527254
(Trimethylsilyl)diazomethane solution
2.0 M in diethyl ether
Synonym(s):
TMS-Diazomethane solution, (Diazomethyl)trimethylsilane
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Linear Formula:
(CH3)3SiCHN2
CAS Number:
Molecular Weight:
114.22
Beilstein:
1902903
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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
Looking for similar products? Visit Product Comparison Guide
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
related product
Product No.
Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
Supplementary Hazards
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
-31.0 °F - closed cup
Flash Point(C)
-35 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
监管及禁止进口产品
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Homologation reaction of ketones with diazo compounds.
Candeias N R
Chemical Reviews, 116(5), 2937-2981 (2016)
Hélène Lebel et al.
The Journal of organic chemistry, 73(17), 6828-6830 (2008-07-30)
Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group
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
Natalia Migowska et al.
Analytical and bioanalytical chemistry, 397(7), 3029-3034 (2010-06-22)
Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most common groups of pharmaceuticals detected in environmental matrices. Although several derivatization procedures have been employed in the gas chromatographic analysis of NSAIDs, the application of trimethylsilyldiazomethane has never yet been reported. This
Sean K J Devine et al.
Organic letters, 10(10), 1909-1911 (2008-04-12)
Palladium catalysts are shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and stabilized carbon nucleophiles. The reaction is believed to proceed through a palladium-carbene intermediate LX(R)PdCHSiMe 3 that undergoes migration of the vinyl substituent to the electrophilic carbene
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service