This compound belongs to the class of organic compounds known as 2-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 2-position of the benzene ring.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Empfindlichkeit
Light sensitive
Schmelzpunkt (°C)
159-162
Molekulargewicht
215.590 g/mol
XLogP3
1.000
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
215.01 Da
Monoisotopic Mass
215.01 Da
Topological Polar Surface Area
101.000 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
243.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Lösungsrechner
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Application Protocols
Item-specific, validated bioassay protocols (WB, IHC, IF, FC, etc.) are not applicable to this small-molecule reagent.
General laboratory usage notes (literature/practice):
For hydrazone derivatization of aldehydes: Dissolve the compound in EtOH (5–50 mM), combine with the carbonyl substrate (1.0–1.2 equiv), add catalytic AcOH, and stir at rt–reflux until completion (TLC/LC–MS). Isolate by filtration (if precipitates) or standard workup and purification (trituration/crystallization/column chromatography).
For cross-coupling sequences: Dry solvents and bases, employ inert atmosphere (argon; product is supplied argon-charged), and degas reaction media. Monitor by LC–MS to detect partial reduction of the nitro group or hydrazide modifications.
These are generic planning guidelines and not validated protocols for this specific catalog item.
Biological Roles
Item-specific biological roles are not assigned. This product is designated for research use only.
General biochemical context (literature; not specific to this item):
Hydrazide functionality: Frequently used to capture aldehyde-containing biomolecules via hydrazone formation (e.g., oxidized glycans on glycoproteins/polysaccharides). This reversible covalent chemistry is exploited in bioconjugation workflows and affinity probes. The aromatic acyl hydrazide here could, in principle, engage in such condensations under appropriate conditions.
Nitroaromatic and haloaromatic motifs: These substituents do not confer a known endogenous biological role. Nitro groups can be bioreductively transformed in cellular environments, but that behavior is highly context-dependent and not claimed for this item.
Physicochemical properties: Multiple heteroatoms support hydrogen bonding, which can influence binding interactions in screening libraries; however, any target engagement would be empirical and is not specified here.
Use limitations:
No claims are made regarding enzyme inhibition, cellular activity, or therapeutic relevance. Any use in biochemical assays should be accompanied by appropriate controls and verification of purity/identity for the specific lot employed.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare buffer systems.
Practical note:
If the hydrazide is to be used in aqueous reactions (e.g., hydrazone formation with biomolecules), select a suitable buffer for the chemistry rather than using the compound itself as a buffer. Common choices (literature) include acetate buffer (pH ~4–5.5) to catalyze hydrazone formation, or phosphate buffer (pH ~6–7.4) for bioconjugations employing aniline catalysts. These are general guidelines and not item-specific specifications.
Green Alternatives
Greener choices focus on solvent/reagent selection for transformations of this hydrazide; the molecule itself is fixed.
Solvents (literature-oriented suggestions):
Replace DMF/NMP with:
• Cyrene or GBL in some coupling steps (check compatibility with dehydrating agents).
• 2-MeTHF or CPME for cross-couplings and extractions—lower toxicity and better sustainability than dioxane/toluene.
Use ethanol or water–ethanol mixtures for hydrazone condensations instead of chlorinated solvents.
Reagents/process changes:
Cyclodehydration to oxadiazoles: Favor CDI or green dehydrative couplings where feasible over POCl3/SOCl2; employ catalytic Mukaiyama-type dehydrations with benign co-products when substrates allow (literature).
Nitro reduction: Prefer catalytic hydrogenation (H2/Pd-C in EtOH) over stoichiometric tin/iron salts to reduce inorganic waste load. Implement flow hydrogenation for improved safety and gas utilization.
Cross-coupling: Nickel catalysis with biobased solvents (2-MeTHF) can reduce Pd usage; aqueous micellar catalysis (TPGS-750-M) has shown success for some aryl chloride couplings (literature).
Comparison snapshot (literature):
DMF vs EtOH/H2O for hydrazone:
• EHS: DMF (reprotoxic) vs EtOH/H2O (benign).
• Performance: Similar conversions often achievable with mild acid catalysis.
POCl3 vs CDI for cyclizations:
• Waste: POCl3 generates corrosive waste; CDI yields imidazole byproduct.
• Scope: POCl3 broader but harsher; CDI milder, substrate-dependent.
Note: Validate green substitutions on small scale; the hydrazide can undergo hydrolysis or over-acylation under strongly basic/acidic conditions.
Pharmaceutical Uses
Item-specific pharmacopeial status and excipient roles: Not specified for this item; refer to CoA/Spec Sheet. Research use only.
General context (non-clinical; literature):
As a synthetic intermediate: Aromatic acyl hydrazides are common building blocks in medicinal chemistry for preparing hydrazones, azoles (e.g., 1,3,4-oxadiazoles), and amide/urea analogs after nitro reduction. The ortho-chloro substituent provides an orthogonal handle for cross-coupling diversification, enabling library generation.
As an analytical derivatization reagent: Hydrazides can derivatize carbonyl-containing APIs/intermediates to stabilize and detect them by HPLC/LC–MS (hydrazone formation).
No claims are made regarding therapeutic activity, dosage forms, or clinical applications of this product. Any use in drug development should remain at the discovery/analytical stage unless supported by further qualification and regulatory assessment.
Physical Properties
Item-specific physico-chemical specifications (mp, bp, density, solubility, UV cutoff, metals, water content, etc.): Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for 2-chloro-4-nitrobenzohydrazide and closely related benzohydrazides (for planning only):
Physical state: typically a crystalline solid (literature, by analogy to benzohydrazides).
Melting point: commonly observed for aromatic acyl hydrazides in the range ~150–220 °C, depending on substitution (literature range; specific value for this item not established).
Boiling point: not applicable; compound expected to decompose before boiling at atmospheric pressure (literature expectation for acyl hydrazides).
Solubility profile:
• Good solubility in polar aprotic solvents (DMF, DMSO, NMP) and hot polar protic solvents (EtOH, MeOH) (literature).
• Poor solubility anticipated in nonpolar hydrocarbons (hexanes, toluene) due to multiple heteroatoms (literature).
• Aqueous solubility: variable/limited; can increase under mildly acidic/basic conditions owing to protonation/deprotonation of hydrazide nitrogens (literature).
pKa: hydrazide nitrogens typically pKaH ~2–4 (conjugate acid) and ~10–12 (deprotonation) depending on substitution (literature ranges; not measured for this item).
LogP: aromatic acyl hydrazides with one halogen and one nitro group often exhibit moderate lipophilicity (literature qualitative note; no exact value for this item).
Refractive index, viscosity, and other solvent-only parameters: not applicable (solid).
Always verify critical parameters experimentally or via the item’s CoA prior to scale-up.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and analytical limits.
Guidance on typical quality considerations for aromatic acyl hydrazides:
Identity confirmation: Usually supported by 1H/13C NMR, IR (amide C=O ~1650–1700 cm−1; N–H stretches), MS, and HPLC/GC purity. Elemental analysis may be informative when halogens and nitro groups are present.
Residual solvents/water: Karl Fischer moisture and residual solvent analysis are often reported on CoAs for hydrazides due to hygroscopic tendencies in some members of the class. For this specific item, water/solvent limits are Not specified for this item; refer to CoA/Spec Sheet.
Metals/ash/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: None indicated in product data. If present, would be declared on CoA; stabilizers are generally not used for this class.
What “research use only” means (product data): The material is intended for laboratory R&D. Not for drug, diagnostic, or household use.
Practical notes:
If using for coupling/cyclization chemistry, confirm residual acidic/basic impurities by titration or HPLC, as these can impact yields in carbodiimide- or acid chloride-mediated processes.
For quantitative work, verify assay on receipt and use argon-blanketed storage (as provided) to maintain lot integrity.
Reaction and Applications
2-Chloro-4-nitrobenzohydrazide combines an acyl hydrazide handle with a deactivated, functionally rich aryl ring. Typical laboratory uses (literature/practice):
Hydrazide-centered transformations:
Hydrazone formation: Condensation with aldehydes/ketones to give aryl benzoyl hydrazones. Useful for derivatization, ligand scaffolds, and as precursors to heterocycles. Catalyzed by AcOH or other acids in alcohol/water or polar aprotics.
1,3,4-Oxadiazole synthesis: Cyclodehydration of acyl hydrazides with carboxylic acid equivalents or via intramolecular activation (e.g., POCl3, SOCl2, P2O5, CDI+DCC strategies) affords 1,3,4-oxadiazoles—important motifs in materials and medicinal chemistry (literature).
Acyl transfer/activation: Conversion to acid chlorides (via POCl3/SOCl2) followed by intramolecular or intermolecular transformations; formation of acyl azines/azo derivatives via nitrosation or coupling (literature).
Aryl ring elaboration (considering substitution pattern):
Nitro reduction: The 4-nitro group can be chemoselectively reduced (H2/Pd-C, Fe/AcOH, SnCl2) to the corresponding 4-amino derivative, opening access to amide/urea/sulfonamide libraries. The ortho-chloro remains a potential cross-coupling handle.
Cross-coupling at aryl chloride: With modern Pd catalysts/ligands (e.g., BrettPhos/XPhos-type), aryl chlorides undergo Buchwald–Hartwig amination, Suzuki–Miyaura (after borylation), or direct C–C coupling. Electronic deactivation from nitro/carbonyl may require elevated temperatures and strong bases.
Electrophilic aromatic substitution is generally disfavored (ring is deactivated by nitro and acyl groups); metalation strategies must consider directing effects and potential hydrazide sensitivity.
Applications context:
Building block for SAR libraries where hydrazide participates in reversible covalent capture (hydrazone) and orthogonal aryl diversification via reduction/cross-coupling.
Derivatization agent for carbonyl analysis (hydrazone formation) in analytical workflows (literature), with chloro/nitro offering spectroscopic handles.
Reaction Conditions
The following are literature-derived, general conditions to guide planning. Optimize per substrate and scale; not item-specific specs.
Hydrazone formation (with aldehydes/ketones):
• Solvent: EtOH, MeOH, or EtOH/H2O.
• Catalyst: AcOH (0.1–1 equiv) or aniline catalysts for bioconjugation.
• Temperature/time: rt–reflux, 1–16 h.
• Notes: Remove water (Dean–Stark for less reactive ketones) or use molecular sieves to drive equilibrium.
1,3,4-Oxadiazole synthesis from acyl hydrazide:
• Reagent: POCl3 or SOCl2 (3–6 equiv) or CDI with coupling partners.
• Solvent: Neat reagent or chlorinated solvent/MeCN.
• Temperature: 60–110 °C, 2–12 h.
• Workup: Careful quench to avoid exotherm and HCl/POCl3 hydrolysis hazards.
Nitro reduction (to aniline):
• H2 (1–3 bar) with 5–10 wt% Pd/C in EtOH or MeOH at rt–50 °C, 2–8 h; or Fe/AcOH or SnCl2/EtOH under reflux (stoichiometric).
• Monitor for over-reduction or N–N bond cleavage; protect hydrazide if necessary.
Aryl chloride cross-coupling:
• Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol%), XPhos/BrettPhos (2–4 mol%), NaOtBu/K3PO4, dioxane or toluene, 90–120 °C, 6–24 h.
• Suzuki–Miyaura (after borylation or direct if boronic partner available): Pd(PtBu3)2 or Pd-PEPPSI, K3PO4/K2CO3, 2-MeTHF/dioxane/H2O, 80–110 °C.
• Notes: Ortho substitution may slow oxidative addition; ligand choice is critical.
Protection strategies: Boc or Cbz protection of the terminal hydrazide nitrogen can improve chemoselectivity under acylation/coupling conditions (literature).
Safety and Handling
GHS/CLP item-specific classifications, pictograms, and H-statements: Not specified for this item; refer to SDS.
Known hazards and prudent practices for aromatic acyl hydrazides and nitroaromatics (general guidance; not a substitute for the SDS):
Potential hazards: May cause irritation to skin, eyes, and respiratory tract; hydrazide functionality can be harmful if swallowed or inhaled. Nitroaromatic motifs can present toxicity concerns in prolonged exposure (literature). Avoid dust formation.
PPE: Use lab coat, appropriate chemical-resistant gloves (e.g., nitrile), safety goggles/face shield. Handle in a fume hood.
Storage (item-specific): Store at room temperature, protected from light, under an argon atmosphere (product data). Keep container tightly closed; minimize air/moisture exposure.
Incompatibilities (general): Strong oxidizers or reducing agents (depending on context), strong acids/bases may induce decomposition or hydrolysis; reactive acylation/condensing agents can modify the hydrazide. Avoid prolonged heating without ventilation.
Special risks:
• Thermal decomposition may produce nitrogen oxides, HCl, and other irritant fumes (literature).
• Dust explosion risk is generally low for this class but minimize airborne particulates.
First aid (overview; follow institutional protocols):
• 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; obtain medical attention.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the current SDS for authoritative hazard, exposure limits, spill, and disposal procedures.
Solvent Selection
This product is a solid reagent; solvent selection concerns dissolution for reactions, derivatizations, or analytical measurements.
Recommended dissolution solvents:
• DMSO, DMF, NMP – usually provide rapid dissolution at ambient or mild warming.
• Alcohols (MeOH, EtOH, i-PrOH) – often effective, especially warm; may participate in H-bonding.
• Acetonitrile – moderate solubility; may require sonication/warming.
• Water – limited and pH-dependent; mild acid (e.g., 0.1–1% AcOH) can aid wetting/dispersion, while mild base can increase deprotonation of the hydrazide (caution: hydrolysis at high pH/temperature).
Poor solvents: Aliphatic hydrocarbons and toluene/EtOAc frequently give low solubility at room temperature.
Selection by application:
Hydrazone formation with aldehydes/ketones: EtOH, MeOH, or EtOH/H2O with catalytic acetic acid (literature).
Cyclodehydration to 1,3,4-oxadiazoles: POCl3, SOCl2, or P2O5-mediated reactions typically run in chlorinated solvents or neat reagent; DMF/DCM sometimes used as co-solvents (literature).
Reductions/cross-couplings on the aryl ring: For Pd-catalyzed steps, dioxane, toluene, or DMF with suitable ligands/bases (literature). For nitro reductions, EtOH or MeOH under H2/Pd-C are common.
Comparison (literature):
DMSO vs DMF: DMSO offers higher solvency and greener profile but can participate in some oxidations; DMF is more volatile but has reprotox concerns. Choose per downstream removal and EHS constraints.
Storage and Reconstitution
Storage conditions (product data): Store at room temperature, protected from light, under an argon atmosphere. Shipments are sent under normal conditions.
Container handling: Keep tightly closed. Purge headspace with inert gas after each use to maintain the argon blanket. Minimize exposure to ambient humidity and air.
Stability: Item-specific stability data are Not specified for this item; refer to CoA/Spec Sheet. As a general note, hydrazides are typically stable solids when kept dry and protected from light; avoid prolonged heating.
Reconstitution/dissolution (general guidance):
• Prepare stock solutions in DMSO or DMF (typ. 10–100 mM) for synthetic or analytical work.
• Alternatively, dissolve in EtOH/MeOH with gentle warming and sonication.
• Filter through 0.2 µm PTFE syringe filter if particulate is present.
• For aqueous applications, consider co-solvent systems or pH adjustment; avoid strong base/acid that may hydrolyze the hydrazide.
Freeze–thaw: For solution stocks, aliquot to avoid repeated freeze–thaw. Store DMSO/DMF stocks at −20 °C in amber vials when extended storage is required (general recommendation; verify solubility and stability experimentally).
Always consult the product’s CoA/SDS for lot-specific guidance and confirm solution stability before critical experiments.
Structure and Identity
A substituted benzohydrazide featuring an ortho chloro and para nitro substituent on the benzoyl ring; the acyl hydrazide (–C(=O)–NH–NH2) is directly attached to the aromatic ring.
SKU: C708810
Product name: 2-Chloro-4-Nitrobenzohydrazide
CAS: 67345-78-2 (product data)
PubChem CID: 3685650 (product data)
InChIKey (product data): 420724 (note: appears nonstandard/incomplete; verify against CoA/SDS)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/stoichiometric estimate based on the name: C7H6ClN3O3 (to be verified)
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature estimate (from formula above): ~215.60 g/mol (to be verified)
Key structural features (general description):
Aromatic ring bearing three substituents: (1) a benzoyl carbonyl at C-1, (2) a chloro at C-2 (ortho to the carbonyl), and (3) a nitro at C-4 (para to the carbonyl).
Acyl hydrazide functionality: –C(=O)–NH–NH2, providing two nitrogen centers (one amide-like, one terminal hydrazide) for condensation and derivatization chemistry.
Nitro group (–NO2) strongly deactivating and meta-directing for electrophilic aromatic substitution; can be reduced to an aniline derivative under standard conditions (literature).
No defined stereocenters; planar aromatic core with rotatable C(=O)–N bonds in the hydrazide tail.
Synthetic Utility
Functional group leverage:
Hydrazide (–CONH–NH2):
• Nucleophilic terminal –NH2 condenses with aldehydes/ketones to hydrazones (precursors to heterocycles).
• Intramolecular cyclodehydration with carboxylates to 1,3,4-oxadiazoles (literature).
• Acyl activation (e.g., via SOCl2/POCl3) enables rearrangements or further coupling.
• Selective N-acylation on the terminal nitrogen offers access to diacylhydrazides.
Nitro (para):
• Chemoselective reduction to an aniline, enabling urea/sulfonamide/amide formation and directing-group strategies.
• Participates in Meisenheimer complexes in strongly activated systems; here, meta to Cl relative positioning reduces SNAr activation of the 2-Cl site (literature insight).
Aryl chloride (ortho):
• Cross-coupling handle (Buchwald–Hartwig, Suzuki–Miyaura after borylation, Ullmann-type under copper catalysis). Ortho position may influence reactivity/sterics; robust ligands and elevated temperatures are typically required for aryl chlorides.
Retrosynthetic value:
Disconnection at the hydrazide reveals the corresponding acid chloride or activated ester of 2-chloro-4-nitrobenzoic acid reacting with hydrazine or a protected hydrazine derivative (literature). Protecting group strategies (e.g., Boc-hydrazide) can improve selectivity and handling.
Orthogonality:
Sequential strategies: (1) Hydrazone formation, (2) nitro reduction, (3) cross-coupling at Ar–Cl, or alternate orders depending on compatibility. Protect hydrazide if conditions risk N-acylation or cleavage.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting agent or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies.
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