Phenanthrene - Moligand™, 10 mM in DMSO , CAS No.85-01-8

CAS: 85-01-8 Cat. No.: P1499576 Formula: C₁₄H₁₀ Molecular Weight: 178.23 Beilstein Registry Number: 1905428 EC Number: 201-581-5

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Phenanthrene is an orally active polycyclic aromatic hydrocarbon (PAH) that induces inflammation, oxidative stress, and apoptosis . Additionally, phenanthrene is commonly used to detect or assess PAH pollution in the environment .

Specifications

Specifications & Purity

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

Isomeric SMILES

C1=CC=C2C(=C1)C=CC3=CC=CC=C32

WGK Germany

2

Molecular Weight

178.23

Beilstein

1905428

Reaxy-Rn

1905428

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1905428&ln=

Chemical and Physical Properties

• Flash Point(°F): -0.4℉
• Flash Point(°C): -18 °C
• Boil Point(°C): 340°C
• Melt Point(°C): 100°C

Application Protocols

No vendor-validated bioassay protocols are provided for this small molecule. Typical research uses include small-molecule screening, photophysical measurements, and materials synthesis.

General starting points (research use only; literature/practice-based):

• Stock preparation: Dissolve phenanthrene in toluene, DMF, or DMSO to 10–50 mM. Sonication and mild warming (≤40 °C) aid dissolution. Filter (0.2 µm PTFE) for spectroscopic work.
• Fluorescence measurement: Prepare ~1–10 µM solutions in spectroscopic-grade toluene or acetonitrile; degas by freeze–pump–thaw (3 cycles) or sparge with argon. Use quartz cuvettes and minimize stray light.
• Binding/partition assays: Make concentrated DMSO stocks; dilute into buffer with ≤1% v/v DMSO final (or per assay tolerance). Include solvent-only controls. Equilibrate sufficiently to avoid precipitation.

Any application-specific, lot-specific recommendations: Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

Phenanthrene is not a biomolecule; however, as a representative polycyclic aromatic hydrocarbon, it is frequently used in environmental toxicology and biochemistry research (literature/general).

• Metabolic processing (literature):
  • Oxidatively metabolized by cytochrome P450 monooxygenases to epoxides, dihydrodiols, and phenanthrenequinone derivatives; downstream conjugation (e.g., glucuronidation, sulfation) facilitates excretion.
• Model substrate:
  • Serves as a probe for studying aryl hydrocarbon receptor (AhR) interactions and induction of xenobiotic metabolism pathways in vitro.
• Partitioning/biophysics:
  • Employed as a hydrophobic marker for membrane partitioning, protein binding in hydrophobic cavities, and sorption to natural organic matter and engineered carbons.
• Ecotoxicology:
  • Used to assess bioaccumulation, phototoxicity, and PAH degradation by microbial consortia and enzymes (dioxygenases) under controlled laboratory conditions.

Note: Research use only. No clinical or therapeutic claims are made or implied.

Buffer Applications

Phenanthrene is a nonpolar hydrocarbon with extremely low aqueous solubility and does not function as a buffering agent.

• It is not typically used to prepare buffer systems. For experiments requiring aqueous handling, prepare concentrated stocks in a miscible organic co-solvent (e.g., DMSO or DMF) and dilute into buffer while keeping final organic content within assay tolerance.
• For binding or partition studies, use co-solvent controls and ensure thorough mixing/sonication to avoid precipitation or micelle partitioning artifacts.

Green Alternatives

While phenanthrene itself is the target analyte/scaffold and not easily substituted in PAH-specific studies, greener choices can be made in the surrounding workflow.

• Solvent selection (literature/general):
  • Prefer toluene, anisole, or 2-methyltetrahydrofuran (2-MeTHF) over dichloromethane/chloroform when feasible.
  • Use alcohols (ethanol, isopropanol) or ethyl acetate for workups in place of halogenated solvents if solubility permits.
• Oxidations (literature/general):
  • Replace Cr(VI)-based oxidants with safer alternatives such as DDQ, IBX, or catalytic aerobic systems (e.g., Cu/air) for forming phenanthrenequinone where compatible.
• Halogenation/coupling (literature/general):
  • Employ NBS under photoredox or mild radical conditions instead of Br2/FeBr3; for cross-coupling, use nickel catalysis and aqueous micellar media (e.g., surfactant-enabled) to reduce organic solvent demand.
• Energy and emissions:
  • Consider flow photochemistry for controlled halogenations or oxidations, improving heat/mass transfer and reducing solvent volumes.

Trade-offs:

• Greener solvents may reduce solubility or reaction rates for PAHs; careful optimization (temperature, catalyst loading) is required.
• Micellar catalysis can limit substrate concentration for highly hydrophobic PAHs; co-solvents or surfactant choice may be necessary.

Pharmaceutical Uses

Phenanthrene is not used as a pharmaceutical excipient or active in approved formulations; however, in research and development contexts it may serve analytical or materials roles (literature/general).

• Potential R&D roles:
  • Fluorescence/UV standard for instrument qualification and method development.
  • Hydrophobic probe to challenge formulations (e.g., studying solubilization by surfactants, cyclodextrins, or lipid-based systems) in pre-formulation research.
  • Structural motif: the phenanthrene ring system appears in certain APIs as part of larger frameworks, but phenanthrene itself is not formulated for therapeutic use.

Regulatory status and pharmacopeia monographs: Not specified for this item; refer to CoA/Spec Sheet.

Note: For research use only; not for human or veterinary use.

Physical Properties

The following properties are literature values or general references; they are not product specifications for this specific lot.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: ~99–101 °C (literature)
• Boiling point: ~340–342 °C at 1 atm (literature)
• Density: ~1.18 g/cm³ at 25 °C (literature)
• Vapor pressure: very low at ambient temperature (literature)
• Water solubility: ~1–1.3 mg/L at 25 °C (very low) (literature)
• Solubility in organics: soluble in benzene, toluene, xylene, chloroform, dichloromethane, carbon disulfide; sparingly soluble in ethanol and acetonitrile (literature)
• logP (octanol/water): ~4.5–4.6 (literature)
• pKa: not applicable (non-ionizable hydrocarbon) (literature)
• UV/Vis: strong π→π* absorption in the near-UV; structured fluorescence with emission in the blue region (literature)

Notes for practitioners (general):

• Low volatility and high hydrophobicity facilitate handling as a solid; however, dust control is advisable.
• Due to strong π-conjugation, phenanthrene is fluorescent and light-absorbing; for photophysical work, use spectroscopic-grade solvents and control dissolved oxygen for reproducibility.

Quality & Grades

• Grade/Purity: Moligand™ (per Product Data)

About Moligand™ (context):

• Moligand™ denotes inclusion in a curated small-molecule/ligand screening collection intended for research discovery, cheminformatics, and assay development. It emphasizes identity, library compatibility, and handling suitability rather than analytical-chromatography solvent grades.

What this means in practice:

• Identity confirmation and library readiness are prioritized (e.g., structure-verified for screening). Specific impurity profiles, residual solvent limits, metal content, or spectrophotometric cutoffs are not implied by the Moligand™ designation.
• Item-specific assays such as water content (KF), residual peroxide, metal traces, or UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

When to choose Moligand™ phenanthrene:

• Suitable for high-throughput screening, binding studies in hydrophobic pockets, host–guest testing, photophysics benchmarking, or as a nonpolar probe in partition experiments.
• For trace-analysis calibration, regulatory submission, or materials manufacturing where defined impurity limits are critical, consult the CoA/Spec Sheet or request a lot with the required specification.

Stabilizers/additives:

• None stated. Any stabilizer or inhibitor content: Not specified for this item; refer to CoA/Spec Sheet.

Reaction & Applications

Phenanthrene serves as a prototypical PAH scaffold in synthesis, materials, and analytical chemistry.

• Scaffold in organic materials:
  • Used to construct extended π-systems via Scholl cyclodehydrogenation or oxidative coupling, enabling graphene nanoribbon and OLED/OPV component synthesis (literature).
• Electrophilic substitution (literature):
  • The 9,10-positions exhibit enhanced reactivity; halogenation, nitration, and Friedel–Crafts acylation preferentially occur there under controlled conditions.
• Halogenation and cross-coupling (literature):
  • 9-Bromophenanthrene prepared via Br2/FeBr3, NBS, or radical conditions is a versatile partner for Suzuki, Stille, Negishi, and Kumada couplings to elaborate PAHs.
• Directed metalation (literature):
  • 9-Lithiophenanthrene forms with n-BuLi (often with TMEDA) at low temperature; subsequent quench with electrophiles affords 9-substituted derivatives.
• Oxidation (literature):
  • Oxidation at 9,10 yields phenanthrene-9,10-quinone, a valuable intermediate for further nucleophilic additions and annulations.
• Hydrogenation (literature):
  • Partial hydrogenation gives dihydro/tetrahydro derivatives for reactivity studies and as intermediates.
• Analytical/photophysical uses (literature):
  • Employed as a fluorescence standard, probe for solvatochromism, and model for π–π interactions and host–guest inclusion (e.g., cyclodextrins, MOFs).

Manufacturer Applications: None provided beyond inclusion in a small-molecule/compound library. Typical expansions include its use as a hydrophobic probe ligand in biophysical binding and as a rigid aromatic core in fragment-based materials discovery (research use only).

Reaction Conditions

Representative literature conditions for transforming phenanthrene (guidance only; optimize per system):

• 9-Bromination (electrophilic):
  • Br2 (1.0–1.2 equiv) in CCl4 or CHCl3, catalytic FeBr3 or light; 0–25 °C; hours. Alternative: NBS (1.1–1.5 equiv) with AIBN or photochemical initiation in CCl4/CH2Cl2.
• 9-Lithiation/electrophile trapping:
  • n-BuLi (1.1–1.3 equiv) in THF or Et2O at −78 to −40 °C, often with TMEDA; quench with DMF (formylation), Me3SiCl (silylation), B(OMe)3 then oxidative workup (borylation). Typical times: 0.5–2 h lithiation; yields variable (50–80%).
• Oxidation to phenanthrene-9,10-quinone:
  • DDQ or nitric acid/acetic acid; 0–25 °C to reflux depending on reagent; or catalytic Cu/air under oxidative conditions. Monitor by TLC/UV.
• Cross-coupling from 9-bromophenanthrene:
  • Suzuki–Miyaura: Pd(PPh3)4 or Pd2(dba)3/XPhos; base K2CO3/K3PO4 in toluene/H2O or dioxane/H2O, 80–110 °C, 4–16 h.
  • Stille/Negishi: standard Pd catalysts in DMF/toluene; 60–110 °C.
• Hydrogenation:
  • H2 (1–5 bar) over Pd/C in ethanol or ethyl acetate at ambient to 50 °C; control equivalents/time to achieve di- vs tetrahydro products.
• Scholl cyclization (ring fusion):
  • FeCl3 or AlCl3 in dichloromethane/nitromethane/CS2 at 0–25 °C to reflux; inert atmosphere; water-sensitive.

General tips:

• Ensure complete dissolution in an appropriate solvent before initiating reactions; gentle heating and sonication help.
• Protect from strong light during radical brominations unless photoinitiated intentionally.
• For photophysical assays, rigorously degas to avoid oxygen quenching.

Safety & Handling

Safety information below provides general guidance for phenanthrene (PAH) handling. Item-specific hazards, GHS classification, and pictograms: Not specified for this item; refer to SDS.

• Anticipated hazards (general, literature):
  • Polycyclic aromatics may be harmful if inhaled or ingested; dust may irritate eyes/skin/respiratory tract.
  • Environment: hazardous to aquatic organisms; prevent release to the environment.
  • Combustible solid; burning may produce soot and irritating fumes.
• Storage conditions: Store at −80 °C (per Product Data). Protect from light and sources of ignition. Keep container tightly closed.
• Incompatibilities (general): strong oxidizers (risk of vigorous oxidation); nitrating mixtures; halogens under catalytic conditions.
• Engineering controls: handle in a fume hood; minimize dust formation; use closed transfers for solutions when possible.
• PPE: safety glasses or goggles, lab coat, appropriate chemically resistant gloves (e.g., nitrile); consider double-gloving for extended handling of PAHs.
• First aid (general overview; defer to 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; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Waste: collect solids/solutions as hazardous organic waste; avoid drains; follow institutional and local regulations.

Solvent Selection

Phenanthrene is highly hydrophobic and non-ionizable; solvent choice centers on achieving adequate solubility and matrix compatibility.

• Polarity class: nonpolar aromatic hydrocarbon (literature)
• Miscibility/solubility profile (literature):
  • Good: toluene, xylene, benzene, dichloromethane, chloroform, carbon disulfide, THF, dioxane.
  • Moderate/limited: acetonitrile, ethyl acetate, ethanol, isopropanol.
  • Poor: water and aqueous buffers.
• Practical guidance:
  • For stock solutions in screening: DMSO is often used, but phenanthrene has limited solubility in DMSO at room temperature; pre-warm (≤40 °C) and sonicate to reach 10–50 mM, or use DMF/toluene as primary stock then back-dilute.
  • For photophysical measurements: use spectroscopic-grade toluene, cyclohexane, or acetonitrile depending on polarity needs; rigorously degas to minimize oxygen quenching of fluorescence.
  • For electrophilic substitution or radical halogenation: aromatic solvents (toluene) or chlorinated solvents (DCM/CHCl3) are common; choose based on catalyst and safety constraints.
• Comparison (general):
  • Toluene vs DCM: toluene is less volatile/toxic and often dissolves PAHs well; DCM provides faster mass transfer and lower viscosity but with higher EHS burden.
  • Cyclohexane/hexanes useful when precipitation or crystallization is desired after reaction or for fluorescence in nonpolar medium.

Storage & Reconstitution

• Storage conditions (per Product Data): Store at −80 °C. Keep container tightly sealed. Protect from light to preserve photophysical integrity.
• Shipping: Shipped with dry ice packs + cold packs (per Product Data), supporting maintenance of low temperature during transit.
• Stability: Phenanthrene is a stable PAH; at ambient conditions it is not especially labile, but low-temperature storage can help maintain consistent properties for screening libraries. Long-term stability or retest period: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/preparation:
  • For screening stocks: Prepare in dry DMSO, DMF, or toluene at 10–50 mM. Sonication and mild heating (≤40 °C) can assist dissolution. Store aliquots in amber vials to minimize light exposure; backfill with inert gas if possible.
  • Avoid repeated freeze–thaw of stock solutions; aliquot upon first dissolution. For DMSO stocks, store at −20 to −80 °C depending on assay cadence; verify solubility upon thaw.
• Handling after thaw:
  • Warm to room temperature before opening to prevent moisture condensation. Mix thoroughly and inspect for crystallization/precipitate; if present, re-warm and sonicate to redissolve.

Research Use Note: For research use only. Not for human or veterinary use.

Structure & Identity

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) composed of three fused benzene rings in an angular arrangement.

• SKU: P1499576
• CAS: 85-01-8 (literature)
• PubChem CID: 995 (literature)
• Molecular formula: C14H10 (literature)
• Molecular weight: 178.23 g/mol (literature)
• SMILES: c1ccc2c(c1)ccc3ccccc23 (literature)
• InChIKey: YWWGFRZPVNNQJQ-UHFFFAOYSA-N (literature)
• Structural features:
  • Aromatic system: three fused benzene rings; fully conjugated π-system.
  • Topology: angular fusion (unlike linear anthracene), giving distinct reactivity at the 9,10-positions.
  • Functional groups: none beyond aromatic C–H; nonpolar hydrocarbon.
• 2D description in words: two outer benzene rings share individual edges with a central ring, forming a bent tricyclic framework; the most reactive positions are typically the bridgehead-like 9 and 10 carbons.

Item-specific identifiers or specifications not listed above: Not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

The rigid, angular, π-rich phenanthrene core is a valuable building block for PAH elaboration and functional materials (literature/general).

• Key reactivity handles:
  • 9,10-positions: enhanced reactivity enables selective halogenation, oxidation to quinones, and addition reactions.
  • Directed metalation: formation of 9-lithiophenanthrene allows installation of electrophiles (formylation, silylation, borylation via trapping strategies).
• Named/typical transformations:
  • Scholl cyclodehydrogenation to generate larger fused aromatics and nanographenes.
  • Radical bromination/chlorination leading to cross-coupling handles for Suzuki–Miyaura, Stille, Negishi, Sonogashira.
  • Oxidation to phenanthrene-9,10-quinone followed by nucleophilic additions (e.g., Wittig-like annulations) to craft heteroacenes.
  • Photochemical reactions (e.g., [4+4] dimerizations under constrained conditions) as mechanistic probes.
• Retrosynthetic value:
  • Readily available, stable, and scalable; its derivatives serve as synthons toward helicenes, phenacenes, and donor–acceptor architectures by sequential halogenation/coupling and oxidative ring fusion.
• Materials interface:
  • Phenanthrene derivatives tune HOMO/LUMO levels and packing for OFETs, OLEDs, and OPVs; substitution patterns at 3,6- or 9,10-positions modulate solid-state π–π stacking and emission.

Target Specificity

This product is a small molecule (phenanthrene), not an antibody or biological targeting reagent. No target specificity data (antigen, epitope, clone, isotype, species reactivity) apply.

• Targeting details: Not applicable.
• Any item-specific bioactivity panel: Not specified for this item; refer to CoA/Spec Sheet.