376159
(Trimethylsilyl)methyl isocyanide
97%
Synonym(s):
(Isocyanomethyl)trimethylsilane
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About This Item
Linear Formula:
(CH3)3SiCH2NC
CAS Number:
Molecular Weight:
113.23
Beilstein:
3930556
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
liquid
refractive index
n20/D 1.416 (lit.)
bp
52-53 °C/35 mmHg (lit.)
density
0.803 g/mL at 25 °C (lit.)
functional group
amine
isonitrile
storage temp.
−20°C
SMILES string
C[Si](C)(C)C[N+]#[C-]
InChI
1S/C5H11NSi/c1-6-5-7(2,3)4/h5H2,2-4H3
InChI key
OLSTVZKPVGMQKB-UHFFFAOYSA-N
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General description
Synthesis of (trimethylsilyl)methyl isocyanide and its reaction with protic nucleophiles has been reported. An improved preparation of (trimethylsilyl)methyl isocyanide is reported. Reaction of (trimethylsilyl)methyl isocyanide with (η2-formaldehyde)zirconocene complex is reported to yield insertion products.
Application
(Trimethylsilyl)methyl isocyanide may be used in the preparation of isocyanomethylenetriphenylphosphorane.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
<59.0 °F - closed cup
Flash Point(C)
< 15 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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A (η1-iminoacyl) zirconocene complex formed by alkyl isocyanide insertion into the metal-to-carbon bond of (η2-formaldehyde) zirconocene.
Erker G, et al.
Organometallics, 10(4), 1201-1203 (1991)
An Improved Synthesis of Trimethylsilylmethyl Isocyanide.
Brouwer AC and Van Leusen AM.
Synthetic Communications, 16(8), 865-869 (1986)
Isocyanomethylenetriphenylphosphorane.
Zinner G and Fehlhammer WP.
Angewandte Chemie (International Edition in English), 24(11), 979-980 (1985)
An improved synthesis of trimethylsilylmethyl isocyanide and some of its reactions with nucleophiles.
Smith R and Livinghouse T.
Synthetic Communications, 14(7), 639-646 (1984)
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