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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/REAXYS Number:
1902903
MDL number:
MFCD00053946
UNSPSC Code:
12352302
PubChem Substance ID:
24874613
NACRES:
NA.22

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

Related product

Referencia del producto
Descripción
Precios

08168

Timestrip Plus™ 8 °C

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

EUH019,EUH066

Storage Class

3 - Flammable liquids

wgk_germany

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

Certificados de análisis (COA)

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A new, stable, and safe reagent for the homologation of ketones.
Hashimoto N
Tetrahedron Letters, 21(48), 4619-4622 (1980)
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
Konrad Kowalewski et al.
Journal of chromatography. A, 1218(41), 7264-7274 (2011-09-13)
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)
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
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