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153583

Sigma-Aldrich

1-(Trimethylsilyl)imidazole

96%

Sinónimos:

N-Trimethylsilylimidazole, TMSI, TSIM

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About This Item

Fórmula empírica (notación de Hill):
C6H12N2Si
Número de CAS:
18156-74-6
Peso molecular:
140.26
Beilstein:
606148
Número CE:
242-040-3
Número MDL:
MFCD00005280
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
24849355
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

grado

synthesis grade

Nivel de calidad

200

Ensayo

96%

Formulario

liquid

índice de refracción

n20/D 1.475 (lit.)

bp

93-94 °C/14 mmHg (lit.)

densidad

0.956 g/mL at 25 °C (lit.)

temp. de almacenamiento

2-8°C

cadena SMILES

C[Si](C)(C)n1ccnc1

InChI

1S/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3

Clave InChI

YKFRUJSEPGHZFJ-UHFFFAOYSA-N

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Aplicación

1-(Trimethylsilyl)imidazole (TMSI) was used for derivatization of carbohydrates into trimethylsilyl ethers[1]. It was also used to synthesize polysubstituted chiral spirotetrahydropyrans[2] and as silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.[3]
Silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.[3]

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Pictogramas

FlameExclamation mark
GHS02,GHS07

Palabra de señalización

Danger

Frases de peligro

H225,H302,H315,H319

Clasificaciones de peligro

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

42.8 °F - closed cup

Punto de inflamabilidad (°C)

6 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
SDBB0828
STBK8588
SDBB1367
STBL2287
STBK3062

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Visite la Librería de documentos

Marijana M Ačanski et al.
Food chemistry, 145, 743-748 (2013-10-17)
Gas chromatography with mass spectrometry was used for carrying out a qualitative analysis of the ethanol soluble flour extract of different types of cereals bread wheat and spelt and pseudocereals (amaranth and buckwheat). TMSI (trimethylsilylimidazole) was used as a reagent
Synthetic Communications, 23, 2191-2191 (1993)
Maiwenn Jacolot et al.
Organic letters, 14(1), 58-61 (2011-12-02)
We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
Silylated N,O-ketals from the reaction of ketones with N-trimethylsilylimidazole.
P A Andrews et al.
Journal of chromatography, 419, 271-274 (1987-08-07)
S Kulkarni et al.
Steroids, 53(1-2), 131-147 (1989-01-01)
The reaction of trimethylsilylimidazole (TSIM) and 3-keto-5,10-epoxy-nor-19-methylandrostanone 3 and its 17-acetate analog 4 was examined at two different temperatures. In both compounds, reaction at 90 degrees C gave predominantly a delta 3-silyl-enol ether plus a minor product as a result
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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