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B82200

Sigma-Aldrich

4-Bromtoluol

98%

Synonym(e):

1-Methyl-4-bromobenzene, 4-Bromo-1-methylbenzene, 4-Methyl-1-bromobenzene, 4-Methylbromobenzene, 4-Tolyl bromide, p-Bromo(methyl)benzene, p-Methylbromobenzene, p-Tolyl bromide

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5 G
CHF 33.00
100 G
CHF 57.30
500 G
CHF 139.00

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5 G
CHF 33.00
100 G
CHF 57.30
500 G
CHF 139.00

About This Item

Lineare Formel:
CH3C6H4Br
CAS-Nummer:
106-38-7
Molekulargewicht:
171.03
Beilstein:
1903636
EG-Nummer:
203-391-8
MDL-Nummer:
MFCD00000109
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24892060
NACRES:
NA.22

CHF 33.00

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Qualitätsniveau

200

Assay

98%

Form

solid

bp

184 °C (lit.)

mp (Schmelzpunkt)

26-29 °C (lit.)

Dichte

1.39 g/mL at 25 °C (lit.)

SMILES String

Cc1ccc(Br)cc1

InChI

1S/C7H7Br/c1-6-2-4-7(8)5-3-6/h2-5H,1H3

InChIKey

ZBTMRBYMKUEVEU-UHFFFAOYSA-N

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Verwandte Kategorien

Allgemeine Beschreibung

4-Bromotoluene is a p-substituted aryl bromide.[1] 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.[2] 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.[1] Palladium catalyzed C-N cross-coupling reaction of 4-bromotoluene with piperidine in a microstructured continuous reactor has been described.[3] 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.[4]

Anwendung

4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction.[5]

Piktogramme

Exclamation markEnvironment
GHS07,GHS09

Signalwort

Warning

H-Sätze

H332,H411

Gefahreneinstufungen

Acute Tox. 4 Inhalation - Aquatic Chronic 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
STBL3488
STBK2551
STBJ9475
STBH8117
STBG1123V

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Die Dokumentenbibliothek aufrufen

Synthesis of ketones from alpha-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling.
Lukas J Goossen et al.
Angewandte Chemie (International ed. in English), 47(16), 3043-3045 (2008-03-11)
Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction.
Wang A-E, et al.
Tetrahedron, 61(1), 259-266 (2005)
Successful application of microstructured continuous reactor in the palladium catalysed aromatic amination.
Mauger C, et al.
Journal of Organometallic Chemistry, 690(16), 3627-3629 (2005)
Hong-Jie Chen et al.
Dalton transactions (Cambridge, England : 2003), 43(29), 11410-11417 (2014-06-18)
The C-O coupling reaction between 2,4-dimethylphenol and 4-bromotoluene catalyzed by the CuI/K2CO3/phen system can be inhibited by the radical scavenger cumene. Complexes [Cu(i)(phen)(1-(2,4-dimethylphenoxy)-4-methylbenzene)](+) (denoted as A), {H[Cu(i)(phen)(2,4-dimethylphenoxy)]}(+) and [Cu(i)(2,4-dimethylphenoxy)2](-) (denoted as B) were observed by in situ electrospray ionization mass
Naoya Kishikawa et al.
Journal of chromatography. A, 1216(40), 6873-6876 (2009-09-01)
The fluorogenic derivatization method for aryl halide was developed for the first time. This method was based on the formation of fluorescent biphenyl structure by Suzuki coupling reaction between aryl halides and non-fluorescent phenylboronic acid (PBA). We measured the fluorescence
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    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?

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    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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