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527254

Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in diethyl ether

Synonyme(s) :

TMS-Diazomethane solution, (Diazomethyl)trimethylsilane

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About This Item

Formule linéaire :
(CH3)3SiCHN2
Numéro CAS:
18107-18-1
Poids moléculaire :
114.22
Numéro Beilstein :
1902903
Numéro MDL:
MFCD00053946
Code UNSPSC :
12352302
ID de substance PubChem :
24874613
Nomenclature NACRES :
NA.22

Concentration

2.0 M in diethyl ether

Densité

0.773 g/mL at 25 °C

Température de stockage

2-8°C

Chaîne SMILES 

C[Si](C)(C)C=[N+]=[N-]

InChI

1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3

Clé InChI

ONDSBJMLAHVLMI-UHFFFAOYSA-N

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Description générale

(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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

08168

Timestrip Plus™ 8 °C

Pictogrammes

FlameSkull and crossbonesHealth hazard
GHS02,GHS06,GHS08

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Flam. Liq. 2 - STOT SE 1 Inhalation - STOT SE 3

Organes cibles

Central nervous system, Lungs

Risques supp

EUH019,EUH066

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

-31.0 °F - closed cup

Point d'éclair (°C)

-35 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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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