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Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in hexanes

Synonym(s):

(Diazomethyl)trimethylsilane

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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

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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’.

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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)
Synlett, 107-107 (1994)
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)
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