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Key Documents

563048

Sigma-Aldrich

2-Bromo-6-methylaniline

95%

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About This Item

Linear Formula:
Br(CH3)C6H3NH2
CAS Number:
Molecular Weight:
186.05
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

95%

refractive index

n20/D 1.6030 (lit.)

bp

105-107 °C/205 mmHg (lit.)

density

1.4780 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

Cc1cccc(Br)c1N

InChI

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

InChI key

LDUCMSVRKKDATH-UHFFFAOYSA-N

Application

2-Bromo-6-methylaniline can be used as a reactant to synthesize:
  • Alkyl substituted bromoindazole building blocks by Pd-catalyzed Suzuki coupling reaction with various vinyl boronic acids.
  • Difluoropyridoindole via Pd-catalyzed intramolecular Heck reaction with difluoropiperidinone.
  • 4-Methyl-N-phenyl-1H-benzo[d]imidazol-2-amine by one-pot Cu-catalyzed domino C-N cross-coupling reaction with iodobenzene and thiourea.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

215.1 °F - closed cup

flash_point_c

101.7 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Synthesis and evaluation of indazole based analog sensitive Akt inhibitors
Okuzumi T, et al.
Molecular Biosystems, 6(8), 1389-1402 (2010)
Novel synthesis of 4, 4-difluoropyrido [4, 3-b] indoles via intramolecular Heck reaction
Madaiah M, et al.
Tetrahedron Letters, 54(11), 1424-1427 (2013)
Copper-promoted one-pot approach: Synthesis of benzimidazoles
Boddapati SN, et al.
Molecules (Basel), 25(8), 1788-1788 (2020)

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