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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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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)
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)
Synthetic studies on arene-olefin cycloadditions. ii. total synthesis of (?)-isocomene.
Wender PA and Geoffrey BD.
Tetrahedron, 37(25), 4445-4450 (1981)
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)
Maryam Shokrollahi et al.
Combinatorial chemistry & high throughput screening, 22(8), 570-576 (2019-10-18)
Phencyclidine (PCP, I) is a synthetic drug with remarkable physiological properties. PCP and its analogues exert many pharmacological activities and interact with some neurotransmitter systems in the central nervous system like particular affinity for PCP sites in NMDA receptors or
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Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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