Description

3-Bromo-5-nitro-1H-indole (CAS No. 525593-33-3) is a high-purity heterocyclic organic compound with the molecular formula C₈H₅BrN₂O₂. This brominated nitroindole derivative is a versatile building block in medicinal chemistry, pharmaceutical research, and material science applications. The compound features a reactive bromine substituent at the 3-position and an electron-withdrawing nitro group at the 5-position of the indole scaffold, making it an excellent intermediate for cross-coupling reactions, nucleophilic substitutions, and other synthetic transformations.

Our product is rigorously tested for quality, with ≥95% purity confirmed by HPLC and NMR spectroscopy. It is supplied as a crystalline solid with proper storage recommendations to ensure stability. Ideal for researchers developing novel drug candidates, agrochemicals, or functional materials, this compound is available in various packaging options to suit laboratory-scale needs.

Properties

• CAS Number: 525593-33-3
• Complexity: 219
• IUPAC Name: 3-bromo-5-nitro-1H-indole
• InChI: InChI=1S/C8H5BrN2O2/c9-7-4-10-8-2-1-5(11(12)13)3-6(7)8/h1-4,10H
• InChI Key: LBTWTOYAMQQAKO-UHFFFAOYSA-N
• Exact Mass: 239.95344
• Molecular Formula: C8H5BrN2O2
• Molecular Weight: 241.04
• SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=CN2)Br
• Topological: 61.6
• Monoisotopic Mass: 239.95344
• Synonyms: 3-bromo-5-nitro-1H-indole, 525593-33-3, DTXSID60655590, DTXCID60606340, 860-871-5, 3-BROMO-5-NITROINDOLE, MFCD11110951, 1H-Indole, 3-bromo-5-nitro-, SCHEMBL981675, LBTWTOYAMQQAKO-UHFFFAOYSA-N, AKOS009322817, CS-W007030, AC-30545, DS-15215, SY006253, DB-014613, EN300-62801, Z382706826

Application

3-Bromo-5-nitro-1H-indole serves as a key intermediate in the synthesis of pharmacologically active indole derivatives, particularly in developing kinase inhibitors and antimicrobial agents. The bromo and nitro functional groups allow for sequential functionalization via Suzuki-Miyaura coupling or nucleophilic aromatic substitution reactions. Researchers utilize this compound to construct complex heterocyclic systems for drug discovery programs targeting cancer and CNS disorders. It also finds use in materials science as a precursor for organic electronic materials.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.