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| | (TRIMETHYLSILYL)ACETONITRILE Basic information |
| Product Name: | (TRIMETHYLSILYL)ACETONITRILE | | Synonyms: | TMSAN;(TRIMETHYLSILYL)ACETONITRILE;trimethylsilanyl-acetonitrile;(Trimethylsilyl)acetonitrile,(Cyanomethyl)trimethylsilane, TMSAN;2-(Trimethylsilyl)acetonitrile;2-Trimethylsilylacetonitrile;Einecs 242-169-5;Acetonitrile, 2-(triMethylsilyl)- | | CAS: | 18293-53-3 | | MF: | C5H11NSi | | MW: | 113.23 | | EINECS: | 242-169-5 | | Product Categories: | | | Mol File: | 18293-53-3.mol |  |
| | (TRIMETHYLSILYL)ACETONITRILE Chemical Properties |
| Boiling point | 65-70 °C20 mm Hg(lit.) | | density | 0.827 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.420(lit.) | | Fp | 122 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | Sol most common organic solvents. | | form | Liquid | | color | Clear colorless to straw | | Specific Gravity | 0.829 | | Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions | | BRN | 1738845 | | InChIKey | WJKMUGYQMMXILX-UHFFFAOYSA-N |
| | (TRIMETHYLSILYL)ACETONITRILE Usage And Synthesis |
| Physical properties | bp 84–85 °C/54 mmHg, 66 °C/35 mmHg,
65–70 °C/20 mmHg;3 d 0.827 g cm?3. | | Uses | (Trimethylsilyl)acetonitrile has been used in catalytic cyanomethylation of various carbonyl compounds in the presence of Lewis bases. | | Uses | α-carbanion is a useful alternative to LiCH2CN for nucleophilic
cyanomethylation; (Z)-selective Peterson alkenation). Trimethylsilylacetonitrile participates in the following synthesis reactions: Metalation, Peterson Alkenation (Cyanomethylenation), Michael Addition, Reactions with Other Electrophiles, Cyanomethylation, Metal-Catalyzed Reactions etc. | | 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.] |
| | (TRIMETHYLSILYL)ACETONITRILE Preparation Products And Raw materials |
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