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Merck
CN

376159

(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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863423
MDL number:
MFCD00043056
Beilstein/REAXYS Number:
3930556
Assay:
97%
Form:
liquid

Key Documents

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InChI

1S/C5H11NSi/c1-6-5-7(2,3)4/h5H2,2-4H3

SMILES string

C[Si](C)(C)C[N+]#[C-]

InChI key

OLSTVZKPVGMQKB-UHFFFAOYSA-N

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

Quality Level

200

Related Categories

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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBG0627V
1375040
05628JE
11312KD
18030DO

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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)
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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