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227234

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

Quality Level

100

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, diindenoanthracene, teranthene and dimesitylindeno[2,1-a]fluorene by kinetically blocking reactive molecular sites. It is also used in a variety of aromatic cross-coupling reactions.

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
SHBM7886
SHBM2057
SHBK1556
SHBH8478
SHBG9168V

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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)
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)
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)
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)
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)
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