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Sigma-Aldrich

2-Mesitylmagnesium bromide solution

1.0 M in THF

Synonym(s):

2,4,6-Trimethylphenylmagnesium bromide

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About This Item

Linear Formula:
(CH3)3C6H2MgBr
CAS Number:
2633-66-1
Molecular Weight:
223.39
MDL number:
MFCD00009663
UNSPSC Code:
12352103
PubChem Substance ID:
24853266
NACRES:
NA.22
Pricing and availability is not currently available.

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

density

1.005 g/mL at 25 °C

SMILES string

Cc1cc(C)c([Mg]Br)c(C)c1

InChI

1S/C9H11.BrH.Mg/c1-7-4-8(2)6-9(3)5-7;;/h4-5H,1-3H3;1H;/q;;+1/p-1

InChI key

YXVSITSUDRGILL-UHFFFAOYSA-M

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Application

2-Mesitylmagnesium bromide is a Grignard reagent generally used to synthesize stable aromatic radical species such as dibenzoheptazethrene,[1] diindenoanthracene,[2] teranthene[3] and dimesitylindeno[2,1-a]fluorene[4] by kinetically blocking reactive molecular sites. It is also used in a variety of aromatic cross-coupling reactions.[5][6]

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17.0 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000411730
0000411730
0000265828
SHBQ6259
0000265828

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Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals.
Rudebusch, Gabriel E et al.
Nature Chemistry, 8(8), 753-753 (2016)
Indeno [2, 1-a] fluorene: An Air-Stable ortho-Quinodimethane Derivative.
Shimizu A and Tobe Y
Angewandte Chemie (International Edition in English), 123(30), 7038-7042 (2011)
Highly selective biaryl cross-coupling reactions between aryl halides and aryl Grignard reagents: a new catalyst combination of N-heterocyclic carbenes and iron, cobalt, and nickel fluorides.
Hatakeyama T, et al.
Journal of the American Chemical Society, 131(33), 11949-11963 (2009)
Dibenzoheptazethrene isomers with different biradical characters: an exercise of Clar?s aromatic sextet rule in singlet biradicaloids.
Sun, Zhe et al.
Journal of the American Chemical Society, 135(48), 18229-18236 (2013)
Iron-catalyzed selective biaryl coupling: Remarkable suppression of homocoupling by the fluoride anion.
Hatakeyama T and Nakamura M
Journal of the American Chemical Society, 129(32), 9844-9845 (2007)
View All Related Papers

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/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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