This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl 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.
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
245.100 g/mol
XLogP3
1.900
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
244.017 Da
Monoisotopic Mass
244.017 Da
Topological Polar Surface Area
41.100 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
250.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Not applicable to this product.
No validated immunoassay or bioassay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block in the Product Data.
For compound handling in screening: prepare DMSO stock (e.g., 10–50 mM), filter-sterilize if needed (0.22 µm PTFE), and dilute into assay buffer with careful mixing to avoid precipitation. Determine final DMSO tolerance of the assay system independently.
Biological Roles
Item-specific biological information: Not specified for this item; refer to primary literature if pursuing biochemical studies.
General context (non-clinical, literature-based)
2-Piperazinone motifs are common in medicinal chemistry as conformationally constrained piperazine surrogates. The lactam reduces basicity compared with free piperazines, potentially modulating permeability and off-target ion channel interactions; however, these are design principles rather than established biological roles for this exact compound.
The 3,4-dichlorophenyl group is a prevalent hydrophobic/aromatic vector used to tune potency and metabolic stability in structure–activity relationships.
Research use only note
This product is intended exclusively for research and laboratory use. It has no approved biological, diagnostic, or therapeutic application. Any evaluation of biochemical interactions (e.g., receptor binding, enzyme inhibition) must be experimentally determined and is outside the scope of this catalog entry.
If biological assessment is planned, generate compound-specific data (e.g., aqueous solubility across pH, stability in assay buffers, potential aggregation) prior to screening to avoid artifactual readouts.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare classical laboratory buffers.
Practical note
The secondary amine allows salt formation (e.g., hydrochloride, mesylate, citrate) to increase aqueous solubility for biological assays; however, these salts function for solubilization rather than pH buffering.
If dissolution in assay media is required, prepare DMSO stock solutions (e.g., 10–50 mM) and dilute into buffered systems (PBS, HEPES) with attention to final DMSO percentage and potential precipitation.
For true buffering applications, select dedicated buffers with defined pKa and buffering ranges (e.g., phosphate, HEPES, Tris).
Green Alternatives
While the compound is a solid building block rather than a solvent, greener choices concern reaction media, reagents, and workups used with it.
Greener solvent options (general guidance)
Replace DMF/NMP with safer polar aprotics when feasible: 2-MeTHF, CPME, propylene carbonate, or green esters (e.g., ethyl acetate) for certain couplings or N-acylations.
For Suzuki couplings: aqueous ethanol or 2-MeTHF/H2O systems can substitute dioxane/toluene; micellar catalysis (TPGS-750-M in water) has growing precedent for Ar–Cl couplings.
Catalysis and bases
Use highly active Pd/ligand systems (e.g., tBuBrettPhos, XPhos precatalysts) to lower catalyst loadings and temperatures, reducing energy demand.
Carbonate bases (K2CO3, K3PO4) in water-rich media are preferable over strong alkoxides for EHS profile.
Workup/waste minimization
Salt formation/crystallization (e.g., HCl/Et2O, fumarate) can replace chromatographic purification, cutting solvent use.
Employ solvent recovery and switch to greener eluents (heptane/EtOAc) when chromatography is unavoidable.
Trade-offs (balanced view)
2-MeTHF/CPME are flammable and can form peroxides over time; manage peroxide testing and stabilization.
Aqueous micellar systems may complicate isolation of moderately water-soluble amine salts; plan phase-split strategies.
Summary: For most derivatizations of 3-(3,4-dichlorophenyl)piperazin-2-one, prioritize 2-MeTHF or EtOAc where possible, employ water/ethanol blends for couplings, and consider crystallizable salts to reduce chromatography.
Pharmaceutical Uses
Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. No compendial monograph is indicated.
General formulation/manufacturing context (non-clinical)
3-(3,4-Dichlorophenyl)piperazin-2-one is best categorized as a synthetic intermediate or discovery compound. It is not used as an excipient. Its secondary amine enables formation of crystalline salts (e.g., HCl), which can be advantageous for handling during process development if the scaffold is embedded in a route to a drug candidate.
If adopted in a development route, standard pharmaceutical considerations would include impurity control (aryl chlorination byproducts, over-alkylation), polymorph/solvate screening if isolated as a salt, and residual solvent limits per ICH Q3C.
No therapeutic or clinical claims are made for this material. It is offered strictly for research and development use.
Physical Properties
Item-specific specs (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations (for reference; not item-specific specifications)
State: Typically an organic solid at ambient conditions (aromatic dichloro substituents often confer crystallinity; the lactam and secondary amine add polarity).
Melting/boiling: Specific MP/BP not located in public domain sources for this CAS at the time of writing; expect a definite MP and negligible volatility at room temperature typical of aryl-lactam scaffolds.
Density/refractive index: Not applicable/rarely reported for non-liquid solids of this class.
Solubility profile (qualitative):
Good solubility in polar aprotic solvents (DMSO, DMF, NMP) and chlorinated organics (DCM, chloroform).
Moderate in acetonitrile/ethyl acetate; limited in nonpolar hydrocarbons (hexane/heptane).
Water: limited for the free base; aqueous solubility increases markedly upon protonation (e.g., HCl salt) due to the secondary amine.
Acid–base behavior: Contains one basic secondary amine (amine pKaH typically in the 7–9 range for piperazinone derivatives; literature values vary with substitution) and one amide nitrogen that is not basic.
LogP/cLogP: Expected to be moderate due to the dichlorophenyl ring offset by a polar lactam; commonly suitable for organic/medchem applications. Use experimental measurement or validated prediction tools for exact values.
Always consult the CoA/SDS for definitive, lot-specific physical data before process design.
Quality and Grades
Item-specific quality status (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research/analytical grade materials are typically controlled for identity (NMR/LC–MS/HPLC), purity, and relevant residuals/impurities. When “HPLC grade” is used for solvents, it implies low UV/background; for solids like this building block, purity is often provided as an assay (% area by HPLC/GC) with impurity profiling.
Absence of a specified stabilizer suggests the neat solid is supplied without added inhibitors unless noted on the CoA.
Recommendations for this item
Verify lot-specific assay, water content, and residual solvents on the CoA prior to use in regulated or critical synthesis steps.
If used for structure–activity relationship (SAR) studies, consider in-house verification by 1H NMR, 13C NMR, and HRMS, and confirm chloride substitution pattern (3,4-) via aromatic splitting and/or HMBC/NOESY.
If chiral or polymorph concerns existed, they would be noted; this scaffold is achiral, and polymorphism risk is generally lower than for flat amides but can still occur—confirm solid form if crystallinity matters for scale-up.
Reaction and Applications
This scaffold is a versatile medchem/intermediate building block with two orthogonal handles: (a) a secondary amine within the piperazinone; (b) two aryl chlorides on the 3,4-dichlorophenyl ring.
Transformations on the ring nitrogen (secondary amine)
N-alkylation: Alkyl halides or sulfonates under basic conditions (K2CO3, Cs2CO3, DIPEA) in DMF/MeCN; consider protection (Boc/CBz) if selective alkylation is needed.
Acylation/sulfonylation: Acyl chlorides, anhydrides, or sulfonyl chlorides in DCM/MeCN with base; yields ureas, amides, or sulfonamides for SAR expansion.
Reductive amination: After prior formylation or with aldehydes if a suitable activation strategy is used (e.g., NaBH(OAc)3 in DCE/MeOH), though the lactam diminishes nucleophilicity—optimize conditions.
Buchwald–Hartwig amination: Pd catalysts (XPhos/SPhos/tBuBrettPhos) enable coupling of Ar–Cl with amines to replace one or both chlorides selectively.
Suzuki–Miyaura coupling: Boronic acids/esters can be installed on Ar–Cl with Pd/SPhos or related ligands to append (hetero)aryl fragments.
Other cross-couplings: Negishi/Kumada under optimized systems for Ar–Cl if stronger activation is available.
Orthogonality and protection
The lactam is generally stable to many cross-coupling conditions. If interference from the secondary amine occurs (Pd binding), temporary protection (Boc) improves reproducibility.
Applications (general)
Common in discovery chemistry libraries as a constrained piperazine motif offering H-bonding (lactam) with controlled basicity. Useful for probing polarity/permeability balance without over-basicity of free piperazines.
All conditions above are literature-style guidance; optimize for your specific substrate and scale.
Reaction Conditions
The following conditions are literature-style, general guidance for scaffolds bearing aryl chlorides and a secondary amine/lactam. Optimize for your substrates and scale.
Buchwald–Hartwig amination (Ar–Cl on the 3,4-dichlorophenyl)
Catalyst/ligand: Pd2(dba)3 (1–2 mol% Pd) or Pd(OAc)2 (2–4 mol% Pd) with tBuBrettPhos, XPhos, or RuPhos (2–6 mol% ligand).
Base: NaOtBu or K3PO4 (2–3 equiv).
Solvent: Toluene, dioxane, or 2-MeTHF.
Temperature/time: 80–110°C, 2–16 h.
Suzuki–Miyaura coupling (Ar–Cl → Ar–Ar′)
Catalyst: Pd(dppf)Cl2·DCM (1–2 mol%) or Pd-precatalysts with SPhos/XPhos.
Nucleophile: Boronic acid/ester (1.2–1.5 equiv).
Base: K3PO4 or K2CO3 (2–3 equiv).
Solvent: 1,4-dioxane/H2O or toluene/H2O; greener options include EtOH/H2O.
Temperature/time: 70–100°C, 3–12 h.
N-alkylation of the ring secondary amine
Electrophile: Alkyl bromides/iodides or mesylates (1.1–1.5 equiv).
Base: K2CO3 or Cs2CO3 (2–3 equiv).
Solvent: DMF or MeCN; 20–60°C, 2–18 h.
Tip: Boc-protect prior to aryl couplings to prevent Pd poisoning; deprotect with TFA in DCM or HCl in dioxane.
N-acylation/sulfonylation
Reagents: Acyl chlorides/anhydrides or sulfonyl chlorides (1.1–1.3 equiv).
Base: DIPEA, Et3N, or pyridine (2–3 equiv).
Solvent: DCM or MeCN; 0–25°C, 0.5–4 h.
Workup/isolation
Quench with aqueous NH4Cl or NaHCO3; extract with EtOAc/DCM. Consider forming an HCl salt (IPA/Et2O) for crystallization.
Note: The lactam is generally stable under these conditions; avoid strong base at high temperature for prolonged times to prevent ring opening.
Safety and Handling
Item-specific hazard data (from Product Data)
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl-dichloro lactam amines (literature/analog-based; not a certificate of analysis)
Likely hazards: May cause skin/eye irritation and respiratory irritation if dust is generated. Avoid inhalation, ingestion, and contact.
PPE: Use lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle solids in a fume hood to minimize dust exposure.
Handling: Avoid generating dust; use antistatic measures when weighing. For solutions, cap tightly to minimize evaporation and contamination. The secondary amine can react with strong electrophiles—avoid uncontrolled contact with acid chlorides/anhydrides unless intended.
Incompatibilities: Strong oxidizers; strong acids/bases may cause degradation under forcing conditions (lactam hydrolysis under strong base/high temperature; N-chlorination possible with strong chlorinating agents).
First aid (overview; defer to SDS):
Skin/eye contact: 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: Organic solid; treat fires with CO2, dry chemical, or foam. Combustion may produce HCl, NOx, and CO/CO2—use SCBA.
Always consult the product-specific SDS for authoritative hazard, exposure limits, and emergency procedures.
Solvent Selection
Selecting solvents for 3-(3,4-dichlorophenyl)piperazin-2-one balances its moderate polarity (lactam + secondary amine) and hydrophobic aryl dichloro group.
Polarity/miscibility (general)
Polar aprotic: DMSO, DMF, NMP—typically excellent solubility; ideal for stock solutions and coupling chemistry.
Moderately polar: Acetonitrile, ethyl acetate, isopropanol—moderate solubility; useful for workups and crystallizations.
Nonpolar: Toluene, MTBE, CPME—variable; often limited but can be improved as salts or at elevated temperature.
Aqueous: Free base has low solubility; protonated salts (e.g., HCl) dissolve readily in water and aqueous alcohols.
Practical choices by task
N-alkylation/acylation: DMF or acetonitrile with K2CO3/DIPEA; DCM for acylations using acyl chlorides with base.
Cross-coupling on the aryl chloride(s): Toluene, dioxane, or 2-MeTHF with water/cosolvent for Suzuki; anisole/PhMe for high-temp Buchwald–Hartwig.
Purification: Ethyl acetate/hexane or DCM/MeOH gradients; reverse phase (C18) using MeCN/H2O with 0.1% formic acid for polar impurities.
Small comparison (general)
DMSO vs DMF: DMSO offers superior solubilization but is harder to remove; DMF balances solubility and workup.
Toluene vs dioxane: Toluene tolerates higher temps; dioxane/water aids Suzuki phase transfer.
Select solvent considering downstream isolation: form a crystalline salt (e.g., HCl in IPA/Et2O) to improve handling and stability if needed.
General storage guidance (solid, organic amide/amine)
Keep tightly closed in the original container, stored dry and away from direct light. Use desiccation if ambient humidity is high. Avoid prolonged exposure to air if frequent opening leads to moisture uptake.
If long-term storage (>12 months) is planned, consider aliquoting to minimize repeated air/moisture exposure, especially if forming salts that may be hygroscopic.
Reconstitution/stock preparation (general, not item-specific specifications)
Prepare concentrated stocks in anhydrous DMSO (e.g., 10–100 mM) for biological assays or library storage. Filter through 0.22 µm PTFE if particulate is present.
For synthetic use, dissolve in DMF, DMSO, MeCN, DCM, or EtOAc as appropriate. Warming (30–40°C) and sonication can aid dissolution.
Aqueous work: Convert to a soluble salt (e.g., HCl) prior to dissolution in water/buffer if needed.
Stability considerations
The lactam is generally robust; avoid strong acids/bases and high temperatures for extended periods, which may promote hydrolysis or N-dealkylation (if derivatized). Store away from strong oxidizers.
Always consult the CoA/SDS for lot-specific stability and handling recommendations.
Structure and Identity
Brief description: 3-(3,4-Dichlorophenyl)piperazin-2-one is a dichloroaryl-substituted 2-piperazinone (six-membered lactam) featuring both a cyclic amide and a secondary amine within the piperazinone ring.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity (for reference; not item-specific specifications)
Core scaffold: 2-piperazinone (lactam) substituted at C3 with a 3,4-dichlorophenyl group.
Functional groups: cyclic amide (lactam), secondary amine (ring N), dichloroaryl (two aryl C–Cl bonds ortho/para to each other at 3,4-positions on the ring).
Typical molecular formula (literature): C10H10Cl2N2O
2D structure described in words (general): A six-membered ring containing two nitrogens at the 1,4-positions and a carbonyl at the 2-position (2-piperazinone). The carbon at the 3-position bears a phenyl ring substituted with chlorines at the 3- and 4-positions. One ring nitrogen is amide-bound (lactam N adjacent to the carbonyl), the other is a secondary amine available for derivatization (e.g., N-alkylation/acylation). No stereocenters are present; the compound is achiral.
Synthetic Utility
Key features enabling broad synthetic utility:
Functional group portfolio
Secondary amine (nucleophilic, basic): amenable to N-alkylation, acylation, sulfonylation, carbamoylation; can be protected (Boc/CBz) to direct chemoselectivity.
Lactam (amide): hydrogen bond acceptor; generally inert under many coupling conditions; can be reduced (e.g., with borane) under forcing conditions to give piperazine derivatives; can be opened under strong basic/acidic hydrolysis though typically avoided.
Aryl dichlorides: two C(sp2)–Cl bonds suitable for Pd-catalyzed cross-coupling (Buchwald–Hartwig, Suzuki, Heck) with modern ligands that activate aryl chlorides.
Retrosynthetic value
Serves as a convergent junction: heterocycle installed via cyclization, then late-stage diversification on the aryl chlorides and ring nitrogen to access libraries.
Orthogonal derivatization allows stepwise vector exploration (e.g., selectively couple para-Cl first, then meta-Cl) using ligand-controlled selectivity.
Named reaction contexts (general)
Buchwald–Hartwig amination (Ar–Cl → Ar–NR2), Suzuki–Miyaura (Ar–Cl → Ar–Ar′), and Chan–Lam variants after prefunctionalization.
Reductive acylation/amination sequences on the ring nitrogen to introduce alkyl side chains.
Practical notes
If catalyst inhibition is observed (amine binding to Pd), Boc-protect the ring NH prior to cross-coupling; deprotect under mild acid post-coupling.
Control over-alkylation on the secondary amine by using hindered bases, phase-transfer conditions, or stoichiometric control.
These features make the compound a robust platform for rapidly assembling diverse analogs in discovery chemistry.
Target Specificity
Not applicable to this product.
No antigen/epitope/clone/isotype information is relevant. This material is a small-molecule research chemical and not an antibody, protein, or diagnostic reagent. Any biological target interactions must be established experimentally and are not provided in the Product Data.
Domande frequenti
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.
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 334477-10-0, the molecular formula is C10H10Cl2N2O, and the molecular weight is 245.1 g/mol. InChIKey PYBLTGJGVAFJCT-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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