Skip to Content
Merck
CN

Key Documents

View All Documentation

362832

(Trimethylsilyl)diazomethane solution

2.0 M in hexanes

Synonym(s):

(Diazomethyl)trimethylsilane

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

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
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

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

Synthetic applications include metathesis and cycloaddition reactions.
Regioselective dipolar cycloadditions to give amino acids and azakainoids.
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

Preparation Note

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

signalword

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library