6-Hydroxymethaqualone - ≥95% , CAS No.5060-51-5

CAS: 5060-51-5 Cat. No.: H988781 PubChem CID: 64016

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: CC1=CC=CC=C1N2C(=NC3=C(C2=O)C=C(C=C3)O)C
• IUPAC Name: 6-hydroxy-2-methyl-3-(2-methylphenyl)quinazolin-4-one
• InChIKey: NHGHFELYOIWDRR-UHFFFAOYSA-N
• INCHI: 1S/C16H14N2O2/c1-10-5-3-4-6-15(10)18-11(2)17-14-8-7-12(19)9-13(14)16(18)20/h3-9,19H,1-2H3
• Isomere SMILES: CC1=CC=CC=C1N2C(=NC3=C(C2=O)C=C(C=C3)O)C
• Alternative CAS-Nummer: 5060-51-5
• PubChem CID: 64016

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Diazanaphthalenes
      • Subclass Benzodiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Diazanaphthalenes
• Subclass: Benzodiazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Quinazolines
• Alternative Parents: Toluenes Pyrimidones 1-hydroxy-2-unsubstituted benzenoids Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinazoline - 1-hydroxy-2-unsubstituted benzenoid - Pyrimidone - Toluene - Monocyclic benzene moiety - Pyrimidine - Benzenoid - Heteroaromatic compound - Lactam - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as quinazolines. These are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 266.290 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 266.106 Da
• Monoisotopic Mass: 266.106 Da
• Topological Polar Surface Area: 52.900 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 421.000
• 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

No vendor-verified application protocols are provided for this SKU. The following are general, non-binding examples for analytical use:

• LC–MS/MS calibration standard

  • Prepare a 1.0 mg/mL stock in acetonitrile or DMSO.
  • Serially dilute with 50:50 MeCN:water (0.1% formic acid or 5 mM ammonium formate) to desired calibration levels (e.g., 0.5–500 ng/mL).
  • Store aliquots at −20 °C protected from light; avoid repeated freeze–thaw.

• Sample preparation (biological matrices)

  • Protein precipitation: add 3–4 volumes of cold MeCN or MeOH containing internal standard; vortex, centrifuge, and analyze supernatant.
  • SPE: condition RP cartridge, load sample, wash with aqueous buffer, elute with MeCN containing 0.5–2% NH4OH for phenolic analytes; evaporate and reconstitute for LC–MS.

Validate all conditions (linearity, recovery, matrix effects, stability) in your laboratory. For any application beyond analytical research, consult appropriate regulations and your institutional guidelines.

Biological Roles

• Context (informational; no clinical claims): 6‑Hydroxymethaqualone is a documented Phase‑I metabolite of methaqualone formed by cytochrome P450‑mediated aromatic hydroxylation of the quinazolinone ring system.
• Metabolic fate (literature-based):
  • Subsequent Phase‑II conjugation (e.g., O‑glucuronidation or O‑sulfation) of the phenolic OH is typical, enhancing aqueous solubility for excretion.
  • Can be detected in biological matrices (urine, plasma) in forensic/toxicology investigations of methaqualone exposure, often as conjugates.
• Biochemical properties:
  • The phenolic functionality alters hydrogen-bonding and acidity compared with the parent, potentially affecting protein binding and partitioning.
  • Compared with methaqualone, hydroxylation generally reduces lipophilicity and can modify metabolic stability.
• Research utility:
  • Serves as an authentic analytical standard to verify biotransformation pathways, support enzyme phenotyping (CYP isoform involvement), and calibrate LC–MS/MS quantitation of metabolites.

Note: All statements describe general biochemical behavior of methaqualone metabolites for research context only; this product is not intended for diagnostic or therapeutic use.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare biological buffers. For analytical workflows, it may be spiked into existing buffers (e.g., ammonium formate/acetate for LC–MS) as an analyte. Choose buffers that are MS-compatible and avoid high pH unless deliberate phenolate formation is desired.

Green Alternatives

This product is a solid reference compound rather than a process solvent. Greener considerations pertain to the choice of solvents and reagents used with it.

• Preferred greener solvents (when compatible with your method):

  • Ethanol or isopropanol instead of chlorinated solvents for simple dissolution or cleaning steps.
  • Acetonitrile (readily recyclable) over DMF/DMAc for LC sample prep when solubility permits.
  • Supercritical CO2 or ethyl acetate for preparative chromatography when feasible.

• Derivatization and workup alternatives:

  • Use carbonate bases (K2CO3) in acetone/MeCN rather than strong bases in DMF for O‑alkylations.
  • Prefer enzymatic glucuronidation assays (aqueous buffers) to study phase‑II metabolism over organic-intensive chemistries when the goal is biological relevance.

Comparison (illustrative; literature guidance):

• DMF/DMSO vs MeCN/EtOH
  • Worker exposure: lower with MeCN/EtOH (better volatility/evaporation control) vs high-boiling polar aprotics.
  • Waste: MeCN/EtOH easier to recover; DMF/DMSO often end up as incineration waste.
  • Performance: DMF/DMSO offer higher solubility; MeCN/EtOH may require sonication or warming.

Adopt microscale procedures and solvent recycling where possible to minimize environmental footprint.

Pharmaceutical Uses

• Not an excipient or formulated ingredient. No pharmacopeial grade is indicated for this item.
• Typical role (research/manufacturing QA, informational): analytical reference standard or system suitability standard for method development and validation related to methaqualone and its metabolites.
• Application notes:
  • Useful for establishing calibration curves, retention time windows, and ion transitions in LC–MS/MS.
  • Employed to assess extraction recovery, matrix effects, and stability in sample preparation procedures (e.g., SPE, protein precipitation).

No therapeutic claims are made; this material is for laboratory research and analytical method support only.

Physical Properties

Item-specific specifications are not provided in the Product Data for this catalog entry. Do not treat the following as specifications; consult the CoA/Spec Sheet for certified values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/guidance):
  • Expected to be sparingly soluble in water due to the hydrophobic quinazolinone/o‑tolyl framework, with modest ionizable character only under strongly basic conditions (phenolate formation).
  • Typically soluble in polar aprotic organics such as DMSO and DMF; moderately soluble in MeOH/EtOH and readily soluble in MeCN for analytical sample prep (literature/experience with phenolic quinazolinones).
• Acid–base behavior (literature): phenolic pKa commonly ~9–10 for related quinazolinone phenols; lactam N is non-basic; ring nitrogens weakly basic at best.
• Partitioning (literature expectation): overall lipophilic with an estimated logP in the low‑to‑mid single digits typical of methaqualone analogs; phenolic OH slightly reduces lipophilicity versus the parent.

Note: If exact numeric values (mp, solubility, water content, metal content, UV cutoff, etc.) are required, request the lot-specific CoA.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• What to expect from research-grade analytical/reference materials:
  • Lot-specific assay/purity determined by HPLC/GC and confirmed by spectroscopic methods (NMR, MS, IR) where applicable.
  • Control of identity via CAS/CID cross-reference, and, when available, retention time/MS fragmentation matching to literature standards.
  • Residual solvents and inorganics are typically controlled; exact limits are lot-specific.
• Stabilizers: None indicated in Product Data. If stabilizers or salt forms are used for this SKU, they will be declared on the CoA/label.
• UV/LC considerations: For LC–MS reference use, low non-volatile residue and minimal UV-active impurities are important; verify with CoA chromatograms.
• Documentation: Each lot ships with or has access to a Certificate of Analysis (CoA) that states the analytical methods, acceptance criteria, and results. For regulated workflows (forensic/toxicology method validation), retain the CoA and lot traceability info.

If you require specific compendial grades or impurity profiles, contact Aladdin with your application needs prior to ordering.

Reaction and Applications

• Research applications (non-clinical):
  • Commonly used as a reference standard or metabolite marker for method development/validation in forensic toxicology and environmental/biotransformation studies involving methaqualone metabolism.
  • Useful in metabolic pathway elucidation (CYP‑mediated aromatic hydroxylation) and phase‑II conjugation studies (e.g., glucuronidation of the phenolic OH) in liver microsomes or hepatocyte systems.
• Synthetic/derivatization applications:
  • The phenolic OH enables O‑derivatization (e.g., silylation with BSTFA or MTBSTFA; acylation/alkylation) to enhance GC–MS volatility or tailor LC–MS ionization.
  • Conversion to aryl triflate/mesylate from the phenol permits cross-coupling (Suzuki, Buchwald–Hartwig via subsequent amination) on the benzenoid ring.
  • The lactam (quinazolin-4-one) can participate in N‑acylation or act as a directing group for electrophilic substitution under specific conditions (literature precedents for quinazolinone chemistry).
• Practical tips:
  • For GC–MS, derivatize the phenol to minimize tailing and thermal degradation; validate with authentic standard.
  • For LC–MS/MS, both ESI(+/-) modes can work; phenolate formation often enhances ESI(−) response.
  • When performing O‑alkylations, use mild bases (e.g., K2CO3/Cs2CO3) in acetone/MeCN with an alkyl halide; avoid over-alkylation or N‑alkylation by controlling conditions.

All uses are for research and analytical method development; not for human/animal administration.

Reaction Conditions

General literature-guidance for common manipulations of phenolic quinazolinones (verify experimentally for your system):

• O‑Alkylation (ether formation)

  • Solvent: acetone, MeCN, or DMF
  • Base: K2CO3 (1.5–2.0 eq) or Cs2CO3
  • Electrophile: primary alkyl bromides/iodides; tosylates
  • Temp/time: 25–60 °C, 2–16 h
  • Notes: Minimize N‑alkylation by using weaker bases and polar aprotic solvents; monitor by HPLC.

• O‑Acylation

  • Reagents: acyl chloride or anhydride; catalyst DMAP (5–10 mol%)
  • Base: pyridine or Et3N
  • Solvent: DCM, THF, or MeCN; 0–25 °C, 0.5–4 h

• Silylation (for GC or protection)

  • Reagents: BSTFA/BSA (for TMS), or TBSCl + imidazole for protection
  • Solvent: pyridine/MeCN; RT to 60 °C, 0.5–2 h

• Triflation and cross-coupling

  • Triflation: Tf2O (1.2 eq), base (2,6‑lutidine) in DCM at −20 to 0 °C
  • Suzuki: Pd(PPh3)4 (2–5 mol%), base (K2CO3), solvent (dioxane/H2O or toluene/EtOH/H2O), 60–100 °C

• Analytical prep (LC–MS stocks)

  • Dissolve 1–10 mg/mL in MeCN or DMSO; dilute with aqueous mobile phase (0.1% formic acid or 5–10 mM ammonium acetate) to working concentrations.

The above are literature-style conditions and should be optimized for scale, purity, and specific substitution patterns.

Safety and Handling

• GHS classification, signal word, H‑statements, pictograms: Not specified for this item; refer to the SDS for authoritative hazard information.
• General hazards (class-based, informational): Aromatic phenolic and lactam heterocycles can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid dust and aerosols.
• PPE recommendations: Use lab coat, nitrile gloves, and safety glasses or goggles. Handle powders in a fume hood or ventilated enclosure. Avoid inhalation and contact with skin/eyes.
• Incompatibilities: Strong oxidizers (may oxidize phenols), strong bases (can form phenolates, increasing solubility/reactivity), and strong acids (possible hydrolysis under forcing conditions). Avoid prolonged exposure to light and air to minimize oxidative discoloration.
• First-aid (overview; see SDS for details):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eyes: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice for persistent irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Hygiene/storage: Keep container tightly closed, dry, and well ventilated. Prevent contamination of work surfaces. Dispose via approved chemical waste streams.

Always consult the Aladdin SDS for this SKU for definitive hazard, exposure limits, and response guidance.

Solvent Selection

• Compound class and polarity: Aromatic quinazolinone with a phenolic OH; predominantly nonpolar/aromatic with one H‑bond donor and one carbonyl acceptor.
• Practical dissolution guidance (literature/experience-based):
  • Preferred for stock solutions: DMSO or DMF (good solubility at 10–50 mg/mL typical for related phenolic heteroaromatics).
  • Chromatography/sample prep: Acetonitrile or methanol, optionally with 0.1% formic acid or ammonium acetate for LC–MS compatibility.
  • Poor water solubility is expected at neutral pH; aqueous solubility can improve in basic media via phenolate formation, but this may alter chromatographic behavior.
• Miscibility and handling tips:
  • Avoid high water content in initial dissolution; prepare a concentrated stock in DMSO/MeCN, then dilute into aqueous buffers if needed, keeping final organic ≤1–2% for bioassays.
  • For solid-phase extraction (SPE) methods, phenolic character favors retention on reversed-phase sorbents; elute with MeOH/MeCN with a small base modifier.
• Comparison (selection context):
  • Versus parent methaqualone, the phenolic OH makes 6‑hydroxy analog slightly more polar and hydrogen-bonding; it may elute earlier on RP‑HPLC and ionize more efficiently in ESI negative mode.

Note: For critical quantitation work, verify solvent effects on recovery and ionization with your specific matrix.

Storage and Reconstitution

• Storage (from Product Data): Room temperature. Keep tightly closed in a dry, well-ventilated place. Protect from light and moisture to minimize oxidative discoloration of the phenolic functionality.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Shelf-life: Not specified; assess periodically by HPLC/LC–MS for purity and degradation.
• Reconstitution/preparation of solutions (guidance):
  • Prepare concentrated stocks (1–50 mg/mL) in DMSO or acetonitrile. For NMR, use DMSO‑d6, CD3CN, or CDCl3 if soluble.
  • For aqueous work, first dissolve in organic solvent, then dilute into buffer while vortexing; final organic content typically ≤1–2% for bioassays or as required for LC–MS.
  • For GC–MS, consider silylation (e.g., BSTFA) after dissolution in anhydrous solvent to improve volatility and peak shape.
• Freeze–thaw: If solutions are stored cold (e.g., −20 °C), aliquot to avoid repeated freeze–thaw cycles.
• Compatibility: Avoid strong bases/acids in storage solutions; use neutral, anhydrous solvents and amber vials when possible.

Research Use Only: As stated in Product Data, this material is for research use only; not for drug, household, or other uses.

Structure and Identity

Brief overview: 6‑Hydroxymethaqualone is a hydroxylated quinazolin-4-one derivative and a known Phase‑I metabolite of methaqualone. It features a phenolic OH on the quinazolinone core and an o‑tolyl substituent typical of methaqualone analogs.

• Item-specific identifiers (from Product Data)

  • SKU: H988781
  • Product Name: 6-Hydroxymethaqualone
  • CAS: 5060-51-5
  • CID (PubChem): 64016
  • InChIKey: 238500 (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.

• Literature/typical structural features (informational)

  • Core scaffold: quinazolin-4-one (a bicyclic lactam; benzo-fused diazine) with a 2‑methyl and 3‑(2‑methylphenyl) substitution in methaqualone; the “6‑hydroxy” indicates a phenolic OH on the benzannulated ring (position 6).
  • Functional groups: phenolic OH, lactam (amide carbonyl), two ring nitrogens (diazine), and aryl–aryl connectivity.
  • 2D description: a fused benzodiazine ring bearing a 4‑oxo (lactam) and a para‑related phenolic OH (at C6) on the benzenoid portion, with an adjacent heteroaromatic ring junction; an o‑tolyl substituent attached at N3 and a methyl at C2 in the methaqualone framework.

• Stereochemistry: none (achiral scaffold).

Synthetic Utility

From a synthetic standpoint, 6‑Hydroxymethaqualone offers two reactive handles on an otherwise rigid heteroaromatic scaffold:

• Phenolic OH
  • O‑Alkylation/O‑acylation to access ether/ester derivatives; conditions: alkyl halide + K2CO3/Cs2CO3 in acetone/MeCN; or acyl chloride/anhydride + base (pyridine, DMAP catalysis).
  • Silylation (TMS, TBDMS, TBS) to protect the phenol for multistep sequences or to enhance GC volatility.
  • Sulfonate activation (triflate/mesylate) enabling cross-couplings (e.g., Suzuki–Miyaura to diversify substitution at C6 after phenol activation).
• Quinazolin-4-one lactam
  • Functions as a hydrogen-bond acceptor and can undergo N‑acylation or selective reduction under forcing conditions (literature precedents). The lactam can serve as a directing group for certain electrophilic substitutions.
• Retrosynthetic value
  • Provides access to a family of methaqualone metabolites/analogs by late-stage functionalization at the phenolic site or by modifying the o‑tolyl substituent through cross-coupling after suitable activation.

Caveat: The heteroaromatic core can be sensitive to harsh conditions; favor milder bases and avoid strong nucleophiles that might attack the lactam carbonyl.

Target Specificity

Not applicable. This product is a small-molecule reference compound, not a biological macromolecule or antibody. No target-binding specificity data are provided in the Product Data.