Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

362832

Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in hexanes

Synonym(s):

(Diazomethyl)trimethylsilane

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)3SiCHN2
CAS Number:
18107-18-1
Molecular Weight:
114.22
Beilstein:
1902903
MDL number:
MFCD00053946
UNSPSC Code:
12352302
PubChem Substance ID:
24862335
NACRES:
NA.22

form

liquid

concentration

2.0 M in hexanes

density

0.718 g/mL at 25 °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, a methylating agent, is generally used for the methylation of carboxylic acids. It is also used as a derivatization agent for the analysis of carboxylic acids and polyphenols by the GC-MS method.

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
Synthetic applications include metathesis and cycloaddition reactions.
Regioselective dipolar cycloadditions to give amino acids and azakainoids.

Preparation Note

Preparation of substituted cyclopentenones via [4+1] annulation with vinylketenes.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Aquatic Chronic 2 - Asp. Tox. 1 - Carc. 1B - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 Inhalation - STOT SE 1 Inhalation - STOT SE 3

Target Organs

Central nervous system, Lungs, Nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-9.4 °F - closed cup

Flash Point(C)

-23 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

Analysis of catechins and condensed tannins by thermally assisted hydrolysis/methylation-GC/MS and by a novel two step methylation
Shadkami F, et al.
Journal of Analytical and Applied Pyrolysis, 85(1-2), 54-65 (2009)
Boon-Hooi Tan et al.
Chemical communications (Cambridge, England), 45(45), 4703-4705 (2006-11-17)
Hexagonal columnar liquid-crystalline phases are induced for a new fan-shaped spiropyran compound as the result of an acidichromism effect of spiro-merocyanine isomerisation through protonation upon incorporation of 4-methylbenzenesulfonic acid.
Journal of Organometallic Chemistry, 476, C27-C27 (1994)
Trapping of carbamic acid species with (trimethylsilyl) diazomethane
Ito Y and Ushitora H
Tetrahedron, 62(1), 226-235 (2006)
Adv. Use Synthons Org. Chem., 1, 51-51 (1993)
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