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362832

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/REAXYS Number:
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.[1] It is also used as a derivatization agent for the analysis of carboxylic acids and polyphenols by the GC-MS method.[2][3]

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[4][5] include metathesis[6] and cycloaddition reactions.[7]
Regioselective dipolar cycloadditions to give amino acids and azakainoids.[8]

Preparation Note

Preparation of substituted cyclopentenones via [4+1] annulation with vinylketenes.[9]

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_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM5564
SHBM3797
SHBH9823
SHBG3451V
SHBF5862V

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Synlett, 107-107 (1994)
Adv. Use Synthons Org. Chem., 1, 51-51 (1993)
Trapping of carbamic acid species with (trimethylsilyl) diazomethane
Ito Y and Ushitora H
Tetrahedron, 62(1), 226-235 (2006)
Andreas Ranz et al.
Journal of chromatography. A, 1192(2), 282-288 (2008-04-15)
Microwave radiation is used to speed up chemical derivatization. In the present study, three microwave-assisted techniques for the methylation of chlorophenoxy acid herbicides prior to analysis by gas chromatography coupled with mass spectrometry are compared. Derivatization was performed with the
Journal of Organometallic Chemistry, 476, C27-C27 (1994)
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