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196940

Sigma-Aldrich

1-(2-Aminophenyl)pyrrole

≥98%

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About This Item

Empirical Formula (Hill Notation):
C10H10N2
CAS Number:
6025-60-1
Molecular Weight:
158.20
EC Number:
227-884-2
MDL number:
MFCD00005344
UNSPSC Code:
12352100
PubChem Substance ID:
24851811
NACRES:
NA.22

Quality Level

100

Assay

≥98%

form

solid

mp

96-98 °C (lit.)

SMILES string

Nc1ccccc1-n2cccc2

InChI

1S/C10H10N2/c11-9-5-1-2-6-10(9)12-7-3-4-8-12/h1-8H,11H2

InChI key

GDMZHPUPLWQIBD-UHFFFAOYSA-N

General description

1-(2-Aminophenyl)pyrrole participates in Pt(IV)-catalyzed hydroamination triggered cyclization reaction to yield fused pyrrolo [1,2-a] quinoxalines. It reacts with aromatic or heteroaromatic aldehydes in ethanol and catalytic amounts of acetic acid to yield 4,5-dihydropyrrolo[1,2-a]quinoxalines. Thin films of poly(1-(2-aminophenyl)pyrrole) has been prepared via oxidative electropolymerization.

Application

1-(2-Aminophenyl)pyrrole was used in the synthesis of 4-substituted pyrrolo[1,2-a]quinoxaline derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - 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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW9582
MKCS8082
MKCQ6285
MKCP0401
MKCN3984

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Jean Guillon et al.
Bioorganic & medicinal chemistry, 15(1), 194-210 (2006-10-20)
An original series of 4-substituted pyrrolo[1,2-a]quinoxaline derivatives, new structural analogues of Galipea species quinoline alkaloids, was synthesized from various substituted 2-nitroanilines via multistep heterocyclizations and tested for in vitro antiparasitic activity upon Leishmania amazonensis and Leishmania infantum strains. Structure-activity relationships
Photoelectrochemical studies on poly [1-(2-aminophenyl) pyrrole]-Creation of a photoactive inorganic-organic semiconductor interface (IOI).
Kasem KK, et al.
Canadian Journal of Chemistry, 87(8), 1109-1116 (2009)
Nitin T Patil et al.
The Journal of organic chemistry, 75(10), 3371-3380 (2010-04-16)
A PtCl(4)-catalyzed hydroamination-triggered cyclization strategy to access biologically interesting N-containing heterocycles such as pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines is described. The reaction makes use of aminoaromatics such as 1-(2-aminophenyl)pyrroles, N-(2-aminophenyl)indoles, 2-(2-aminophenyl)indoles, and alkynes having a tethered hydroxyl group. Mechanistically, the reaction
A Versatile Synthesis of 4, 5-Dihydropyrrolo [1, 2-a] quinoxalines.
Abonia R, et al.
Journal of Heterocyclic Chemistry, 38(3), 671-674 (2001)

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