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Sigma-Aldrich

(Trimethylsilyl)methyl isocyanide

97%

Synonym(s):

(Isocyanomethyl)trimethylsilane

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About This Item

Linear Formula:
(CH3)3SiCH2NC
CAS Number:
30718-17-3
Molecular Weight:
113.23
Beilstein/REAXYS Number:
3930556
MDL number:
MFCD00043056
UNSPSC Code:
12352100
PubChem Substance ID:
24863423
NACRES:
NA.22

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.)

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.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

<59.0 °F - closed cup

flash_point_c

< 15 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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)
Isocyanomethylenetriphenylphosphorane.
Zinner G and Fehlhammer WP.
Angewandte Chemie (International Edition in English), 24(11), 979-980 (1985)
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)

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