B82006
2-Bromotoluene
99%
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About This Item
Linear Formula:
CH3C6H4Br
CAS Number:
Molecular Weight:
171.03
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-421-7
Beilstein/REAXYS Number:
1904176
MDL number:
Assay:
99%
Form:
liquid
InChI key
QSSXJPIWXQTSIX-UHFFFAOYSA-N
InChI
1S/C7H7Br/c1-6-4-2-3-5-7(6)8/h2-5H,1H3
SMILES string
Cc1ccccc1Br
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
Quality Level
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Application
2-Bromotoluene was used in the synthesis of (±)-isocomene.
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Chronic 2
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
174.2 °F
flash_point_c
79 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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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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