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Sigma-Aldrich

(Trimethylsilyl)isocyanate

85%

Synonym(s):

Isocyanatotrimethylsilane

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About This Item

Linear Formula:
(CH3)3SiNCO
CAS Number:
1118-02-1
Molecular Weight:
115.21
Beilstein/REAXYS Number:
1744962
EC Number:
214-256-8
MDL number:
MFCD00001993
UNSPSC Code:
12352100
PubChem Substance ID:
24855227
NACRES:
NA.22

Quality Level

100

assay

85%

form

liquid

impurities

<15% hexamethyldisiloxane

refractive index

n20/D 1.396 (lit.)

bp

90-92 °C (lit.)

density

0.851 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)N=C=O

InChI

1S/C4H9NOSi/c1-7(2,3)5-4-6/h1-3H3

InChI key

NIZHERJWXFHGGU-UHFFFAOYSA-N

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Application

Trimethylsilyl isocyanate was used in:
  • postsynthetic modification of isoreticular metal-organic framework-3
  • synthesis of 1-unsubstituted 4-(dialkylamino) imidazolin-2-ones
  • conversion of isocyanates to carbodiimides with cyclopentadienyl Fe(CO)2 or -Mn(CO)3 catalysis
  • carbamoylation of aromatic hydrocarbons and alcohols

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Eye Irrit. 2 - Flam. Liq. 2 - Resp. Sens. 1 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

23.0 °F - closed cup

flash_point_c

-5 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Tetrahedron Letters, 48, 6002-6002 (2007)
Reactions of trimethylsilyl isocyanate and isothiocyanate with 3-(dialkylamino)-2H-azirines. A facile synthesis of 1-unsubstituted 4-(dialkylamino) imidazolin-2-ones and 4-(dialkylamino) imidazoline-2-thiones
Handke I, et al.
The Journal of Organic Chemistry, 53(22), 5298-5300 (1988)
J. Prakt. Chem./Chem.-Ztg., 335, 558-558 (1993)
S Manfredini et al.
Journal of medicinal chemistry, 37(15), 2401-2405 (1994-07-22)
As a continuation of previous studies on the synthesis and antitumor activity of geiparvarin analogues bearing a carbamate moiety in the alkyl side chain, a series of N-substituted [(E)-3-(4,5-dihydro-5,5-dimethyl-4-oxo-2-furanyl)-2- butenyl]carbamates (15a-f) were synthesized and tested with the objective to investigate
SiNCO+ and SiNCS+ and their neutral counterparts.
Srinivas R, et al.
Chemical Physics Letters, 316(3), 243-247 (2000)
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