1-Trimethylsilyl-1,2,4-triazole - CAS 18293-54-4

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Category
Main Product
Product Name
1-Trimethylsilyl-1,2,4-triazole
Catalog Number
18293-54-4
Synonyms
2,4-Triazole,1-(trimethylsilyl)-1H-1; 4-triazole,1-(trimethylsilyl)-1h-2; N-TRIMETHYLSILYL-1,2,4-TRIAZOLE; 1-TRIMETHYLSILYL-1,2,4-TRIAZOLE; Trimethylsilyl-1,2,3-triazole; 1-Trimethylsilyl-1H-1,2,4-triazole
CAS Number
18293-54-4
Molecular Weight
141.25
Molecular Formula
C5H11N3Si
COA
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MSDS
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Canonical SMILES
C[Si](C)(C)N1C=NC=N1
InChI
InChI=1S/C5H11N3Si/c1-9(2,3)8-5-6-4-7-8/h4-5H,1-3H3
InChIKey
WPSPBNRWECRRPK-UHFFFAOYSA-N
Structure
CAS 18293-54-4 1-Trimethylsilyl-1,2,4-triazole
Specification
Purity
95%
Boiling Point
73ºC(12 torr)
Density
0.989 g/mL at 25 °C(lit.)
Appearance
Clear clear liquid
Storage
2-8ºC
Related Products
Reference Reading
1.Highly asymmetric coordination of trimethylsilyl groups to tetrazole and triazole rings: an experimental and computational study in gaseous and crystalline phases.
Wann DA1, Gronde I, Foerster T, Hayes SA, Masters SL, Robertson HE, Mitzel NW, Rankin DW. Dalton Trans. 2008 Aug 7;(29):3817-23. doi: 10.1039/b803091j. Epub 2008 Jun 16.
1-Trimethylsilyltetrazole, 1, has been synthesised from chlorotrimethylsilane and tetrazole in the presence of triethylamine as an auxiliary base. The structure of this compound has been determined in the crystalline phase by X-ray diffraction of a crystal grown in situ. The gas-phase structures of 1 and 1-trimethylsilyl-1,2,4-triazole, 2, have been determined by gas-phase electron diffraction (GED). An extensive investigation of these and related compounds by ab initio calculations is also reported. The angles between the rings and the substituents on N were of particular interest. It was found that the calculated difference of 15.5 degrees between the CNSi and NNSi angles in 1 was mostly, but not entirely, an inherent property of the tetrazole ring and not due to a short SiN interaction.
2.Azoles as reactive nucleophiles with cyclic perfluoroalkenes.
Garg S1, Twamley B, Zeng Z, Shreeve JM. Chemistry. 2009 Oct 12;15(40):10554-62. doi: 10.1002/chem.200901508.
Di- and multiazole-substituted fluorocyclic products (2-13) were readily synthesized in good to high yields. These were synthesized by nucleophilic substitution reactions of perfluorocycloalkenes with azoles (i.e., imidazole, triazole) involving simple reaction procedures. Interestingly, these azoles were later found to be reactive not only with the vinylic, but also with the allylic fluorine atoms. This resulted in the substitution of up to six azoles on the fluorinated rings. Stoichiometry plays a key role in determining the degree of substitution. For comparison, the analogous reactions of N-substituted 1-(trimethylsilyl)-imidazole and 1-(trimethylsilyl)-1,2,4-triazole were also investigated. All of the new compounds were fully characterized by elemental, spectral ((19)F, (1)H, (13)C NMR), and thermal differential scanning calorimetry (DSC) analyses.
3.Syntheses and Structures of Bis(azole)difluorosulfuranes.
Wessel J1, Behrens U, Lork E, Watson PG, Schröter M, Mews R. Inorg Chem. 1999 Oct 18;38(21):4789-4794.
Bis(imidazole)sulfur difluoride (4), bis(pyrazole)sulfur difluoride (6), and bis(1,2,4-triazole)sulfur difluoride (8) are formed in the reactions of N-(trimethylsilyl)imidazole, N-(trimethylsilyl)pyrazole, and 1-(trimethylsilyl)-1,2,4-triazole with SF(4), in high yield. The ring systems in these three molecules occupy equatorial positions in the pseudo-trigonal-bipyramidal coordination sphere of the central sulfur atoms. The angles between the planes of the ring substituents and the FSF axis for 4 and 6 are in the range 23.6-35.3 degrees, and in 8 the triazole rings are almost parallel (deviation 1.7 degrees ). The interaction between the heterocyclic substituents and the sulfur centers and their influence on the axial and equatorial bonds is discussed.
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