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Safety Information

92360

Sigma-Aldrich

Chlorotrimethylsilane

puriss., ≥99.0% (GC)

Synonym(s):

TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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About This Item

Linear Formula:
(CH3)3SiCl
CAS Number:
Molecular Weight:
108.64
Beilstein:
1209232
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.7 (vs air)

Quality Level

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

Silylating agent

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-18.4 °F - closed cup

Flash Point(C)

-28 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

92360-500ML:
92360-6X500ML:
92360-25ML:
92360-100ML:
92360-BULK:
92360-VAR:
92360-6X100ML:
92360-INTR:


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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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