362832

(Trimethylsilyl)diazomethane solution

2.0 M in hexanes

• Synonym(s): (Diazomethyl)trimethylsilane
• Linear Formula: (CH₃)₃SiCHN₂
• CAS Number: 18107-18-1
• Molecular Weight: 114.22
• UNSPSC Code: 12352302
• NACRES: NA.22
• PubChem Substance ID: 24862335
• MDL number: MFCD00053946
• Beilstein/REAXYS Number: 1902903
• Form: liquid

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H225,H304,H315,H330,H336,H350,H361f,H370,H372,H411
• pcodes: P202 - P210 - P273 - P303 + P361 + P353 - P304 + P340 + P310 - P331
• 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: 3 - Flammable liquids
• wgk: WGK 3
• flash_point_f: -9.4 °F - closed cup
• flash_point_c: -23 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter