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442178

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:
636491
MDL number:
MFCD00000040
UNSPSC Code:
12352103
PubChem Substance ID:
24867733
NACRES:
NA.22

Quality Level

100

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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Application

p-Tolylmagnesium bromide is a common Grignard reagent. It can also be used in a variety of 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,EUH018,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F

Flash Point(C)

-17 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium-catalyzed cross coupling of Grignard reagents with in situ-derived enol phosphates.
Miller JA
Tetrahedron Letters, 43(39), 7111-7114 (2002)
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-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)
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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