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Trimethylsilyl iodide information


Trimethylsilyl iodide
Names
Preferred IUPAC name
Iodotri(methyl)silane
Other names
Iodotrimethylsilane; TMSI; TMS-I; Jung reagent
Identifiers
CAS Number
  • 16029-98-4
3D model (JSmol)
  • Interactive image
ChemSpider
  • 76879
ECHA InfoCard 100.036.503 Edit this at Wikidata
PubChem CID
  • 85247
UNII
  • 7A65KRZ6NV checkY
CompTox Dashboard (EPA)
  • DTXSID4065997 Edit this at Wikidata
InChI
  • InChI=1S/C3H9ISi/c1-5(2,3)4/h1-3H3
    Key: CSRZQMIRAZTJOY-UHFFFAOYSA-N
  • InChI=1/C3H9ISi/c1-5(2,3)4/h1-3H3
    Key: CSRZQMIRAZTJOY-UHFFFAOYAB
SMILES
  • I[Si](C)(C)C
Properties
Chemical formula
C3H9ISi
Molar mass 200.094 g·mol−1
Appearance Clear colorless liquid[1]
Density 1.406 g/mL[1]
Boiling point 106–109 °C (223–228 °F; 379–382 K)[1]
Hazards
Flash point −31 °C (−24 °F; 242 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylsilyl iodide (iodotrimethylsilane or TMSI) is an organosilicon compound with the chemical formula (CH3)3SiI. It is a colorless, volatile liquid at room temperature.

  1. ^ a b c d Michael E. Jung, Michael J. Martinelli, George A. Olah, G. K. Surya Prakash, Jinbo Hu (October 15, 2005). "Iodotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ri043.pub2. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)CS1 maint: multiple names: authors list (link)

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Trimethylsilyl iodide

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Trimethylsilyl iodide (iodotrimethylsilane or TMSI) is an organosilicon compound with the chemical formula (CH3)3SiI. It is a colorless, volatile liquid...

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Trimethylsilyl chloride

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fluoride, trimethylsilyl bromide, trimethylsilyl iodide, trimethylsilyl cyanide, trimethylsilyl azide, and trimethylsilyl trifluoromethanesulfonate (TMSOTf)...

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TMSI

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Subscriber Identity, data sent between a mobile phone and its network Trimethylsilyl iodide, a chemical compound This disambiguation page lists articles associated...

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Methyl pivalate

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the parent acid. Hydrolysis can be effected with a solution of trimethylsilyl iodide in hot acetonitrile followed by aqueous workup. Olah, George A.;...

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Beckmann rearrangement

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pentachloride, phosphorus pentoxide, triethylamine, sodium hydroxide, trimethylsilyl iodide among others. The Beckmann fragmentation is another reaction that...

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Benzyl group

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temperature Ozone N-Bromosuccinimide (NBS) N-Iodosuccinimide (NIS) Trimethylsilyl iodide (Me3SiI) in dichloromethane at ambient temperature (selectivity...

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Cefquinome

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N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA). Treatment of this intermediate with trimethylsilyl iodide gives the allylic iodide (3). Displacement...

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Hexamethyldisilane

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react as follows: Si2Me6 + RLi → RSiMe3 + LiSiMe3 Iodine gives trimethylsilyl iodide. Me3Si−SiMe3 + I2 → 2 SiMe3I Tamejiro Hiyama, Manabu Kuroboshi,...

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Danishefsky Taxol total synthesis

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conjugated vinyl iodide 28 was produced in an unexpected dehydrogenation. The ketone was converted into cyanohydrin 29 with trimethylsilyl cyanide, potassium...

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Grepafloxacin

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removes a proton from the 8 position; treatment of that anion with trimethylsilyl iodide leads to the silylated intermediate (4). A second round of LDA then...

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NanoPutian

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of the desired products. To remedy this, the bromide was replaced with iodide through lithium-halogen exchange and quenching by using 1,2-diiodoethane...

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Deoxygenation

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are deoxygenated by strongly reducing silyl reagents such as N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene. Phosphorus occurs in nature as oxides, so to...

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Holton Taxol total synthesis

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the trimethylsilyl enol ether 29, which was subsequently oxidized in a Rubottom oxidation using m-chloroperbezoic acid to give the trimethylsilyl protected...

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Organozinc chemistry

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Frankland prepared the first organozinc compound, diethylzinc, by heating ethyl iodide in the presence of zinc metal. This reaction produced a volatile colorless...

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Diacetylene

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HC#C-C#CH + 2 KCl + 2 H2O}}} The bis(trimethylsilyl)-protected derivative may be prepared by the Hay coupling of (trimethylsilyl)acetylene: 2 Me 3 Si − C ≡ CH...

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Organosilicon chemistry

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with methyl lithium to give trimethylsilyl lithium: (CH3)6Si2 + CH3Li → (CH3)3SiLi + (CH3)4Si Similarly, tris(trimethylsilyl)silyl lithium is derived from...

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Phosphine

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occurs at around 200 °C. Alternative methods are the hydrolysis of tris(trimethylsilyl)phosphine, or of metal phosphides such as aluminium phosphide, or calcium...

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Group 2 organometallic chemistry

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Dimethylcalcium is obtained by metathesis reaction of calcium bis(trimethylsilyl)amide and methyllithium in diethyl ether: C a [ N { S i ( C H 3 ) 3...

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Abiological nitrogen fixation using homogeneous catalysts

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a related process, trimethylsilyl chloride, lithium and nitrogen react in the presence of a catalyst to give tris(trimethylsilyl)amine, which can be...

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