This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro 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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No application protocols are specified for this item. As a small-molecule building block, usage conditions depend on the chosen synthetic transformation (see Reaction Conditions and Synthetic Utility tabs for general guidance).
For analytical quality control, typical non-item-specific methods include: HPLC purity assay, LC–MS for identity, IR for CN/NO2 bands, and NMR for aromatic substitution pattern.
Refer to your project’s SOPs and optimize conditions empirically.
Biological Roles
This product is a small halogenated nitrobenzonitrile used as a synthetic building block. It does not serve a known endogenous biological role.
General notes (literature/general):
Nitro- and cyano-substituted aromatics are not typical metabolites and are generally foreign to biological systems. When present, such motifs are often introduced synthetically for probe or material applications rather than as natural ligands.
The nitrile group can act as a metabolically stable bioisostere in medicinal chemistry; however, any biological activity would be compound- and context-specific and cannot be inferred for this reagent.
Nitro groups are strong electron-withdrawing substituents and can modulate binding or reactivity in biochemical assay development, but they also carry structural alerts in drug design due to potential reduction and reactivity under bioreductive conditions.
For lab use only. No medical, diagnostic, or therapeutic uses are claimed or implied for this item.
Buffer Applications
Not typically applicable. 6-Chloro-2-nitrobenzonitrile is a neutral aromatic solid used as a synthetic intermediate and does not function as a buffering agent or pH stabilizer.
Practical guidance: If deploying in aqueous biochemistry workflows, dissolve first in a suitable co-solvent (e.g., DMSO or acetonitrile) and add to buffers at low percentages to avoid precipitation, ensuring compatibility with the downstream assay or reaction.
Green Alternatives
While 6-chloro-2-nitrobenzonitrile is itself a target intermediate rather than a solvent, process chemists can improve sustainability by selecting greener media and conditions for its transformations.
Greener solvent choices (literature/general):
Replace DMF/NMP/DMAc with 2-MeTHF, CPME, propylene carbonate, dimethyl carbonate, or ethyl acetate where solubility and reactivity permit.
Favor water or water-rich biphasic systems with phase-transfer catalysis for SNAr when nucleophile solubility is adequate.
Energy and reagent efficiency:
Use microwave or continuous-flow heating to shorten reaction times and reduce energy input.
Choose highly active Pd catalysts/ligands for aryl chloride couplings (e.g., Pd-PEPPSI, XPhos/SPhos systems) to run at lower temperatures and lower catalyst loadings.
Alternative transformations:
For nitro-to-amine reduction, catalytic hydrogenation (H2/Pd-C) in EtOAc/EtOH is generally greener than stoichiometric tin or iron salts; transfer hydrogenation (e.g., with formate) can avoid compressed gas.
Enzymatic or biocatalytic nitrile hydrolysis (nitrilases) may be considered for converting the nitrile to amide/acid under mild aqueous conditions, if compatible with the chloro/nitro substituents.
Comparison snapshot (general):
DMF/DMSO/NMP: excellent solvation; regulatory and EHS concerns; difficult to remove.
2-MeTHF/CPME: bio-based or safer ethers; good for extractions and many couplings; form peroxides over time—monitor and inhibit.
Propylene carbonate: high-boiling, low toxicity; limited nucleophile solubility in some cases.
Optimize with solvent selection guides (GSK/ACS), balancing performance, safety, environment, and cost.
Pharmaceutical Uses
This product is intended for research use only.
General context (literature/industry practice, not item-specific):
Halogenated nitrobenzonitriles serve as versatile intermediates in the synthesis of pharmaceutical candidates and agrochemical actives due to the orthogonal reactivity of aryl–Cl, –NO2, and –CN groups.
The compound may be used to assemble substituted anilines (via nitro reduction), benzo-fused heterocycles (through intramolecular cyclizations), and aryl coupling products (via Pd-catalyzed activation of the aryl chloride).
Excipient or formulation uses are not typical for this structural class; usage is primarily as a starting material or intermediate in API process development.
Compliance considerations:
For GMP or clinical manufacturing, additional qualification (impurity profile, residual solvents, elemental impurities, robust analytical methods) would be required beyond standard research-grade material.
No therapeutic claims are made. Any application in regulated manufacturing must be supported by appropriate specifications and validation.
Acid–base: non-basic, non-acidic; nitrile pKa for conjugate acid typically < −10 (literature/general).
Data not provided for this specific catalog item (do not assume; check CoA/SDS if needed):
Melting point, boiling point, density, refractive index, logP, water content, residual metals, UV cutoff, and any spectroscopic purity metrics.
Always rely on the item’s CoA/specification sheet for release specifications and on the SDS for safe handling-related physical data.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grades (general guidance):
Research/technical grade: suitable for most synthetic applications; impurity profile may be broader.
High-purity/assay-specified grade: tighter control of assay, related aromatics, halide content, and residual solvents.
Chromatography (HPLC/GC) grades typically refer to solvents; for solids, “≥98%” or similar assay is more relevant.
Typical impurity considerations for 6-chloro-2-nitrobenzonitrile (general):
Positional isomers (other chloro/nitro placements), unreacted precursors (chloro-benzonitriles, dinitro species), hydrolyzed products (amides/acids) from nitrile, and trace inorganic salts from nitration/chlorination steps.
Residual metals are generally low unless produced via catalytic halogenation; if metal-sensitive applications are planned, request ICP data.
Quality control recommendations:
Identity: 1H/13C NMR (aromatic region deactivated by EWG), IR (sharp CN stretch ~2220–2250 cm−1; strong NO2 asymmetric/symmetric ~1520/1350 cm−1; literature/general), MS (M+ with Cl isotopic pattern).
Purity: HPLC/GC as applicable; melting point (if crystalline) as a rapid check; LC–MS to resolve isomeric impurities.
Documentation:
For exact acceptance criteria (assay, residual solvents, water content, metals, UV), consult the item’s CoA/Specification Sheet. No specific stabilizers or additives are indicated in the Product Data.
Reaction and Applications
As an electron-poor aryl chloride with ortho nitro and nitrile substituents, 6-chloro-2-nitrobenzonitrile is a versatile electrophilic building block.
Nucleophilic aromatic substitution (SNAr): Nitro and nitrile groups activate the ring toward displacement of chloride by amines, alkoxides, thiolates, and other hard nucleophiles, typically under heating in polar aprotic solvents. Ortho-nitro further stabilizes Meisenheimer intermediates.
Cross-coupling: The aryl–Cl bond can engage in Pd-catalyzed Buchwald–Hartwig amination, Suzuki–Miyaura, Sonogashira, and Negishi couplings with appropriate catalysts/ligands optimized for aryl chlorides (e.g., Pd/XPhos, SPhos).
Nitro group manipulation: Reduction to the aniline (2-amino-6-chlorobenzonitrile) provides a handle for diazotization, urea/carbamate formation, or subsequent intramolecular cyclizations.
Nitrile group transformations: Hydrolysis to the corresponding amide/acid, reduction to benzylamine analogs, or addition chemistry (e.g., nucleophilic additions under strong conditions).
Strategic applications:
Preparation of densely functionalized anilines and benzo-fused heterocycles through sequential nitro reduction followed by intramolecular SNAr or amidation.
Divergent parallel synthesis: orthogonal reactivity of Cl vs NO2 vs CN enables stepwise functionalization, facilitating SAR libraries for agrochemical/materials leads.
Practical tips:
For selectivity between SNAr and cross-coupling, tune conditions: strong nucleophiles/base favor SNAr; milder nucleophiles with Pd catalysis favor C–X activation.
Nitro group can survive many coupling conditions; however, highly reducing environments (e.g., Ni/RANEY with hydrogen) may partially reduce NO2.
Monitor for hydrolysis of the nitrile during prolonged heating in aqueous or strongly basic media.
Reaction Conditions
General literature guidance for transforming 6-chloro-2-nitrobenzonitrile (verify and optimize experimentally):
Solvents: DMF, DMSO, NMP, sulfolane; sometimes MeCN for reactive nucleophiles.
Bases: NaOMe/NaOtBu/K2CO3/Cs2CO3; phase-transfer catalysts can assist in less polar media.
Temperature/time: 60–140 °C, 1–24 h depending on nucleophile strength; monitor by HPLC/LC–MS.
Pd-catalyzed couplings (on aryl–Cl):
Suzuki–Miyaura: Pd(dba)2 or Pd2(dba)3 (0.5–2 mol%) with SPhos/XPhos; base K3PO4 or Cs2CO3; solvents dioxane/H2O, toluene/H2O, or CPME/H2O; 60–110 °C, 2–16 h.
Buchwald–Hartwig amination: Pd2(dba)3 or Pd(OAc)2 with BrettPhos/XPhos ligands; NaOtBu or K3PO4; toluene/dioxane; 80–120 °C.
Sonogashira: Pd(PPh3)2Cl2/CuI; Et3N or iPr2NEt; toluene/THF/DMF; 50–90 °C.
Nitro reduction:
H2 (1–5 bar) with Pd/C (5–10 wt%) in EtOH/EtOAc at RT–50 °C, 1–6 h; monitor to avoid over-reduction of the nitrile under forcing conditions.
Fe/AcOH or SnCl2·2H2O in EtOH/H2O at 50–90 °C for chemoselective reduction to aniline.
Nitrile transformations:
Hydrolysis: aqueous acid (6 M HCl) reflux or base (NaOH) with co-solvent (dioxane) to amide/acid; times 4–24 h.
Reduction: BH3·THF or catalytic hydrogenation (Raney Ni/Co) to primary amine; control to prevent nitro group interference (reduce nitro first or protect as needed).
Notes:
Order of operations matters; reducing nitro before cross-coupling can change electronic properties and catalyst performance.
Electron-withdrawing groups facilitate SNAr but can also alter regioselectivity—validate substitution pattern by NMR.
Safety and Handling
Product Data safety fields (GHS, pictograms, H-statements, signal word) are not specified for this item; refer to the SDS for authoritative information.
General hazard profile for nitro- and cyano-substituted aryl chlorides (literature/general):
May cause skin/eye irritation and respiratory tract irritation; harmful if swallowed or inhaled. Nitroaromatics can present methemoglobinemia risk upon significant exposure; avoid inhalation/ingestion.
Combustible solid; dust may form explosive mixtures with air. Not self-reactive, but avoid heating above decomposition temperatures.
Handling guidance (general best practices):
Use in a fume hood; avoid dust generation. Wear appropriate PPE: lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles. Where dust/insufficient ventilation is possible, use a particulate respirator per institutional policy.
Avoid contact with strong bases and strong nucleophiles at elevated temperature unless intended (may undergo SNAr). Keep away from strong reducing agents (risk of nitro reduction) and strong oxidizers (incompatible mixing).
For reactions, ensure appropriate temperature control and inert atmosphere when using moisture-sensitive bases.
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; obtain medical attention for persistent irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting measures (general):
Use dry chemical, CO2, or foam; avoid high-pressure water jets. Thermal decomposition may release NOx, HCl, and CN-containing fumes; firefighters should wear SCBA.
Always defer to the current SDS for this catalog item for classification, exposure limits, and emergency measures.
Solvent Selection
This compound is a moderately polar, electron-deficient aryl chloride bearing nitro and nitrile groups.
Polarity and miscibility (literature/general):
Limited aqueous solubility; enhanced solubility in polar aprotic media (DMSO, DMF, NMP, sulfolane) and in acetonitrile. Moderate solubility in chlorinated (DCM, DCE) and aromatic solvents (toluene, chlorobenzene), especially on warming.
Choosing a solvent by application:
SNAr and base-promoted substitutions: DMF, DMSO, NMP, or sulfolane support high basicity and elevated temperatures; CPME or toluene with phase-transfer catalysts can work for less nucleophilic partners.
Pd-catalyzed cross-coupling on aryl chloride: polar, high-boiling solvents (NMP, DMAc, dioxane, toluene, anisole); chlorobenzene or xylene advantageous for >130 °C.
Reductions (nitro→amine): alcoholic solvents (EtOH, iPrOH) or EtOAc under catalytic hydrogenation; Fe/AcOH or SnCl2 in ethanol/water for chemoselective metal-mediated reductions.
Nitrile transformations: hydrolysis in aqueous mixed solvents (dioxane/H2O); reductions in THF, MeOH, or EtOH with borohydrides or catalytic hydrogenation.
Practical notes:
Ensure dryness for strong-base chemistry (t-BuOK, NaH). Nitro and nitrile groups withstand many solvents but can undergo side reactions in strongly protic/basic media at high temperature.
If crystallization is desired for purification, consider EtOAc/hexane or toluene/hexane mixtures; adjust based on solubility screening.
Environmental/operational tradeoffs:
When feasible, prefer greener solvents (2-MeTHF, CPME, EtOAc, propylene carbonate) over DMF/DMSO/NMP, balancing solubility and reaction kinetics.
Storage and Reconstitution
Storage (Product Data): Room temperature. Ship under normal conditions.
General storage guidance (literature/best practice):
Keep tightly closed in a dry, well-ventilated place. Store in original container or in amber glass with a desiccant to minimize moisture uptake and photolysis.
Avoid prolonged exposure to strong light and heat. Segregate from strong oxidizers and strong reducing agents.
Stability notes:
Nitro and nitrile groups are generally stable under ambient, dry conditions. Under strongly basic, hot, or aqueous conditions, nitrile hydrolysis may occur; under reducing environments, the nitro can be converted to an amine.
Reconstitution/Preparation:
Solid; no reconstitution required for storage. For solution preparation, dissolve in a compatible organic solvent (e.g., DMF, DMSO, acetonitrile, dichloromethane, toluene) at the desired concentration. Filter if particulates are present.
For long-term stock solutions, store in sealed amber vials at 2–8 °C and protect from moisture; validate stability by LC–MS/HPLC periodically.
Always consult the item’s CoA and SDS for any additional storage precautions specific to the supplied batch.
Structure and Identity
6-Chloro-2-nitrobenzonitrile is an electron-deficient halogenated aromatic bearing both nitrile and nitro groups ortho to each other, plus a chloro substituent para to the nitrile across the ring.
Item identifiers (Product Data):
SKU: C113586
CAS: 6575-07-1
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (catalog lists a nonstandard key)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed identifiers (for reference; not item-specific):
Molecular formula (literature): C7H3ClN2O2
Molecular weight (literature): ~182.56 g/mol
Structural features (general chemistry description):
Core: monosubstituted benzonitrile scaffold (aromatic phenyl ring fused to a nitrile, –C≡N).
Substituents: chloro (–Cl) and nitro (–NO2) groups; the nitro at the 2-position (ortho to –CN) and chloro at the 6-position (ortho to –CN on the opposite side).
Functional groups: aryl chloride (electrophilic under cross-coupling), nitro (reducible to anilines), and nitrile (hydrolyzable/reducible; strong electron-withdrawing group).
Electronic profile: highly deactivated ring due to –CN and –NO2; facilitates nucleophilic aromatic substitution (SNAr) at activated positions; alters cross-coupling kinetics of the aryl–Cl bond.
2D description: a benzene ring bearing, in order around the ring, a nitrile, an ortho nitro, and a distal ortho chloro; remaining ring positions are hydrogen.
Note: Where exact structure strings (SMILES/InChI) are critical for informatics, consult the certificate of analysis (CoA) or authoritative databases for this CAS entry.
Synthetic Utility
Key functional groups and reactivity map:
Aryl chloride (C–Cl):
Acts as a cross-coupling handle (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira, Negishi). Electron-withdrawing –NO2 and –CN enhance oxidative addition to Pd(0) in some ligand systems, enabling milder conditions relative to electron-rich aryl chlorides.
Under SNAr conditions, the C–Cl can be displaced by hard nucleophiles, particularly when ortho/para to strong EWGs, as in this scaffold.
Nitro group (–NO2):
Readily reduced to an aniline, unlocking downstream transformations (diazotization/Sandmeyer, urea/carbamate formation, heterocycle construction through intramolecular attack onto the nitrile or aryl chloride when suitably arranged).
Nitrile (–C≡N):
Hydrolysis to amide/acid (acidic or basic conditions; or via catalytic hydration), reduction to primary amine (BH3, LiAlH4, catalytic hydrogenation), or addition chemistry (organometallics under forcing conditions).
Strategic sequences (literature/general):
Orthogonal functionalization: selective Pd-catalyzed C–Cl coupling in the presence of NO2 and CN, followed by nitro reduction and derivatization of the aniline; final-stage nitrile conversion for polarity tuning.
Divergent SNAr: install O-, S-, or N-nucleophiles at the activated chloro position; nitro reduction later affords anilides for ring-closure to benzoxazoles/benzothiazoles/benzimidazoles.
MS: isotopic pattern diagnostic for Cl; HRMS supports formula confirmation.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and is not an antibody, enzyme prep, or biological targeting agent. No antigen/epitope specificity, clone, or isotype information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
C1827134