This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
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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Application Protocols
Not applicable. No immunoassay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block.
Tested applications, recommended dilutions, controls: Not specified for this item; not applicable.
Biological Roles
This product is a synthetic small-molecule building block and is not intended for biological use as a metabolite or ligand.
Item-specific biological function: Not specified for this item; refer to CoA/Spec Sheet.
General notes (contextual, not usage claims)
Pyridinecarboxylic acids occur in biology (e.g., nicotinic acid derivatives), but the presence of a 2-nitro and 5-bromo substituent makes this compound a non-natural, highly functionalized scaffold typically used only in chemical synthesis.
Any biochemical assays involving this compound should be considered exploratory research only; no clinical or diagnostic use is implied.
Buffer Applications
Not typically used as a buffering agent. As a carboxylic acid on a pyridine ring, it can form salts for solubilization, but it does not comprise a standard laboratory buffer system.
If aqueous handling is required: Prepare dilute alkaline solutions (e.g., with NaOH) to form the carboxylate for dissolution. Confirm pH empirically; do not rely on this compound to maintain pH as a primary buffer.
Green Alternatives
Greener choices mainly involve solvent and reagent selection, as the substrate is a fixed heteroaromatic building block.
Solvent substitutions (general guidance)
Replace dioxane/DMF with bio-derived ethers/esters when possible: 2-MeTHF, CPME, and propylene carbonate can substitute in cross-coupling or reductions, depending on base/catalyst compatibility.
Favor aqueous or water-lean couplings: Employ micellar catalysis (e.g., TPGS-750-M) or ethanol/water mixtures to diminish dipolar aprotic solvents.
Coupling reagent choices
Amide formations: Prefer carbodiimide chemistry with catalytic Oxyma/HOAt analogs or direct dehydration protocols to reduce waste relative to uronium/phosphonium reagents.
Cross-coupling: Use ligand-enabled, low-Pd loadings or Ni catalysis; water-tolerant systems enable higher substrate concentrations and reduced organic throughput.
Comparison (illustrative; non-spec)
Dioxane vs 2-MeTHF: 2-MeTHF is bio-based, lower toxicity, and often performs comparably in Suzuki couplings; however, solubility of inorganic bases may be inferior—consider water co-solvent.
DMF/DMAc vs Cyrene/PC: Dipolar aprotic alternatives (Cyrene, propylene carbonate) offer improved EHS profiles but may require different bases/temperatures and careful water control.
Waste minimization
Sequence couplings before reductions to avoid amine-containing waste early. Crystallization-induced purification of carboxylic acids can reduce reliance on chromatographic solvents.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided. This compound is supplied for research use only.
Item-specific information
Pharmaceutical/excipient use: Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical)
Heteroaryl carboxylic acids like isonicotinic derivatives are commonly used as synthetic intermediates in discovery chemistry for SAR exploration. Any formulation-related work would be preclinical research only, not for human or veterinary administration.
Physical Properties
Item-specific physico-chemical specifications were not provided in the Product Data. Do not treat the following as specifications; they are general/literature-style information to aid method development.
Item-specific values
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Computed value from formula C6H3BrN2O4 ≈ 247.00 g/mol provided separately as literature/computed.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not applicable (decomposes before boiling; literature expectation for nitroaromatics). Not specified for this item; refer to CoA/Spec Sheet.
Density, refractive index, UV cutoff, metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed guidance (non-spec)
Ionization/acid-base: One carboxylic acid (weak acid) and a basic ring nitrogen (pyridine). Electron-withdrawing nitro and bromo substituents are expected to lower the pKa of the carboxyl and the basicity of the ring nitrogen relative to isonicotinic acid (qualitative trend, literature rationale).
Solubility profile (qualitative): Typically sparingly soluble in water as the free acid; increased solubility as salts (e.g., Na+, K+). Readily soluble in polar aprotic solvents (DMSO, DMF, NMP) and in basic aqueous media (pH > ~7). Actual solubility for this item: Not specified; verify experimentally.
Stability: Nitroaromatic carboxylic acids are generally stable solids under ambient conditions; avoid prolonged exposure to strong bases/acids when functional integrity is critical.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance)
Research/technical grade: Suitable for most synthetic and screening work; assay and impurity profile may be provided on CoA.
Analytical/AR grade: Tighter control of inorganic/organic impurities; useful when trace metals or UV background matter.
HPLC/LC-MS grade (for solvents): Low UV absorbance and low metal/ion content; generally not applicable to solid building blocks like this compound.
Practical quality notes for this scaffold (general)
Halogenated heteroaromatics used in cross-coupling are sensitive to trace metal contaminants and residual halide salts in the reaction mixture; verifying halogen content by NMR or HRMS is helpful.
For coupling chemistry, dryness and identity confirmation (1H/13C NMR, 19F/Br patterns by HRMS/halogen isotopic clusters) are typically more important than trace water content in the solid.
Refer to the item’s CoA/Spec Sheet for actual assay, residual solvents, and impurity limits.
Reaction and Applications
This substrate is a versatile heteroaryl building block combining three orthogonal handles: an aryl bromide (cross-coupling locus), a nitro group (reduction → aniline; nucleophile precursor), and a carboxylic acid (amidation/esterification site).
Cross-coupling at C5–Br: Suzuki–Miyaura (biaryls/heterobiaryls), Sonogashira (alkynes), Stille/Negishi (vinyl/alkyl). Electron-withdrawing nitro increases oxidative addition rates on pyridines, facilitating Pd-catalysis.
Nitro group transformations: Chemoselective reduction to the 2-aminopyridine using H2/Pd-C, Fe/AcOH, SnCl2/HCl, or Zn/NH4Cl; subsequent acylation, urea formation, or Buchwald–Hartwig amination (via diazonium/other routes) becomes accessible.
Carboxylic acid elaboration: Amide coupling (EDC/HATU), esterification (Fischer or Steglich), or activation to acyl chlorides (e.g., oxalyl chloride) for subsequent acylations.
Divergent synthesis: Orthogonal order—e.g., first couple at C5–Br (Suzuki), then reduce –NO2 to –NH2, then amidate the acid—to minimize protecting-group needs.
Practical tips
Sequence planning: Perform Pd-catalyzed couplings prior to nitro reduction to avoid catalyst poisoning by amines.
Base choice: Carbonate/bicarbonate mixtures balance basicity to maintain acid mostly deprotonated (enhanced solubility) without hydrolyzing sensitive partners.
Solubility management: Convert to a soluble carboxylate salt in situ with K2CO3 for aqueous-organic couplings.
Regioselectivity: The C5–Br is the principal cross-coupling site; direct C–H functionalization at other positions on a nitro-substituted pyridine can also be explored with appropriate directing groups/catalysts.
Reaction Conditions
The following are literature-style, general conditions for compounds of this class; they are not item-specific specifications.
Suzuki–Miyaura coupling at C5–Br
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1–2 mol%) with SPhos/XPhos.
Base: K2CO3 or K3PO4 (2–3 equiv); Cs2CO3 for challenging partners.
Solvent: 1,4-dioxane/H2O or THF/H2O (4:1 to 1:1); DMA or DMF also effective.
Temperature/time: 70–100 C, 2–16 h. Typical isolated yields for well-matched partners: 60–90% (literature range).
Sonogashira coupling
Catalyst: PdCl2(PPh3)2 (1–3 mol%) + CuI (5–10 mol%); base: Et3N or iPr2NH.
Solvent: THF, DMF, or 2-MeTHF; 25–70 C. Protect acid as ester if solubility limits conversion.
Nitro reduction to aniline
Catalytic hydrogenation: H2 (1–3 bar) over Pd/C (5–10 wt% relative to substrate) in EtOH or MeOH; rt–50 C, 2–8 h.
Iron/acid: Fe powder (5–10 equiv) in HOAc/EtOH/H2O, 50–80 C.
Tin(II) chloride: SnCl2·2H2O (3–5 equiv) in EtOH/HCl, reflux.
Amide coupling of the acid
Reagents: HATU or EDC·HCl + Oxyma; base: DIPEA or NMM.
Solvent: DMF, NMP, or DCM (for less polar amines); 0–25 C to start, then rt.
Workup/purification tips
Maintain mildly basic aqueous workups for Pd couplings to keep carboxylate soluble until extraction is desired. Consider pre-esterification to facilitate chromatography if necessary.
Safety and Handling
Item-specific hazard details
Signal word / GHS classification / H-statements / pictograms: Not specified for this item; refer to the SDS for authoritative safety information.
General safety considerations for nitro- and halo-substituted heteroaromatic carboxylic acids (literature-based; not item-specific classifications)
Hazards: May cause irritation to skin, eyes, and respiratory tract. Dust may be harmful if inhaled. Nitroaromatics can present combustion hazards; avoid dust accumulation and ignition sources. Carboxylic acids can be corrosive to eyes/skin depending on acidity.
Peroxide formation: Not applicable; not an ether. No specific peroxide risk expected.
Incompatibilities: Strong oxidizers or reducing agents (can cause exothermic reactions); strong bases/acids (can induce decomposition or salt/ester formation); reactive metals. Avoid contact with acylation or nitration reagents unless controlled.
PPE and handling
Use a chemical fume hood. Wear lab coat, safety glasses or goggles, and appropriate gloves (e.g., nitrile). Avoid breathing dust; handle as a solid with minimal disturbance. Wash thoroughly after handling.
First aid (general): Inhalation—move to fresh air; Skin/Eye—rinse with water for at least 15 minutes; Ingestion—rinse mouth, seek medical advice. Provide SDS to healthcare personnel.
Spills and waste
Collect solids with minimal dust generation; place in appropriate container for hazardous waste. Dispose of according to institutional and local regulations.
Always consult the product-specific SDS for definitive hazard and response guidance.
Solvent Selection
As a heteroaromatic carboxylic acid bearing strong electron-withdrawing substituents, this compound behaves as a moderately polar, hydrogen-bond donating/accepting solid.
Practical dissolution choices (general guidance; not item-specific specs)
Polar aprotic: DMSO, DMF, NMP—excellent for preparing concentrated stock solutions (10–100 mM typical). Warm gently (30–50 C) to accelerate dissolution.
Aqueous alkaline: Readily dissolves upon neutralization to its carboxylate (e.g., 0.01–0.1 M NaOH, or buffered pH ≥ 8). Prepare salts in situ if aqueous work is required.
Alcohols: Methanol/ethanol may dissolve modestly; solubility improves with small amounts of base (e.g., triethylamine) or with heating.
Nonpolar/low polarity: Poor solubility expected in hexanes, toluene, CPME; use these mainly as reaction media for couplings if the substrate is suspended or pre-dissolved with co-solvent.
When to choose specific solvents
Cross-coupling: 1,4-dioxane/H2O, THF/H2O, or DMA/EtOH/H2O mixtures balance base solubility and catalyst stability.
Amide coupling: DMF, NMP, or DCM with coupling reagents (EDC/HOBt, HATU, PyBOP); add base (DIPEA) as needed.
Nitro reduction/hydrogenation: EtOH, MeOH, AcOH, or THF under catalytic hydrogenation; for metal-mediated reductions (Fe, SnCl2), alcoholic solvents with acid co-solvent are common.
Small comparison (general)
DMSO vs DMF: DMSO offers broader solubilization but can coordinate metals; DMF is frequently preferred for Pd couplings to limit DMSO coordination. Water co-solvent often improves base handling and turnover.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Storage conditions: Room temperature.
Shipped in: Normal conditions.
Research use note: For research use only.
General handling recommendations
Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and prolonged light exposure. Use desiccant if ambient humidity is high.
For solution stocks, prepare in dry DMSO, DMF, or NMP at convenient concentrations (e.g., 10–100 mM). Filter if particulates are present. Store aliquots to minimize air/moisture exposure.
Aqueous stocks can be prepared by basification (forming carboxylate salts); use promptly or refrigerate to limit hydrolysis and microbial growth. Avoid repeated freeze–thaw of solutions; aliquot as needed.
Stability notes (general)
Solid nitroaromatic carboxylic acids are typically stable at ambient conditions for extended periods when kept dry. Verify integrity periodically by NMR/HRMS, especially before key cross-coupling or medicinal chemistry steps.
Structure and Identity
A multifunctional, heteroaromatic carboxylic acid bearing both a bromide and nitro substituent on an isonicotinic acid (pyridine-4-carboxylic acid) scaffold; useful as a bifunctional coupling/reduction handle in heteroaryl synthesis.
Item-specific identifiers (from Product Data)
SKU: B190689
Product name: 5-Bromo-2-nitroisonicotinic acid
CAS: 1356412-82-2
PubChem CID: 71464020
InChIKey: 225323 (as provided; truncated/incomplete format in source)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (informational; not item-specific specifications)
Core: pyridine ring (ring N at position 1)
Substituents: carboxylic acid at the 4-position (isonicotinic acid), nitro at the 2-position, bromo at the 5-position
Molecular formula (derived from structure): C6H3BrN2O4 (computed)
Approximate molecular weight: ~247.00 g/mol (computed from formula)
2D description in words
A six-membered aromatic ring containing one ring nitrogen (pyridine). At the para position relative to the ring nitrogen is a carboxylic acid group. Adjacent to the ring nitrogen (ortho) is a nitro group, and at the meta position relative to the nitrogen is a bromine atom.
Synthetic Utility
The convergence of three orthogonal functionalities on the pyridine ring enables modular assembly of densely substituted heteroaromatics.
Functional group handles and reactivity (general literature)
Aryl bromide (C5): Excellent site for Pd/Ni cross-couplings (Suzuki, Sonogashira, Stille, Negishi), with the nitro group further activating the ring toward oxidative addition.
Nitro group (C2): Reductive conversion to an aniline grants entry to ureas, amides, sulfonamides, and intramolecular cyclizations (e.g., to benzodiazines/imidazopyridines under suitable conditions).
Carboxylic acid (C4): Coupling to amides/esters; activation to acyl chloride or mixed anhydrides enables acylations and late-stage diversification.
Retrosynthetic value
Deconvolutes complex heterobiaryl targets: install the C5 partner via Suzuki first, then reduce nitro and couple at nitrogen; end with amide formation for polarity tuning.
Orthogonality permits protection-free sequences if coupling precedes formation of strongly coordinating amines.
Selectivity and compatibility
The acid group can be left unprotected in many Pd couplings (as potassium carboxylate) to aid solubility. For base-sensitive partners, pre-esterification (e.g., methyl ester) may furnish smoother couplings and purifications.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or affinity reagent.
Item-specific biological target, clone, isotype, species reactivity: Not specified for this item; not applicable.
Perguntas frequentes
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 1356412-82-2, the molecular formula is C6H3BrN2O4, and the molecular weight is 247 g/mol. InChIKey MPPXDSQZQIBCRT-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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