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205354

Sigma-Aldrich

(Chloromethyl)trimethylsilane

98%

Synonym(s):

(Trimethylsilyl)methyl chloride

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About This Item

Linear Formula:
(CH3)3SiCH2Cl
CAS Number:
2344-80-1
Molecular Weight:
122.67
Beilstein:
906705
EC Number:
219-058-5
MDL number:
MFCD00000878
UNSPSC Code:
12352103
PubChem Substance ID:
24852326
NACRES:
NA.22
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vapor pressure

~25 mmHg ( 20 °C)

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.418 (lit.)

bp

98-99 °C (lit.)

density

0.879 g/mL at 25 °C (lit.)

functional group

chloro

SMILES string

C[Si](C)(C)CCl

InChI

1S/C4H11ClSi/c1-6(2,3)4-5/h4H2,1-3H3

InChI key

OOCUOKHIVGWCTJ-UHFFFAOYSA-N

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Application

(Chloromethyl)trimethylsilane can be treated with aldehydes or ketones in the presence of triphenylphosphine to synthesize terminal alkenes.[1] It can also be used in the preparation of a reagent, trimethylsilylmethyl magnesium chloride, commonly used in Peterson methylenation.[2][3]

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

24.8 °F - closed cup

Flash Point(C)

-4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9948
SHBR7477
27496KJV
35397LJ
39697LJ

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Direct synthesis of terminal olefins from ketones. Application of (chloromethyl) trimethylsilane to a Wittig reaction.
Sekiguchi A and Ando W
The Journal of Organic Chemistry, 44(3), 413-415 (1979)
Methylenation of Perfluoroalkyl Ketones using a Peterson Olefination Approach.
Hamlin T A, et al.
The Journal of Organic Chemistry, 79(3), 1145-1155 (2014)
Synthesis of alkenes from carbonyl compounds and carbanions alpha to silicon. III. Full report and a synthesis of the sex pheromone of gypsy moth.
Chan T H and Chang E
The Journal of Organic Chemistry, 39(22), 3264-3268 (1974)

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Single-Electron Oxidation Transformations

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Questions

1–2 of 2 Questions  

  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/449/386/product-dating-information-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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