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376868

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

376868-1G:
376868-250MG:
376868-VAR:
376868-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP4670V
U16846
19326CR
14724EA
12429JQ

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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)
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.
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)

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