6-Ethyl-3-formylchromone - ≥98% , CAS No.42059-78-9

CAS: 42059-78-9 Cat. No.: E473297 Formula: C₁₂H₁₀O₃ Molecular Weight: 202.21 EC Number: 623-597-5

GRADE & PURITY ≥98%

Synonyms

EN300-22561 | 6-Ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde | MFCD00192155 | UPCMLD0ENAT5522482:001 | 6-Ethylchromone-3-carboxaldehyde | 6-Ethyl-3-formylchromone | AKOS000268942 | 6-Ethyl-3-formylchromone, 98% | DTXSID10374522 | 6-ethyl-3-formyl chromone

Storage

Room temperature

Overview

Description

6-Ethyl-3-formylchromone (6-Ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde) is a benzopyran derivative. It is a bicyclic heterocyclic molecule made up of a benzene ring fused to a heterocyclic pyran ring.6-Ethyl-3-formylchromone is the suitable reagent used in the synthesis of uridine-based library. It may be used in the synthesis of ethyl 3-acetyl-5-(5-ethyl-2-hydroxybenzoyl)-2-hydroxybenzoate.

Specifications

Synonyms

EN300-22561 | 6-Ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde | MFCD00192155 | UPCMLD0ENAT5522482:001 | 6-Ethylchromone-3-carboxaldehyde | 6-Ethyl-3-formylchromone | AKOS000268942 | 6-Ethyl-3-formylchromone, 98% | DTXSID10374522 | 6-ethyl-3-formyl chromone

Specifications & Purity

≥98%

Storage

Room temperature

Purity

≥98%

Names and Identifiers

Pubchem Sid

504761543

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504761543

Canonical Smiles

CCC1=CC2=C(C=C1)OC=C(C2=O)C=O

IUPAC Name

6-ethyl-4-oxochromene-3-carbaldehyde

InChIKey

XCKTXKYXKJJGBA-UHFFFAOYSA-N

INCHI

1S/C12H10O3/c1-2-8-3-4-11-10(5-8)12(14)9(6-13)7-15-11/h3-7H,2H2,1H3

Isomeric SMILES

CCC1=CC2=C(C=C1)OC=C(C2=O)C=O

WGK Germany

3

Molecular Weight

202.21

Reaxy-Rn

1372005

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1372005&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzopyrans
      • Subclass 1-benzopyrans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Not available
• Direct Parent: Chromones
• Alternative Parents: Pyranones and derivatives Aryl-aldehydes Benzenoids Heteroaromatic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Chromone - Aryl-aldehyde - Pyranone - Benzenoid - Pyran - Heteroaromatic compound - Oxacycle - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aldehyde - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as chromones. These are compounds containing a benzopyran-4-one moiety.
• 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

• x_melt_point_char: 108-110 °C
• Molecular Weight: 202.210 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 202.063 Da
• Monoisotopic Mass: 202.063 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 306.000
• 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

Item-specific validated protocols/applications: Not specified for this item.

General laboratory usage examples (literature/general):

• Stock solution preparation: Dissolve at 10–50 mM in dry DMSO or acetonitrile. Filter (0.22 µm PTFE) if needed. Store small aliquots at ambient or 4 °C desiccated and protected from light for short-term use.
• Knoevenagel screening: Combine aldehyde (0.5 mmol), malononitrile (0.55 mmol), piperidine (10 mol%) in EtOH (5 mL). Stir at rt; monitor by TLC (254 nm). Quench with water, filter or extract, and purify by crystallization or flash.
• Wittig test reaction: In dry THF (5 mL), cool to 0 °C under N2. Add ylide solution (1.2 eq) to aldehyde (0.5 mmol). Warm to rt, stir 2 h, quench with saturated NH4Cl, extract, and purify.
• Analytical HPLC: Utilize a C18 column with a water/acetonitrile gradient containing 0.1% formic acid; detect at 254–360 nm where chromones absorb strongly.

These are non-binding, representative procedures. Optimize conditions for your substrate, scale, and compliance requirements.

Biological Roles

Item-specific biological/biochemical role claims: Not specified; this product is for research use only.

Literature/general context:

• Chromone core: The chromone (1-benzopyran-4-one) scaffold is a privileged structure found across flavones and related natural products. Substitution at the 3-position (including formylation) modulates conjugation and electronics, influencing interactions with biomacromolecules in model studies.
• Chemical biology utility: 3-Formylchromones serve as versatile handles for Schiff base formation with amines, enabling conjugation to peptides or aminosugars under mild conditions for probe development. The aldehyde can be further elaborated to fluorophores or affinity tags.
• Photophysics: Conjugated chromone systems exhibit strong UV absorbance; certain 3-alkenyl/aryl-extended derivatives display intramolecular charge-transfer behavior. These features can be exploited in spectroscopic assays as internal standards or reporters (non-clinical, research-only).
• Metabolic considerations (general): Aldehydes in biological milieu may be reactive toward nucleophiles (lysine side chains, glutathione) or undergo oxidation to acids via aldehyde dehydrogenases. Such reactivity should be considered when designing in vitro experiments.

Important note: No clinical, diagnostic, or therapeutic uses are claimed or supported. Any biological evaluations should be conducted under appropriate institutional approvals with a clear recognition of aldehyde reactivity.

Buffer Applications

This compound is a neutral organic aldehyde/heteroaromatic and is not a buffering agent. It does not form defined conjugate acid/base pairs in aqueous media suitable for pH control. Consequently, standard buffer recipes (phosphate, Tris, HEPES, acetate, etc.) do not apply.

Practical guidance:

• For biochemical assays, dissolve first in a compatible co-solvent (e.g., DMSO or acetonitrile), then dilute into the chosen buffer, keeping final organic content within assay tolerances (commonly ≤1–2%).
• Verify solubility and stability at the working pH; aldehydes can hydrate in water and may undergo imine formation with amine-containing buffers (e.g., Tris), potentially depleting free compound. Prefer phosphate or HEPES if aldehyde integrity must be preserved.

Green Alternatives

Context: While the molecule itself is a target/building block, greener choices mainly involve solvent and reagent selection during its use (literature/general).

Greener solvent options and trade-offs:

• Replace chlorinated solvents: Use ethyl acetate or 2-MeTHF instead of dichloromethane where possible (e.g., for extractions and some reactions). Note: Polarity differences may affect rates/selectivities.
• Swap DMF/DMSO where feasible: Acetonitrile, propylene carbonate, Cyrene, or ethanol can be effective in condensations; verify solubility and catalyst compatibility.
• Use bio-based ethers: 2-MeTHF often substitutes for THF in Wittig/HWE and organometallic steps; lower peroxide propensity and better phase separation are advantages.

Reagent choices:

• Base catalysis: Employ organic bases (piperidine, DBU) catalytically rather than stoichiometric inorganic bases when possible; or use solid-supported bases to simplify workup.
• Oxidations/reductions: Prefer TEMPO/bleach or oxygen-mediated oxidations and transfer hydrogenations (isopropanol, catalytic) over chromium reagents and high-pressure hydrogen.

Small comparison (literature/general):

• DCM vs EtOAc: EtOAc has lower toxicity and environmental impact; DCM often gives faster olefinations but poses higher worker exposure risk.
• THF vs 2-MeTHF: 2-MeTHF is bio-derived, less volatile, and facilitates separations; ensure water content control for air/moisture-sensitive steps.

Waste minimization:

• Leverage the strong UV response of chromones for in-process control (HPLC/UPLC), reducing trial runs and solvent use.
• Consider crystallization-induced purification rather than silica chromatography when feasible.

Pharmaceutical Uses

Item-specific pharmacopeial/excipient status: Not specified for this item.

Literature/general context:

• Role: 6-Ethyl-3-formylchromone is best regarded as a synthetic intermediate or research building block rather than a formulated excipient. Its aldehyde functionality and chromone core enable rapid derivatization toward libraries of heteroaromatics and chromophores.
• Process chemistry: The strong UV chromophore facilitates in-process monitoring by HPLC/UPLC, supporting route scouting and impurity tracking in medicinal chemistry campaigns.
• Pre-formulation in research: For in vitro tool compound development, stocks are commonly prepared in DMSO or acetonitrile and aliquoted; no clinical formulation claims are made or implied.

Compliance reminder:

• For research use only. Not for human or veterinary use, not for diagnostic procedures, and not intended as an API or excipient without further qualification and regulatory assessment.

Physical Properties

Item-specific physical properties: Not specified for this item; refer to CoA/Spec Sheet.

Literature/typical properties for 6-ethyl-3-formylchromone and closely related 3-formylchromones (values vary by source and substitution pattern):

• Physical state/appearance: Typically a pale yellow to yellow crystalline solid due to extended conjugation.
• Molecular formula: C12H10O3 (literature)
• Molecular weight: ~202.21 g/mol (literature)
• Solubility: Sparingly soluble in water; soluble in common organic solvents such as DMSO, DMF, acetone, acetonitrile, ethyl acetate, dichloromethane, and alcohols (literature, qualitative).
• Partitioning: Expected moderate lipophilicity (logP estimated in the 2–3 range for similar chromone aldehydes; literature estimates vary).
• UV–Vis: Chromones typically show strong UV absorbance with π→π* bands in the 240–280 nm region and extended absorbance into 320–380 nm due to conjugation; the 3-formyl group often causes a bathochromic shift (literature/general).
• IR features: Strong C=O stretches near ~1660–1720 cm−1 for the aldehyde and lactone, aromatic C=C stretches, and aldehydic C–H around ~2720–2830 cm−1 (literature/general).

Practical notes:

• For solution preparations, DMSO or DMF stock solutions are commonly used at 10–100 mM, then diluted into the reaction medium or assay solvent as needed.
• Always verify lot-specific purity, residual solvents, and water content from the CoA before critical applications.

Quality and Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on grades and what to look for with chromone aldehydes (literature/general):

• Research grade vs. higher-purity: For synthetic applications (e.g., Knoevenagel, Wittig), standard research grade often suffices. For photophysical measurements or trace-level applications, consider material with low UV-absorbing impurities and well-defined assay purity.
• Purity reporting: Look for assay by HPLC/GC/NMR, and impurity profiles (particularly residual starting chromone, over-oxidized acids, or polymeric byproducts). If stabilizers are used, they should be declared; none are specified for this item.
• Water content: Aldehydes can engage in hydrate formation; Karl Fischer water is sometimes reported. For this item, water content is not specified—consult the CoA.
• Metals/peroxides: Not typically relevant unless a metal-catalyzed step was used upstream. If critical, request a certificate with ICP/Peroxide tests.
• Batch consistency: Check melting behavior and HPLC retention time against reference spectra; chromone scaffolds give characteristic UV traces that facilitate identity confirmation.

Takeaway for this product: Use the CoA for lot-specific purity, residual solvents, and chromatographic identification. If your application is particularly sensitive (e.g., photophysics or medicinal chemistry SAR with tight impurity control), consider re-crystallization or preparative HPLC polishing as needed.

Reaction and Applications

Manufacturer Applications: Not specified in the Product Data.

Literature/general synthetic applications of 6-ethyl-3-formylchromone (and related 3-formylchromones):

• Knoevenagel condensations: The aldehyde undergoes base- or acid-catalyzed condensation with active methylenes (e.g., malononitrile, ethyl cyanoacetate, barbiturates) to give push–pull alkenes and extended chromone dyes. Secondary amines (piperidine, morpholine) or ammonium acetate in EtOH/MeCN are typical catalysts.
• Wittig/Horner–Wadsworth–Emmons: Olefination furnishes 3-vinylchromones with control over E/Z and electron-withdrawing substituents, enabling access to styrylchromones.
• Reductive transformations: NaBH4 or catalytic hydrogenation can reduce the aldehyde selectively to the corresponding benzyl alcohol; stronger conditions may reduce the chromone carbonyl or open the lactone.
• Oxidation: Mild oxidants (e.g., Ag2O, TEMPO/bleach) can yield the corresponding carboxylic acid; care to avoid over-oxidation of the chromone ring.
• Cycloadditions/annulations: The α,β-unsaturated system of chromones participates in Michael additions and [4+2]/[3+2] annulations with azomethine ylides, nitrones, and dienophiles, constructing polycyclic frameworks.
• Electrophilic substitution on the ring: The 6-ethyl group provides a handle for benzylic functionalizations (e.g., oxidation to acetyl, bromination) without perturbing the core.

Use-cases:

• Building block for flavone-like scaffolds and chromophore tuning in materials.
• Intermediate in library synthesis for SAR around chromone cores.
• UV-active tag/handle for analytical method development.

Reaction Conditions

General literature guidance for typical reactions of 3-formylchromones (optimize per substrate; values are indicative, not specifications):

• Knoevenagel condensation:

  • Conditions: 1.0 eq aldehyde, 1.1–1.5 eq active methylene (e.g., malononitrile), catalytic piperidine (5–20 mol%), solvent EtOH or MeCN, rt to reflux, 1–6 h.
  • Notes: Monitor by TLC/HPLC (strong UV). Water removal (Dean–Stark in toluene) can drive equilibrium for less reactive partners. Typical isolated yields: 70–95% with malononitrile.

• Wittig/Horner–Wadsworth–Emmons:

  • Conditions: Aldehyde (1.0 eq), phosphonium ylide or phosphonate (1.2–1.5 eq), base (NaH or t-BuOK for unstabilized; NaHMDS for stabilized), dry THF or toluene, 0 °C to rt, 1–4 h.
  • Notes: Stabilized ylides favor E-olefins. Control moisture rigorously.

• Reductive amination:

  • Conditions: Amine (1.2–2.0 eq), AcOH (0–1.0 eq) as promoter, NaBH3CN (1.2–1.5 eq) or NaBH(OAc)3 (2.0–3.0 eq), solvent MeOH, EtOH, or DCE, 0–25 °C, 2–16 h.
  • Notes: Avoid strong acids to protect the chromone lactone.

• Selective reduction to alcohol:

  • Conditions: NaBH4 (1.1–2.0 eq) in MeOH or THF/MeOH at 0–5 °C to rt, 0.5–2 h.
  • Notes: Low temperature minimizes over-reduction of the chromone carbonyl.

• Oxime/hydrazone formation:

  • Conditions: Hydroxylamine hydrochloride (1.2–2.0 eq) or hydrazine derivatives in EtOH/AcOH or buffer (pH 4.5–5.5), rt to 50 °C, 1–4 h.

Always validate on small scale and tailor to your substrate and equipment.

Safety and Handling

Item-specific GHS data (from Product Data): Not specified for this item; refer to the SDS for authoritative information.

General safety guidance for aromatic aldehydes and conjugated lactones (literature/general):

• Likely hazards: May cause skin and eye irritation; aldehydes can be sensitizers/irritants. Avoid inhalation of dust; use in a chemical fume hood.
• PPE: Safety glasses or goggles, lab coat, appropriate gloves (e.g., nitrile). Change gloves regularly; aldehydes can permeate some elastomers.
• Handling: Minimize dust formation. Keep containers tightly closed. Avoid prolonged exposure to air/moisture which can lead to slow surface oxidation/polymerization in some aldehydes.
• Incompatibilities: Strong bases (can induce aldol/Knoevenagel self-reactions), strong oxidizers (oxidation of the aldehyde), strong reducing agents (may reduce carbonyls), and strong acids (may catalyze undesired condensations).
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air, seek medical advice 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 and easy to do; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Storage: Room temperature as per Product Data; protect from light and moisture to preserve chromophore integrity (general best practice). Always consult the product SDS and institutional protocols.

Solvent Selection

Applicability: 6-Ethyl-3-formylchromone is a neutral, moderately lipophilic, conjugated heteroaromatic aldehyde. It dissolves well in polar aprotic and common organic solvents; aqueous solubility is limited (literature/general).

Solubility/miscibility profile (literature/general):

• Highly suitable: DMSO, DMF, NMP, acetone, acetonitrile, ethyl acetate, dichloromethane, THF.
• Moderately suitable: Methanol, ethanol, isopropanol (warming/sonication may help).
• Poor: Water and highly nonpolar alkanes (unless cosolvent or surfactants are used).

Selection guidance:

• For synthetic condensations (e.g., Knoevenagel): Ethanol, acetonitrile, or toluene with a base catalyst, or solvent-free under mechanochemical conditions.
• For Wittig/olefination: Dry THF, toluene, or CH2Cl2 under inert atmosphere.
• For reductions (NaBH4, selective): Alcohols or MeOH/THF mixtures are common; watch for competitive lactone reduction under stronger conditions.
• For analytical stocks: Prepare 10–50 mM in DMSO or acetonitrile and dilute into mobile phases.

Quick comparison (literature/general):

• DMSO vs DMF: DMSO gives broader solubility and is easier to remove at high vacuum temperatures; DMF often better for amidination/couplings.
• MeCN vs EtOAc: MeCN is fully miscible with water and supports base-catalyzed condensations; EtOAc is greener and easier to remove but less polar.
• THF vs 2-MeTHF: 2-MeTHF offers greener profile and improved phase behavior; both solvate organolithiums and ylides effectively when dry.

Storage and Reconstitution

Item-specific storage/shipping:

• Storage Conditions: Room temperature (as provided in Product Data)
• Shipped In: Not specified for this item; refer to product label.

General best practices for this class of compounds (literature/general):

• Protection: Store tightly closed in an inert atmosphere or with desiccant; protect from prolonged light exposure to preserve the conjugated chromophore and prevent slow oxidation of the aldehyde.
• Stability: Aromatic aldehydes are generally stable at ambient conditions when dry; avoid extended exposure to moisture to minimize hydrate/oligomer formation.

Reconstitution/solution handling:

• Solvents: Prepare stocks in dry DMSO, DMF, acetonitrile, or ethanol depending on downstream use. For biological assays, DMSO stocks are typical.
• Concentration: 10–100 mM stocks are common. Filter through PTFE (0.2 µm) if particulate is observed.
• Aliquoting: Divide into single-use aliquots to avoid repeated opening; limit freeze–thaw cycles if storing solutions at 0–4 °C or −20 °C.
• Shelf-life: For solutions, use within days to weeks depending on solvent and storage; monitor by HPLC/UV for degradation.

Always consult the product CoA and SDS for lot-specific guidance and institutional safety requirements.

Research Use Note: For research use only.

Structure and Identity

Item-specific identifiers (from Product Data):

• CAS: 42059-78-9
• SKU: E473297
• InChIKey: 414311 (as provided)
• Storage: Room temperature

Literature/computed structural information (for reference; not item-specific specifications):

• Preferred name: 6-Ethyl-3-formylchromone (a substituted chromone/flavone scaffold)
• Core scaffold: Chromone (4H-1-benzopyran-4-one) bearing an aldehyde at C-3 and an ethyl group at C-6 (on the benzene ring)
• Functional groups: Conjugated lactone (chromone carbonyl), conjugated aldehyde (–CHO), aromatic benzopyran system
• Molecular formula (literature): C12H10O3
• Molecular weight (literature): ~202.21 g/mol
• Representative SMILES (literature): CCc1ccc2oc(=O)c(C=O)cc2c1
• 2D description: A bicyclic benzopyran-4-one ring where the pyrone ring (α,β-unsaturated lactone) is fused to a benzene ring; the aldehyde is vinylogously conjugated at position 3 of the pyrone, and an ethyl substituent is para to the lactone carbonyl on the benzene portion (position 6 overall).

Notes:

• The literature identifiers are provided to aid search and cheminformatics. For regulatory/lot-specific identification, refer to the product label and CoA.

Synthetic Utility

Functional group synopsis:

• Electrophilic aldehyde at C-3: amenable to imine formation, reductive amination, oxime/hydrazone formation, Wittig/HWE olefination, and nucleophilic additions.
• Conjugated chromone lactone: participates in Michael additions at C-2, cycloadditions, and can undergo selective ring transformations.
• 6-Ethyl substituent: benzylic C–H functionalization (oxidation to acyl, halogenation) provides diversification without perturbing the aldehyde.

Representative transformations (literature/general):

• Knoevenagel with malononitrile or ethyl cyanoacetate (piperidine, EtOH/MeCN) to give E-alkenyl nitriles/esters.
• Wittig with stabilized ylides in dry THF to form 3-alkenylchromones; HWE enables access to E-olefins bearing EWGs.
• Reductive amination with anilines/aliphatic amines to furnish benzylic amines; NaBH3CN or NaBH(OAc)3 in DCE/MeOH commonly used.
• 1,3-dipolar cycloadditions (azomethine ylide, nitrone) across the chromone to provide spiro- or fused heterocycles.
• Oxidation of the aldehyde to acid (e.g., TEMPO/NaClO or Pinnick oxidation) to access 3-carboxychromones.

Retrosynthetic value:

• The 3-formyl handle serves as a linchpin for convergent introduction of side chains via C=C or C–N bond formation late in a sequence, enabling rapid SAR exploration around a stable chromone core.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, ligand standard with defined receptor selectivity). No antigen, epitope, isotype, or species reactivity information applies. For applications involving biochemical assays, see Biological Roles and Application Protocols for general handling guidance.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 42059-78-9, the molecular formula is C12H10O3, and the molecular weight is 202.21 g/mol. InChIKey XCKTXKYXKJJGBA-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.