This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
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
246.090 g/mol
XLogP3
1.100
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
245.024 Da
Monoisotopic Mass
245.024 Da
Topological Polar Surface Area
103.000 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
264.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No manufacturer‑validated application protocols are provided for this SKU.
General lab guidance (adapt to your use case)
Stock solution preparation: Dissolve in DMSO (e.g., 10–100 mM) or prepare an acidified aqueous stock (e.g., 1–10 mg/mL in water with 0.1–1.0 equiv HCl) to form a soluble biguanidinium salt. Filter (0.22 µm) if required.
Reaction setup: For N‑functionalization, dry solvents and maintain inert atmosphere to avoid moisture‑induced variability in protonation state.
Analytical: Use LC with acidic modifiers; confirm identity by NMR and HRMS. If salt form is critical, verify counterion content (ion chromatography or titration).
Handling: Minimize exposure to ambient humidity; store tightly closed. Use single‑use aliquots for moisture‑sensitive steps.
For assay‑specific or method‑specific protocols, consult domain literature and validate conditions with small pilot experiments.
Biological Roles
Scope and caution
No biological/clinical claims are made for this SKU. The following are general, literature‑level notes about aryl biguanide chemistry relevant to research contexts only.
General features (literature/general)
Biguanides are polybasic, cationic at physiological pH, and capable of strong electrostatic and hydrogen‑bonding interactions with biomolecules (e.g., phospholipids, polyanions).
Aromatic substitution (here, 3,5‑dichloro) can modulate hydrophobicity and membrane association relative to unsubstituted phenyl biguanides.
Biguanidinium species often display salt‑dependent aqueous solubility and can engage in ion‑pairing, which may be leveraged in delivery studies and analytical separations.
Research relevance (non‑clinical)
Aryl biguanides and related cationic guanidinium compounds have been explored as tools in chemical biology for probing binding to acidic biomolecular surfaces and as components of cell‑penetrating motifs (literature).
The protonation state and counterion critically influence binding, aggregation, and partitioning; characterize these parameters explicitly for any biological assay.
Experimental considerations
Prepare well‑defined salt forms (e.g., HCl) to ensure consistent dosing concentration in aqueous media.
Filter sterilize solutions (0.22 µm) for cell‑free assays if needed; avoid adsorption losses by using low‑binding plastics.
Item‑specific biological function data are not provided in the Product Data; consult primary literature if mechanistic targeting information is required for your study.
Buffer Applications
This compound is not a standard buffering agent. While biguanides are polybasic and can be protonated, their pKa profile and reactivity are not optimized for maintaining a narrow pH range in classical biochemical buffers.
Applicability
Not typically used to formulate buffer systems. For pH control, use established buffers (e.g., phosphate, HEPES, Tris) appropriate to your pH window.
Practical note
If preparing aqueous solutions of this compound for assays, adjust pH with a suitable acid (e.g., HCl) to form a soluble biguanidinium salt, but use a separate buffer component to control pH.
No item‑specific buffer recipes or pKa values are provided for this SKU.
Green Alternatives
Context
This SKU is a functionalized biguanide building block rather than a solvent. “Green alternatives” therefore focus on greener media and processing choices when using this compound.
Solvent considerations (general/literature)
Prefer water or aqueous ethanol when feasible by employing the protonated (salt) form to enhance solubility.
When aprotic media are required, consider Cyrene, propylene carbonate, or ethyl acetate/EtOH blends as greener alternatives to DMF/DMSO/NMP, balancing solubility and reaction needs.
Processing strategies
Use salt‑switch crystallizations to avoid chlorinated solvents in purifications.
Employ microscale, high‑throughput experimentation to minimize material and solvent use during condition screening.
Evaluate continuous flow for hazardous electrophile steps to reduce exposure and improve heat/mass transfer.
Tradeoffs
Aqueous systems may change selectivity and complicate extractions with cationic species; greener aprotics (e.g., Cyrene) can be less stable under strong basic conditions and may require temperature limits.
Comparison snapshot (general)
DMF/DMSO: excellent solubility, but high EHS burden; disposal is costly.
Water/EtOH: best EHS profile; requires salt form and pH control.
Propylene carbonate/Cyrene: improved sustainability; viscosity and base sensitivity must be managed.
Adopt solvent‑selection guides (e.g., CHEM21/ACS GCI) alongside experimental solubility tests for this specific substrate.
Pharmaceutical Uses
Item-specific regulatory/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
General (non‑clinical, formulation science context)
Biguanide derivatives are often handled as salts (e.g., hydrochloride, acetate) to improve aqueous solubility and solid‑state stability for research formulations.
In preformulation studies, evaluate: hygroscopicity of the chosen salt, polymorphism, counterion equivalence, and solution stability across pH 1–7.
For analytical development, use buffered mobile phases with acidic modifiers for LC to minimize tailing of basic analytes.
Practical guidance
Prepare small‑scale salt screens (HCl, mesylate, sulfate, fumarate) to identify a robust solid form for handling in discovery workflows.
Avoid making any clinical or therapeutic inferences; this product is supplied strictly for research use only, as indicated by the Product Data.
No pharmacopeial monograph or excipient designation is stated for this SKU.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for aryl biguanides (informational only; verify experimentally)
Physical state: typically solid, often off‑white to tan due to conjugation and salt formation tendencies.
Ionization: biguanide motif is strongly basic; readily forms biguanidinium salts with mineral or organic acids; pKa values for biguanide conjugate acids commonly >10 (literature, scaffold‑level), promoting water solubility as salts.
Solubility profile: free bases of aryl biguanides are variably soluble in polar aprotic solvents (DMSO, DMF) and protic solvents (MeOH, EtOH); limited solubility in nonpolar hydrocarbons; salts show enhanced aqueous solubility (literature/general).
Thermal behavior: biguanides may char/melt with decomposition rather than exhibit a sharp boiling point (literature/general). Specific MP/BP for this item: Not specified for this item; refer to CoA/Spec Sheet.
Partitioning: aryl chlorides increase lipophilicity relative to unsubstituted phenyl biguanides; overall logP depends strongly on protonation state and counterion (literature/general).
Other parameters (density, refractive index, UV cutoff, water, metals): Not specified for this item; refer to CoA/Spec Sheet.
Note: Provide exact, lot‑specific properties using the product CoA/SDS. Do not rely on generalized values for method validation.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research grade: Suitable for discovery chemistry, screening, and method development where trace impurity levels are acceptable within the research context.
High‑purity/≥98% organic building blocks: Prioritized for structure–activity studies and sensitive reactions; lower background in analytical assays.
HPLC/LC‑MS grade (when applicable to solvents/reagents): Implies low UV absorbance and volatile impurity control; not claimed for this item unless stated on the label/CoA.
Analytical expectations for aryl biguanides (general)
Typical quality controls include NMR (1H/13C), HRMS/ESI, HPLC/UPLC purity, and verification of salt form (free base vs. specific counterion) by titration or ion chromatography.
Water content (Karl Fischer), residual solvent, and inorganic residue are often reported; for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives
No stabilizers are indicated in the Product Data. If present in a specific lot, they will be declared on the CoA. Absence/presence of stabilizers can influence analytical baselines and solubility.
Salt formation: Readily forms biguanidinium salts with mineral/organic acids, enabling tunable solubility and crystallinity for isolation/purification.
N‑acylation and N‑alkylation: The biguanide nitrogens can be selectively functionalized to access urea/biguanide derivatives; control of chemo‑selectivity requires protecting group strategy and careful base choice.
Complexation/H‑bonding: Multiple donor/acceptor sites make aryl biguanides useful as supramolecular recognition motifs and in ion‑pairing extractions for anionic species.
Ligand/organocatalysis roles: Guanidinium and biguanidinium species serve as Brønsted base or H‑bond donor catalysts in certain additions and ring‑opening reactions (e.g., nitro‑Michael additions; literature precedents for biguanide scaffolds).
Use scenarios in discovery chemistry (general)
As a cationic, aromatic scaffold for SAR exploration where charge–aromatic balance is desired.
As a building block toward bis‑biguanides (by linker introduction) or heterobifunctional constructs via acylation/alkylation.
Practical tips
Protonation state control is key; conduct reactions under anhydrous conditions when using strong electrophiles, and pre‑convert to an appropriate salt to improve handling when needed.
Monitor by HPLC with acidic modifiers (e.g., 0.1% TFA or formic acid) to sharpen peaks of basic analytes.
Workup: Neutral/basic washes may lead to emulsion with cationic species; instead, use pH‑controlled liquid–liquid partitioning or solid‑phase extraction.
Note: No manufacturer‑specific application notes were provided; the above reflects general practice with aryl biguanides.
Reaction Conditions
The following are literature‑style, general conditions relevant to aryl biguanides; adapt to this substrate and verify experimentally.
Salt formation
Conditions: dissolve in MeOH, EtOH, or IPA; add stoichiometric HCl or other acid at 0–25 °C; concentrate and recrystallize from alcohol/ether. Typical isolations are high‑yielding for biguanidinium salts.
N‑Acylation
Reagents: acyl chlorides or anhydrides (1.0–1.5 equiv), base such as DIPEA or pyridine, solvent DMF/CH2Cl2.
Temperature/time: 0–25 °C, 1–16 h. Monitor by LC. Competing multi‑acylation may occur; use protecting groups to control site selectivity.
N‑Alkylation
Reagents: alkyl halides (1.2–2.0 equiv), carbonate or Cs2CO3 base in DMF/DMSO.
Temperature/time: 25–60 °C, 2–24 h. Over‑alkylation possible; titrate equivalents.
SNAr on aryl dichloride (if pursued)
Nucleophiles: strong amines/alkoxides; polar aprotic solvents (DMSO/DMF), 80–140 °C.
Note: 3,5‑dichloro substitution is less activated; success depends on ring electronics and additional activators.
Purification and analysis
Use acidified mobile phases (e.g., 0.1% formic acid) for LC to reduce tailing of basic analytes.
Crystallize as salts or purify by ion‑exchange chromatography when normal silica gives broad bands.
No item‑specific optimal conditions or yields are provided in the Product Data; perform small‑scale scouting first.
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 biguanides (literature/general guidance; not a substitute for SDS)
Hazards: May cause irritation to skin, eyes, and respiratory tract. Biguanidinium salts can be corrosive to eyes/skin depending on concentration. Avoid inhalation of dust/particulates.
PPE: Use appropriate laboratory PPE – lab coat, safety glasses or splash goggles, and chemical‑resistant gloves (e.g., nitrile). Employ dust control and local exhaust ventilation when weighing.
Handling: Prevent moisture uptake; biguanides are basic and hygroscopic behavior is possible. Avoid contact with strong oxidizers and strong bases/acids unless salt formation is intended and controlled.
First aid (overview): 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. Ingestion – rinse mouth; seek medical advice. Always follow institutional procedures.
Fire safety: Use standard extinguishing media (CO2, dry chemical, foam). Combustion/thermal decomposition may produce nitrogen oxides, HCl (due to aryl chlorides), and carbon oxides.
Spill/cleanup: Avoid dust generation; collect mechanically and place in appropriate waste container. Decontaminate area with mild detergent.
Always consult the official SDS for authoritative hazard classifications, exposure limits, and emergency measures for this specific SKU.
Solvent Selection
This compound is an aryl biguanide (strong organic base). Solvent choice should balance basicity, hydrogen‑bonding capability, and desired ionization state.
Polarity/miscibility (literature/general)
Free base: often dissolves in DMSO, DMF, NMP, methanol, ethanol, and aqueous acidic media; limited in ethers and hydrocarbons.
Protonated forms (salts): enhanced solubility in water and aqueous buffers; consider counterion effects (e.g., HCl, acetate, sulfate).
Practical selection tips
For stock solutions in screening assays: DMSO or water (acidified, pH ~2–4) are typical. Filter through 0.22 µm if particulates persist.
For coupling or derivatization: DMF or DMAc allow good solvation of both nucleophilic and electrophilic partners under basic or mildly acidic conditions.
For crystallization/purification: Employ antisolvent systems (e.g., methanol/MTBE or ethanol/ethyl acetate). Salt formation can greatly aid crystallinity and handling.
Brief comparison (general)
DMSO vs DMF: DMSO offers broader solubility and biocompatibility in assays; DMF preferred when minimizing sulfoxide reactivity.
Alcohols vs water: Alcohols solvate both aromatic and cationic centers; water (acidified) maximizes ionization and dissolution but can complicate moisture‑sensitive downstream steps.
Note: Specific solubility values for this SKU are not provided; verify empirically for your application.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for aryl biguanides
Keep container tightly closed, in a dry place away from direct light. Consider using desiccant to limit moisture uptake and maintain the defined protonation/salt state.
If provided as a free base, avoid prolonged exposure to acidic vapors; if provided as a salt (e.g., HCl), avoid strong bases during storage.
Reconstitution/solution stability (general)
For organic stocks: Dissolve in DMSO, DMF, or alcohols. Filter if needed. Prepare aliquots and store at 2–8 °C or −20 °C (solid back‑up at RT as per Product Data). Avoid repeated freeze–thaw; use single‑use aliquots.
For aqueous use: Adjust pH with a suitable acid to form a biguanidinium salt for improved solubility. Aqueous solutions are typically most stable at mildly acidic pH; prepare fresh when possible.
Shelf life and specs
Specific shelf life, assay/purity limits, and permissible impurities: Not specified for this item; refer to CoA/Spec Sheet and lot‑specific labeling.
Always follow institutional chemical hygiene practices and consult the SDS for stability and incompatibility details specific to this SKU.
Structure and Identity
Brief description: This item is an aryl–biguanide (N‑aryl imidodicarbonimidic diamide), specifically bearing a 3,5‑dichlorophenyl substituent on the biguanide scaffold.
Item-specific (from Product Data)
CAS: 1672-93-1
PubChem CID: 558969
InChIKey: 34957 (as provided)
SMILES: 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.
Structural features (general/interpretive)
Core functionality: biguanide (imidodicarbonimidic diamide) – a linear array of two guanidino units (–NH–C(=NH)–NH–C(=NH)–NH–) conferring high basicity and multiple hydrogen‑bond donors/acceptors.
Substituent: 3,5‑dichlorophenyl ring attached via an exocyclic nitrogen, increasing hydrophobicity and potential π–π interactions while retaining cationic character upon protonation.
Functional groups: multiple imino (C=NH) and amino (–NH–) sites; potential to form biguanidinium salts under acidic conditions.
2D description in words: a monosubstituted phenyl ring (chlorine atoms at meta positions 3 and 5) bonded through an anilide‑type nitrogen to a linear biguanide chain terminating in an –NH2/–NH functionality; no stereocenters; fully achiral.
Synonym notes (literature/general)
Often described as a “3,5‑dichlorophenyl biguanide” or “N‑(3,5‑dichlorophenyl)biguanide,” consistent with the imidodicarbonimidic diamide nomenclature.
Synthetic Utility
Functional group behavior (literature/general)
The biguanide unit provides multiple nucleophilic nitrogens and C=NH centers, enabling derivatization via acylation, alkylation, and formation of coordination complexes.
The aryl chloride substituents (3,5‑dichloro) are positioned meta to each other; while deactivated toward oxidative addition relative to electron‑rich rings, they can still participate in SNAr (with strong nucleophiles) or cross‑couplings under optimized conditions (e.g., Pd with tailored ligands) if orthogonal handles are introduced.
Retrosynthetic value
Aryl biguanides are commonly accessed from the corresponding anilines via dicyandiamide or carbodiimide routes; this scaffold can serve as a progenitor for bis‑biguanides or tethered cationic ligands.
Transformations
Formation of biguanidinium salts for purification and subsequent counterion exchange.
Protective group strategies (e.g., Boc on guanidine nitrogens) to direct selectivity in N‑functionalization.
Conjugation to acids/activated esters to yield cationic conjugates; attachment to polymers or surfaces exploiting multidentate H‑bonding.
Utility in materials/recognition
Multisite H‑bonding and charge assist in anion recognition, phase transfer, and ion‑pair catalysis motifs.
Note: Specific reactivity/yields for this exact substrate should be established experimentally; no item‑specific reaction data were provided.
Target Specificity
This product is a small‑molecule chemical and not an antibody, enzyme, or targeted biological reagent.
Item-specific targeting data: Not applicable; no antigen/epitope/clone/isotype information applies.
If using in biochemical assays, any observed target engagement should be established empirically and supported by primary literature specific to your system.
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