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
Beilstein:
1902903
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
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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
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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
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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
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A new, stable, and safe reagent for the homologation of ketones.
Hashimoto N
Tetrahedron Letters, 21(48), 4619-4622 (1980)
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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
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
Konrad Kowalewski et al.
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A novel three-step analytical method was developed which enables the simultaneous detection and identification of multifunctional oxygenated products resulting from the reaction of α-pinene with ozone. The method consists of the following steps: conversion of carbonyl groups to methyloximes using
Homologation reaction of ketones with diazo compounds.
Candeias N R
Chemical Reviews, 116(5), 2937-2981 (2016)
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