6-Nitroindole

Name: 6-Nitroindole
Brand: ChemScene
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CAS No. 4769-96-4
Cat. No. CS-W001576
Purity≥96%
MDL No.MFCD00051497

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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General Information

CAS No. 4769-96-4
Cat. No. CS-W001576
Purity ≥96%
MDL No. MFCD00051497
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆N₂O₂
Molecular Weight None
Synonym(s) None
SMILES O=[N+](C1=CC2=C(C=C1)C=CN2)[O-]

Description

6-Nitroindole features a nitro group at the 6-position of the indole scaffold, imparting strong electron-withdrawing character. This functionalization enhances reactivity in transition-metal-catalyzed couplings and facilitates incorporation into bioactive scaffolds. The compound exhibits bench-stable handling properties and serves as a key building block in medicinal chemistry and materials science applications.

Application

6-Nitroindole serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C6 position via electrophilic substitution or transition-metal-catalyzed coupling. Its electron-deficient indole core enhances reactivity in Pd- and Ni-mediated cross-couplings, while the nitro group facilitates selective reduction to an amine or further derivatization. Bench-stable and readily purified by column chromatography, it functions as a key scaffold for heterocyclic libraries and API intermediates.

Safety Information

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GHS Pictogram :	GHS No : GHS08
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H341
Precautionary Statements : P280-P405-P501

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Computational Chemistry Data

TPSA 58.93
LogP 2.0761
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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6-Nitroindole

CAS No. 4769-96-4

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