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B82200

Sigma-Aldrich

4-Bromotoluene

98%

Synonyme(s) :

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
26,50 €
100 G
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500 G
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About This Item

Formule linéaire :
CH3C6H4Br
Numéro CAS:
106-38-7
Poids moléculaire :
171.03
Beilstein:
1903636
Numéro CE :
203-391-8
Numéro MDL:
MFCD00000109
Code UNSPSC :
12352100
ID de substance PubChem :
24892060
Nomenclature NACRES :
NA.22

26,50 €

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Niveau de qualité

200

Essai

98%

Forme

solid

pb

184 °C (lit.)

Pf

26-29 °C (lit.)

Densité

1.39 g/mL at 25 °C (lit.)

Chaîne SMILES 

Cc1ccc(Br)cc1

InChI

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

Clé InChI

ZBTMRBYMKUEVEU-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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]

Application

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

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H332,H411

Classification des risques

Acute Tox. 4 Inhalation - Aquatic Chronic 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
STBL3488
STBK2551
STBJ9475
STBH8117
STBG1123V

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Consulter la Bibliothèque de documents

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
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 réponse

    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 réponse

    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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