3-Ethoxy-4-methoxybenzoyl chloride - ≥98% , CAS No.82613-08-9

CAS: 82613-08-9 Cat. No.: E963311 Summenformel: C₁₀H₁₁ClO₃ Molekulargewicht: 214.640

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

CCOC1=C(C=CC(=C1)C(=O)Cl)OC

IUPAC Name

3-ethoxy-4-methoxybenzoyl chloride

InChIKey

FVPSRCQVHSLSOT-UHFFFAOYSA-N

INCHI

1S/C10H11ClO3/c1-3-14-9-6-7(10(11)12)4-5-8(9)13-2/h4-6H,3H2,1-2H3

Molekulargewicht

214.640

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acids and derivatives
• Alternative Parents: Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers Acyl chlorides Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoic acid or derivatives - Phenoxy compound - Methoxybenzene - Phenol ether - Anisole - Benzoyl - Alkyl aryl ether - Acyl chloride - Acyl halide - Ether - Organic oxygen compound - Organohalogen compound - Organochloride - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzoic acids and derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene 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: 214.640 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 214.04 Da
• Monoisotopic Mass: 214.04 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 196.000
• 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. No validated bioassay protocols (WB, IHC, IF, FC, etc.) are associated with this small-molecule reagent. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

This is a synthetic aryl acyl chloride and does not have established natural biological roles. It is not a metabolite or cofactor in known biochemical pathways.

• General context (literature):
  • Aromatic acyl chlorides are reactive electrophiles that rapidly acylate nucleophiles (e.g., amines, thiols) and therefore are not typically encountered in biological systems due to hydrolytic instability.
  • The corresponding acid or amide/ester derivatives of the 3-ethoxy-4-methoxybenzoyl motif may be encountered as synthetic intermediates in medicinal chemistry research; however, no biological function is implied.

Note: For research use only (per Product Data). No clinical or diagnostic applications are claimed.

Buffer Applications

Not typically applicable. As a moisture-sensitive acylating reagent, this material is incompatible with aqueous buffer systems and will hydrolyze to the corresponding acid with HCl release. For aqueous work, consider first converting it to a stable derivative (e.g., amide or ester) and then formulate that derivative in appropriate buffers.

Green Alternatives

While acyl chlorides are highly efficient acyl donors, they pose environmental, safety, and handling burdens (HCl release, corrosivity, moisture sensitivity). Consider the following greener strategies where feasible.

• Alternative acylating agents (literature):
  • Carboxylic acids with coupling reagents (e.g., CDI, DMTMM, EDC/HOBt substitutes): Avoids HCl but introduces other auxiliaries; waste profile may be improved depending on solvent choices.
  • Acid anhydrides or mixed anhydrides: Often less volatile/corrosive than acyl chlorides; can offer milder handling.
  • Acid fluorides via DAST/Deoxo-Fluor are not greener and generally discouraged.
• Greener solvents for acylations:
  • Replace DCM with 2-MeTHF, CPME, or ethyl acetate when compatible with reactivity and base.
  • Employ water or water-rich biphasic media (Schotten–Baumann) to minimize organic solvent volumes; control pH to 8–10 to capture HCl.

Comparison (general trade-offs):

• Parameter | Acyl chloride | Coupling reagent route
• Waste | HCl, hydrolysis by-products | Urea or imidazole by-products
• Hazard | Corrosive, lachrymator | Typically less corrosive; some sensitizers
• Rate | Fast, high-yielding | Often fast; reagent cost higher
• Solvent | DCM/THF common | Broader choice; greener options feasible

Practical recommendation: If EHS drivers are strong, evaluate the 3-ethoxy-4-methoxybenzoic acid + CDI in 2-MeTHF or EtOAc as a first alternative.

Pharmaceutical Uses

No excipient or formulation roles are indicated for this item. In a process-chemistry or medicinal-chemistry context, aryl acyl chlorides like 3-ethoxy-4-methoxybenzoyl chloride can serve as synthetic intermediates to prepare amides, esters, and ketones that may be evaluated during route scouting or lead optimization.

• Notes (general, non-clinical):
  • If used in GMP settings as a starting material or intermediate, control of residual acid chloride and HCl is critical; validated quench and purge steps are required.
  • Downstream product specification typically includes confirmation of complete acyl chloride consumption (e.g., by IR/derivatization), and control of 3-ethoxy-4-methoxybenzoic acid as a potential hydrolysis impurity.

No therapeutic claims are made. Research use only (per Product Data).

Physical Properties

• Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general expectations for aryl acid chlorides with dialkoxy substitution (for guidance only; not product specs):
  • Physical state: Typically colorless to pale yellow liquid or low-melting solid; may fume in moist air due to HCl release.
  • Density/refractive index: Often higher than aliphatic analogs; exact values not established here.
  • Solubility profile: Hydrolytically unstable in water; soluble in common aprotic organic solvents (e.g., dichloromethane, toluene, THF, acetonitrile, ethyl acetate). Reacts with lower alcohols and amines.
  • Volatility: Moderate; handle in well-ventilated fume hood to minimize exposure.
  • Stability: Moisture-sensitive; gradual hydrolysis to the corresponding acid with HCl evolution. Stable to brief ambient handling when dry and sealed.
• Practical notes:
  • Avoid aqueous workup until the acylation reaction is complete; quench carefully with ice-cold, buffered or basic media to control HCl.
  • For analytical tracking, IR typically shows a strong acyl chloride C=O band near 1780–1800 cm⁻¹ and a C–Cl stretch in the 600–800 cm⁻¹ region (literature).

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpretation guidance (general):
  • For acyl chlorides used in synthesis, key quality markers typically include assay/purity by GC or NMR, hydrolyzable chloride content, color (APHA/Hazen), and moisture content (Karl Fischer). Low moisture is critical to avoid premature hydrolysis.
  • Where stated, stabilizers (e.g., trace acid scavengers or inhibitors) can affect reactivity and downstream purification; none are specified for this item.
  • If offered as “anhydrous” or “for synthesis,” expect tighter limits on water and low acid content. If “HPLC grade” is ever indicated for similar aromatic reagents, that usually refers to low UV-absorbing impurities for analytical compatibility rather than suitability as a mobile phase.
• Recommendations:
  • Verify current lot specifications (assay, moisture, color, residual solvents) on the CoA before use in moisture-sensitive couplings.
  • For demanding applications (e.g., medicinal chemistry route scouting), consider re-distillation under reduced pressure immediately prior to use to remove trace acid and hydrolysis products, if compatible with safety protocols.

Reaction and Applications

As an electron-rich aryl acyl chloride, 3-ethoxy-4-methoxybenzoyl chloride is a versatile benzoylating agent in organic synthesis.

• Core transformations (literature/general):
  • Amide formation: Coupling with primary/secondary amines to afford 3-ethoxy-4-methoxybenzamides. Bases such as TEA, DIPEA, or pyridine scavenge HCl; catalytic DMAP can accelerate acyl transfer.
  • Esterification: Reaction with alcohols/phenols to give the corresponding 3-ethoxy-4-methoxybenzoates. Conduct under anhydrous conditions with base or in the presence of DMAP.
  • Anhydride formation: With carboxylate salts to provide symmetrical or mixed anhydrides.
  • Friedel–Crafts acylation: With activated aromatics in the presence of Lewis acids (AlCl3, FeCl3) to generate aryl ketones bearing the 3-ethoxy-4-methoxybenzoyl fragment.
• Electronic effects:
  • The ring’s methoxy and ethoxy groups are strong donors; they do not diminish the intrinsic reactivity of the acyl chloride but can influence the stability and UV properties of the products (useful for analytical detection).
• Practical tips:
  • Add the acyl chloride slowly to a cooled solution of nucleophile and base to control exotherm and suppress side hydrolysis.
  • For sensitive amines, pre-form the amine hydrochloride salt and neutralize in situ with excess base in a biphasic setup (Schotten–Baumann conditions).
  • Monitor by IR (loss of ~1800 cm⁻¹ acyl chloride band) or LC/GC. Quench cautiously with cold, basic aqueous media after completion.

Reaction Conditions

The following ranges are literature-style guidance for acyl chlorides and should be optimized per substrate. They are not product specifications.

• Amide formation:
  • Solvent: DCM, THF/2-MeTHF, DMF, toluene, or EtOAc (anhydrous).
  • Base: 1.0–2.0 equiv TEA or DIPEA; 0.1 equiv DMAP optional.
  • Temperature: 0–25 °C for addition, then 20–40 °C until completion.
  • Time: 0.5–6 h typical; sterically hindered amines may require longer.
  • Workup: Quench with cold, aqueous NaHCO3 or dilute Na2CO3; extract; wash to neutrality.
• Esterification (alcohols/phenols):
  • Solvent: DCM, THF, or EtOAc; catalytic DMAP (5–10 mol%) often beneficial.
  • Base: Pyridine/TEA (1.5–2.0 equiv) or biphasic NaHCO3 for phenols.
  • Temperature: 0–25 °C addition; then 20–50 °C.
• Thioester formation:
  • Solvent: DCM or acetonitrile; base: TEA.
  • Temperature: 0–25 °C; rapid reactions; minimize air exposure due to odor/toxicity of thiols.
• Friedel–Crafts acylation:
  • Catalyst: AlCl3 (1.2–2.0 equiv) or FeCl3.
  • Solvent: DCM or CS2/toluene (per substrate/catalyst); strictly anhydrous.
  • Temperature: –20 to 25 °C for initiation; may warm to reflux as needed.
• Monitoring and analytics:
  • IR: Disappearance of acyl chloride band (~1780–1800 cm⁻¹) and appearance of amide/ester C=O (1640–1740 cm⁻¹).
  • LC/MS or GC/MS for conversion and impurity profiling.
• Expected outcomes:
  • Many amide/ester formations with aryl acyl chlorides reach high conversions (often >80–90% in literature) under mild conditions; actual yields depend on substrate and workup efficiency.

Safety and Handling

• Item-specific hazard data (GHS, H-phrases, pictograms): Not specified for this item; refer to SDS.
• General hazards for acyl chlorides (literature; for guidance only):
  • Corrosive; generates HCl upon contact with moisture, alcohols, and amines; causes severe skin and eye burns; respiratory irritation. Often a lachrymator.
  • Hydrolysis is exothermic; vapors may be irritating.
• PPE and engineering controls:
  • Use in a certified chemical fume hood.
  • Wear chemical-resistant gloves (e.g., butyl rubber or laminated film for acyl chlorides), splash goggles/face shield, lab coat; consider respiratory protection per institutional policy.
• Incompatibilities:
  • Water, protic solvents (alcohols), amines, strong bases (uncontrolled exotherm and HCl release), strong oxidizers. Avoid contact with active metals if HCl could be generated.
• First-aid overview (consult SDS for details):
  • Skin/eye contact: Immediate 15+ min water flush; remove contaminated clothing; seek medical attention.
  • Inhalation: Move to fresh air; monitor breathing; obtain medical attention.
  • Ingestion: Rinse mouth; do not induce vomiting; urgent medical care.
• Handling tips:
  • Maintain anhydrous conditions; use oven-dried glassware and dry solvents.
  • Add acyl chloride last and slowly, with external cooling if needed, to control exotherms.
  • Keep spill control neutralizers (e.g., sodium bicarbonate solution) and absorbents readily available.

Solvent Selection

This product is a reactive aryl acyl chloride, not a solvent. The discussion below addresses solvent choices for using it as a reagent.

• Polarity/solvent class preference (general):
  • Polar aprotic solvents with low water content are preferred: dichloromethane (DCM), THF, 2-MeTHF, acetonitrile, ethyl acetate, toluene. Avoid protic solvents unless conducting intentional solvolysis/esterification.
• Miscibility and practicality:
  • DCM: Excellent substrate solubility and heat removal; easy workup; low boiling point advantageous for temperature control.
  • THF/2-MeTHF: Useful when base-soluble; good for amide couplings with organic bases (e.g., DIPEA, TEA).
  • Toluene: Higher temperature operations or Lewis acid-mediated Friedel–Crafts acylations.
  • Acetonitrile: Suitable for nucleophilic acyl substitutions with salts; ensure base compatibility.
• When to choose alternatives:
  • For greener profiles, consider 2-MeTHF or CPME over THF/DCM; ethyl acetate can be a benign medium for Schotten–Baumann-style biphasic reactions with controlled aqueous base.
• Additives:
  • Employ amine bases (triethylamine, DIPEA) or pyridine as HCl scavengers in homogeneous media; aqueous Na2CO3/NaHCO3 in biphasic protocols.
• Drying and conditioning:
  • Dry solvents thoroughly (molecular sieves or distillation). Degas if moisture/CO2 sensitive steps are anticipated.

Storage and Reconstitution

• Item-specific storage (from Product Data): Room temperature.
• Additional handling guidance (general for acyl chlorides):
  • Store tightly sealed under dry inert gas (nitrogen/argon) to minimize hydrolysis; include a desiccant in the outer container where possible.
  • Protect from moisture; avoid prolonged exposure to ambient humidity. If available, use septum-sealed bottles for syringe transfers.
  • Do not refrigerate in humid environments without secondary containment; moisture ingress can occur upon warming (condensation).
  • If partial hydrolysis is suspected (odor change, IR band changes), consider purifying by quick vacuum distillation under dry conditions before critical use, observing all safety precautions.
• Reconstitution: Not applicable; supplied neat. If dilution is needed, prepare anhydrous stock solutions (e.g., in DCM, THF, toluene, or acetonitrile) immediately before use. Discard solutions that show signs of HCl formation or haze.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Research use only (per Product Data).

Structure and Identity

Aryl acyl chloride featuring two electron-donating alkoxy substituents on the ring (ethoxy at C-3 and methoxy at C-4) relative to the benzoyl chloride carbonyl.

• Item-specific (from Product Data):
  • Product name: 3-Ethoxy-4-methoxybenzoyl chloride
  • CAS: 82613-08-9
  • InChIKey: 93373 (provided; appears truncated — consult CoA for full key)
  • Storage: Room temperature
• Literature/computed identifiers (for reference; not item specifications):
  • Molecular formula (computed from name): C10H11ClO3
  • Molecular weight (computed): ~214.65 g/mol
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general description):
  • Core: Benzoyl chloride (–C(=O)Cl) directly attached to an anisole-type ring.
  • Substitution pattern: Ethoxy (–OCH2CH3) at the meta position (3-) and methoxy (–OCH3) para (4-) to the acyl chloride. Two strong +M donors render the ring electron-rich.
  • Functional groups: Acid chloride (acyl chloride), two aryl alkyl ethers (anisole/phenetole type). No stereocenters.
  • 2D depiction (verbal): A benzene ring bearing at position 1 a –C(=O)Cl; at position 3 an –O–CH2–CH3; at position 4 an –O–CH3.

Synthetic Utility

• Functional handle: The acyl chloride (–C(=O)Cl) is a high-energy acyl donor enabling rapid formation of C–N and C–O acyl derivatives under mild conditions.
• Derivatization map:
  • Amides: Primary/secondary amines, anilines, heteroarylamines → 3-ethoxy-4-methoxybenzamides. Use base (TEA/DIPEA/pyridine) ± catalytic DMAP.
  • Esters: Aliphatic, benzylic, and phenolic alcohols → 3-ethoxy-4-methoxybenzoates. Consider DMAP catalysis for hindered substrates.
  • Thioesters: Thiols (RSH) under basic conditions; useful acyl transfer intermediates.
  • Anhydrides: Carboxylates (RCO2–) → symmetrical/mixed anhydrides for subsequent coupling.
  • Aryl ketones: Friedel–Crafts acylation on activated arenes with AlCl3/FeCl3; installs the 3-ethoxy-4-methoxybenzoyl fragment.
• Strategic value:
  • The dialkoxy pattern imparts electron-rich character to the aromatic ring of the products, tuning polarity and UV response, aiding chromatographic detection and purification.
  • The benzoyl group can sometimes function as a temporary protecting/activating group removable via hydrolysis or reductive conditions depending on the derivative formed.
• Practical guidance:
  • Exclude moisture rigorously; pre-dry nucleophile solutions.
  • For base-sensitive substrates, use non-nucleophilic bases (Proton sponge, collidine) or biphasic NaHCO3 to limit side reactions.
  • Monitor for hydrolysis to the carboxylic acid; include scavengers and maintain low temperature during additions.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biologic or affinity reagent. No antigen/epitope/clone/isotype information applies.

Häufig gestellte Fragen

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 82613-08-9, the molecular formula is C10H11ClO3, and the molecular weight is 214.640 g/mol. InChIKey FVPSRCQVHSLSOT-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.