Skip to Content
Merck
CN

527254

(Trimethylsilyl)diazomethane solution

2.0 M in diethyl ether

Synonym(s):

TMS-Diazomethane solution, (Diazomethyl)trimethylsilane

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Linear Formula:
(CH3)3SiCHN2
CAS Number:
18107-18-1
Molecular Weight:
114.22
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24874613
MDL number:
MFCD00053946
Beilstein/REAXYS Number:
1902903

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

(Trimethylsilyl)diazomethane solution, 2.0 M in diethyl ether

InChI

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

SMILES string

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

InChI key

ONDSBJMLAHVLMI-UHFFFAOYSA-N

concentration

2.0 M in diethyl ether

density

0.773 g/mL at 25 °C

storage temp.

2-8°C

Looking for similar products? Visit Product Comparison Guide

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

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.

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

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
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBL5650
SHBH2203V
SHBG3825V
SHBF3890V
SHBF2954V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

A new, stable, and safe reagent for the homologation of ketones.
Hashimoto N
Tetrahedron Letters, 21(48), 4619-4622 (1980)
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
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
Sean Flaherty et al.
Electrophoresis, 23(14), 2327-2332 (2002-09-05)
The investigation of emerging contaminant issues is a proactive effort in environmental analysis. As a part of this effort, sewage effluent is of current analytical interest because of the presence of pharmaceuticals and their metabolites and personal care products. The
View All Related Papers

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