This compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Recensioni
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Application Protocols
Not applicable. No standardized bioassay or immunoassay protocols are associated with this small-molecule building block. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.
Biological Roles
Contextualizing the indole motif in biology while clarifying the intended use of this item.
Item-specific
Research Use Note: For research use only.
General indole biology (literature; not specific to this compound)
Indole is a privileged scaffold in biochemistry: the side chain of L-tryptophan, the chromophore core of many natural products, and a key fragment in signaling molecules (e.g., indole-3-acetic acid in plants, serotonin precursors).
Halogenation on the benzene ring modulates lipophilicity, polarizability, and potential halogen-bonding interactions, properties often explored in medicinal chemistry SAR to tune permeability and target recognition.
Relevance of 5,7-disubstitution (general)
Orthogonal reactivity of C–I and C–Br enables rapid access to libraries of 5,7-disubstituted indoles for probing structure–activity relationships in enzyme or receptor studies conducted in vitro (no clinical or therapeutic claims).
This product is supplied strictly as a synthetic building block; no biological activity is claimed or implied.
Buffer Applications
This compound is a neutral, poorly water-soluble heteroaromatic building block and is not used as a buffering agent. For aqueous experimental work, dissolve in a miscible organic co-solvent (e.g., DMSO) before dilution into buffered systems if solubility and assay design permit.
Green Alternatives
Opportunities to reduce environmental footprint while maintaining reactivity for dihalogenated indole couplings.
Solvent substitutions (literature/general)
Replace DMF/NMP with 2-MeTHF, CPME, cyclopentyl methyl ether, or toluene/dioxane mixtures; consider aqueous micellar media (TPGS-750-M, Savie) for Suzuki couplings.
Swap DCM with EtOAc or MTBE for extractions and chromatography where feasible.
Base and reagent choices
Favor inorganic carbonates (K2CO3, K3PO4) in water-containing media over strong alkoxides where compatible.
Employ boronic acids/esters over stannanes to avoid organotin waste (i.e., Suzuki vs Stille).
Catalyst and loading
Use modern Pd catalysts with bulky biaryl phosphines (SPhos/XPhos) at low loadings (0.1–1 mol%) or nickel catalysis for certain couplings to reduce precious metal use (literature-dependent).
Energy and process
Microwave or continuous-flow heating can shorten reaction times and improve space–time yields, lowering energy per mole.
Illustration (general comparison)
Conventional: DMF, 100–120 °C, Pd(PPh3)4 (2–5 mol%), chlorinated extraction.
Greener variant: 2-MeTHF/H2O, 70–90 °C, Pd–SPhos (0.5–1 mol%), EtOAc extraction, micellar catalysis where applicable.
Note: Optimize with small-scale trials; actual solvent/catalyst choices depend on coupling partner and protecting group stability.
Pharmaceutical Uses
Formulation and manufacturing context without therapeutic claims.
Intended use
Research-use building block for discovery chemistry. Not an active pharmaceutical ingredient.
Potential roles in drug development workflows (general)
Intermediate for synthesizing 5,7-disubstituted indole cores during hit-to-lead and lead optimization.
Enables installation of two distinct vectors via sequential couplings, facilitating rapid preparation of analog sets for ADME and potency screening.
Regulatory status
No pharmacopeial monograph is expected for this specialized intermediate. Any GMP usage would require custom qualification; this catalog listing is for research use only.
Developability considerations (general)
Residual Pd/Ni from cross-couplings should be controlled by scavengers or metal-sensitive workups if downstream pharmaceutical assessment is anticipated.
Choice of N-protecting group (Boc, SEM) can affect crystallinity and purification profiles of advanced intermediates.
Physical Properties
Key physicochemical attributes relevant to handling and method development.
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for this scaffold (not specifications for this item)
Physical state: typically a pale to off-white crystalline solid for dihalogenated indoles.
Solubility profile: expected sparing solubility in water; soluble in polar aprotic organics (DMSO, DMF, NMP) and moderately in chlorinated/aromatic solvents (DCM, chloroform, toluene). Actual solubility depends on sample and temperature.
Acid–base: pyrrolic NH is weakly acidic (indole pKa ~16–17 in DMSO, literature). N–H can hydrogen bond; deprotonation requires strong base.
Lipophilicity: aryl bromide/iodide substitution generally increases logP vs indole (qualitative, literature).
Volatility: negligible; thermal stability typical of aryl halides, but prolonged heating may cause decomposition/halogen loss.
Not specified for this item; refer to CoA/Spec Sheet
Melting point, boiling point (decomposes), density, refractive index, UV–Vis cutoff/ε, water content, residual metals: Not specified for this item; refer to CoA/Spec Sheet.
Note: Use measured values from the item’s CoA for method validation, DSC/TGA, or formulation; literature values are only heuristic starting points.
Quality and Grades
Understanding grade and analytical expectations helps match the material to your application.
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (not item-specific specifications)
Research grade small-molecule building blocks are commonly supplied at ≥95% purity by HPLC or NMR assay. For demanding cross-couplings, trace metal and halide content, water, and residual solvents can influence outcomes.
If UV transparency is relevant (e.g., for photochemistry or analytical detection), verify UV–Vis background on the CoA. For medicinal chemistry, additional release tests (residual Pd, KF water, LC–MS purity, HRMS) may be desired.
Stabilizers: None are typical for indole solids; however, protection from light and moisture (as specified for this item) helps maintain integrity and limits adventitious oxidation or hydrolysis.
Recommendations
Request and review the batch CoA for assay method, purity, and impurity profile before route-critical couplings.
For chromatography-sensitive work, consider an extra recrystallization or short silica plug if the CoA indicates marginal purity.
If metal content matters (e.g., in photocatalysis or after catalytic coupling), consider ICP-MS screening post-reaction; item-specific metal limits are Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
This dihalogenated indole is a versatile bifunctional electrophile enabling sequential, site-selective functionalization on the indole benzene ring.
Chemoselectivity: The C–I bond at C7 is more reactive than the C–Br at C5, allowing stepwise installation of two different substituents. Typical sequence: couple at I (Suzuki/Sonogashira/Buchwald–Hartwig), then couple at Br under slightly harsher conditions.
Suzuki–Miyaura: Pd(PPh3)4 or Pd-PEPPSI-type catalysts; bases K2CO3, Cs2CO3, or K3PO4; solvents dioxane/H2O, toluene/H2O, or DMF. Aryl/alkenyl/heteroaryl boron partners commonly deliver 60–90% yields on the iodide (literature).
Sonogashira: Pd/Cu co-catalysis (Pd(PPh3)2Cl2 + CuI) or copper-free systems; amine base (Et3N, DIPEA); THF/Et3N or DMF; alkyne installs at C7 first.
Buchwald–Hartwig: Aryl amination at C7 using Pd2(dba)3 + BINAP/XPhos; NaOtBu or Cs2CO3; toluene/dioxane. Follow with C5 coupling using stronger ligands (BrettPhos, RuPhos) and higher temperature.
N-protection strategies (general)
The indole NH can coordinate to Pd or undergo N-arylation. Installing Boc, Cbz, or SEM often improves yields and regioselectivity. Boc can be removed under acid after couplings.
Metalation/halogen–metal exchange (general)
Selective activation of the C–I site with iPrMgCl·LiCl at −30 to 0 °C enables subsequent electrophile trapping (e.g., formylation, acylation), while leaving C–Br intact.
Applications
Efficient entry to 5,7-disubstituted indoles found in materials, dye chemistry, and as advanced intermediates in medicinal chemistry SAR campaigns (research use only).
Reaction Conditions
Representative, literature-sourced conditions to exploit the I/Br differentiation on the indole ring. These are general guidelines; optimize for your substrates.
Suzuki–Miyaura at C7–I (general literature)
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI/iPr·XPhos systems.
Base: K2CO3, Cs2CO3, or K3PO4 (2–3 equiv).
Solvent: 1,4-dioxane/H2O (3:1) or toluene/H2O; 60–90 °C.
Time/Yields: 2–12 h; often 70–90% for the iodide stage with aryl boronic acids.
Sonogashira at C7–I (general)
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (5–10 mol%) or copper-free Pd/XPhos.
Base/Solvent: Et3N or DIPEA in THF, DMF, or toluene; 25–80 °C.
Buchwald–Hartwig amination (general)
Catalyst/Ligand: Pd2(dba)3 (1–2 mol%) with BINAP/XPhos/BrettPhos.
Base: NaOtBu or Cs2CO3.
Solvent: Toluene or dioxane; 80–110 °C. After C7 amination, C5–Br coupling typically requires more active ligands (BrettPhos/RuPhos) and 90–120 °C.
Halogen–metal exchange (selective at I) (general)
Reagent: iPrMgCl·LiCl (1.0–1.2 equiv) in THF or 2-MeTHF.
Temperature: −78 to −20 °C.
Electrophiles: DMF (formylation), CO2 (carboxylation), aldehydes/ketones (addition), acid chlorides (acylation).
Protecting group notes
Boc protection prior to coupling improves chemoselectivity; remove with TFA after couplings. SEM protection is robust to basic conditions and removed with fluoride reagents.
Workup (general)
Quench with aqueous NH4Cl/NaHCO3, extract with EtOAc, charcoal/metal scavenger polish, and silica or neutral alumina chromatography.
All parameters above are literature/general guidance, not specifications for this item.
Safety and Handling
Safety guidance for laboratory use of a halogenated heteroaromatic solid. Always consult the product SDS for authoritative information.
Item-specific (from Product Data)
Storage: Store at 2–8 °C, protected from light, desiccated.
Shipping: Shipped on wet ice.
GHS signal word, hazard statements, pictograms, classification: Not specified for this item; refer to SDS.
General hazards and precautions (literature/general; not item-specific classification)
Expected hazards: May cause skin/eye irritation and respiratory tract irritation if dust is generated. Avoid inhalation of particulates and contact with skin/eyes.
Light sensitivity: Protect from light to minimize potential degradation/halogen exchange.
Combustibility: Organic solid; combustible dust hazard if finely divided. Avoid ignition sources and dust accumulation.
PPE: Lab coat, safety glasses, and nitrile gloves as minimum. Use local exhaust/hood when weighing or dissolving.
Incompatibilities: Strong bases (can deprotonate the indole NH), strong oxidizers, and strong nucleophiles under forcing conditions (risk of substitution/decomposition). Avoid prolonged exposure to strong light/UV.
First aid overview (general)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation develops.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste handling
Halogenated organic waste: Collect solutions/solids in halogenated waste streams per institutional and regulatory guidelines.
Solvent Selection
Solubility and solvent effects for halogenated indole scaffolds influence both handling and reactivity.
Polarity and miscibility (literature/general)
The compound is nonpolar–moderately polar aromatic with a hydrogen-bond donor NH. It is typically soluble in polar aprotic solvents (DMSO, DMF, NMP) and moderately soluble in chlorinated (DCM, CHCl3) and aromatic solvents (toluene, xylenes). Aqueous solubility is expected to be very low.
Practical choices by use-case
Stock solutions for screening: DMSO for 10–50 mM libraries (literature practice); filter if needed. For lower background in photophysics, use anhydrous acetonitrile or toluene.
Pd-catalyzed couplings: 1,4-dioxane, toluene, THF, CPME, or mixtures with water/EtOH depending on base (K2CO3/Cs2CO3) and ligand (SPhos/XPhos). DMF or NMP can be used for challenging aryl bromide steps.
Metal–halogen exchange or magnesiation: Ethers (THF, 2-MeTHF) at −78 to −20 °C with iPrMgCl·LiCl (Turbo Grignard) for selective activation of the C–I site (literature practice).
Comparison notes (general)
DMSO/DMF maximize solubility but complicate workup and may retain Pd; toluene/dioxane offer cleaner extractions and easier removal.
Aqueous co-solvents can accelerate Suzuki couplings of aryl iodides; too much water may precipitate bases or deprotect N-protecting groups.
Item-specific solvent data: Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Practical guidance for maintaining material integrity and preparing solutions.
Item-specific (from Product Data)
Storage Conditions: Store at 2–8 °C, protected from light, desiccated.
Shipped In: Wet ice.
General handling (not item-specific specifications)
Minimize exposure to ambient humidity and light during weighing; re-cap promptly. Use amber glassware or foil wrap for light protection.
If long-term storage is anticipated, consider subdividing into aliquots under dry inert gas to reduce open–close cycles.
Reconstitution/solution preparation (general)
Prepare stock solutions in dry DMSO, DMF, THF, or acetonitrile. Filter through a PTFE syringe filter if particulates are present.
For aqueous assays, dissolve first in a water-miscible organic co-solvent (e.g., DMSO) before diluting into buffer; verify that final organic content and solubility suit the assay.
For moisture/air-sensitive transformations (e.g., metal–halogen exchange), transfer under inert atmosphere and use anhydrous solvents.
Stability notes (general)
Solid halogenated indoles are typically stable for months at 2–8 °C when protected from light and moisture. Monitor for discoloration or unexpected TLC/LC peaks as signs of degradation.
Specifications not provided
Exact shelf life, retest period, and solution stability: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Concise overview of the heteroaromatic scaffold and identifiers for a dihalogenated indole building block.
Item-specific (from Product Data)
SKU: B166642
Product Name: 5-Bromo-7-iodoindole
CAS: 123020-20-2
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed identifiers and features (for reference; not item specifications)
Molecular formula (literature): C8H5BrIN
Molecular weight (literature): ~321.94 g/mol (calculated from atomic weights)
Synonymy: Indole substituted with bromine at C5 and iodine at C7 on the benzene ring (indole numbering).
Structural features: bicyclic indole (fused benzene–pyrrole), one endocyclic nitrogen (pyrrolic NH), two aryl C–halogen bonds of differing leaving-group ability (C–I > C–Br), enabling stepwise cross-coupling.
2D structure description (general)
Indole core: a six-membered benzene ring fused to a five-membered pyrrole containing NH at position 1.
Substitution pattern: bromine para to the indole N across the benzene ring (position 5) and iodine meta to it (position 7), placing the two halogens 1,3-related around the benzene perimeter.
Aromatic C–Br and C–I bonds suitable for Pd- or Ni-catalyzed cross-couplings.
Pyrrolic NH is mildly acidic and often protected (e.g., Boc, SEM) to direct chemoselectivity and prevent N-arylation/metal coordination during coupling.
Synthetic Utility
Reactivity features that make 5-bromo-7-iodoindole a powerful bifunctional handle in synthesis.
Orthogonal electrophilicity (general)
The C–I (C7) site undergoes oxidative addition fastest, enabling first-stage couplings (Suzuki, Sonogashira, Heck, Buchwald–Hartwig). The C–Br (C5) site is reserved for a second-stage transformation under more forcing or ligand-optimized conditions.
Indole NH management
Protect NH (Boc, Cbz, SEM) to suppress N-arylation and improve catalyst turnover. Boc is acid-labile; SEM is fluoride-labile; choice depends on downstream steps.
Diversification pathways (literature/general)
Arylation/alkenylation at C7 followed by C5 borylation (Ir-catalyzed) or vice versa creates versatile linchpins.
Selective halogen–metal exchange at the iodide with iPrMgCl·LiCl at sub-ambient temperatures allows formylation (DMF), acylation (acid chlorides), or electrophile trapping (I2/Br2 for tri/reh halogenation) while retaining C5–Br.
Direct C–H functionalization on the pyrrole ring (C2/C3) can be explored after protecting/deactivating strategies, providing tri- or tetrasubstituted indoles.
Retrosynthetic value
Serves as a convergent junction where two orthogonal coupling partners define 5- and 7-vectors late-stage, reducing protecting-group manipulations and chromatography passes.
Purification/workup tips (general)
Halogenated indoles can tail on silica; add 0.1–1% Et3N to eluents or use neutral alumina. For metal removal, apply Pd scavengers (Si-TMT, silica–thiourea) or activated carbon before concentration.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and not a biological reagent (e.g., antibody, enzyme, or ligand with defined target binding) in this catalog context.
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