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124087

Sigma-Aldrich

2-Bromo-4-methylaniline

98%

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Synonym(s):
2-Bromo-p-toluidine, 4-Amino-3-bromotoluene
Linear Formula:
BrC6H3(CH3)NH2
CAS Number:
583-68-6
Molecular Weight:
186.05
Beilstein:
1931711
EC Number:
209-515-7
MDL number:
MFCD00007635
UNSPSC Code:
12352100
PubChem Substance ID:
24847595
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.602 (lit.)

bp

240 °C (lit.)

mp

14-16 °C (lit.)

density

1.5 g/mL at 25 °C (lit.)

SMILES string

Cc1ccc(N)c(Br)c1

InChI

1S/C7H8BrN/c1-5-2-3-7(9)6(8)4-5/h2-4H,9H2,1H3

InChI key

UVRRJILIXQAAFK-UHFFFAOYSA-N

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General description

2-Bromo-4-methylaniline participates in palladium catalyzed selective amination of 3-bromoquinoline to yield 3-(2-bromo-4-methylphenylamino) quinoline. It reacts with ethyl and methyl imidazo[1,2-a]pyridine-2-carboxylates in the presence of Me3Al to form amide.

Application

2-Bromo-4-methylaniline has been used in the synthesis of iminophosphoranes.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Synthesis of 7H-indolo [2, 3-c] quinolines: study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino) quinolines under microwave irradiation.
Koubachi J, et al.
Tetrahedron, 66(10), 1937-1946 (2010)
Synthesis of 7H-indolo [2, 3-c] quinolines: study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino) quinolines under microwave irradiation.
Hostyn S, et al.
Tetrahedron, 62(19), 4676-4684 (2006)
Synthesis and reactivity of ortho-palladated arylcarbodiimides and aryl isothiocyanates. Formation of C-palladated quinazolines. Synthesis of 2-aminoquinolines.
Vicente J, et al.
Organometallics, 23(20), 4711-4722 (2004)

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