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B82006

Sigma-Aldrich

2-Bromotoluene

99%

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About This Item

Linear Formula:
CH3C6H4Br
CAS Number:
95-46-5
Molecular Weight:
171.03
Beilstein:
1904176
EC Number:
202-421-7
MDL number:
MFCD00000068
UNSPSC Code:
12352100
PubChem Substance ID:
24892059
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.555 (lit.)

bp

58-60 °C/10 mmHg (lit.)

mp

−27 °C (lit.)

density

1.422 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

Cc1ccccc1Br

InChI

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

InChI key

QSSXJPIWXQTSIX-UHFFFAOYSA-N

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General description

2-Bromotoluene is an an electron rich heteroaryl bromide. Heck reactions of 2-bromo toluene with cycloalkene (cyclododecene) and linear alkenes (dec-1-ene, allylbenzene) catalyzed by tedicyp (cis,cis,cis -1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane)-palladium complex has been studied. Vibrational spectral analysis of 2-bromobenzene by Raman and infrared spectroscopy at 50-4000cm-1 has been investigated. Suzuki cross-coupling of 2-bromobenzene with benzeneboronic acid catalyzed by the Tedicyp-palladium complex has been studied. Suzuki coupling of 2-bromotoluene with phenylboronic acid using palladium nanoparticles supported on alumina-based oxides as catalyst has been reported.

Application

2-Bromotoluene was used in the synthesis of (±)-isocomene.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F

Flash Point(C)

79 °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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Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids.
Feuerstein M, et al.
Tetrahedron Letters, 42(38), 6667-6670 (2001)
Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst.
Berthiol F, et al.
Tetrahedron Letters, 44(6), 1221-1225 (2003)
Palladium nanoparticles supported on alumina-based oxides as heterogeneous catalysts of the Suzuki-Miyaura reaction.
Gniewek A, et al.
J. Catal., 254(1), 121-130 (2008)
Synthetic studies on arene-olefin cycloadditions. ii. total synthesis of (?)-isocomene.
Wender PA and Geoffrey BD.
Tetrahedron, 37(25), 4445-4450 (1981)
Sven Herbers et al.
Physical chemistry chemical physics : PCCP, 22(20), 11490-11497 (2020-05-12)
The internal rotation of methyl groups and nuclear quadrupole moments of the halogens Cl, Br, I in o-halotoluenes cause complex spectral fine and hyperfine structures in rotational spectra arising from angular momentum coupling. Building on the existing data regarding o-fluorotoluene
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