(diazomethyl)trimethylsilane

• ChemBase ID: 130014
• Molecular Formular: C4H10N2Si
• Molecular Mass: 114.2211
• Monoisotopic Mass: 114.06132486
• SMILES: C[Si](C)(C)C=[N+]=[N-]
• Canonical SMILES: C[Si](C=[N+]=[N-])(C)C
• InChI: InChI=1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
• InChIKey: ONDSBJMLAHVLMI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (diazomethyl)trimethylsilane
• IUPAC Traditional name: trimethylsilyldiazomethane
• Synonyms: (Trimethylsilyl)diazomethane, 2M in hexanes; Trimethylsilyldiazomethane; Diazo(trimethylsilyl)methane; Trimethylsilyldiazomethane; (Diazomethyl)trimethylsilane; (Trimethylsilyl)diazomethane solution; (三甲硅烷)重氮甲烷, 2M 正己烷溶液; (三甲硅烷)重氮甲烷; 三甲基硅烷化重氮甲烷 溶液

Database IDs

• CAS Number: 18107-18-1
• MDL Number: MFCD00053946
• Beilstein Number: 1902903
• PubChem SID: 24889702; 24862335; 24874613; 162224300
• PubChem CID: 167693
• Chemspider ID: 146699
• MeSH Name: Trimethylsilyldiazomethane
• Wikipedia Title: Trimethylsilyldiazomethane

CALCULATED PROPERTIES

• Acid pKa: 9.643465
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.25019383
• LogD (pH = 7.4): 0.24987915
• Log P: 0.25019786
• Molar Refractivity: 25.2227 cm^3
• Polarizability: 12.320663 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: greenish-yellow liquid
• Flash Point: -14.8 °F; -23 °C; -23°C(-10°F); -26 °C; -31 °F; -35 °C; -9.4 °F
• Density: 0.718; 0.718 g/mL at 25 °C; 0.773 g/mL at 25 °C

Safety Information

• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); Highly toxic (T+); Harmful (Xn)
• UN Number: 1992; UN1992
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 1; 2; I
• Risk Statements: 45-11-19-22-26-39/26-66-67; 45-11-26-38-39/26-51/53-62-65-67; 62-11-23-36/38-48/20-51/53-65
• Safety Statements: 4-9-16-20-23-26-33-36/37/39-45-57-60; 53-16-28-36/37-45; 53-28-36/37-45-61-62
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H330-H336-H350-H370; H225-H304-H315-H330-H336-H350-H361f-H370-H411; H225-H330-H315-H319-H304-H361-H373-H411-H401
• GHS Precautionary statements: P201-P210-P260-P273-P281-P284; P201-P210-P260-P284-P310; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 1; UN 1992 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides., Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target Organ: Lungs

Product Information

• Concentration: ~2 M in hexane; 2.0 M in diethyl ether; 2.0 M in hexanes; 2M in hexanes
• Grade: technical
• Linear Formula: (CH3)3SiCHN2

DETAILS

Sigma Aldrich - 527254

Packaging
5, 25, 100 mL in Sure/Seal™
Application
Reactant for preparation of:
• Macrolactam analogs of the natural product macrolide (-)-A26771B with improved metabolic stability and antibacterial activity1
• Aigialomycin D analogues as protein kinase inhibitors for cancer treatment2
• Unnatural α-amino acid derivatives containing gem-bisphosphonates via Michael addition reaction3
• Capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates4
• Stictamides A-C as matrix metallopeptidase 12 (MMP12) inhibitors with antitumor invasion activity5
• Endothelin converting enzyme (ECE) Inhibitors WS 75624A and WS 75624B via a cross-metathesis approach6
• Ent-kaurene derivatives as anti-inflammatory agents7
• Desmosdumotin C analogs as potent antitumor agents acting via activation of spindle assembly checkpoint8
• Imidazolo[2,1-b]benzothiazole derivatives as potential p53 inhibitors9

Sigma Aldrich - 362832

Packaging
5, 25, 100, 500 mL in Sure/Seal™
Preparation Note
Preparation of substituted cyclopentenones via [4+1] annulation with vinylketenes.10
Application
Reactant for preparation of:
• Macrolactam analogs of the natural product macrolide (-)-A26771B with improved metabolic stability and antibacterial activity1
• Aigialomycin D analogues as protein kinase inhibitors for cancer treatment2
• Unnatural α-amino acid derivatives containing gem-bisphosphonates via Michael addition reaction3
• Capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates4
• Stictamides A-C as matrix metallopeptidase 12 (MMP12) inhibitors with antitumor invasion activity5
• Endothelin converting enzyme (ECE) Inhibitors WS 75624A and WS 75624B via a cross-metathesis approach6
• Ent-kaurene derivatives as anti-inflammatory agents7
• Desmosdumotin C analogs as potent antitumor agents acting via activation of spindle assembly checkpoint8
• Imidazolo[2,1-b]benzothiazole derivatives as potential p53 inhibitors9
Synthetic applications include metathesis and cycloaddition reactions.Regioselective dipolar cycloadditions to give amino acids and azakainoids.

Sigma Aldrich - 92738

Application
Reactant for preparation of:
• Macrolactam analogs of the natural product macrolide (-)-A26771B with improved metabolic stability and antibacterial activity1
• Aigialomycin D analogues as protein kinase inhibitors for cancer treatment2
• Unnatural α-amino acid derivatives containing gem-bisphosphonates via Michael addition reaction3
• Capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates4
• Stictamides A-C as matrix metallopeptidase 12 (MMP12) inhibitors with antitumor invasion activity5
• Endothelin converting enzyme (ECE) Inhibitors WS 75624A and WS 75624B via a cross-metathesis approach6
• Ent-kaurene derivatives as anti-inflammatory agents7
• Desmosdumotin C analogs as potent antitumor agents acting via activation of spindle assembly checkpoint8
• Imidazolo[2,1-b]benzothiazole derivatives as potential p53 inhibitors9