This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
266.120 g/mol
XLogP3
3.700
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
265.006 Da
Monoisotopic Mass
265.006 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
266.000
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
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Recensioni
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Application Protocols
No item-specific tested application protocols are provided for this small-molecule building block. Typical laboratory uses would follow standard organic synthesis procedures.
For solution preparation in research assays (general guidance):
Prepare a concentrated stock (e.g., 10–100 mM) in dry DMSO or DMF.
Filter through 0.2 µm PTFE if needed; store aliquots to minimize freeze–thaw.
Dilute into reaction or assay media ensuring final vehicle (e.g., DMSO) remains within tolerated limits.
Always adapt to your institutional SOPs and consult the product CoA/SDS for any constraints specific to your lot.
Biological Roles
Item-specific biological/biochemical roles: Not specified for this item; refer to primary literature if a biological application is intended.
General context:
Diaryl amides are common motifs in bioactive molecules due to conformational rigidity, H-bonding capability, and tunable lipophilicity. However, N-(2,3-dichlorophenyl)benzamide is provided for research use only and has no assigned biological function in this listing.
Metabolic expectations (general): aromatic amides may undergo hydrolysis by amidases to liberate the corresponding aniline and carboxylic acid; aromatic ring hydroxylation and dechlorination are possible in advanced oxidative systems.
Protein interactions: the amide can form H-bonds (as donor and acceptor), but specific target binding or biochemical pathways are not established here.
For any biological testing, ensure compound identity/purity by orthogonal methods (NMR, LC-MS) and evaluate solubility and vehicle effects (e.g., DMSO) on assay performance.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biological buffers. If used in biochemical assays, it would generally be dissolved in an organic co-solvent (e.g., DMSO) and then diluted into the assay buffer. Refer instead to the Solvent Selection and Storage & Reconstitution sections for practical handling guidance.
Green Alternatives
While N-(2,3-dichlorophenyl)benzamide itself is a target molecule, greener choices can be made in its use and in transformations upon it.
Greener solvent choices for common operations (general guidance):
Cross-coupling media:
Greener options: 2-MeTHF, CPME, propylene carbonate, or water/ethanol mixtures (with micellar catalysis) vs traditional toluene/DMF/dioxane.
Tradeoffs: catalyst solubility/activity and base choice may require optimization; product isolation can be simpler from greener ethers (2-MeTHF, CPME) than from DMSO/DMF.
Workup and crystallization:
Favor EtOAc/IPA/heptane systems over chlorinated solvents when feasible.
Hydrolysis studies:
Use aqueous ethanol or water/MeCN with minimized organic content.
Comparison snapshot (general):
DMF vs 2-MeTHF: DMF offers higher polarity and solubility but is more challenging to remove and has a worse EHS profile; 2-MeTHF is biorenewable and easier to separate, though less polar and sometimes requires elevated temperature.
CH2Cl2 vs EtOAc: CH2Cl2 has higher solvency and density (aids phase separations) but poorer environmental metrics; EtOAc is biodegradable with lower toxicity.
Process considerations:
Employ catalytic rather than stoichiometric activations (e.g., catalytic amidation protocols) and flow chemistry to reduce solvent volumes.
Use high-activity Pd–NHC or biaryl phosphine ligands to lower catalyst loadings and temperatures, improving energy efficiency.
Pharmaceutical Uses
Item-specific pharmacopeial status, excipient roles, or formulation uses: Not specified for this item; refer to CoA/Spec Sheet.
General note:
Aromatic amide motifs are prevalent in medicinal chemistry. Compounds like N-(2,3-dichlorophenyl)benzamide may be used as research intermediates during structure–activity relationship (SAR) exploration or as synthetic building blocks toward more complex candidates. No clinical or therapeutic claims are made for this product.
If used in formulation research (preclinical only), confirm solubility and stability in the intended vehicle, and assess potential for crystallinity-driven precipitation upon dilution.
Physical Properties
Item-specific numeric specifications (mp, bp, density, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for diaryl amides like N-(2,3-dichlorophenyl)benzamide (for planning only):
Physical state: typically a crystalline solid due to strong amide H-bonding and planarity (literature/general)
Polarity: moderately polar (amide) yet overall hydrophobic because of two aryl rings and two chlorines (general)
Solubility profile (general):
Water: very low to practically insoluble
Organic: good solubility in polar aprotic solvents (DMSO, DMF, NMP); moderate in acetone/ethyl acetate; variably soluble in chlorinated solvents (CH2Cl2, CHCl3); limited in hexanes/aliphatics
Acid/base: neutral secondary amide; non-basic due to resonance; can form H-bonds as donor (N–H) and acceptor (C=O) (general)
Partitioning: expected cLogP in the moderate range for diaryl amides bearing two chlorines (qualitative; consult specific computational tools if needed)
Thermal behavior: amides generally show high melting points; decomposition may occur before boiling under ambient pressure (general guidance)
Notes:
When preparing solutions for assays or reactions, DMSO or DMF typically provide rapid dissolution; gentle warming (≤40–50 °C) and sonication can assist.
Always verify critical values (mp, solubility limits) against primary literature or the product CoA before scale-up.
Quality and Grades
Item-specific grade/purity, stabilizers, and analytical limits: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on quality for aromatic amide building blocks:
Research grade: suitable for most synthetic and discovery workflows. For high-sensitivity applications (e.g., trace analytics or photophysics), review UV cutoff and metal content on the CoA.
Purity reporting: typically validated by 1H/13C NMR and LC/GC purity. For halogenated aromatics, GC may under-report heavy, non-volatile residues; LC-UV or LC-MS often provides the most reliable purity trace.
Residual solvents: common crystallization/processing solvents include ethyl acetate, acetone, toluene, or alcohols; confirm limits on CoA if relevant to downstream steps.
Stabilizers: none are typically required for diaryl amides; if present, the CoA will list them explicitly.
Impurities to consider (general): unreacted anilines/acid chlorides, over-acylated species, positional isomers, or hydrolysis products. Chlorinated aromatics may carry trace inorganic chloride; ash/metals should be checked if using in catalysis-sensitive steps.
Recommendation: If using for catalysis (e.g., Pd-catalyzed couplings on the aryl chloride), consider a pre-wash or recrystallization and request metal content or halide assay data as needed.
Reaction and Applications
This compound is primarily a synthetic building block. The two aryl chlorides and the amide functionality enable diverse transformations.
Transformations on the 2,3-dichlorophenyl ring (literature/general):
Pd-catalyzed cross-couplings at C–Cl: Suzuki–Miyaura (to arylate), Buchwald–Hartwig amination, or Sonogashira alkynylation using modern catalysts/ligands active for aryl chlorides (e.g., Pd/XPhos, Pd/SPhos, Pd–NHC). Sequential/orthogonal couplings at the two chlorine sites allow regiocontrol.
Nucleophilic aromatic substitution (SNAr): generally limited on anilide rings unless additionally activated; consider electron-withdrawing activating groups if SNAr is desired.
Transformations at the amide (literature/general):
Hydrolysis (acidic or basic) to yield 2,3-dichloroaniline and benzoic acid; useful for protecting-group-like applications or labeling studies.
Reduction: LiAlH4 or borane can reduce the amide to the corresponding amine (e.g., N-(2,3-dichlorophenyl)benzylamine). Catalytic hydrogenolysis protocols for amide reduction may also be applicable.
Transamidation/activation: via CDI, Mukaiyama reagents, or thionyl chloride to form the acid chloride (from the benzamide parent), enabling further derivatization when used in a synthetic sequence.
Directing effects:
The amide can act as a directing group for metalation or C–H activation on the benzamide phenyl ring (orthometalation under strong base or transition-metal catalysis; literature-dependent).
Practical notes:
Employ anhydrous, degassed solvents for Pd-catalyzed couplings; aryl chlorides often require higher temperatures or more active ligands versus bromides/iodides.
For sequential couplings on the dichloro ring, map relative reactivity (2- vs 3-position) under candidate conditions to design orthogonal steps.
Reaction Conditions
General literature-style conditions for common transformations of aryl chlorides and amides (guidance only; optimize per substrate and scale):
Suzuki–Miyaura coupling at aryl C–Cl:
Catalyst/ligand: Pd2(dba)3 (1–2 mol% Pd) with XPhos/SPhos (2–4 mol%) or Pd-PEPPSI (1–2 mol%)
Base: K2CO3 or K3PO4 (2–3 equiv), often with H2O (10–20%)
Solvent: 1,4-dioxane, toluene/H2O, or CPME/H2O
Temperature/time: 80–110 °C, 4–16 h
Notes: aryl chlorides may require higher temp or more active ligands vs bromides; sequential couplings feasible.
Buchwald–Hartwig amination of aryl C–Cl:
Catalyst/ligand: Pd(OAc)2 (1–2 mol%) + BrettPhos or RuPhos; or Pd-PEPPSI-IPr
Base: NaOtBu or Cs2CO3 (2–3 equiv)
Solvent: toluene, dioxane, or tAmOH
Temperature/time: 90–120 °C, 6–18 h
Notes: monitor for potential competitive amide N–H involvement; N is less nucleophilic (resonance) but may require base management.
Sonogashira coupling:
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (5–10 mol%) or copper-free systems
Base/solvent: Et3N or iPr2NH in THF/DMF
Temperature: rt–80 °C
Amide reduction to amine:
Reagent: LiAlH4 (2–4 equiv) in dry THF or Et2O
Temperature: 0 °C to reflux, 2–6 h; careful quench protocol required
Alternative: BH3·THF (excess), reflux, 6–16 h
Amide hydrolysis:
Conditions: 2–6 M HCl or NaOH, reflux (aqueous ethanol or dioxane co-solvent), 4–24 h
Outcome: benzoic acid + 2,3-dichloroaniline
Expected yields depend strongly on ligands, base, and substitution; consult primary literature for closely related dichloroanilide substrates.
Safety and Handling
Item-specific hazard classification (GHS, pictograms, H-statements, signal word): Not specified for this item; refer to SDS.
General safety guidance for aromatic amides (informational; not a substitute for SDS):
Likely hazards: may cause skin/eye irritation or respiratory irritation as a dust; aromatic chlorinated solids are often harmful if swallowed or inhaled. Avoid dust formation and inhalation.
PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control dust and solvent vapors.
Incompatibilities: strong oxidizers (risk of reaction); strong bases or acids under reflux can hydrolyze the amide; avoid reactive metals when using strong reducing agents (e.g., LiAlH4) in subsequent chemistry.
Handling tips:
Weigh in a ventilated enclosure (balance enclosure) to minimize dust exposure.
For solution prep, add solvent slowly with stirring; warm gently if needed.
First aid overview (follow institutional protocols):
Skin/eyes: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: treat as a combustible organic solid; use CO2, dry chemical, or foam extinguishers. Thermal decomposition may release HCl/HCl-containing fumes.
Always consult the product SDS for authoritative hazard, exposure limits, and response measures.
Solvent Selection
As a neutral, moderately polar, hydrophobic diaryl amide, N-(2,3-dichlorophenyl)benzamide dissolves best in polar aprotic media and some chlorinated solvents.
Miscibility/solubility guidance (general):
Excellent: DMSO, DMF, NMP
Good: CH2Cl2, CHCl3, acetone, ethyl acetate
Fair/variable: toluene, MeCN, THF (warming may be needed)
Poor: water, hexanes
Selection by application:
Reaction medium for cross-coupling on the aryl chlorides: toluene, dioxane, or DMF are common; addition of water (Suzuki) may be beneficial with phase-transfer/base.
Hydrolysis studies: aqueous acid/base with a co-solvent (MeCN, dioxane) to assist dissolution.
Analytical prep/stock solutions: DMSO (biochemistry assays) or DMF/MeCN (chromatography). Filter through 0.2 µm PTFE when preparing standard solutions.
Practical tips:
If solids persist, gentle heating (≤50 °C) and sonication accelerate dissolution.
For moisture-sensitive downstream reactions, dry solvents thoroughly (molecular sieves, distillation) prior to use.
Small comparison (general):
DMSO vs DMF: DMSO offers superior solvating power but can complicate workup; DMF is easier to remove under high vacuum. For air-sensitive Pd catalysis, toluene/dioxane may afford higher catalyst longevity than DMF in some systems.
Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to light and moisture. Use a desiccator if humidity is high.
For long-term archival, many labs store aromatic amide solids at ambient temperature in desiccation; refrigeration is typically unnecessary unless the CoA indicates otherwise.
Reconstitution/solution preparation (general):
Preferred solvents: DMSO, DMF, or CH2Cl2 depending on application.
To prepare stock solutions: weigh accurately, dissolve with gentle stirring; warm to 30–40 °C or sonicate if needed. Record the exact concentration and solvent.
Working solution stability: aromatic amides are generally stable in aprotic solvents for weeks at 2–8 °C; for maximum stability, aliquot and store stocks at −20 °C to minimize hydrolysis. Avoid repeated freeze–thaw cycles.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Always defer to the lot-specific CoA/SDS for definitive storage and handling instructions.
Structure and Identity
Brief overview: N-(2,3-dichlorophenyl)benzamide is an anilide (diaryl amide) featuring a benzamide carbonyl bound to an anilide nitrogen bearing a 2,3-dichlorophenyl substituent. Two aryl rings and two ortho/meta chlorines provide useful synthetic handles.
From Product Data (item-specific):
SKU: N1035960
Product name: N-(2,3-dichlorophenyl)benzamide
CAS: 10286-77-8
Storage conditions: Room temperature
Research use note: For research use only
Literature/computed identity (general reference values; not item specifications):
Synonym class: 2,3-dichloroanilide of benzoic acid (anilide)
Molecular formula (literature): C13H9Cl2NO
Molecular weight (literature): ~266.13 g/mol
SMILES (literature): O=C(Nc1cccc(Cl)c1Cl)c2ccccc2
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (descriptive):
Functional groups: secondary amide (benzamide), two aryl chlorides (o- and m- to the amide N on the aniline ring)
Ring systems: two phenyl rings linked via an amide (Ar–CO–NH–Ar)
Stereochemistry: achiral; no stereogenic centers
2D description: a benzamide carbonyl (C=O) attached to a phenyl ring; the amide N is bonded to a second phenyl ring bearing chlorine atoms at the 2- and 3-positions relative to the N–aryl bond.
Synthetic Utility
Functional handles and strategies (literature/general):
Aryl chlorides (2,3-positions):
Cross-coupling manifold: Suzuki–Miyaura (C–B), Buchwald–Hartwig (C–N), Sonogashira (C–C≡C), Negishi/Kumada (C–Zn/Mg) using catalysts active for aryl chlorides (e.g., Pd–NHC, BrettPhos/SPhos systems). Sequential couplings can construct densely substituted aniline frameworks.
Halogen–metal exchange (under carefully controlled conditions) to access organolithium intermediates, then quench with electrophiles (requires low temperature and protection of the amide if needed).
Amide functionality:
Chemoselective reduction to the corresponding amine with LiAlH4 or BH3·THF; catalytic systems (e.g., Raney Ni/borrowing hydrogen; Ru or Ir catalysts) may operate under milder conditions depending on substrate tolerance.
Hydrolysis (acid/base) as a deprotection-like step to 2,3-dichloroaniline + benzoic acid.
Activation to more reactive acyl species via chlorination (SOCl2, oxalyl chloride) of the benzoic acid precursor in synthetic routes; transamidation via coupling reagents (CDI, EDCI) when constructing analogs.
Directing-group chemistry:
The amide can direct ortho-functionalization on the benzamide ring through lithiation or transition-metal-catalyzed C–H activation protocols, enabling elaboration distal from the dichloroaniline ring.
Selectivity/practical points:
Map the relative reactivity of the two C–Cl sites; steric and electronic differences often enable stepwise, regioselective functionalization.
Maintain anhydrous, oxygen-free conditions for metalation/cross-coupling; pre-dry the amide to avoid catalyst inhibition via adventitious water.
Target Specificity
Not applicable — this product is a small-molecule chemical and not a biological targeting reagent (e.g., antibody, enzyme, or probe). No antigen/epitope or species reactivity is relevant.
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