≥95% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Room temperature Ships Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Übersicht
Description
4-Amino-9-fluorenone was used in a study on determination of major contaminants in water samples from gas plant by using particle beam interface LC-coupled to a single quadrupole mass spectrometer. It was used as starting reagent for the synthesis of 4-methoxy-9-fluorenone.
This compound belongs to the class of organic compounds known as fluorenes. These are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
195.220 g/mol
XLogP3
2.400
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
195.068 Da
Monoisotopic Mass
195.068 Da
Topological Polar Surface Area
43.100 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
276.000
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
Lösungsrechner
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Application Protocols
No antibody/assay protocols apply to this small-molecule building block.
General laboratory use notes:
For solution preparation, weigh accurately and dissolve in a suitable organic solvent (e.g., DMSO, DMF, MeCN) under inert atmosphere if required by the downstream chemistry.
For spectroscopic studies, prepare stock solutions (e.g., 10–50 mM in dry DMSO) and store aliquots protected from light to minimize photoinduced changes.
For combinatorial synthesis, consider parallel N‑acylation or reductive amination platforms; monitor by LC–MS with dual‑wavelength detection (254/365 nm).
Biological Roles
This compound is a synthetic polycyclic aromatic ketone bearing an aniline functionality and has no known endogenous biological role.
General context (literature):
Polycyclic aromatic frameworks are used in research on fluorescence probes, charge‑transfer materials, and as model systems for π–π interactions with biomacromolecules. The 4‑amino substituent can tune donor–acceptor properties, impacting photophysics in sensing constructs.
The primary amine allows conjugation to biomolecules or polymers (via amide or urea linkages) for materials and imaging research; the conjugated ketone can participate in Schiff base chemistry with biomolecule amines under controlled conditions.
Metabolic/biochemical considerations:
Not a metabolite; no participation in recognized metabolic pathways.
Aromatic amines in general can undergo bioactivation in vivo; however, this product is supplied strictly for research use in controlled laboratory settings. No clinical or toxicological claims are made here.
Use in bioassays (research context):
Can serve as a chromophoric core in synthetic ligands or as a scaffold for sensor development; spectral properties are solvent and substituent dependent.
Note: For any work involving biological systems, ensure appropriate risk assessments and approvals. This product is labeled “For research use only.”
Buffer Applications
Not typically applicable. 4-Amino-9-fluorenone is a hydrophobic, non-buffering aromatic building block and is not used to prepare aqueous buffer systems.
Practical note:
If dissolution into aqueous media is needed for assay development, solubilize first in a miscible organic co‑solvent (e.g., DMSO) and then dilute into buffer while controlling final organic content (commonly ≤1–2% v/v) to avoid precipitation. Adjust pH only to manage the protonation state of the aniline (acidic media increase apparent solubility by forming the ammonium salt).
Green Alternatives
Greener choices pertain mainly to solvent and reagent selection around this scaffold, as the substrate itself is a specialty aromatic building block.
Preferred solvents (when feasible):
2‑MeTHF or CPME in place of THF/dioxane for reductions, imine formation, and acylations (better safety, lower peroxide tendency than ethers like dioxane; higher boiling than THF).
Ethyl acetate or MeCN as workup/reaction media in place of chlorinated solvents where solubility permits.
Propylene carbonate for high‑polarity needs (alternative to DMF/DMSO) when downstream removal is acceptable.
Reagent choices:
Reductive amination: choose NaBH(OAc)3 in AcOH/MeCN rather than cyanoborohydride when cyanide waste is a concern.
Acylations: use acid anhydrides or CDI‑mediated couplings to avoid acid chlorides/phosgene derivatives.
Diazotization/Sandmeyer variants: copper‑free photoredox procedures can replace heavy‑metal salts in some cases (literature-dependent).
Comparison (general considerations):
DMF vs. MeCN: MeCN is less problematic in some regulatory frameworks and easier to remove; DMF offers superior solvency but is a reproductive toxin.
Chlorobenzene/DCM vs. EtOAc/2‑MeTHF: the latter have improved environmental and safety profiles but may require temperature or additives for solubility.
Trade‑offs:
Higher‑boiling green solvents (2‑MeTHF, propylene carbonate) can complicate removal/crystallization.
Substrate solubility may limit chlorinated solvent replacement for highly conjugated aromatics; mixed‑solvent systems can be a workable compromise.
Always validate green substitutions at small scale to confirm kinetics, selectivity, and crystallization behavior.
Pharmaceutical Uses
No pharmacopeial monograph or excipient role is indicated for this specialty aromatic building block. It is not supplied as a drug substance or excipient.
Research/manufacturing context (general):
May be used as a chemical intermediate in discovery chemistry to build donor–acceptor chromophores, ligands, or scaffolds that can later be elaborated into targets of interest.
The primary aniline allows rapid parallel synthesis of amide/urea libraries; the conjugated ketone enables reductive amination or formation of heterocycles.
Compliance:
Provided strictly for research and laboratory use. Not for human or veterinary use, diagnostic procedures, or clinical applications.
If used in a GMP environment as an intermediate, users should qualify the material per internal quality systems, including identity/purity testing and impurity profiling per ICH guidance where applicable.
Physical Properties
Item-specific specs (for this catalog entry):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Exact purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values for 4-amino-9-fluorenone (not product specifications):
Physical state: typically a crystalline aromatic solid (often yellow to orange due to extended conjugation).
Molecular formula: C13H9NO (literature)
Molecular weight: ~195.22 g/mol (literature)
Acid–base behavior: primary aniline (weak base) with conjugate acid pKa typically in the 4–6 range for para‑substituted anilines; the amine basicity can be attenuated by conjugation with the fluorenone carbonyl (literature, qualitative).
Solubility: sparingly soluble in water; soluble in polar organic solvents (e.g., DMF, DMSO, NMP) and moderately in hot alcohols and chlorinated aromatics; limited solubility in nonpolar alkanes (literature, qualitative).
UV–Vis: conjugated donor–acceptor system; shows π→π* and n→π* bands in the near‑UV/visible region; exact λmax depends on solvent and substitution pattern (literature).
Melting point, boiling point, density, refractive index, logP, and vapor pressure: Not specified for this item; consult primary literature or CoA.
Practical notes (general):
The conjugated ketone/amine framework can exhibit solvatochromism; spectral properties are sensitive to solvent polarity and acid/base conditions.
For quantitative properties required for method development (e.g., DSC/TGA, partition data), verify experimentally with your batch and refer to the CoA.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for exact assay, trace metals, residual solvents, and chromatographic purity.
How to interpret common grades for this class of reagent (general guidance):
Research/technical grade: suitable for synthetic method development and material screening; typical characterization by NMR/IR/HRMS; may contain residual isomeric or oxidative impurities for highly conjugated aromatics.
AR/ACS grade (if offered): emphasizes assay and inorganic impurity limits; not typically assigned to specialty building blocks but may be stated for consistency in analytical applications.
HPLC grade: rarely used for solids like this; when stated, denotes low UV‑absorbing impurities appropriate for trace analysis or as a fluorescence probe precursor.
Stabilizers: Not typically added for aminofluorenones; if present, will be listed on the CoA. Stabilizer-free material may slowly discolor on air/light; this generally does not impact reactivity but can be removed by recrystallization if needed.
Batch-to-batch considerations (general):
Polycyclic aromatics can carry trace quinone/azoxy byproducts; verify by HPLC/UPLC at 254/365 nm and by 1H NMR aromatic region integration.
If you require low-water or low-peroxide specifications, request the current CoA; otherwise treat as a dry solid and confirm KF/peroxide as needed.
Documentation: Always consult the item’s CoA/Spec Sheet for authoritative specifications and recommended analytical acceptance criteria.
Reaction and Applications
4-Amino-9-fluorenone is a versatile bifunctional building block combining a conjugated aryl ketone and a para‑aniline. Typical research uses include:
Imine/enamine formation at C=O:
Condense with primary amines/anilines to form imines or with active methylenes to give enamines; subsequent reduction (NaBH3CN, NaBH(OAc)3, catalytic hydrogenation) affords 9‑alkyl/aryl‑substituted fluorenylamines.
Tips: drive imine formation by removing water (molecular sieves, Dean–Stark) and monitor by IR (C=N band) and 1H NMR (imine CH shift).
N‑Functionalization of the aniline:
Acylation (acyl chlorides/anhydrides, DMAP/Et3N) to give amides that can modulate electronics/solubility.
Alkylation under Mitsunobu‑type or SNAr conditions using the aniline as nucleophile after deprotonation (careful with overalkylation).
Diazotization of the aniline (NaNO2/HCl) to a diazonium salt enables Sandmeyer‑type diversification (Ar–X, –CN) after appropriate protection of the ketone if needed.
Electrophilic/nucleophilic aromatic substitution:
The –NH2 group activates the ring toward EAS (e.g., nitration, sulfonation) at ortho/para sites; the carbonyl can direct reactivity on the adjacent ring. Protecting the amine (e.g., acetamide, Boc) can control regioselectivity.
Cross‑coupling after functional group interconversion:
Transform the aniline to aryl triflate/boronate via diazonium or other routes for Suzuki/Heck/Sonogashira elaboration on the fluorenone framework.
Photophysics/materials:
The donor–acceptor motif supports charge‑transfer chromophores and sensing motifs; substitution at N4 or C9 tunes emission/absorption (literature applications).
Practical tips:
The conjugated core can be reduced (NaBH4, catalytic hydrogenation) to the corresponding alcohol (9‑fluorenol derivatives) prior to further transformations.
Maintain anhydrous conditions for organometallic additions to the carbonyl; amine may need protection (e.g., as carbamate) to avoid coordination or side reactions.
Reaction Conditions
General, literature-based guidance for common transformations on 4-amino-9-fluorenone (not product specifications):
Reductive amination at C9:
Conditions: amine (1.2–2.0 eq), AcOH (0.5–1 eq) in MeCN/DMF or 2‑MeTHF; NaBH(OAc)3 (2–3 eq) added portionwise at 0–25 °C; 2–16 h. Workup by basification and extraction. Typical isolated yields for related fluorenones: 60–90% depending on nucleophile.
N‑Acylation of the aniline:
Conditions: acyl chloride or anhydride (1.1–1.5 eq), base (Et3N or DIPEA, 2 eq), catalytic DMAP in DCM/MeCN at 0–25 °C; 1–4 h. For greener variant, use EtOAc or MeCN. Monitor by TLC/HPLC (loss of aniline NH stretch in IR, downfield shift of amide NH in 1H NMR).
Carbonyl reduction:
NaBH4 (2–4 eq) in MeOH/THF at 0–25 °C, 0.5–3 h affords the corresponding 9‑alcohol; chemoselectivity over the aryl ring is usually high. Alternatively, Pd/C hydrogenation (H2, 1–3 bar) in EtOH/AcOH mixtures reduces the imine in a two‑step, one‑pot reductive amination sequence.
Diazotization/Sandmeyer from the aniline:
Conditions: NaNO2 (1.1 eq) in 2–4 M HCl at 0–5 °C to form diazonium; trap with Cu(I)/Cu(II) salts and appropriate nucleophiles (Cl−, Br−, CN−) at 0–25 °C. Protect carbonyl as needed if sensitive to conditions.
Organometallic additions to C=O:
Use dry THF/Et2O at −78 to 0 °C for RMgX/RLi; pre‑protect the aniline (e.g., Boc) to avoid acid–base quenching and coordination. Quench at low temperature to control exotherm.
Always optimize on small scale; yields and selectivities depend strongly on substituents, solvent, and protection strategy.
Safety and Handling
Item-specific hazard data from Product Data:
GHS signal word: Not specified for this item; refer to SDS.
H-statements / pictograms / classification: Not specified for this item; refer to SDS.
General safety guidance for aromatic amine/ketone solids (literature; not product-specific):
Likely hazards: aromatic amines can cause skin/eye irritation and may be harmful if swallowed or inhaled; dust may cause respiratory irritation. Conjugated ketones can be photosensitive.
PPE: wear lab coat, appropriate gloves (e.g., nitrile), and safety glasses; use a fume hood to avoid dust and vapor exposure. Avoid contact with skin and eyes.
Handling: minimize dust generation; avoid breathing dust; prevent contamination of work surfaces. Use tools/spatulas dedicated to aromatic amines if cross‑contamination is a concern.
Storage incompatibilities: keep away from strong oxidizers (amine oxidation), strong acids (can form ammonium salts), and strong bases (can promote side reactions such as aldol‑type condensations at the carbonyl under certain conditions). Avoid prolonged light exposure if spectral properties are critical.
Fire safety: organic solid; combustible. Use CO2, dry chemical, or foam to extinguish. Avoid high heat; decomposition can produce irritating fumes.
First aid (overview):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical advice for persistent irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Definitive hazard classification, exposure limits, and reactivity information must be taken from the product’s SDS.
Solvent Selection
Solubility/miscibility profile (general, literature-based for 4-aminofluorenone):
Polar aprotic solvents (DMF, DMSO, NMP): typically provide highest solubility; good for coupling, condensation, and spectroscopic measurements.
Chlorinated aromatics (chlorobenzene, o‑DCB) and aromatic solvents (toluene): moderate solubility, useful for high‑temperature reactions involving electrophilic substitution or cross‑coupling after functional group interconversion.
Alcohols (MeOH, EtOH, i‑PrOH): low to moderate solubility; heat may be required for dissolution or recrystallization.
Water: generally poor solubility due to hydrophobic PAH core; solubility increases upon protonation of the aniline in acidic aqueous media.
Polarity and selection tips:
The molecule is amphoteric in function but dominated by a rigid, hydrophobic, π‑rich core; treat as a weakly basic, moderately polar aromatic solid.
For nucleophilic chemistry on the carbonyl (e.g., imine formation/reductive amination), select dehydrating polar aprotics (dry toluene with Dean–Stark; or 3 Å molecular sieves in MeCN/DMF).
For N‑acylation/alkylation of the aniline, use mildly basic conditions in DMF/MeCN/THF with soluble bases (DIPEA, K2CO3) and ensure adequate solubility of reagents.
Quick comparison (general):
DMSO/DMF: maximize solubility and rate; harder to remove.
MeCN/THF: easier workup; may require heating or additives for solubility.
Toluene/chlorobenzene: good for higher‑temperature processes and crystallizations of products derived from this scaffold.
Note: Verify actual solubility with your lot; for precise solubility and UV cutoff in specific solvents, refer to experimental determination or the CoA.
Storage and Reconstitution
Item-specific storage (from Product Data):
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for aromatic amine/ketone solids:
Keep tightly closed in a dry, inert container. Protect from excessive light and humidity. Desiccation is recommended if long-term storage is anticipated.
If spectral/purity stability is critical, store under nitrogen/argon and avoid prolonged exposure to air to limit slow oxidative discoloration.
Reconstitution and solution handling (general):
Solvents: DMSO, DMF, NMP, MeCN, or warm alcohols/aromatics depending on application.
Suggested stock concentrations: 10–100 mM in dry DMSO/DMF for screening chemistry or spectroscopic work.
Filtration: If particulates are present, pass solutions through 0.2 µm PTFE filters.
Freeze–thaw: If storing solutions, aliquot and freeze at −20 to −80 °C to minimize freeze–thaw cycles; allow to equilibrate to room temperature before opening to avoid moisture ingress.
Stability notes:
No stabilizer is indicated for this item. For exact shelf life and any item-specific stability studies, consult the current CoA/SDS.
Research use only: Not for human or veterinary use.
Structure and Identity
Brief description: 4-Amino-9-fluorenone is an aminated polycyclic aromatic ketone (fluorenone core) bearing a primary aniline substituent at the 4‑position of the aromatic framework.
Item-specific identifiers (from Product Data):
SKU: A467288
CAS: 4269-15-2
InChIKey: 81733 (as provided)
Storage conditions: Room temperature
Category: Chemical and Biochemical Reagents (research use only)
Literature structural information (for reference; not item-specific specifications):
Common name: 4-Aminofluorenone; 4-aminofluoren-9-one
Molecular formula (literature): C13H9NO
Molecular weight (literature): ~195.22 g/mol
SMILES (literature): Nc1ccc2c(c1)C(=O)c1ccccc12
Structural features: polycyclic fluorenone scaffold (tricyclic fused arene with a 9‑one carbonyl) and a para‑oriented aniline (–NH2) on the outer ring relative to the bridgehead carbonyl. Contains one ketone (conjugated to the aromatic system) and one primary amine. Planar, rigid aromatic framework conducive to π–π interactions and charge‑transfer behavior.
2D structure in words:
A tricyclic aromatic system (two benzene rings fused through a five‑membered bridge) bearing a carbonyl at the bridgehead (position 9, “fluorenone”) and an –NH2 group at the 4‑position of one outer benzene ring. The amine is conjugated across the ring system toward the 9‑ketone, enabling intramolecular donor–acceptor resonance.
Notes:
Where an exact identifier is needed for regulatory or analytical purposes, consult the item’s CoA/SDS for definitive canonical identifiers.
Synthetic Utility
Functional group leverage:
Ketone at C9 (fluorenone):
Nucleophilic additions (organolithium/Grignard) to form tertiary/secondary alcohols on the fluorenyl framework; subsequent dehydration can access alkenes.
Imine formation with amines followed by reduction (reductive amination) provides 9‑substituted amino derivatives.
Selective reduction to 9‑fluorenol derivatives (NaBH4, catalytic hydrogenation); chemoselectivity can be tuned against the aniline.
Aniline at C4:
Acylation (acyl chlorides/anhydrides, CDI) for amide libraries; carbamate protection (Boc, Cbz) to control reactivity in multi‑step routes.
Diazotization to aryl diazonium enables Sandmeyer transformations (Ar–Cl/Br/CN) or azo coupling to form push–pull chromophores.
Oxidative couplings (e.g., with hypervalent iodine reagents) to form biaryl or N–O structures under controlled conditions.
Retrosynthetic value:
Serves as a convergent node: orthogonal derivatization at N4 and C9 allows dual diversification from a single scaffold.
Electronics: the donor (–NH2) to acceptor (C=O) axis supports intramolecular charge transfer; tuning these ends modulates optoelectronic properties for materials or sensing.
Practical considerations:
Protect the aniline when performing strong‑base organometallic steps on the carbonyl (e.g., Boc protection resists many conditions and is readily removed with acid).
For electrophilic substitutions on the ring, control regioselectivity via temporary amine protection and solvent/temperature.
The rigid PAH core aids purification by recrystallization or normal‑phase chromatography; monitor at 254/365 nm due to strong absorbance.
Target Specificity
Not applicable. This product is a small-molecule aromatic building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity applies.
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