. The molecular structures of N-methyl-N,N-bis(silatranylmethyl)amine (1), N-methyl-N-[(trimethylsilyl)methyl]-N,N-bis(silatranylmethyl)ammonium iodide (4) and N-methyl-N-N,N-tris(silatranylmethyl)ammonium iodide (6) were determined by single-crystal X-ray diffraction. Compound 1 exists as mix of the conformers 1A (values lN→Si are equal 2.212 ? and 2.274 ?), 1B (values of lN→Si are equal 2.252 ? and 2.272 ?) and 1C (values lN→Si are equal 2.273 ? and 2.291 ?). The length of dative bond N→Si of molecules 1A-1C is longer than in molecules 4 and 6 (Δl lie between 0.105 ? and 0.199 ?), but length of Si–CH2 bond is shorter on 0.001–0.034 ?.
Cyanide initiated perfluoroorganylations with perfluoroorgano silicon compounds
Panne, Patricia,Naumann, Dieter,Hoge, Berthold
, p. 283 - 286 (2007/10/03)
Cyanophenylphosphanes, Ph2PCN or PhP(CN)2, do not react with Me3SiCF3 or Me3SiC6F5 in the absence of cyanide ions. Catalytic amounts of ionic cyanides such as [NEt4]CN
