Skip to Content
Merck
All Photos(1)

Documents

376159

Sigma-Aldrich

(Trimethylsilyl)methyl isocyanide

97%

Synonym(s):

(Isocyanomethyl)trimethylsilane

Sign Into View Organizational & Contract Pricing


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

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service