Trimethylsilyldiazomethane

Trimethylsilyldiazomethane
Ball-and-stick model of the trimethylsilyldiazomethane molecule
Names
IUPAC name
(Diazomethyl)trimethylsilane
Other names
Trimethylsilyldiazomethane
Diazo(trimethylsilyl)methane
Identifiers
3D model (JSmol)
1902903
ChemSpider
ECHA InfoCard 100.131.243 Edit this at Wikidata
EC Number
  • 605-915-4
MeSH Trimethylsilyldiazomethane
UNII
  • InChI=1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3 checkY
    Key: ONDSBJMLAHVLMI-UHFFFAOYSA-N checkY
  • InChI=1/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
    Key: ONDSBJMLAHVLMI-UHFFFAOYAN
  • C[Si](C)(C)[CH-][N+]#N
  • [N-]=[N+]=C[Si](C)(C)C
Properties
C4H10N2Si
Molar mass 114.223 g·mol−1
Appearance greenish-yellow liquid[1][2]
Boiling point 96.0[1] °C (204.8 °F; 369.1 K)
Hazards
GHS labelling:[3]
GHS02: FlammableGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H330, H350, H370
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P284, P302+P352, P303+P361+P353, P304+P340, P307+P311, P308+P313, P310, P311, P314, P320, P332+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS) External MSDS[dead link]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Trimethylsilyldiazomethane is the organosilicon compound with the formula (CH3)3SiCHN2. It is classified as a diazo compound. Trimethylsilyldiazomethane, which is a commercially available, reagent used in organic chemistry as a methylating agent of carboxylic acids. Its behavior is akin to the reagent diazomethane, but the trimethylsilyl (TMS) analog is nonexplosive.[4]

  1. ^ a b Seyferth, Dietmar.; Dow, Alan W.; Menzel, Horst.; Flood, Thomas C. (1968). "Trimethylsilyldiazomethane and trimethylsilylcarbene". J. Am. Chem. Soc. 90 (4): 1080–1082. doi:10.1021/ja01006a055.
  2. ^ Seyferth, Dietmar; Menzel, Horst; Dow, Alan W.; Flood, Thomas C. (1972). "Trimethylsilyl-substituted diazoalkanes I. Trimethylsilyldiazomethane". J. Organomet. Chem. 44 (2): 279–290. doi:10.1016/S0022-328X(00)82916-2.
  3. ^ "Trimethylsilyldiazomethane". pubchem.ncbi.nlm.nih.gov.
  4. ^ Shioiri, Takayuki; Aoyama, Toyohiko; Snowden, Timothy (2001). "Trimethylsilyldiazomethane". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt298.pub2. ISBN 0471936235.