527254

(Trimethylsilyl)diazomethane solution

2.0 M in diethyl ether

• Synonym(s): TMS-Diazomethane solution, (Diazomethyl)trimethylsilane
• Linear Formula: (CH₃)₃SiCHN₂
• CAS Number: 18107-18-1
• Molecular Weight: 114.22
• Beilstein: 1902903
• MDL number: MFCD00053946
• UNSPSC Code: 12352302
• PubChem Substance ID: 24874613
• NACRES: NA.22

Properties

• concentration: 2.0 M in diethyl ether
• density: 0.773 g/mL at 25 °C
• storage temp.: 2-8°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

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

Safety Information

• Pictograms: GHS02,GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H225,H302,H330,H336,H350,H370
• Precautionary Statements: P202 - P210 - P233 - P240 - P301 + P312 - P304 + P340 + P310
• 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
• Supplementary Hazards: EUH019,EUH066
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): -31.0 °F - closed cup
• Flash Point(C): -35 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves