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Sigma-Aldrich

p-Tolylmagnesium bromide solution

1.0 M in THF

Synonym(s):

4-Methylphenylmagnesium bromide

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About This Item

Linear Formula:
CH3C6H4MgBr
CAS Number:
4294-57-9
Molecular Weight:
195.34
Beilstein/REAXYS Number:
636491
MDL number:
MFCD00000040
UNSPSC Code:
12352103
PubChem Substance ID:
24867733
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

bp

65-67 °C

density

1.002 g/mL at 25 °C

SMILES string

Cc1ccc([Mg]Br)cc1

InChI

1S/C7H7.BrH.Mg/c1-7-5-3-2-4-6-7;;/h3-6H,1H3;1H;/q;;+1/p-1

InChI key

ZRJNGFJIBZKXTP-UHFFFAOYSA-M

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Related Categories

Application

p-Tolylmagnesium bromide is a common Grignard reagent. It can also be used in a variety of cross-coupling reactions.

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system, Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

1.4 °F

flash_point_c

-17 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Palladium-and Nickel-Catalyzed Kumada Cross-Coupling Reactions of gem-Difluoroalkenes and Monofluoroalkenes with Grignard Reagents.
Dai W
The Journal of Organic Chemistry, 79(21), 10537-10546 (2014)
Dinuclear Iron Complex-Catalyzed Cross-Coupling of Primary Alkyl Fluorides with Aryl Grignard Reagents.
Mo Z, et al.
Organometallics, 31(18), 6518-6521 (2012)
Palladium-catalyzed cross coupling of Grignard reagents with in situ-derived enol phosphates.
Miller JA
Tetrahedron Letters, 43(39), 7111-7114 (2002)
Takuji Hatakeyama et al.
Journal of the American Chemical Society, 131(33), 11949-11963 (2009-07-31)
Combinations of N-heterocyclic carbenes (NHCs) and fluoride salts of the iron-group metals (Fe, Co, and Ni) have been shown to be excellent catalysts for the cross-coupling reactions of aryl Grignard reagents (Ar(1)MgBr) with aryl and heteroaryl halides (Ar(2)X) to give

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