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362832 Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in hexanes

Synonym: (Diazomethyl)trimethylsilane

  • CAS Number 18107-18-1

  • Linear Formula (CH3)3SiCHN2

  • Molecular Weight 114.22

  •  Beilstein/REAXYS Number 1902903

  •  MDL number MFCD00053946

  •  PubChem Substance ID 24862335

  •  NACRES NA.22



Related Categories Alkylation Reagents, Analytical Reagents, Analytical/Chromatography, C-X Bond Formation (Non-Halogen), Chemical Synthesis,
Quality Level   200
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


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.


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.


5, 25, 100, 500 mL in Sure/Seal™

Preparation Note

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

Safety & Documentation

Safety Information

Signal word 
Target organs 
Central nervous system, Lungs, Nervous system
UN 3383 6.1(3) / PGI
WGK Germany 
Flash Point(F) 
-9.4 °F - closed cup
Flash Point(C) 
-23 °C - closed cup


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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