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563048

Sigma-Aldrich

2-Bromo-6-methylaniline

95%

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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.)

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

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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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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