527254
(Trimethylsilyl)diazomethane solution
2.0 M in diethyl ether
Synonym(s):
TMS-Diazomethane solution, (Diazomethyl)trimethylsilane
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About This Item
Linear Formula:
(CH3)3SiCHN2
CAS Number:
Molecular Weight:
114.22
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1902903
InChI
1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
SMILES string
C[Si](C)(C)C=[N+]=[N-]
InChI key
ONDSBJMLAHVLMI-UHFFFAOYSA-N
concentration
2.0 M in diethyl ether
density
0.773 g/mL at 25 °C
storage temp.
2-8°C
General description
(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.
Application
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
signalword
Danger
Hazard Classifications
Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Flam. Liq. 2 - STOT SE 1 Inhalation - STOT SE 3
target_organs
Central nervous system, Lungs
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
-31.0 °F - closed cup
flash_point_c
-35 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
监管及禁止进口产品
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A new, stable, and safe reagent for the homologation of ketones.
Hashimoto N
Tetrahedron Letters, 21(48), 4619-4622 (1980)
Sussan Ghassabian et al.
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
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
Andreas Ranz et al.
Journal of chromatography. A, 1192(2), 282-288 (2008-04-15)
Microwave radiation is used to speed up chemical derivatization. In the present study, three microwave-assisted techniques for the methylation of chlorophenoxy acid herbicides prior to analysis by gas chromatography coupled with mass spectrometry are compared. Derivatization was performed with the
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