1-Chrysenol - ≥95% , CAS No.63019-38-5

CAS: 63019-38-5 Cat. No.: C1338949 Formula: C₁₈H₁₂O Molecular Weight: 244.29 PubChem CID: 44284

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1=CC=C2C(=C1)C=CC3=C2C=CC4=C3C=CC=C4O

IUPAC Name

chrysen-1-ol

InChIKey

ISHBWEUQYFEVES-UHFFFAOYSA-N

INCHI

1S/C18H12O/c19-18-7-3-6-14-16-9-8-12-4-1-2-5-13(12)15(16)10-11-17(14)18/h1-11,19H

Isomeric SMILES

C1=CC=C2C(=C1)C=CC3=C2C=CC4=C3C=CC=C4O

PubChem CID

44284

Molecular Weight

244.29

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenanthrenes and derivatives
      • Subclass Chrysenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenanthrenes and derivatives
• Subclass: Chrysenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Chrysenes
• Alternative Parents: Phenanthrols Naphthols and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Chrysene - Phenanthrol - 1-naphthol - Naphthalene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as chrysenes. These are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.
• 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

Chemical and Physical Properties

• Molecular Weight: 244.300 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 244.089 Da
• Monoisotopic Mass: 244.089 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 326.000
• 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 to this product category.

• No validated immunoassay or histological application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.

General laboratory notes (if using in assays)

• Prepare concentrated stocks in a suitable organic solvent (e.g., DMSO, DMF, ethanol) and dilute into assay media with rigorous mixing to avoid precipitation. Include solvent-only controls and keep final co-solvent below assay tolerance (commonly ≤0.5–1% v/v). Protect solutions from light.

Biological Roles

General literature context (not item-specific, no medical claims)

• Chemical class: Hydroxylated polycyclic aromatic hydrocarbon (OH-PAH). Hydroxychrysenes can arise as oxidative metabolites of chrysene in environmental and biological systems (e.g., via cytochrome P450-mediated hydroxylation).
• Interactions: Phenolic PAHs often exhibit high affinity for organic matter and lipid phases due to hydrophobicity; some OH-PAHs can bind to proteins and DNA non-covalently through π–π interactions and intercalation-like behavior in vitro.
• Receptor engagement: Certain OH-PAHs are studied as ligands/modulators of aryl hydrocarbon receptor (AhR) and related pathways in biochemical assays (literature), though activity is structure- and position-dependent.
• Biotransformation: Conjugation via phase II metabolism (glucuronidation, sulfation) increases polarity for excretion in biological systems; the phenolic OH is the locus for such conjugations.
• Environmental fate: Strong sorption to particulates/soils; photolytic and microbial transformation are typically slow relative to more polar organics.

Note

• The above reflects general biochemistry of OH-PAHs like 1-hydroxychrysene. This product is supplied strictly for research use only, and no biological performance or safety is implied. Consult the SDS and institutional biosafety guidance when designing experiments.

Buffer Applications

Not typically applicable.

• 1-Chrysenol is a hydrophobic polycyclic phenol and is not used as a buffering agent. It lacks the water solubility and defined pKa window in aqueous media necessary for practical buffer systems.
• For aqueous experimentation, dissolve first in a miscible co-solvent (e.g., DMSO) before dilution into buffer if absolutely required for assays; confirm solubility and avoid exceeding the critical micelle/co-solvent percentage to prevent precipitation.

Green Alternatives

Context

• 1-Chrysenol itself is a hydrophobic PAH phenol; its inherent environmental persistence risk suggests minimizing release and selecting greener solvents/conditions when feasible.

Greener choices in processing (literature-based guidance)

• Solvent selection: Prefer bio-derived ethers/esters (2-MeTHF, CPME, EtOAc) or water/MeOH with micellar catalysis when reaction compatibility allows, instead of chlorinated aromatics or DMF/DMSO.
• Bases and reagents: Use inorganic carbonates (K2CO3, Cs2CO3) over strong alkoxides where possible; consider enzyme-mimetic or phase-transfer systems to reduce temperature and energy input.
• Energy: Employ flow chemistry or microwave for shorter residence times and decreased solvent volumes.
• Workup: Use minimal halogenated solvents; opt for heptane/EtOAc gradients for chromatography; explore recrystallization to reduce silica waste.

Illustrative comparison (general)

• Traditional: O-alkylation in DMF with NaH, 0–25 °C → good yields; DMF waste and hydride hazards.
• Greener: O-alkylation in 2-MeTHF or EtOAc under K2CO3 and phase-transfer catalyst at mild heat → comparable yields for activated electrophiles; improved EHS profile.

Note

• These are general recommendations; verify solubility/reactivity with small-scale screens. For environmental compliance, manage PAH-containing waste per local regulations.

Pharmaceutical Uses

Not a formulated excipient (general context)

• 1-Chrysenol is not a common pharmaceutical excipient and is not described in major pharmacopeias for formulation use.
• In research settings, hydroxylated PAHs may be used as analytical standards, probe molecules in ADME/toxicology modeling, or photophysical reference compounds. Such uses are strictly non-clinical and for laboratory research only.

Regulatory note

• No medical or therapeutic claims are made. For any GLP/GMP or regulated application, verify lot-specific quality attributes (identity, purity, residual solvents, elemental impurities) with CoA and applicable compendial tests if relevant to your workflow.

Physical Properties

Item-specific specifications

• Boiling point, melting point, density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for 1-hydroxychrysene (for reference only; not item specifications)

• Physical state: Typically a crystalline polycyclic aromatic phenol; high aromaticity and planarity.
• Melting point: Reported in the approximate 180–200 °C range depending on isomer assignment, polymorph, and purity (literature, varies by source).
• Boiling point: Not commonly tabulated due to thermal lability; sublimation/decomposition may occur before true boiling (literature).
• Solubility: Very low in water; soluble in aromatic solvents (toluene, xylene), chlorinated solvents (DCM, CHCl3), and moderately in ethers/esters; enhanced solubility in hot polar aprotics (DMF, DMSO) (literature).
• LogP/logKow: High hydrophobicity expected; reported/calculated values typically around 4.5–5.5 for monohydroxylated PAHs of this size (literature/estimates; specific values vary by method).
• pKa (phenolic OH): Typically in the range pKa ≈ 9.3–10.2 depending on solvent/ionic strength (literature for PAH phenols).
• Spectral features: Strong π–π* absorptions in the UV region characteristic of chrysene derivatives; phenolic OH exhibits IR O–H stretch and 13C/1H shifts consistent with hydrogen bonding (literature).

Practical notes

• Due to planarity and strong π-stacking, solids may show limited wettability; gentle warming and selection of a good π-solvent (e.g., toluene) can assist dissolution. Dry media prevent oxidative discoloration.

Quality & Grades

Item-specific

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

Guidance on grades for aromatic building blocks (general)

• Research grade vs. analytical grade: Research grade material typically supports synthetic and discovery workflows; analytical grade may include tighter controls on trace contaminants and UV-Vis background for spectroscopic applications.
• Impurities of note for PAH phenols: Unsubstituted PAHs (e.g., chrysene), isomeric hydroxychrysenes, oxidative dimers/quinones, and residual metals/halides from synthesis. UV absorbance baselines and fluorescence background can be important if using in photophysical studies.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Phenolic PAHs are commonly shipped without stabilizers; if present (e.g., trace BHT) this should be disclosed on the CoA.
• What to check on receipt: Verify identity by 1H/13C NMR (phenolic OH often broad, aromatic region diagnostic), HRMS, and HPLC/UPLC for isomeric purity. For photophysics or toxicology research, request fluorescence background and PAH impurity profile if critical.

Reaction & Applications

Use domains (literature/general)

• Building block for PAH functional materials: The phenolic handle enables O-alkylation, O-acylation, and etherification to tailor solubility and electronic properties of chrysene frameworks for organic electronics and fluorescence studies.
• Ligand/chelating motifs: Phenolate formation (with base) can bind metals; used to construct O,O- or O,N-chelates on PAH scaffolds for photophysical investigation.
• Protective chemistry: Phenolic OH can be protected as silyl ethers (TBS, TBDPS) or benzyl/methoxymethyl ethers during multi-step PAH elaborations.
• Cross-coupling after activation: Conversion to triflate/nonaflate from the phenol (via Tf2O or NfF) affords aryl electrophiles for Suzuki–Miyaura, Negishi, or Buchwald–Hartwig couplings on the chrysene core.
• Oxidation pathways: Controlled oxidation to quinone-like PAH derivatives (e.g., chrysene-1,4-dione analogs) expands redox-active materials.

Practical tips

• Deprotonation: Use K2CO3/Cs2CO3 in DMF/DMSO for alkylation; stronger bases (NaH, t-BuOK) enable sluggish substrates—exclude moisture/oxygen.
• Electrophile choice: Benzylic/allylic/sulfonate electrophiles give higher yields in Williamson-type ether formation; for less reactive alkyl halides, phase-transfer catalysis can help.
• Aryl activation: Triflation at the phenolic site typically requires low-temperature base (e.g., 2,6-lutidine) in DCM to suppress overreaction; follow with Pd-catalysis under standard conditions.
• Purification: Strong π–π interactions can cause tailing on silica; add a small % of polar modifier (e.g., 0.5–2% Et3N) or use neutral alumina when compatible.

Reaction Conditions

General literature guidance (illustrative; adjust per substrate and scale)

• O-alkylation (Williamson):
  • Typical: 1-chrysenol (1.0 eq), K2CO3 (2–3 eq), DMF or acetone, alkyl bromide/iodide (1.2–2.0 eq), 50–80 °C, 4–16 h; inert atmosphere recommended. Yields often moderate to high with activated electrophiles.
  • Strong base variant: NaH (1.2–2.0 eq) in THF/DMF at 0–25 °C then add electrophile; shorter times; rigorous anhydrous conditions.
• O-acylation: Pyridine or triethylamine base in DCM/toluene at 0–25 °C with acid chloride/anhydride; catalytic DMAP accelerates; minutes to hours; typically high yields.
• Triflation for cross-coupling: Tf2O (1.2–1.5 eq), base (2,6-lutidine or pyridine), DCM at −20 to 0 °C → aryl triflate; follow with Suzuki–Miyaura (Pd(PPh3)4 1–3 mol%, base K3PO4, dioxane/H2O 80–100 °C) or Buchwald–Hartwig amination (Pd2(dba)3 + BINAP/Buchwald ligands, NaOtBu, toluene 90–110 °C).
• Protection (silyl ether): TBSCl (1.2–1.5 eq), imidazole, DMF or DCM, 0–25 °C; hours.

Workup/purification tips

• Use minimal light exposure; include antioxidants only if compatible. For chromatography, consider neutral alumina or silica with 0.5–2% Et3N to mitigate tailing. Recrystallization from toluene/EtOH or chlorobenzene/hexanes can be effective depending on substitution.

Disclaimer

• Conditions above are compiled from general PAH phenol literature and are not specifications for this item. Optimize on small scale.

Safety & Handling

Item-specific hazard information

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS for authoritative safety data.

General safety considerations for PAH phenols (literature/industry practice; not item-specific)

• Hazard profile: Polycyclic aromatic phenols may be harmful if swallowed, inhaled, or in contact with skin and can be irritants to eyes/skin/respiratory tract. Some PAHs are suspected mutagens or environmental hazards; handle with care and minimize dust/aerosol generation.
• PPE: Laboratory coat, nitrile gloves (change regularly), safety glasses or splash goggles. Use a chemical fume hood to avoid inhalation of dust or solvent vapors.
• Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong bases (can form phenolates; exothermic dissolution), and strong reducing agents (in presence of catalysts may lead to hydrogenation). Avoid prolonged UV/visible light exposure that can induce photooxidation/polymerization in PAH systems.
• Handling tips: Keep containers tightly closed; dispense with anti-static and dust control measures. Use amber glassware or protect from light when storing solutions.
• First aid (overview; consult SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect as halogen-free organic waste unless contaminated otherwise; PAH-containing waste should be managed per local environmental regulations.

Solvent Selection

Context

• 1-Chrysenol is a hydrophobic, planar PAH phenol. Solvent choice is driven by π-solubility and desired ionization state (phenol vs phenolate).

General guidance (literature-based)

• Nonpolar/aromatic solvents: Toluene, xylenes, chlorobenzene often provide good solubility due to π–π interactions; useful for thermal O-alkylation/acylation.
• Polar aprotic solvents: DMF, DMAc, DMSO, NMP enhance solubility at moderate temperatures and support base-mediated reactions (e.g., Williamson ether synthesis of aryl–O–R via activated systems).
• Halogenated solvents: DCM, chloroform are good for preparative workup and chromatography compatibility; mind light exposure.
• Alcohols/ethers/esters: THF, 2-MeTHF, MTBE, EtOAc offer variable solubility; THF/2-MeTHF favored for metalations and phase-transfer operations when compatible.
• Aqueous systems: Very low aqueous solubility; biphasic or micellar catalysis may be used if green constraints demand, but expect limited partitioning without surfactants.

Small comparison (qualitative)

• Toluene: High solubility, thermal stability; poor polarity for ionic bases.
• DMSO/DMF: Excellent solvating power; facilitates deprotonation; more challenging removal.
• 2-MeTHF: Greener ether option; moderate solubility; suitable for base-mediated steps under anhydrous conditions.

Tips

• Warm gently (40–80 °C) to dissolve; avoid prolonged strong base with air/oxygen to limit oxidative byproducts. Use amberware for solutions.

Storage & Reconstitution

Item-specific storage

• Storage conditions: Room temperature (per Product Data).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General handling and solution preparation (literature/best practice)

• Solid storage: Keep tightly closed in a dry place, preferably under inert atmosphere or with desiccant. Protect from prolonged light exposure to limit photooxidation.
• Solution stability: In oxygenated solvents, phenolic PAHs may slowly discolor due to oxidation; prepare fresh solutions when possible. Store working solutions in amber vials at 2–8 °C or −20 °C as appropriate to solvent, under inert gas.
• Reconstitution: If required, dissolve in a minimal volume of an appropriate organic solvent (e.g., DMSO, DMF, toluene, or DCM), warming gently (≤50–60 °C) to aid dissolution. Filter through PTFE (0.2–0.45 µm) to remove particulates prior to sensitive uses.
• Freeze–thaw: Avoid repeated freeze–thaw of solutions; aliquot stocks to single-use vials.

Research use note

• For research use only. Not for human or veterinary use. Always consult the product’s CoA and SDS for lot-specific guidance before use.

Structure & Identity

Item-specific (from Product Data)

• SKU: C1338949
• Product name: 1-Chrysenol (also known as 1-hydroxychrysene; phenolic PAH derivative)
• CAS: 63019-38-5
• PubChem CID: 44284
• InChIKey: 149206 (as provided; full InChIKey not specified for this item; refer to CoA/Spec Sheet.)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Storage conditions: Room temperature

Computed/literature structural identity (general information for 1-hydroxychrysene)

• Molecular formula: C18H12O (literature)
• Molecular weight: 244.29 g/mol (literature; calculated from formula)
• Core scaffold: Polycyclic aromatic hydrocarbon (PAH) with four fused benzene rings (chrysene framework).
• Functional group: One phenolic hydroxyl (–OH) at the 1-position on the chrysene backbone.
• 2D structural description: A planar, four-ring PAH (arranged as a bent anthracene-like tricyclic system fused with a fourth ring) bearing a phenolic OH on the terminal ring (position 1). No heteroatoms aside from the single oxygen; no stereocenters; fully aromatic π-system.

Notes

• The identity above under “Computed/literature” reflects the commonly accepted structure of 1-hydroxychrysene and is provided for context. Always confirm exact structure and identity against the item’s CoA/SDS for your lot.

Synthetic Utility

Functional group leverage

• Phenolic OH: Enables protection (silyl/benzyl/MOM), O-alkylation/acylation to tune solubility/electronics, and conversion to leaving groups (aryl triflates/nonaflates) for cross-coupling.
• Aromatic π-system: Susceptible to electrophilic substitution at positions activated by the OH (ortho/para orientation on the ring bearing OH, with the PAH topology dictating regiochemistry). Directed lithiation can be challenging but feasible under strong base with appropriate blocking/protection.

Named/standard transformations (literature)

• Williamson ether synthesis (phenolate + alkyl electrophile) to access aryl ethers on a chrysene core.
• Triflation → Suzuki–Miyaura/Negishi/Heck/Buchwald–Hartwig couplings for C–C/C–N bond formation on the PAH.
• Fries/Claisen-type rearrangements after O-acylation/O-allylation to introduce C–C bonds ortho to the phenol.
• Oxidations to quinone-like PAH derivatives for redox-active materials.
• Silyl protection (TBS/TBDPS) facilitating harsh conditions (e.g., halogen–lithium exchange elsewhere on the scaffold) without OH interference.

Retrosynthetic value

• 1-Chrysenol serves as a nodal intermediate allowing late-stage diversification of the chrysene core: the phenol can be toggled between nucleophile (phenolate), electrophile (triflate), or masked functionalities, streamlining access to libraries of substituted chrysenes for materials and mechanistic studies.

Target Specificity

Not applicable to this product category.

• 1-Chrysenol is a small-molecule chemical reagent, not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.