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527254

Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in diethyl ether

Sinónimos:

TMS-Diazomethane solution, (Diazomethyl)trimethylsilane

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About This Item

Fórmula lineal:
(CH3)3SiCHN2
Número de CAS:
18107-18-1
Peso molecular:
114.22
Beilstein:
1902903
Número MDL:
MFCD00053946
Código UNSPSC:
12352302
ID de la sustancia en PubChem:
24874613
NACRES:
NA.22

concentración

2.0 M in diethyl ether

densidad

0.773 g/mL at 25 °C

temp. de almacenamiento

2-8°C

cadena SMILES

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

InChI

1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3

Clave InChI

ONDSBJMLAHVLMI-UHFFFAOYSA-N

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Descripción general

(Trimethylsilyl)diazomethane is considered as a non-explosive substitute to diazomethane for the homologation of carbonyl derivatives, mainly ketones, via reactions such as Tiffeneau-Demjanov rearrangement.[1][2]

Aplicación

Reactant for preparation of:
  • Macrolactam analogs of the natural product macrolide (-)-A26771B with improved metabolic stability and antibacterial activity
  • Aigialomycin D analogues as protein kinase inhibitors for cancer treatment
  • Unnatural α-amino acid derivatives containing gem-bisphosphonates via Michael addition reaction
  • Capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates
  • Stictamides A-C as matrix metallopeptidase 12 (MMP12) inhibitors with antitumor invasion activity
  • Endothelin converting enzyme (ECE) Inhibitors WS 75624A and WS 75624B via a cross-metathesis approach
  • Ent-kaurene derivatives as anti-inflammatory agents
  • Desmosdumotin C analogs as potent antitumor agents acting via activation of spindle assembly checkpoint
  • Imidazolo[2,1-b]benzothiazole derivatives as potential p53 inhibitors

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Referencia del producto
Descripción
Precios

08168

Timestrip Plus™ 8 °C

Palabra de señalización

Danger

Clasificaciones de peligro

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Flam. Liq. 2 - STOT SE 1 Inhalation - STOT SE 3

Órganos de actuación

Central nervous system, Lungs

Riesgos supl.

EUH019,EUH066

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

-31.0 °F - closed cup

Punto de inflamabilidad (°C)

-35 °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
SHBL5650
SHBH2203V
SHBG3825V
SHBF3890V
SHBF2954V

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Hashimoto N
Tetrahedron Letters, 21(48), 4619-4622 (1980)
Sean Flaherty et al.
Electrophoresis, 23(14), 2327-2332 (2002-09-05)
The investigation of emerging contaminant issues is a proactive effort in environmental analysis. As a part of this effort, sewage effluent is of current analytical interest because of the presence of pharmaceuticals and their metabolites and personal care products. The
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 881-882, 34-41 (2011-12-27)
Risedronate is a commonly prescribed bisphosphonate for the treatment of bone disorders. Due to its high polarity and low oral bioavailability, low concentrations of risedronate are expected in human plasma and therefore a sensitive assay is required to serve in
T J van 't Erve et al.
Environment international, 36(8), 835-842 (2010-04-14)
Diazomethane is a highly explosive and toxic gas routinely employed for the quantitative and clean derivatization of phenols. We investigated the commercially available trimethylsilyldiazomethane in the presence of diisopropylethylamine as a safe, non-explosive and less-toxic alternative using six phenolic polychlorinated
Y Park et al.
Journal of agricultural and food chemistry, 49(3), 1158-1164 (2001-04-21)
Four different methods for methylating conjugated linoleic acid (CLA) were compared. The HCl/MeOH and BF(3)/MeOH methods were tested under different time and temperature combinations. Increasing temperature and/or incubation time for either method decreased the cis-9,trans-11 and trans-10,cis-12 isomers, but trans-9,trans-11/trans-10,trans-12
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