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B82200 Aldrich

4-Bromotoluene

98%

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Properties

Related Categories Aryl, Building Blocks, C7, Chemical Synthesis, Halogenated Hydrocarbons,
assay   98%
bp   184 °C(lit.)
mp   26-29 °C(lit.)
density   1.39 g/mL at 25 °C(lit.)

Description

Packaging

5, 100, 500 g in glass bottle

Application

4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction.1

General description

4-Bromotoluene is a p-substituted aryl bromide.2 4-Bromotoluene undergoes C-O coupling reaction with 2,4-dimethylphenol catalyzed by the CuI/K2CO3/phen system. Complexes [Cu(phen)(1-(2,4-dimethylphenoxy)-4-methylbenzene)]+, {H[Cu(phen)(2,4-dimethylphenoxy)]}+ and [Cu(2,4-dimethylphenoxy)2]- were reported as intermediates during the reaction by in situ electrospray ionization mass spectrometry (ESI-MS) analysis.3 Suzuki coupling reaction of 4-bromotoluene and non-fluorescent phenylboronic acid (PBA) in the presence of palladium (II) acetate as a catalyst has been studied.2 Palladium catalyzed C-N cross-coupling reaction of 4-bromotoluene with piperidine in a microstructured continuous reactor has been described.4 4-Bromotoluene has been reported to undergo Heck reaction with styrene in the presence of in situ generated palladium complexes of phosphine-functionalized N-heterocyclic carbene ligands.5

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
RTECS 
XS7965600
Flash Point(F) 
185 °F
Flash Point(C) 
85 °C

Protocols & Articles

Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

Peer-Reviewed Papers

References

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1. Synthesis of ketones from alpha-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling. Goossen LJ, Rudolphi F, Oppel C, et al. Angew. Chem. Int. Ed. Engl. 47(16), 3043-5, (2008)

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2. Fluorogenic derivatization of aryl halides based on the formation of biphenyl by Suzuki coupling reaction with phenylboronic acid. Kishikawa N, Kubo K, Hammad SF, et al. J. Chromatogr. A 1216(40), 6873-6, (2009)

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3. Possible intermediates of Cu(phen)-catalyzed C-O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies. Chen HJ, Hsu IJ, Tseng MC, et al. Dalton Trans. 43(29), 11410-7, (2014)

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4. Successful application of microstructured continuous reactor in the palladium catalysed aromatic amination. Mauger C, et al. J. Organomet. Chem. 690(16), 3627-29, (2005)

5. Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction. Wang A-E, et al. Tetrahedron 61(1), 259-66, (2005)

Beil. 5,IV,827

Aldrich MSDS 1, 291:B / Corp MSDS 1 (1), 584:A / FT-IR 1 (1), 991:A / FT-IR 2 (2), 1702:A / FT-NMR 1 (2), 88:C / IR-Spectra (2), 532:A / IR-Spectra (3), 597:C / NMR-Reference 2 (1), 795:C / RegBook 1 (1), 1177:M / Structure Index 1, 180:D:9 / Vapor Phase 3, 909:A

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