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376159

Sigma-Aldrich

(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

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.)

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

Signal Word

Danger

Hazard 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

Certificates of Analysis (COA)

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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)
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)

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