2-Amino-4-hydroxyquinoline hydrate - ≥95% , CAS No.42712-64-1

CAS: 42712-64-1 Cat. No.: B301240 Formula: C₉H₈N₂O•xH₂O Beilstein Registry Number: 124785 Numero EC: 626-776-6

QUALITÀ & PUREZZA ≥95%

Synonyms

2-Aminoquinolin-4(1H)-one | EN300-134240 | 2-amino-1H-quinolin-4-one | 4-hydroxy-aminoquinoline | SCHEMBL10070259 | 2-amino-4-1H-Quinoline | A825990 | FT-0704430 | 2-AMINO-4-HYDROXYQUINOLINE HYDRATE | SCHEMBL482375 | Q209450 | AF-0735 | AKOS016001111 | Z1

Storage

Room temperature

Shipped In

Normal

Specifiche

Sinonimi

2-Aminoquinolin-4(1H)-one | EN300-134240 | 2-amino-1H-quinolin-4-one | 4-hydroxy-aminoquinoline | SCHEMBL10070259 | 2-amino-4-1H-Quinoline | A825990 | FT-0704430 | 2-AMINO-4-HYDROXYQUINOLINE HYDRATE | SCHEMBL482375 | Q209450 | AF-0735 | AKOS016001111 | Z1

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥95%

Nomi e identificatori

Pubchem Sid

488190568

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488190568

Sorrisi canonici

C1=CC=C2C(=C1)C(=O)C=C(N2)N

IUPAC Name

2-amino-1H-quinolin-4-one

InChIKey

LWGUCIXHBVVATR-UHFFFAOYSA-N

INCHI

1S/C9H8N2O/c10-9-5-8(12)6-3-1-2-4-7(6)11-9/h1-5H,(H3,10,11,12)

Isomeri SMILES

C1=CC=C2C(=C1)C(=O)C=C(N2)N

CAS alternativo

2089378-34-5

Beilstein

124785

Reaxy-Rn

4387103

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4387103&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Quinolines and derivatives
      • Subclass Aminoquinolines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Quinolines and derivatives
• Subclass: Aminoquinolines and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Aminoquinolines and derivatives
• Alternative Parents: Hydroquinolones Hydroquinolines Aminopyridines and derivatives Benzenoids Vinylogous amides Heteroaromatic compounds Azacyclic compounds Primary amines Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aminoquinoline - Dihydroquinolone - Quinolone - Dihydroquinoline - Aminopyridine - Pyridine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Azacycle - Amine - Organic nitrogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Obiettivi associati (non umani)

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTR1 Pteridine reductase 1 (345 Activities)

Discover Target: PTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Meccanismi d'azione

Proprietà chimiche e fisiche

• Punto di fusione (°C): 298℃
• Peso molecolare: 160.170 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 160.064 Da
• Monoisotopic Mass: 160.064 Da
• Topological Polar Surface Area: 55.100 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 235.000
• 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

Application Protocols

Not applicable.

• No tested bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data.

General lab usage notes

• For biochemical assays, prepare concentrated stocks in DMSO (e.g., 10–100 mM), then dilute into assay buffer while maintaining acceptable final DMSO levels (typically ≤1–2%). Verify solubility and stability at working pH.
• For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for literature-based starting points.

Biological Roles

Item-specific (from Product Data)

• No biological role claims are provided. For research use only.

Literature/General context

• Quinolinol/quinolinone scaffolds are prevalent in natural products and research tool compounds. The 4-hydroxy- (4-quinolinol) motif can exist in tautomeric equilibrium with 4-quinolinone, influencing hydrogen bonding and metal-binding properties.
• The presence of both an aryl amine and a phenolic group permits dual H-bond donor/acceptor behavior, affecting interactions with nucleic acids, proteins, and metal ions in biochemical assays.
• Chelation: N,O-bidentate coordination to metal ions (e.g., Al3+, Zn2+, Cu2+) is well-documented for quinolinone-type ligands, enabling use as chromogenic/fluorogenic probes and in metalloenzyme model studies.
• Photophysics: Many quinoline derivatives exhibit UV absorption and environment-dependent fluorescence, which can be exploited in binding or localization studies; actual spectral properties for this specific hydrate should be determined experimentally.

Important notes

• No clinical or therapeutic claims are made. Any discussion of biological activity should be restricted to in vitro or biophysical studies and requires empirical validation with this exact material/lot.
• Hydration state can modulate solubility and ionization behavior in aqueous buffers; characterize pH-dependent speciation before quantitative biochemical work.

Buffer Applications

Not typically applicable.

• 2-Amino-4-hydroxyquinoline hydrate is not a conventional buffering agent and is not supplied with buffer-system specifications.
• For experiments requiring aqueous use, the compound may be dissolved by forming salts (e.g., HCl salt) or by using co-solvents (DMSO) and then diluting into the target buffer. Determine pH-dependent solubility and stability empirically.
• If pH control is needed, use established buffers (e.g., phosphate, HEPES, Tris) and assess compound stability in those systems (monitor for O/N-acyl migration or tautomer shifts as relevant).

Green Alternatives

Context

• The compound is a solid heteroaromatic building block; “green alternatives” pertain mainly to solvent and reagent choices in its use, since the substrate itself is fixed.

Greener solvent choices (literature/general)

• Replace DMF/NMP with: Cyrene (dihydrolevoglucosenone), propylene carbonate, or dimethyl carbonate when reaction compatibility allows (e.g., acylation, alkylation). 2-MeTHF or CPME can substitute for THF/Et2O in extractions and some O-alkylations.
• Replace DCM/CHCl3 with: EtOAc, Me-THF, or toluene for workups/chromatography; aqueous biphasic systems with green surfactants for extractions, where applicable.
• Replace MeCN with: Acetonitrile alternatives such as EtOAc or green alcohols for certain reactions; or water/ethanol mixtures using phase-transfer catalysis when feasible.

Reagent/catalyst considerations

• Use organic carbonates (dimethyl/diethyl carbonate) for O-alkylations as milder, greener alkylating agents versus alkyl halides, when scope permits.
• Employ catalytic methods (e.g., enzymatic acylations, organocatalysis) to reduce waste. For cross-couplings, consider ligand/catalyst systems enabling ppm-level Pd or Ni and aqueous micellar media.

Process intensification

• Microwave or flow processing can cut reaction times and energy use. Solvent recycling (distillation, nanofiltration) and real-time analytics (PAT) help minimize solvent volumes and rework.

Trade-offs

• Cyrene/propylene carbonate have higher viscosity and sometimes reduced solubility for bases; 2-MeTHF is flammable and forms peroxides over time (manage with inhibitor testing). Validate green substitutions at small scale before scale-up.

Pharmaceutical Uses

Item-specific (from Product Data)

• No pharmacopeial or excipient status is specified. For research use only.

Literature/General context

• Role in discovery chemistry: 2-Amino-4-hydroxyquinoline scaffolds are frequently used as intermediates in the synthesis of heteroaromatic libraries and as fragments for SAR around quinolinone cores.
• Potential formulation considerations for research samples: As a weak base/phenol, the compound may be converted to salts (e.g., hydrochloride) to enhance aqueous solubility for in vitro assays. Solid-dispersion or cyclodextrin inclusion strategies can also be explored at research scale.
• Manufacturability: Hydration state and polymorphism can affect flow, compressibility, and drying; define solid form during process development. However, this product is not designated for clinical use, GMP manufacture, or as an API/excipient.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (as supplied, hydrate): Not specified for this item; refer to CoA/Spec Sheet.

Literature/General properties for the anhydrous base (2-amino-4-hydroxyquinoline)

• Typical acid–base behavior: Contains a weakly basic anilide-like amino group and a weakly acidic phenolic OH. The quinolinol/quinolinone tautomerism can influence apparent pKa values; specific numeric pKa values vary by source and measurement method (consult primary literature/CoA for definitive values).
• Solubility tendencies: Commonly soluble in polar aprotic solvents (DMSO, DMF, NMP) and in dilute aqueous mineral acids (via protonation/salt formation). Sparingly soluble in nonpolar hydrocarbons; variable solubility in alcohols and acetone depending on hydration, polymorph, and salt state.
• Hydrate influence: Hydration can elevate measured mass fraction of water and alter melting behavior (often depressed or broadened relative to anhydrous material) and hygroscopicity. Reported mp/bp/density and refractive index should be taken from the item’s CoA for the supplied hydrate.

Notes

• For any critical use (e.g., quantitative formulation, thermal processing), rely on the lot-specific CoA/Spec Sheet for melting range, water content (Karl Fischer), and any other specifications. No numeric physical constants are specified in the Product Data for this item.

Quality and Grades

Item-specific (from Product Data)

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades (general)

• Analytical/AR-grade: Typically controls on assay, residue on ignition, and common impurities; suitable for most synthesis and analytical work.
• “>98%” or “>99%” organic synthesis grade: Emphasis on assay and targeted organic impurities; may include HPLC or GC purity profile and residual solvent limits.
• HPLC grade (for solvents): Not applicable to this solid; however, “HPLC-tested” can indicate low UV background if a material is intended for reference standard or chromatographic use.
• Hydrate designation: Presence of crystalline water. The exact stoichiometry influences calculated assay on “as-is” basis versus “anhydrous basis.” The CoA should clarify water content (e.g., KF) and the effective purity on anhydrous basis.

What to look for on the CoA for this item

• Assay method (e.g., HPLC area%, qNMR), water content (KF), identification (1H NMR/IR/MS), residual solvents, and limits on inorganic matter (sulfated ash).
• Polymorph/hydrate form and lot-specific melting behavior. If your application is stoichiometrically sensitive (e.g., salt formation, metal chelation), use the assay on anhydrous basis in calculations.

Reaction and Applications

Item-specific (from Product Data)

• Manufacturer applications: Not specified for this item.

Literature/General applications of 2-amino-4-hydroxyquinoline scaffolds

• Heterocycle building block: Serves as a bifunctional handle for assembling quinolinone/quinolinol-based libraries. The –NH2 enables N-acylation/sulfonylation/urea formation; the –OH enables O-alkylation/acylation and carbonate/carbamate formation.
• Electrophilic aromatic substitution (EAS): The amino group is ortho/para-directing on the quinoline ring, enabling selective halogenation, nitration (mild), or formylation on activated positions, mindful of the deactivating influence of the ring nitrogen.
• Nucleophilic aromatic substitution (SNAr) on pre-halogenated quinolines: Useful for installing the 2-amino moiety through amination or for further functionalization when the ring bears leaving groups.
• Tautomeric reactivity: 4-hydroxy/4-quinolinone tautomerism can favor acylation at oxygen vs. nitrogen under different conditions, enabling access to O-acyl and N-acyl isomers.
• Metal chelation and ligand design: The 4-hydroxy(quinolinone) motif can chelate main-group and transition metals (e.g., Al3+, Zn2+, Cu2+) through N,O-coordination—useful in materials, fluorescence probes, and catalysis ligand development.
• Cross-coupling after activation: Installation of halides (e.g., 5- or 7-bromo derivatives) allows Suzuki, Buchwald–Hartwig, or Sonogashira elaboration to diversify the scaffold.

Practical tips

• Protecting groups: Boc/CBz on the aniline and silyl or carbonate protection on the phenol can manage chemoselectivity.
• Avoid strong bases at high temperature if tautomer-control is critical; use mild inorganic bases and polar aprotic solvents to steer O- vs N-functionalization.

Reaction Conditions

General guidance (literature)

• N-acylation/sulfonylation: 0–25°C, 1–4 h (often), in DCM/DMF/MeCN with organic base (Et3N, DIPEA) or under Schotten–Baumann biphasic conditions. Carbodiimide couplings (EDCI/HOBt/HOAt) or CDI (for ureas/carbamates) commonly proceed at rt to 50°C.
• O-alkylation: K2CO3 or Cs2CO3 (1.5–2.0 equiv) in DMF/MeCN/acetone, 25–80°C, 2–16 h, with primary alkyl bromides/iodides or dialkyl carbonates (often requiring 80–120°C in DMC/DEC, sealed system). Competing N-alkylation is mitigated by weaker bases and polar aprotic solvents.
• Electrophilic substitution: Halogenation (NBS/NCS) at activated positions under mild conditions (0–25°C) in polar solvents; regioselectivity depends on substitution pattern and protonation state.
• Cross-coupling (after halogen installation): Suzuki–Miyaura (Pd(0), XPhos/SPhos, K2CO3/K3PO4, 60–100°C, dioxane/H2O or Me-THF/H2O), Buchwald–Hartwig amination (Pd2(dba)3 or Pd(OAc)2, BrettPhos/RuPhos, 80–110°C), Sonogashira (Pd/Cu co-catalysis, 40–80°C). Protect –NH2/–OH if necessary.
• Metal complexation: Typically performed in alcohols/DMF with metal salts (e.g., Zn(OAc)2, Cu(OAc)2) and base to deprotonate the phenol; rt to reflux, 1–12 h.

Notes

• These conditions are general literature guidance for the quinolinol/aniline class; optimize for this substrate. Pay attention to hydrate water content in stoichiometry and to tautomer control (monitor by NMR). No item-specific validated conditions are provided in the Product Data.

Safety and Handling

Item-specific (from Product Data)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General safety guidance (literature/chemical class)

• Likely hazards by analogy: Aromatic amines and phenolic heteroaromatics can cause skin/eye irritation and may be harmful if swallowed or inhaled. Dust may be irritating to the respiratory tract. Avoid creating dust and avoid inhalation.
• PPE: Wear appropriate laboratory PPE at all times—lab coat, safety glasses or goggles, and suitable chemically resistant gloves (e.g., disposable nitrile). Use in a fume hood to control dust and vapors.
• Handling: Avoid heat, sparks, and open flame when processing powders. Prevent contact with oxidizing agents and strong acids/bases unless intentionally performing a reaction. Minimize exposure to moisture for materials where hydration state matters for stoichiometry.
• First aid (overview; defer to SDS): If inhaled—move to fresh air; seek medical attention if symptoms occur. Skin contact—wash with soap and water. Eye contact—rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists. If swallowed—rinse mouth; seek medical attention.
• Spill/cleanup: Avoid raising dust; collect mechanically (HEPA-filtered vacuum or damp disposable towels). Dispose of in accordance with institutional and local regulations.
• Fire response: Use standard dry chemical, CO2, or foam extinguishers. Combustion may produce nitrogen oxides and carbon oxides.

Always consult the official SDS for authoritative hazard, first aid, and disposal guidance for this specific item/lot.

Solvent Selection

Item-specific (from Product Data)

• No item-specific solubility specifications are provided. Refer to CoA/Spec Sheet.

Literature/General guidance for 2-amino-4-hydroxyquinoline scaffolds

• Polarity class: Moderately polar heteroaromatic with one basic (–NH2) and one acidic (phenolic –OH) site; capable of intramolecular H-bonding and tautomerism.
• Likely good solvents: DMSO, DMF, NMP, and hot ethanol or isopropanol. Solubilizes readily in dilute mineral acids (e.g., 0.1–1 M HCl) by protonation of the ring/amine nitrogens.
• Limited solubility expected in: Nonpolar solvents (hexanes, heptane) and sometimes in EtOAc or MTBE unless warmed or with base/acid assistance.
• Salt-assisted solubility: Formation of hydrochloride or sulfate salts enhances water solubility; phenoxide salts (with NaOH/K2CO3) can improve solubility in alcohols/DMF for O-alkylation/acylation workflows.

Selection tips

• For reaction media prioritizing nucleophilicity of the aniline nitrogen, use dry polar aprotics (DMF, DMSO, MeCN) and avoid strong acids.
• For O-alkylation/acylation at the phenolic OH, use mildly basic conditions in DMF/MeCN/acetone with a non-nucleophilic base (e.g., K2CO3, Cs2CO3) and an appropriate electrophile.
• For purification, reversed-phase preparative HPLC or normal-phase silica with polar modifiers (MeOH/DCM + 0.1–1% Et3N or AcOH) may be beneficial to manage tailing due to basicity/phenolic H-bonding.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipping: Normal.

General guidance (literature/practice)

• Container: Store in a tightly closed, chemically compatible container to minimize moisture exchange and contamination. Given the hydrate form, avoid unnecessary desiccation cycles that might change solid-state form unless drying is intentional and verified.
• Light/air: Store protected from excessive light and heat. The quinoline chromophore can absorb UV; amber glass is prudent for long-term storage.
• Reconstitution/solution preparation: For stock solutions, dissolve in dry DMSO or DMF; alternatively, dissolve in dilute HCl to form a soluble salt, then adjust pH if needed. Filter through 0.2 µm PTFE/NYLON if particulates are present. Record solvent, concentration, and date.
• Stability of solutions: Assess by LC/HPLC over time; small-molecule stocks in DMSO are often stable for weeks at 2–8°C and months at –20°C, but confirm empirically. Avoid repeated freeze–thaw by aliquoting.

Specifications note

• Appearance, assay, water content, and other item-specific specifications are not provided in the Product Data; consult the CoA/Spec Sheet for lot-specific details before critical use.

Structure and Identity

Item-specific (from Product Data)

• SKU: B301240
• Product name: 2-Amino-4-hydroxyquinoline hydrate
• CAS: 42712-64-1
• InChIKey: 210834
• Storage: Room temperature
• Shipped: Normal
• Category: 全部 / 可售 / 化学和生化试剂
• Research use: For research use only
• 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.

Literature/General identity (for the anhydrous scaffold 2-amino-4-hydroxyquinoline)

• Core scaffold: Quinoline (benzannulated pyridine) bearing a primary amino group at the 2-position and a phenolic hydroxy group at the 4-position on the quinoline ring system.
• Functional groups: Aromatic heterocycle (quinoline), primary aryl amine (–NH2), phenol (–OH). Tautomerism between 4-hydroxyquinoline and 4-quinolinone forms is known in this class.
• 2D description in words: A fused bicyclic system comprising a six-membered benzene ring fused to a six-membered pyridine ring (N at position-1). The amino substituent is ortho to the ring nitrogen (C-2), and the hydroxy substituent is para to C-2 on the benzannulated ring (C-4). For the product offered here, a defined hydrate is present (hydrate stoichiometry not specified in the Product Data).

Synthetic Utility

General synthetic value (literature)

• Bifunctional handle: The juxtaposition of an aniline-type –NH2 and a phenolic –OH on the quinoline core enables orthogonal derivatization. Representative transformations include:
  • N-acylation/sulfonylation to furnish amides and sulfonamides (coupling reagents: EDCI/HOBt, CDI, acid chlorides, sulfonyl chlorides).
  • O-alkylation/acylation to generate ethers/esters (bases: K2CO3, Cs2CO3; electrophiles: alkyl halides, dialkyl carbonates, acyl chlorides/anhydrides).
  • Urea/thiourea formation with isocyanates/isothiocyanates; carbamate formation with chloroformates.
• Tautomer-guided chemistry: The 4-hydroxy/4-quinolinone equilibrium allows access to N1- vs O4-acylated products under condition control (e.g., base strength, solvent polarity, temperature).
• Ring functionalization: Directed lithiation or halogenation at positions 5–8 enables downstream Suzuki/Buchwald–Hartwig/Sonogashira couplings, allowing rapid diversification for SAR.
• Coordination chemistry: The N,O donor set supports complexation to metals, enabling preparation of luminescent or catalytic complexes.

Practical considerations

• Selective protection (Boc on –NH2; silyl or benzyl carbonate on –OH) improves chemoselectivity.
• Control of water: Since the product is a hydrate (item-specific stoichiometry not provided), dry it under mild vacuum if anhydrous conditions are critical, verifying by KF; avoid conditions that alter the heterocycle.
• Analytical: Monitor reactions by HPLC/UPLC with acidic/basic modifiers to reduce peak tailing; qNMR can provide reliable assay independent of chromophore response.

Target Specificity

Not applicable.

• This product is a small-molecule heteroaromatic building block, not an antibody, enzyme, nucleic acid, or affinity reagent. No antigen/epitope/clone/isotype information is associated with this item.