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527254 Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in diethyl ether

Synonym: (Diazomethyl)trimethylsilane, TMS-Diazomethane solution

  • CAS Number 18107-18-1

  • Linear Formula (CH3)3SiCHN2

  • Molecular Weight 114.22

  •  Beilstein/REAXYS Number 1902903

  •  MDL number MFCD00053946

  •  PubChem Substance ID 24874613

  •  NACRES NA.22

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Other Non-Halogen Reagents for C-X Bond Formation,
InChI Key   ONDSBJMLAHVLMI-UHFFFAOYSA-N
Quality Level   100
concentration   2.0 M in diethyl ether
density   0.773 g/mL at 25 °C
storage temp.   2-8°C

Description

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

Packaging

1 L in Sure/Seal™

5, 25, 100 mL in Sure/Seal™

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
May form explosive peroxides., Repeated exposure may cause skin dryness or cracking.
RIDADR 
UN 3383 6.1(3) / PGI
WGK Germany 
3
Flash Point(F) 
-31 °F
Flash Point(C) 
-35 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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