≥95% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Room temperature Spedizione . Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
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
249.650 g/mol
XLogP3
2.900
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Exact Mass
249.019 Da
Monoisotopic Mass
249.019 Da
Topological Polar Surface Area
59.400 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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No tested bioassay or analytical protocols are provided for this item. As a small-molecule reagent, typical usage follows standard organic synthesis procedures:
Prepare stock solutions in dry DMSO or DMF for micro-scale couplings (record exact concentration gravimetrically).
For amide couplings, pre-screen base and coupling reagent on 10–50 mg scale before scale-up.
For cross-couplings on the aryl chloride, run ligand/base screens under inert atmosphere and monitor by LC/MS.
Refer to the Reaction Conditions tab for literature starting points.
Biological Roles
This product is a synthetic heteroaromatic carboxylic acid and is not a known endogenous metabolite.
General context (literature)
Nicotinic acid (pyridine-3-carboxylic acid) is a key motif in biochemistry (precursor to nicotinamide/NAD cofactor). Substituted nicotinic acids, including aryloxy derivatives, are widely explored as pharmacophore fragments and ligating units in coordination chemistry. However, 2-(4-chlorophenoxy) substitution is a research scaffold and does not imply any biological activity for this specific compound.
Protein/ion binding
The carboxylate and ring nitrogen can chelate metals or engage in H-bonding in model systems; binding properties are context dependent and not established for this item.
No biological function or activity is claimed or implied for this product. It is provided strictly for research and laboratory synthesis.
Buffer Applications
Not typically used as a buffering agent. Although it contains a carboxylic acid functionality, 2-(4-chlorophenoxy)nicotinic acid is poorly water-soluble in its neutral form and lacks a defined buffering range for aqueous systems.
For aqueous work, it can be transiently solubilized as its carboxylate salt under basic conditions for extractions or reaction media, but this is not a standardized buffer application.
Green Alternatives
Greener considerations focus on solvent and coupling reagent selection, as the intrinsic hazard profile of a solid heteroaryl carboxylic acid is typically moderate.
Greener solvent swaps (literature guidance)
Replace DMF/NMP with Cyrene, 2-MeTHF, ethyl acetate, propylene carbonate, or CPME when solubility allows.
For Suzuki couplings on the aryl chloride, dioxane can be replaced by 2-MeTHF or water/ethanol mixtures with micellar catalysis.
Suzuki medium | Dioxane/toluene | 2-MeTHF or water/EtOH (micellar) | Comparable outcomes with optimized Pd/ligand.
Practical tips
Use aqueous carbonate or bicarbonate to form soluble carboxylate salts for micellar catalysis.
Crystallization-driven purifications in EtOAc/hexanes or EtOAc/IPA mixtures can reduce reliance on chlorinated solvents.
All substitutions should be validated at small scale; greener conditions may require modest adjustments to base, ligand, and temperature to match performance.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item. This compound is supplied for research use only.
Typical roles in R&D (general)
Heteroaryl acid building block for lead optimization, SAR libraries, or as an intermediate en route to APIs (non-GMP research). The para-chloro phenoxy handle allows late-stage diversification via cross-coupling after temporary protection of the acid.
Formulation considerations
If used in screening, stock solutions are commonly prepared in DMSO or DMF; salts or esters may be generated to adjust solubility and permeability during in vitro assays (research use only). No clinical or therapeutic claims are made.
Physical Properties
Item-specific specifications are not provided in the Product Data. Do not treat the following literature values as specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point (literature): aromatic heteroaryl carboxylic acids of this class typically melt in the 150–250 °C range; specific value for this compound not confirmed.
Boiling point: Not applicable (decomposes before boiling at 1 atm; literature trend for similar compounds).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature, qualitative)
Water: expected very low at neutral pH; soluble as the carboxylate under basic conditions.
Organic: good solubility in polar aprotic solvents (DMSO, DMF, NMP); moderate in MeCN/EtOAc/MeOH; enhanced with gentle heating or salts/bases.
pKa (literature, estimated class value): carboxylic acid ~4–5; pyridine N basicity suppressed by carboxyl meta orientation; exact pKa not confirmed for this compound.
logP/logD: not confirmed; para-chloro phenoxy increases lipophilicity relative to nicotinic acid.
Refractive index: Not applicable (solid) and not specified.
Use the product’s CoA/Spec Sheet for definitive physical data if required for process design or regulatory filings.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance
Without a stated grade, treat this listing as a research chemical intended for general laboratory synthesis. Always verify assay, impurity profile, and residual solvent content on the supplied CoA before use in sensitive applications (e.g., medicinal chemistry SAR, catalyst screening, or analytical reference work).
Stabilizers: None stated. This class of aromatic carboxylic acids typically does not require stabilizers; absence/presence of stabilizers should be confirmed on the CoA if critical for process development.
Typical analytical controls for this class (general)
Identification by NMR/IR/MS; HPLC or GC purity assay.
Water content by Karl Fischer (if relevant to application) — Not specified for this item; refer to CoA/Spec Sheet.
Inorganic/metal content for cross-coupling applications — Not specified for this item; refer to CoA/Spec Sheet.
If low-UV or trace-metal specifications are required (e.g., for photochemistry or catalysis), please request a tailored CoA/Spec Sheet or additional QC documentation.
Reaction and Applications
As a 2-aryloxy-substituted nicotinic acid, this reagent is a versatile heteroaromatic building block for discovery and process chemistry.
Amide formation (primary application)
Convert the acid to amides via carbodiimide couplings (EDC·HCl, DCC) with additives (HOBt/HOAt/Oxyma) or uronium/phosphonium reagents (HATU, HBTU, PyBOP). The 2-aryloxy substituent is typically inert under these conditions.
Esterification
Fischer esterification under acid catalysis or Steglich esterification (DCC/DMAP) affords aryl-oxy nicotinates suitable for further diversification or prodrug studies (research use only).
Acid chloride/anhydride formation
Activation with SOCl2, (COCl)2, or mixed anhydrides (pivaloyl, isobutyl chloroformate) enables rapid acylations.
Cross-coupling on the para-chloro aryl (literature)
The p-chloro substituent on the phenyl ring can undergo Pd-catalyzed Suzuki, Buchwald–Hartwig (after amination), or Negishi couplings to introduce diverse aryl/alkenyl/alkyl groups while retaining the nicotinic acid motif.
Directed metalation/functionalization (advanced)
The pyridine nitrogen and carboxyl can modulate regioselectivity in metalation or electrophilic substitution on suitably protected derivatives (literature precedent with nicotinates).
Applications space (non-clinical)
Common in medicinal chemistry as a heteroaryl acid scaffold; also applicable to materials and agrochemical intermediate synthesis.
Tip: If cross-coupling the aryl chloride first, protect the acid (methyl/tert-butyl ester) to improve solubility and avoid acid–base complications.
Reaction Conditions
General literature guidance for common transformations of heteroaryl carboxylic acids and aryl chlorides. These are not product specifications.
Solvent: DMF, DMA, or NMP (0.05–0.2 M). Temperature: 20–40 °C. Time: 2–18 h. Typical isolated yields: 70–95% with optimized partners.
Acid chloride formation
SOCl2 (3–5 equiv), catalytic DMF; solvent-free or DCM/toluene. 0–70 °C, 1–3 h. Followed by in situ acylation of amines/alcohols with base.
Esterification
Steglich: DCC (1.1–1.3 equiv), catalytic DMAP in DCM, 0–25 °C, 2–12 h.
Fischer: ROH (solvent, 10–50 equiv), catalytic H2SO4/TsOH, reflux, 2–24 h.
Suzuki coupling on the p-chloro phenyl ring
Pd2(dba)3 (1–2 mol%) + SPhos/XPhos (2–4 mol%), base (K3PO4, Cs2CO3), solvent (dioxane/H2O or 2-MeTHF/H2O), 80–110 °C, 4–16 h. Typical yields: 60–90% with suitable boronates.
Pd(OAc)2 (1–3 mol%) + BrettPhos/BINAP, base (NaOtBu), toluene or dioxane, 80–110 °C.
Notes
Protect carboxylic acid when necessary to prevent base-induced issues during Pd-catalyzed steps.
Degas solvents for cross-coupling; rigorously dry conditions improve coupling and acylation outcomes.
Safety and Handling
Safety details specific to this item are not provided in the Product Data; consult the SDS for authoritative information.
GHS/Classification (item-specific): Not specified for this item; refer to SDS.
Anticipated hazards based on structure (general guidance only)
Aromatic carboxylic acids may cause skin/eye irritation; dust may irritate the respiratory tract.
Avoid dust formation and inhalation; handle under adequate ventilation.
PPE
Lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use a dust mask/respirator if airborne particulates may form per institutional risk assessment.
Handling practices
Avoid contact with strong bases and strong oxidizers; neutralization generates heat and salts.
For moisture-sensitive transformations (e.g., acid chloride formation), keep material dry and use anhydrous techniques.
First-aid (general)
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste
Dispose of residues and contaminated materials as halogenated organic waste per local regulations.
Research use only. Not for human or veterinary use.
Solvent Selection
This compound is a moderately lipophilic heteroaryl carboxylic acid. Solvent choice is driven by its ionization state and target operation (coupling, esterification, crystallization).
Polarity/miscibility (general behavior)
Neutral form: sparingly soluble in water; soluble in polar aprotic media (DMSO, DMF, NMP). Moderate solubility in EtOAc, acetone, MeCN, MeOH/EtOH; enhanced with warming.
Carboxylate salt: soluble in aqueous basic media (NaHCO3/Na2CO3/NaOH) and mixed aqueous-organic systems.
Typical use scenarios
Amide couplings: DMF, DMA, NMP, or DCM/DMF mixtures; for greener profiles, 2-MeTHF or ethyl acetate with soluble carbodiimides can work when solubility permits.
Esterifications: DCM, toluene, or MeCN for Steglich/DCC; MeOH/EtOH/IPA for Fischer conditions with catalytic acid.
Cross-coupling on the aryl chloride: dioxane, toluene, or CPME with water co-solvent under Pd catalysis; base-solubilized systems often benefit from t-BuOH/H2O/THF blends.
Practical tips
Pre-dissolve in a small volume of DMSO or DMF to seed into less polar media.
For aqueous workups, deprotonation extracts the carboxylate into water; re-acidify to recover the acid as a solid.
Comparison (general)
DMSO/DMF: best solvating power, hardest to remove.
MeOH/EtOH: useful for salt formation or esterification, may cause transesterification in later steps.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Protect from moisture and strong light. Keep container tightly closed.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and solution handling (general)
Dissolve in dry DMSO, DMF, or NMP to prepare concentrated stock solutions; for less polar media, form a concentrate in DMSO/DMF and seed into the reaction solvent.
For aqueous handling, prepare alkaline solutions (e.g., with NaHCO3/Na2CO3) to form the carboxylate; re-acidify to isolate the free acid.
Stability considerations
Avoid prolonged exposure to strong bases or oxidants. For long-term storage of solutions, prefer anhydrous, oxygen-limited conditions at 2–8 °C; inspect for precipitation or degradation before use.
Always consult the product’s CoA and SDS for definitive storage and handling guidance.
Structure and Identity
A chlorophenoxy-substituted nicotinic acid building block featuring a pyridine-3-carboxylic acid core ether-linked to a para-chlorophenyl ring.
Item-specific identifiers (from Product Data)
CAS: 51362-37-9
CID: 609454
InChIKey: 92955 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Composition
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 structural information (for reference)
Expected molecular formula (literature): C12H8ClNO3
Approximate formula mass (literature): ~249.65 g/mol
Core features: a pyridine ring bearing a carboxylic acid at the 3-position (nicotinic acid) and a 2-aryloxy substituent; the aryloxy group is a para-chlorophenyl ether (–O–C6H4–Cl(p)).
2D description: a six-membered pyridine ring (one ring nitrogen) with the carboxyl group meta to N; adjacent to the ring N (2-position) is an O-aryl ether linking to a 4-chloro-substituted phenyl ring.
All item-specific identifiers above are taken verbatim from Product Data; structural descriptors labeled “literature” are non-spec limits provided for general reference only.
Synthetic Utility
Key functional elements and their reactivity profile make this compound a flexible node in retrosynthesis and diversification.
Functional groups
Carboxylic acid (acyl donor): amide/ester formation; activation to acyl chlorides/anhydrides; coupling under peptide-like conditions.
Pyridine nitrogen (heteroaryl): modulates electronics; can coordinate catalysts; influences regioselectivity in metalation/electrophilic steps.
Para-chloro on phenoxy ring (aryl chloride): cross-coupling handle (Suzuki, Negishi, Kumada, Stille) or nucleophilic aromatic substitution under strong conditions if additional activation is present.
Aryloxy linkage: generally stable; can be modified via demethylation-like strategies only under harsh conditions; primarily treated as inert.
Named reactions (literature usage)
Steglich esterification; Schotten–Baumann acylations (after acid chloride formation); Suzuki–Miyaura coupling on Ar–Cl; Buchwald–Hartwig amination after Ar–Cl activation; Mitsunobu esterifications from corresponding alcohol intermediates.
Strategy tips
Protect the acid (methyl/tert-butyl ester) prior to Pd-catalyzed couplings to improve solubility and avoid base sensitivities.
Exploit differential polarity between acid, amide, and ester to streamline purification by crystallization or trituration.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological macromolecule. No antigen/epitope, species reactivity, clone, or isotype information applies.
Domande frequenti
How should this product be stored?
Store at room temperature.
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.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 51362-37-9, the molecular formula is C12H8ClNO3, and the molecular weight is 249.66 g/mol. InChIKey FVAZJGJEENAKRJ-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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