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Sigma-Aldrich

2-(2-Aminophenyl)indole

97%

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About This Item

Empirical Formula (Hill Notation):
C14H12N2
CAS Number:
32566-01-1
Molecular Weight:
208.26
MDL number:
MFCD00134432
UNSPSC Code:
12352100
PubChem Substance ID:
24863471

assay

97%

mp

154-155 °C (lit.)

SMILES string

Nc1ccccc1-c2cc3ccccc3[nH]2

InChI

1S/C14H12N2/c15-12-7-3-2-6-11(12)14-9-10-5-1-4-8-13(10)16-14/h1-9,16H,15H2

InChI key

IAKRGXQCKYFJCB-UHFFFAOYSA-N

General description

2-(2-Aminophenyl)indole is an indole derivative. It has been reported as an amination reagent. 2-(2-Aminophenyl)indole undergoes condensation with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) to afford new 6-cyanoindolo[3,2-c]quinoline derivatives, having pharmacological applications.

Application

2-(2-Aminophenyl)indole may be used in the preparation of novel indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines. It may be used in the synthesis of mono and bis-indolo[1,2-c] quinazolines.
Reactant in:
  • cascade reactions of benzopyranylidenemalonates with mono- and dinucleophiles

Reactant for preparation of:
  • Mono-, bis-indolo[1,2-c]quinazolines as antimicrobial agents
  • Isocryptolepine alkaloid with antimalarial activity
  • Cyanoindolo[3,2-c]quinolines and benzimidazo[1,2-c]quinazolines as antitumor agents

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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 of some new mono, bis-indolo [1, 2-c] quinazolines: evaluation of their antimicrobial studies.
Rohini R, et al.
Journal of the Brazilian Chemical Society, 21(5), 897-904 (2010)
Novel 6-substituted benzothiazol-2-yl indolo [1, 2-< i> c</i>] quinazolines and benzimidazo [1, 2-< i> c</i>] quinazolines.
Frere S, et al.
Tetrahedron, 59(6), 773-779 (2003)
C Lamazzi et al.
Bioorganic & medicinal chemistry letters, 10(19), 2183-2185 (2000-09-30)
Novel 6-cyanoindolo[3,2-c]quinoline and 6-cyanobenzimidazo[1,2-c]quinazoline derivatives have been synthesised by treatment of the appropriate aromatic amines with 4.5-dichloro-1,2,3-dithiazolium chloride 1 (Appel salt). The cytotoxicity and the effect of these compounds on cellular growth were measured.
Simultaneous and Sensitive HPLC Determination of Mono-and Disaccharides, Uronic Acids, and Amino Sugars after Derivatization by Reductive Amination.
Fischer K, et al.
Acta Hydrochimica et Hydrobiologica, 31(2), 134-144 (2003)

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