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
concentration
2.0 M in diethyl ether
density
0.773 g/mL at 25 °C
storage temp.
2-8°C
SMILES string
C[Si](C)(C)C=[N+]=[N-]
InChI
1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
InChI key
ONDSBJMLAHVLMI-UHFFFAOYSA-N
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