This compound belongs to the class of organic compounds known as nitrophenols. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
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
No assay-specific or bioanalytical application protocols are provided for this item.
General laboratory preparation (non-spec, for convenience):
Stock solutions for screening or chemistry: 10–100 mM in DMSO or DMF; filter through 0.2 µm PTFE if particulate is present. Record exact concentration gravimetrically where precision is required.
Reaction setup: Dry glassware; select solvent as per Reaction Conditions; consider protecting the phenol if using strong base/nucleophiles; monitor by TLC (254 nm) or LC–MS.
For any validated protocols or specific use-cases, please refer to the primary literature or develop internal SOPs based on your equipment and safety standards.
Biological Roles
Item-specific biological information: Not specified for this item.
General context (for researchers; not medical/clinical):
5-hydroxy-2-nitrobenzonitrile is a synthetic aromatic compound; it is not a known endogenous metabolite.
Functional motif rationale:
Nitro- and cyano-substituted phenols are commonly used in chemical biology and medicinal chemistry programs as electron-deficient aromatic cores for probe or inhibitor synthesis; however, any biological activity arises from the final designed molecules, not this starting material itself.
The phenolic OH offers a handle for prodrug or reporter conjugation, while the nitro group can serve as a masked aniline after reduction, expanding SAR exploration.
Caution for bioassays:
Nitroaromatics can display assay interference (redox cycling, absorbance) and should be tested for nonspecific effects when evaluating downstream analogs.
Stock solutions are typically prepared in DMSO; confirm solubility and avoid high DMSO percentages in biological media.
All uses are for research and laboratory development only. No claims are made regarding biological efficacy or therapeutic use.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare laboratory buffer systems. It lacks a suitable conjugate acid–base pair in the physiological pH window for effective buffering.
Practical guidance:
If dissolution into buffered media is required for assays, prepare concentrated stocks in DMSO or MeCN and dilute into the target buffer while monitoring for precipitation.
Select buffers compatible with phenolic/nitro aromatics (e.g., phosphate, HEPES) and avoid strong basic buffers if the free phenol must remain un-ionized.
No buffer recipes or pKa values are specified for this item; consult primary literature if you need quantitative ionization data.
Green Alternatives
While the compound itself is a substrate (not a solvent), greener choices can be made in its processing.
Preferred greener solvents (relative to DMF/DMAc/NMP):
2-Methyltetrahydrofuran (2-MeTHF): bio-based, good for hydrogenations and some O-alkylations; immiscible with water for facile workup.
Ethyl acetate and isopropanol/ethanol: lower toxicity, effective for catalytic hydrogenation and crystallizations.
Acetonitrile: better EHS profile than DMF/NMP in many jurisdictions; good for SNAr and O-alkylation at moderate temperatures.
Process considerations (literature guidance):
Employ catalytic hydrogenation (H2/Pd or transfer hydrogenation with ammonium formate) instead of stoichiometric metal reductions where possible; significantly reduces metal salt waste.
For nitrile hydrolysis, consider aqueous ethanol or water with catalytic acid/base under microwave or flow conditions to shorten times and reduce solvent volumes.
Implement solvent recycling (EtOAc/MeCN) and crystallization-driven purifications to minimize silica waste.
Trade-offs (balanced view):
2-MeTHF may offer lower solubility for this polar aromatic vs DMF; process temperatures or seed-mediated crystallizations may be required.
Alcohols can lead to competitive transesterification/acetal chemistry with sensitive partners; verify compatibility.
Summary table (general, non-spec):
DMF/NMP: high solubility, excellent kinetics; EHS concerns, difficult removal.
MeCN/EtOAc/2-MeTHF: greener profiles, easier workup; may require optimization for solubility and rates.
Pharmaceutical Uses
Item-specific pharmacopeial status or excipient role: Not specified for this item.
Context for process chemists (general, non-clinical):
5-hydroxy-2-nitrobenzonitrile may serve as a synthetic intermediate toward more complex drug substance candidates, owing to its convertible handles (–NO2 → –NH2; –CN → –CONH2/–CO2H; –OH → ethers/esters). Any such use is in the synthetic manufacturing context rather than as an excipient or active on its own.
Considerations for GMP transition:
Define impurity profile (residual metals from catalytic reductions, nitroso/hydroxylamine byproducts, hydrolysis products) and establish purge strategies.
Establish robust crystallization or chromatographic purification to meet specified impurity thresholds.
Validate analytical methods (HPLC/UPLC, residual solvents by GC, ID by IR/NMR/HRMS).
Regulatory note: This product is offered strictly for research use only. It is not intended for human or veterinary use, formulation, or clinical applications.
Physical Properties
Item-specific physical data (spec values): Not specified for this item; refer to CoA/Spec Sheet.
State at ambient conditions: typically a crystalline solid (aromatic nitro phenols are commonly solid).
Molecular weight: ~164.11 g/mol (computed from C7H4N2O3).
Acid–base: phenolic OH expected to be moderately acidic; strong –NO2 and –CN substituents lower phenolic pKa compared with phenol (qualitative literature trend). Exact pKa for this specific isomer: not readily available; consult primary literature if critical.
Solubility profile (qualitative): low in water; generally soluble in polar aprotic organic solvents (DMSO, DMF, DMAc, NMP) and moderately in alcohols/acetone; limited in nonpolar hydrocarbons.
Polarity/logP: electron-withdrawing groups increase polarity relative to benzonitrile; exact logP not located; expect intermediate aromatic polarity.
Spectroscopy (general expectations):
IR: strong C≡N stretch ~2220–2240 cm−1; nitro asymmetric/symmetric stretches ~1520–1550 and ~1340–1370 cm−1; O–H broad band ~3200–3600 cm−1 (intramolecular H-bonding may sharpen/shift).
UV–Vis: nitro-activated phenols show π→π* bands in near-UV; exact λmax solvent-dependent (literature values vary).
All numerical values not explicitly provided here are general literature expectations and should be verified experimentally for your method development.
Quality & Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades for small-molecule research reagents (general):
Research/technical grade: Suitable for routine synthesis and screening; impurity profiles may include residual solvents, trace inorganic salts, and minor isomers. Verify suitability for sensitive catalysis or analytical work.
High-purity (>98–99%) grade: Preferred for medicinal chemistry and analytical workflows; reduces background in spectroscopic assays and improves mass balance in kinetic studies.
Stabilizers: None indicated for this item. For phenolic nitro compounds, stabilizers are rarely used; avoid prolonged exposure to base and light to preserve integrity.
Quality control suggestions for this scaffold (practical tips):
Identity confirmation: 1H/13C NMR in DMSO-d6 or CD3CN; look for phenolic OH (often downfield, may show H-bonding); diagnostic IR C≡N band (~2220–2240 cm−1) and nitro stretches. HRMS for exact mass (~164.11 g/mol, [M+H]+ ~165.1, literature guidance only).
Purity assessment: HPLC/UPLC with UV detection at 254–280 nm; nitro aromatics typically have strong UV response. Consider multiple wavelengths due to phenolic chromophore.
Residual solvents/metals: Not specified for this item; refer to CoA/Spec Sheet if needed for regulatory or sensitive synthetic steps.
Reaction & Applications
With phenol, nitro, and nitrile functions on a single ring, 5-hydroxy-2-nitrobenzonitrile is a versatile synthon for rapid diversification.
Transformations of the nitro group (literature):
Reduction to anilines: H2/Pd-C (EtOH/EtOAc), Fe/AcOH or SnCl2/HCl to give 5-hydroxy-2-aminobenzonitrile; enables subsequent diazotization, coupling, or intramolecular cyclizations (e.g., benzoxazoles after nitrile activation).
Partial reductions or N–O bond manipulations for accessing nitroso or hydroxylamine intermediates (controlled conditions).
Phenolic derivatization:
O-alkylation/acylation: Williamson ether synthesis (K2CO3, DMF/MeCN) or acyl chloride/anhydride acylation (pyridine, DMAP) to tune electronics/solubility or serve as protecting groups for further chemistry at the nitro/cyano.
Protection: Silyl ethers (TBS/TIPS) if base-sensitive steps are planned.
Nitrile transformations:
Hydrolysis to amide/acid: Acidic (H2SO4, HCl; aqueous organic cosolvent) or basic (NaOH/KOH, reflux) conditions.
Nucleophilic additions: Organometallic additions (RMgX/RLi) to give imines/ketimines, then hydrolysis to ketones (requires protection of phenol and control of nitro compatibility).
Aromatic substitution/annulation:
The –NO2 strongly activates the ring toward SNAr at positions ortho/para to itself; phenoxide can intramolecularly attack appropriately placed leaving groups in designed substrates.
Construction of benzoxazole/benzimidazole frameworks via condensation of the aminated derivative (post-reduction) with the nitrile/acid derivatives (literature routes).
Applications include library synthesis for materials or ligand scaffolds, push–pull chromophores (phenol↔nitro/cyano), and precursors to heteroaromatic motifs. All uses are for research and laboratory development only.
Reaction Conditions
The following are literature-style general conditions for common transformations of this scaffold; they are not product specifications and should be optimized for your system.
Nitro reduction → aniline:
H2 (1–5 bar), Pd/C (5–10 wt%), EtOH or EtOAc, 20–40 °C, 1–4 h. Monitor for over-reduction or hydrodecyanation (rare under mild conditions). Work under H2-safe protocols.
Fe (3–5 equiv)/AcOH/H2O or SnCl2·2H2O (2–3 equiv) in EtOH, 50–80 °C, 2–6 h; aqueous workup neutralization required.
O-alkylation (Williamson):
Alkyl halide (1.2–1.5 equiv), K2CO3/Cs2CO3 (2–3 equiv), DMF or MeCN, 25–60 °C, 2–16 h. Alternative greener media: acetone with phase-transfer catalyst.
Phenol acylation:
Acyl chloride (1.1–1.3 equiv), pyridine or Et3N base, catalytic DMAP (0.05–0.1 equiv), DCM or EtOAc, 0–25 °C, 1–3 h.
Nitrile hydrolysis:
Basic: NaOH/KOH (2–5 equiv) in EtOH/H2O (1:1), reflux 4–16 h → carboxylate; acidification to isolate acid. Shorter times under microwave.
Acidic: conc. H2SO4 or HCl in dioxane/H2O, 60–100 °C, 4–16 h → amide/acid depending on conditions.
Organometallic addition to nitrile:
RMgX or RLi (1.5–2.0 equiv) in THF or Et2O at −78 to 0 °C, then acidic quench → ketone after hydrolysis; protect OH first; nitro compatibility is limited (often requires prior reduction/protection).
Typical isolated yields in the literature for well-optimized steps are 60–90%, depending on substitution and protection strategy.
Safety & Handling
Item-specific GHS details: Not specified for this item; refer to SDS.
Signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
General safety considerations for nitro- and nitrile-substituted phenols (literature, not product-specific):
Hazards: Aromatic nitro compounds can present acute toxicity and may cause skin/eye irritation; phenolic compounds can be corrosive/irritant; nitriles can be harmful if inhaled/ingested. Avoid dust generation.
PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, safety goggles; handle in a fume hood to minimize inhalation exposure.
Incompatibilities: Strong bases (may form phenolates; exotherm upon neutralization), strong oxidizers or reducing agents (redox-active nitro group), acid chlorides/anhydrides without control (acylation), reactive metals. Avoid strong heating with reducing metals to prevent uncontrolled nitro reduction.
Handling tips:
Minimize dust; use spatulas and weigh boats in ventilated enclosures.
For solutions, select compatible polar aprotic solvents (e.g., DMSO, DMF). Clearly label with content and hazards.
First aid (overview; consult SDS):
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect organic waste containing nitro/nitrile aromatics in halogen-free organic waste stream unless local rules dictate otherwise; follow institutional and regulatory guidance.
Always consult the product SDS for authoritative hazard classification and response measures.
Solvent Selection
This compound is a solid aromatic building block rather than a process solvent. Solvent discussion here focuses on dissolution and reaction media.
Qualitative solubility and choices (general literature guidance):
Highly suitable: DMSO, DMF, DMAc, NMP — good for stock solutions and polar coupling/reduction chemistry.
Moderately suitable: Acetone, MeCN, EtOAc, methanol/ethanol (solubility varies with temperature and base presence).
Poor: Alkanes and nonpolar ethers (limited solubility at ambient conditions).
Polarity class: Polar aromatic substrate with multiple EWG groups; benefits from polar aprotic environments for SNAr, metal-catalyzed couplings after functional group interconversions, and nitrile hydrolysis.
When to choose which solvent:
Reductions of the nitro group: EtOH, MeOH, or EtOAc with H2/Pd or transfer hydrogenation; avoid strong basicity if the phenol is unprotected.
O-alkylation (Williamson): DMF/MeCN with mild base (K2CO3/Cs2CO3); phase-transfer in acetone/toluene as greener alternatives with PTC.
Nitrile hydrolysis: Aqueous ethanol, dioxane/water, or MeCN/water with acid/base catalysts.
MeCN/EtOAc/2-MeTHF: greener balance with reasonable solubility; validate case-by-case.
Always determine solubility experimentally at your working temperature and concentration.
Storage & Reconstitution
Item-specific storage and shipping (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Normal.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (non-spec):
Storage: Keep tightly closed in the original container, protected from moisture and strong light. Store in a cool, dry, well-ventilated place away from incompatible reagents (strong bases, strong oxidizers/reductants).
Stability: Nitro/cyano aromatics are generally stable under ambient conditions; avoid prolonged exposure to strong base which can lead to phenoxide formation and potential side reactions.
Reconstitution/solution preparation:
Prepare stock solutions in dry DMSO, DMF, MeCN, or EtOAc, depending on the intended application. Typical concentrations: 10–100 mM.
If needed in aqueous systems, dilute organic stock slowly into buffer with vigorous mixing to mitigate precipitation; final organic content often kept ≤1–2% v/v in bioassays (optimize per application).
Freeze–thaw: For solid material, not applicable. For prepared solutions, aliquot and store at 2–8 °C or −20 °C (solvent-dependent) to minimize repeated freeze–thaw cycles; warm to room temperature and check for precipitation before use.
Always consult the product CoA/SDS for definitive handling and storage instructions.
Structure & Identity
5-hydroxy-2-nitrobenzonitrile is a substituted benzonitrile bearing a phenolic OH and an ortho nitro group relative to the nitrile. The combination of a strongly electron-withdrawing nitro and cyano group with a phenolic donor creates a highly polarized aromatic system useful as a synthetic intermediate.
Item-specific identifiers (from Product Data):
SKU: H181287
CAS: 13589-74-7
InChIKey: Provided as “151364” in listing; this appears incomplete. Authoritative identifier: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity data (non-spec, for reference):
Molecular formula: C7H4N2O3 (literature)
Molecular weight: ~164.11 g/mol (computed from formula)
Common 2D description: A benzene ring bearing a nitrile (–C≡N) at C-1, a nitro group (–NO2) at C-2 (ortho to the nitrile), and a phenolic hydroxyl (–OH) at C-5 (meta to nitrile, para to nitro). No stereocenters; fully aromatic.
Structural features and implications (general chemistry):
Functional groups: phenol, nitro, nitrile.
Strong –I/–M effects from –NO2 and –CN increase acidity of the phenol and activate the ring toward nucleophilic aromatic substitution at appropriate positions.
Potential for intramolecular H-bonding between the phenolic OH and the ortho nitro group, influencing conformation, acidity, and spectroscopy.
Note: Structural descriptors above are provided for general chemical understanding and should not be construed as item-specific specifications.
Synthetic Utility
Key reactivity stems from three orthogonal functional groups that can be manipulated in a convergent or stepwise fashion.
Orthogonal handles:
Phenol (–OH): O-alkylation (Williamson), O-acylation (acyl chlorides/anhydrides), carbonate/carbamate formation, silyl protection; late-stage deprotection under fluoride or acid.
Nitro (–NO2): reduction to aniline (gateway to diazonium chemistry, ureas/carbamates, Buchwald–Hartwig couplings), N–O chemistry for diversification (limited scope; careful control required).
Nitrile (–C≡N): hydrolysis to primary amide or carboxylic acid; Pinner reaction to imidates (alcoholic HCl), organometallic addition to afford ketones after hydrolysis.
Reduce NO2 first, then cyclize with nitrile/acid derivatives to benzoxazoles/benzimidazoles, furnishing heteroaromatic scaffolds.
O-alkylate the phenol to tune electronics before SNAr or metal-catalyzed steps.
Electronic effects: The –NO2 and –CN lower the ring’s electron density, enabling SNAr when an appropriate leaving group is present (on suitably positioned substrates), and stabilizing Meisenheimer intermediates.
These features make the compound a compact, modular platform for constructing polyfunctional aromatics and N,O-heteroaromatics in medicinal and materials chemistry campaigns.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, ligand with defined target profile). No antigen/epitope, species reactivity, clone, or isotype information applies.
Frequently Asked Questions
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 13589-74-7, the molecular formula is C7H4N2O3, and the molecular weight is 164.1 g/mol. InChIKey IVDZYHBBWXCWGN-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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