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Sigma-Aldrich

Clorotrimetilsilano

puriss., ≥99.0% (GC)

Sinónimos:

Cloruro de trimetilsililo, TMCS, Trimetilclorosilano

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About This Item

Fórmula lineal:
(CH3)3SiCl
Número de CAS:
75-77-4
Peso molecular:
108.64
Beilstein/REAXYS Number:
1209232
EC Number:
200-900-5
MDL number:
MFCD00000502
UNSPSC Code:
12352101
PubChem Substance ID:
329770119
NACRES:
NA.22

vapor density

3.7 (vs air)

Quality Level

200

vapor pressure

100 mmHg ( 25 °C)

grade

puriss.

assay

≥99.0% (GC)

form

liquid

autoignition temp.

752 °F

expl. lim.

6.4 %

refractive index

n20/D 1.387 (lit.)

bp

57 °C (lit.)

mp

−40 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)Cl

InChI

1S/C3H9ClSi/c1-5(2,3)4/h1-3H3

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

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General description

Chlorotrimethylsilane is a chloro-organosilane compound mainly used for silylation reactions.

Application

  • Chlorotrimethylsilane can be a non-toxic alternative to mercuric chloride as activator in samarium-promoted cyclopropanation of both allylic and α-allenic alcohols.
  • It can be used in combination with hexamethyldisilazane for the protection of alcohols by forming trimethylsilyl ethers via silylation.
  • It is employed in chloromethylation of polysulfones (PSUs).
  • It activates lithium hydride to convert it into a hydride source for the reductive silylation of carbonyl compounds.
  • Chlorotrimethylsilane/lithium bromide forms an effective reagent for the conversion of alcohols to bromides.
  • Chlorotrimethylsilane/sodium iodide in acetonitrile is a better alternative to iodotrimethylsilane for the cleavage of esters, lactones, carbamates, and ethers. It can also be used for the conversion of alcohols to iodides.
  • Chlorotrimethylsilane along with silver or ammonium nitrate forms an efficient regioselective nitrating reagent for the ipso-nitration of arylboronic acids to form the corresponding nitroarenes.
  • Chlorotrimethylsilane along with sodium nitrite or nitrate can be used for deoximation reactions.

Other Notes

Agente sililante

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

-18.4 °F - closed cup

flash_point_c

-28 °C - closed cup

ppe

Faceshields, Gloves, Goggles

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Certificados de análisis (COA)

Lot/Batch Number
BCCG5392
BCCF6132
BCCD9629
BCCD1185
BCCC3094

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Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 4, 261-261 (2014)
ipso-Nitration of Arylboronic Acids with Chlorotrimethylsilane- Nitrate Salts
Prakash GKS, et al.
Organic Letters, 6(13), 2205-2207 (2004)
Chlorotrimethylsilane-sodium nitrite or nitrate. Efficient deoximating reagents for aldoximes and ketoximes.
Jong, Gun Lee and Ki, Hoon Kwak and Je, Pil Hwang
Tetrahedron Letters, 31(46), 6677-6680 (1990)
J. Heberle et al.
Silylating Agents, 2nd ed. (1995)
Use of organosilicon reagents as protective groups in organic synthesis.
Lalonde M & Chan TH.
Synthesis, 1985(09), 817-845 (1985)
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