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167215

Sigma-Aldrich

3-Bromotoluene

98%

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About This Item

Fórmula lineal:
CH3C6H4Br
Número de CAS:
591-17-3
Peso molecular:
171.03
Beilstein/REAXYS Number:
1903633
EC Number:
209-702-3
MDL number:
MFCD00000085
UNSPSC Code:
12352100
eCl@ss:
39060138
PubChem Substance ID:
24850201
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.552 (lit.)

bp

183.7 °C (lit.)

mp

−40 °C (lit.)

density

1.41 g/mL at 25 °C (lit.)

SMILES string

Cc1cccc(Br)c1

InChI

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

InChI key

WJIFKOVZNJTSGO-UHFFFAOYSA-N

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General description

3-Bromotoluene is an electron-rich aryl bromide. It participates in the Heck reaction. 3-Bromotoluene undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It undergoes palladium-catalysed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.

Application

3-Bromotoluene was used in the precise determination of bromine isotope ratio in organic compounds by MC-ICPMS ( Multicollector-Inductively Coupled Plasma Mass Spectrometer).

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

140.0 °F

flash_point_c

60 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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Naoki Ishida et al.
Chemical communications (Cambridge, England), (42)(42), 4381-4383 (2007-10-25)
The palladium-catalysed reaction of alkynyltriarylborates with aryl halides afforded trisubstituted alkenylboranes, in which two different aryl groups were installed across the carbon-carbon double bond in a cis arrangement.
Heck reaction with an alkenylidenecyclopropane: the formation of arylallylidenecyclopropanes.
Fall Y, et al.
Tetrahedron Letters, 48(20), 3579-3581 (2007)
Efficient cyanation of aryl bromides with K4[Fe(CN)6] catalyzed by a palladium-indolylphosphine complex.
Yeung PY, et al.
Tetrahedron Letters, 52(52), 7038-7041 (2011)
High precision determination of bromine isotope ratio by GC-MC-ICPMS.
Gelman F and Halicz L.
International Journal of Mass Spectrometry, 289(2), 167-169 (2010)
Naoyuki Yasaka et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 34(10), 1183-1188 (2018-10-12)
Aryl halides are a very important category of compounds that include many vital drugs and key industrial additives, such as clofibrate and bromobenzene, respectively. Due to their importance, our research group previously developed a novel fluorescence labeling approach for their

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