| Identification | Back Directory | [Name]
(TRIMETHYLSILYL)ACETONITRILE | [CAS]
18293-53-3 | [Synonyms]
TMSAN
2-(Trimethy
Einecs 242-169-5
TRIMETHYLSILYACETONITRILE
(CYANOMETHYL)TRIMETHYLSILANE
2-Trimethylsilylacetonitrile
(TRIMETHYLSILYL)ACETONITRILE
trimethylsilanyl-acetonitrile
2-(Trimethylsilyl)acetonitrile
Acetonitrile, (trimethylsilyl)-
(TriMethylsilyl)acetonitrile 99%
Acetonitrile, 2-(triMethylsilyl)-
(Cyanomethyl)trimethylsilane, TMSAN
(Trimethylsilyl)acetonitrile,(Cyanomethyl)trimethylsilane, TMSAN | [EINECS(EC#)]
242-169-5 | [Molecular Formula]
C5H11NSi | [MDL Number]
MFCD00001882 | [MOL File]
18293-53-3.mol | [Molecular Weight]
113.23 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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.] |
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