6-Chloro-5-nitro-2,3-dihydro-1H-indole: Key Facts & FAQs
6-Chloro-5-nitro-2,3-dihydro-1H-indole: Key Facts & FAQs
6‐chloro‐5‐nitro‐2,3‐dihydro‐1H‐indole is a halogenated, nitro-substituted indoline scaffold widely employed as a reactive building block in medicinal chemistry and heterocyclic synthesis.
- Chemical Name
- 6-chloro-5-nitro-2,3-dihydro-1H-indole
- SKU / Catalog Number
- C174951
- Core Scaffold
- Indoline (2,3-dihydro-1H-indole) with electron-withdrawing chloro and nitro substituents at positions 6 and 5 respectively
- Primary Application
- Pharmaceutical and agrochemical intermediate; used in the synthesis of functionalized indoline and indole derivatives
- Functional Groups
- Secondary amine (NH), aryl chloride, aryl nitro group
- Supplier
- Aladdin Scientific (C174951)
What Is 6-Chloro-5-nitro-2,3-dihydro-1H-indole?
6-Chloro-5-nitro-2,3-dihydro-1H-indole belongs to the indoline family of compounds, which are partially saturated bicyclic heterocycles. The indoline core consists of a benzene ring fused to a saturated five-membered ring containing a secondary nitrogen (NH). In this particular compound, an electron-withdrawing nitro group (–NO2) is installed at the 5-position and a chloro substituent (–Cl) at the 6-position of the aromatic ring, rendering the molecule a useful electrophilic and nucleophilic handle for further chemical elaboration.
The combination of the free NH, the aryl chloride, and the aryl nitro group offers three independent sites for chemical transformation: N-alkylation or N-acylation at the amine, cross-coupling or nucleophilic aromatic substitution at the C-6 chloride, and reduction or further functionalization of the C-5 nitro group to an amine or other functional group. This versatility makes the compound a valued building block in medicinal chemistry programs targeting kinase inhibitors, GPCR ligands, and other biologically active heterocyclic scaffolds.
Handling, Safety, and Storage
As with most aromatic nitro compounds and secondary amines, 6-chloro-5-nitro-2,3-dihydro-1H-indole should be handled with appropriate laboratory precautions. Researchers should consult the product-specific Safety Data Sheet (SDS) provided by Aladdin Scientific before use. General precautions include working in a well-ventilated fume hood, wearing appropriate personal protective equipment (gloves, lab coat, and eye protection), and avoiding inhalation of dust or vapors.
For storage, the compound should be kept in a tightly sealed container away from heat, light, moisture, and incompatible materials such as strong acids, strong bases, and reducing agents. Unless otherwise specified on the certificate of analysis (CoA), storage at room temperature in a dry environment is typically recommended for solid aromatic nitro building blocks; however, researchers should verify recommended storage conditions on the product page or CoA for SKU C174951. Disposal must comply with local regulations governing halogenated and nitro-containing organic waste.
Synthetic Applications and Reactivity
The three reactive sites on 6-chloro-5-nitro-2,3-dihydro-1H-indole can be exploited in a logical sequence to build complex molecular architectures. A common synthetic strategy begins with selective N-functionalization of the indoline nitrogen, followed by palladium-catalyzed cross-coupling (e.g., Suzuki, Buchwald–Hartwig, or Negishi couplings) at the C-6 aryl chloride, and finally reduction of the C-5 nitro group to an aniline for further amide bond formation, cyclization, or diazotization chemistry.
Nitro reduction can be achieved by catalytic hydrogenation (H2/Pd-C), iron/acetic acid, or tin(II) chloride reduction, depending on the functional group tolerance required. The resulting 5-amino-6-chloro-2,3-dihydro-1H-indole intermediate is itself a valuable bifunctional scaffold for building fused ring systems or elaborating kinase-pharmacophore motifs. Researchers exploiting this compound in diversity-oriented synthesis or fragment-based drug discovery should consider protecting the secondary amine prior to cross-coupling steps to avoid catalyst poisoning or undesired N-arylation side reactions.
Ordering and Specifications from Aladdin Scientific
6-Chloro-5-nitro-2,3-dihydro-1H-indole is available from Aladdin Scientific under SKU C174951. To obtain detailed information on available pack sizes, current purity specifications, pricing, and lead times, visit the product listing on the Aladdin Scientific website or contact the Aladdin customer service team directly.
A Certificate of Analysis (CoA) confirming identity (e.g., by 1H NMR and/or HPLC) and purity is available upon request for each lot. Researchers requiring custom quantities, high-purity grades, or isotopically labeled variants are encouraged to submit an inquiry through the Aladdin custom synthesis request portal. For bulk procurement, institutional pricing, or volume discounts, lab managers should contact Aladdin's sales team with anticipated annual consumption volumes.
Frequently asked questions
What is the CAS number and molecular formula of 6-chloro-5-nitro-2,3-dihydro-1H-indole?
The molecular formula of 6-chloro-5-nitro-2,3-dihydro-1H-indole is C₈H₇ClN₂O₂, giving a molecular weight of approximately 198.60 g/mol. The CAS number and exact purity specification for SKU C174951 should be confirmed on the Aladdin Scientific product page or Certificate of Analysis, as these details are lot-dependent.
Which reactions can be performed at the secondary amine (NH) of this indoline?
The secondary amine of 6-chloro-5-nitro-2,3-dihydro-1H-indole can undergo N-alkylation with alkyl halides or aldehydes via reductive amination, N-acylation with acyl chlorides or anhydrides to form amides, N-sulfonylation with sulfonyl chlorides, and N-carbamate formation (Boc, Cbz, Fmoc protection). These transformations are routinely performed under mild to moderate conditions and allow protection or elaboration of the amine prior to further functionalization of the aromatic ring.
How should I store 6-chloro-5-nitro-2,3-dihydro-1H-indole (C174951) to maintain its stability?
Store the compound in a tightly sealed container, protected from light, moisture, and heat. For specific storage temperature recommendations and shelf-life data, always refer to the Aladdin Scientific Certificate of Analysis and Safety Data Sheet supplied with each lot of C174951. Keeping the compound under inert atmosphere (e.g., argon or nitrogen) after opening is advisable if the material will be stored for extended periods.
Can the aryl chloride at C-6 participate in palladium-catalyzed cross-coupling reactions?
Yes. Aryl chlorides are competent partners in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, and Buchwald–Hartwig amination, particularly when electron-withdrawing groups (such as the adjacent nitro group) activate the ring toward oxidative addition. Protecting the indoline NH prior to coupling is generally recommended to avoid catalyst deactivation and to improve yield and selectivity.
Is 6-chloro-5-nitro-2,3-dihydro-1H-indole available in custom pack sizes or higher purity grades?
Aladdin Scientific offers custom quantity and purity options for many of its building blocks. For non-standard pack sizes, high-purity grades, or GMP-quality material, researchers and procurement managers should submit a custom synthesis or bulk inquiry directly to Aladdin's sales or customer service team, referencing SKU C174951.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for nitro reduction and N-functionalization chemistry.)
- Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
- Aladdin Scientific. Product page for 6-chloro-5-nitro-2,3-dihydro-1H-indole, SKU C174951. Aladdin Scientific Corp. (accessed 2024).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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