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92360

Chlorotrimethylsilane

puriss., ≥99.0% (GC)

Synonym(s):

TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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25 ML

$33.80

100 ML

$91.30

500 ML

$252.00

$33.80


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About This Item

Linear Formula:
(CH3)3SiCl
CAS Number:
Molecular Weight:
108.64
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
EC Number:
200-900-5
MDL number:
Beilstein/REAXYS Number:
1209232
Assay:
≥99.0% (GC)
Form:
liquid

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Product Name

Chlorotrimethylsilane, puriss., ≥99.0% (GC)

SMILES string

[H][C@@]12CC(C)(C)CC[C@]1(C)CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C
C[Si](C)(C)Cl

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

InChI

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

vapor density

3.7 (vs air)

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.)

Quality Level

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1 of 4

This Item
9554189595384410
assay

≥99.0% (GC)

assay

≥99.0% (GC)

assay

≥99.0% (GC)

assay

-

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

mp

−40 °C (lit.)

mp

−40 °C (lit.)

mp

−40 °C (lit.)

mp

-

bp

57 °C (lit.)

bp

57 °C (lit.)

bp

57 °C (lit.)

bp

-

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.387 (lit.)

refractive index

n20/D 1.387 (lit.)

refractive index

n20/D 1.387 (lit.)

refractive index

-

Application

  • Chlorotrimethylsilane can be a non-toxic alternative to mercuric chloride as activator in samarium-promoted cyclopropanation of both allylic and α-allenic alcohols.[1]
  • It can be used in combination with hexamethyldisilazane for the protection of alcohols by forming trimethylsilyl ethers via silylation.[2]
  • It is employed in chloromethylation of polysulfones (PSUs).[3]
  • It activates lithium hydride to convert it into a hydride source for the reductive silylation of carbonyl compounds.[4]
  • Chlorotrimethylsilane/lithium bromide forms an effective reagent for the conversion of alcohols to bromides.[5]
  • 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.[6]
  • 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.[7]
  • Chlorotrimethylsilane along with sodium nitrite or nitrate can be used for deoximation reactions.[8]

General description

Chlorotrimethylsilane is a chloro-organosilane compound mainly used for silylation reactions.[9]

Other Notes

Silylating agent[10][11]

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

Storage Class

3 - Flammable liquids

wgk

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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H.H. Hergott et al.
Synthesis, 626-626 (1980)
ipso-Nitration of Arylboronic Acids with Chlorotrimethylsilane- Nitrate Salts
Prakash GKS, et al.
Organic Letters, 6(13), 2205-2207 (2004)
J. Heberle et al.
Silylating Agents, 2nd ed. (1995)
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)
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 4, 261-261 (2014)

Articles

Results of a study involving the ability few Fluka silylating reagents to form GC-MS-compatible trimethylsilylmethyl derivatives of NSAIDs

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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