This compound belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
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
192.210 g/mol
XLogP3
2.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
192.079 Da
Monoisotopic Mass
192.079 Da
Topological Polar Surface Area
46.500 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
203.000
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
Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) are relevant for this small‑molecule building block. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general procedural guidance.
Biological Roles
This product is a synthetic aromatic carboxylic acid used for research and materials synthesis. No endogenous biological role is established for 4‑cyclobutoxybenzoic acid.
General context (literature; not item‑specific)
Benzoic acid derivatives can interact with biological membranes in a hydrophobic, pH‑dependent manner, but para‑alkoxy substitution is primarily used to tune materials properties rather than to target biological pathways.
Carboxylic acids at physiological pH largely exist as carboxylates, which can affect permeability and protein binding; however, this compound is not known as a metabolite or cofactor in recognized pathways.
Use limitations
Research use only (per Product Data). Not intended for diagnostic, therapeutic, or in vivo use.
If a biological assay requires this scaffold
Consider solubilization via co‑solvents (DMSO) or by forming a soluble salt with biocompatible amines; confirm assay compatibility and avoid precipitation upon dilution into aqueous buffers.
Buffer Applications
Not typically applicable. 4‑Cyclobutoxybenzoic acid is not a standard buffering agent.
General note (literature)
Aromatic carboxylic acids have pKa values near 4–5 and can, in principle, form benzoate/benzoic acid buffer pairs around pH ~4.2–4.5; however, limited aqueous solubility and potential hydrophobic interactions make them impractical as routine laboratory buffers.
Recommendation
For buffering near pH 4–5, select conventional systems (e.g., acetate, citrate) rather than this compound. If dissolution into aqueous media is required for research, prepare a dilute solution in DMSO first and then dilute into buffer, monitoring for precipitation.
Green Alternatives
Green chemistry considerations focus on solvent and reagent choices when transforming 4‑cyclobutoxybenzoic acid.
Greener solvent options (literature guidance)
Replace DMF/DMAc with safer polar aprotics where possible: Cyrene, propylene carbonate, or green esters (e.g., ethyl acetate) for some couplings.
Use 2‑MeTHF or CPME instead of DCM/toluene for extractions and recrystallizations when solubility permits.
Aqueous/ethanol media for Fischer esterifications can reduce VOC impact; azeotropic removal of water with bio‑derived solvents (2‑MeTHF) can be effective.
Reagent alternatives
Carbodiimide couplings: substitute DCC with EDC·HCl in water‑tolerant systems to avoid dicyclohexylurea waste. For truly green protocols, explore enzymatic esterifications in solvent‑free or ionic liquid media.
Acid activation: use CDI to form reactive acyl imidazolides under milder, less noxious conditions vs thionyl chloride or oxalyl chloride.
Maximize atom economy by direct esterification where feasible; employ catalytic acids and remove water continuously.
Favor crystallization‑based purifications to minimize silica usage and solvent waste.
Pharmaceutical Uses
No pharmacopoeial or excipient status is specified for this item.
General, non‑clinical context (literature)
Para‑alkoxybenzoic acids and their derivatives may serve as synthetic intermediates in medicinal chemistry campaigns (e.g., for ester or amide linkage installation), but 4‑cyclobutoxybenzoic acid itself is not a recognized pharmacopeial excipient.
The carboxylic acid can be used to generate prodrugs (esters) or amide‑linked analogs during structure–activity exploration in discovery research.
Compliance note
Research use only (per Product Data). Not for use in human or veterinary applications, APIs, or finished dosage forms without appropriate qualification and regulatory evaluation.
If using in preformulation research
Document identity/purity via NMR/HRMS/LC, evaluate residual solvents and water, and assess salt screening if enabling solubility is needed for in vitro assays.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general (non-specification; typical for 4‑alkoxybenzoic acids)
Physical state: usually crystalline solids due to aromatic stacking and carboxylic acid dimerization (literature trend).
Acid–base: weak aromatic carboxylic acid; pKa for para‑alkoxybenzoic acids typically ~4.2–4.5 (literature).
Solubility (qualitative):
Limited in water at neutral pH; increased solubility in basic aqueous media via benzoate formation (literature behavior for benzoic acids).
Good solubility in polar aprotic organics (DMF, DMSO, NMP) and in alcohols upon warming; variable in less polar solvents (EtOAc, toluene) (literature).
Partitioning: aryl carboxylic acids with lipophilic para‑alkoxy substituents exhibit moderate hydrophobicity (logP expected >1; literature trend).
Association: forms hydrogen‑bonded dimers in nonpolar media, influencing melting/boiling behavior (literature observation for benzoic acids).
Notes
Exact BP/MP, density, refractive index, and UV cutoff are not specified for this item; refer to CoA/Spec Sheet.
Where precise numerical values are required for method development or safety assessments, consult the product’s CoA/SDS or measure under your laboratory conditions.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general)
Without a declared grade, treat this listing as a research chemical intended for R&D use. For chromatographic or analytical applications that are purity‑sensitive, request the current CoA specifying assay, residual solvents, and trace impurities.
If HPLC/LC–MS work is planned, look for grades with low UV background and low nonvolatile residue. Para‑alkoxybenzoic acids can show strong π→π* absorption; baseline cleanliness of solvent and solid is important.
Residual moisture: benzoic acids can retain minor moisture via hydrogen bonding in the lattice. If water content is critical, Karl Fischer determination and gentle drying under vacuum at ambient to 40 °C are advisable.
Metal content: Not specified for this item; refer to CoA/Spec Sheet. For catalysis-sensitive applications, consider metal screening or additional purification.
Peroxide content/UV cutoff: Not applicable/not specified for this item; refer to CoA/Spec Sheet.
Documentation
Request batch-specific CoA and, where applicable, a Specification Sheet for assay method, identity (NMR/IR/HRMS), and impurity profile.
Reaction and Applications
Focus: 4‑Cyclobutoxybenzoic acid is a para‑alkoxybenzoic acid. Such motifs are widely used as building blocks for materials (e.g., liquid‑crystal mesogens), esters, and amide derivatives.
Typical applications (literature)
Ester formation: synthesis of para‑alkoxybenzoate esters via Fischer esterification (alcohol, acid catalyst) or via carbodiimide/DMAP coupling. These esters are common components in thermotropic liquid crystals and polymers.
Amide coupling: conversion to amides with anilines or aliphatic amines using EDC/HOBt, HATU, or CDI. Para‑alkoxy substitution modulates electron density and can tune H‑bonding/mesogenic behavior.
Acid chloride/anhydride: activation with SOCl2 or (COCl)2 enables subsequent acylations under milder conditions; useful when substrates are acid‑sensitive to water.
Salt formation: benzoate salts (e.g., with organic amines) can enhance solubility for processing or be used as intermediates in phase‑transfer catalysis.
Supramolecular chemistry: carboxylic acids form robust H‑bonded dimers; para‑alkoxy groups adjust packing, making this scaffold relevant to crystal engineering studies.
Practical tips
Drying: if using coupling reagents, pre‑dry the acid (vacuum, ambient–40 °C) to minimize urea formation and improve conversions.
Acid activation: catalytic DMAP (0.05–0.2 eq) often accelerates esterification/acylation; monitor to avoid over‑acylation of polyfunctional partners.
Protecting group behavior: the aryl ether is generally inert to many conditions; avoid strong Lewis acids or harsh BBr3 which can cleave aryl ethers.
Purification: many derivatives crystallize well; otherwise, use normal‑phase silica with gradients from hexanes/EtOAc to DCM/MeOH.
Reaction Conditions
Literature‑style general conditions for common transformations of para‑alkoxybenzoic acids (guidance only; optimize per substrate):
Fischer esterification: alcohol (3–10 eq), catalytic H2SO4 or p‑TsOH (1–10 mol%), 60–120 °C; remove water (Dean–Stark in 2‑MeTHF/toluene) until completion (4–24 h). Typical isolated yields: 70–95% with primary alcohols.
Carbodiimide coupling (ester or amide): DCC or EDC (1.1–1.5 eq), DMAP (5–20 mol%) in DCM/DMF, 0 °C→rt to 40 °C, 2–18 h. Use EDC for aqueous‑tolerant systems; filter urea byproducts. Typical yields: 70–95%.
HATU/HOAt amidation: HATU (1.1–1.3 eq), DIPEA (2–3 eq) in DMF/DMF–DCM, 0–25 °C, 1–6 h; useful for hindered amines. Typical yields: 75–95%.
Acid chloride formation: SOCl2 (3–5 eq) with catalytic DMF, reflux 1–3 h; remove volatiles under reduced pressure and use in situ. Alternatively, (COCl)2, DCM, rt–reflux. Exercise caution with gas evolution (HCl, SO2/CO).
CDI activation: CDI (1.2–1.5 eq) in THF/DMF, rt–50 °C to form acyl imidazolide; then add nucleophile. Cleaner byproducts (imidazole). Yields often 70–90%.
Notes
Solubility often dictates solvent: DMF/DMSO dissolve the acid well; DCM may require co‑solvent or base.
Base choice: DIPEA/TEA common; avoid excessive base in esterifications to prevent saponification.
Monitoring: TLC/UPLC; aromatic acids show strong UV at 230–280 nm.
Workup: wash with bicarbonate then acidify if recovering unreacted acid; for couplings, sequential acid/base washes remove reagents/byproducts.
Safety and Handling
Item-specific (from Product Data)
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
Hazard (H) Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
Storage Conditions: Room temperature.
General safety guidance (literature/standard practice for aromatic carboxylic acids)
Likely hazards: may cause skin/eye irritation; dust may be irritating to respiratory tract. Avoid inhalation of powders, ingestion, and contact with skin/eyes.
PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use a dust mask/respirator if airborne particulates are generated and engineering controls are insufficient; handle powders in a fume hood.
Handling: avoid creating dust; ground equipment if transferring large quantities of powdered solids. Prevent contact with strong bases (will form benzoate salts) and strong oxidizers.
Incompatibilities: strong oxidizing agents; strong bases (may cause exothermic neutralization); acyl chlorides/anhydrides if accidental activation is undesired.
First aid overview: rinse eyes/skin with water for ≥15 min upon contact; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention. Always follow institutional protocols.
Fire response: aromatic carboxylic acids are combustible; use CO2, dry chemical, or foam. Thermal decomposition can release CO/CO2.
Authoritative information: Always consult the Aladdin SDS for this catalog item before use.
Solvent Selection
Applicability: This product is a solid aromatic carboxylic acid, not a solvent. Selection here refers to dissolving it for reactions, analysis, or processing.
General solubility/miscibility guidance (literature)
Polar aprotic solvents (good): DMF, DMSO, DMAc, NMP readily dissolve aryl acids via strong solvation of the carboxyl group.
Protic solvents: methanol, ethanol, isopropanol dissolve upon warming; solubility increases with slight base (e.g., 0.1–1 eq amine) forming the benzoate.
Moderately polar organics: ethyl acetate, acetone, acetonitrile show variable solubility; warming aids dissolution.
Nonpolar solvents: toluene, hexanes are generally poor unless the acid is converted to an ester or is used at elevated temperature.
Aqueous systems: low solubility at neutral pH; solubility increases markedly above pH ~5 as the carboxylate salt forms.
Practical selection tips
Reaction media: choose DMF or DCM for coupling/activation steps; use MeOH/EtOH for Fischer esterifications; use toluene/xylene only if forming less polar derivatives in situ.
Purification: recrystallization often successful from ethanol/water or ethyl acetate/hexanes, depending on impurity polarity. For base‑labile contexts, avoid strong bases in hot alcohols.
Small comparison (literature trend)
DMSO vs DMF: DMSO offers higher solubility; DMF is easier to remove and less odorous. ACN offers cleaner baselines for HPLC but lower solubility.
Storage and Reconstitution
Item-specific (from Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature/standard practice for aromatic carboxylic acids)
Keep tightly closed in original container; protect from prolonged humidity exposure to prevent clumping or hydrate formation.
Store in a dry place, preferably with a desiccant; ambient temperature is acceptable unless otherwise stated on the CoA.
Avoid contact with strong bases and oxidizers during storage.
Reconstitution and solution handling
Solubility aids: dissolve first in DMSO, DMF, or alcohols; warm gently and sonicate if needed. For aqueous work, adjust pH above the pKa with a suitable base (e.g., NaOH, triethanolamine) to form the benzoate salt, then back‑titrate if required.
Stock solutions: prepare in dry DMSO/DMF at known concentration; filter (0.2 µm) if particulate present. Store aliquots to minimize moisture uptake.
Stability: aryl carboxylic acids are generally stable; avoid prolonged heating >120 °C or strong acidic/basic conditions if the aryl ether must be preserved.
Documentation
For shelf life, allowable storage excursions, and solution stability, consult the batch CoA and SDS for this specific catalog item.
Ring systems: one benzene ring; one cyclobutane ring.
Substitution pattern: para (4-position) relationship between –CO2H and –O–cyclobutyl on the ring.
Stereochemistry: none (achiral) in the neutral acid; cyclobutyl ring is saturated and achiral absent substitution.
2D structure in words
A benzoic acid ring with the –CO2H at C1; at C4 (para) an oxygen connects the ring to a four‑membered cyclobutane ring (the ether linkage is aryl–O–cyclobutyl).
Synthetic Utility
Functional handles and reactivity (literature)
Carboxylic acid: amenable to esterification, amidation, acyl chloride formation, Curtius (via acyl azide), or activation to mixed anhydrides. Robust platform for linking to alcohols/amines.
Para‑alkoxy aryl ether: relatively inert under many conditions; directs electrophilic aromatic substitution (EAS) ortho/para and increases ring electron density, though the para position is occupied. Ortho functionalization (to the ether) may be accessed via directed metalation in advanced settings.
Cyclobutyl substituent: contributes conformational rigidity; can undergo ring‑opening under strongly acidic or radical conditions, offering diversification opportunities in advanced synthesis.
Use cases
Mesogenic building block: coupling with biphenols or bicyclic cores to build liquid‑crystal esters with tailored thermal transitions.
Polymer chemistry: derivatization to diesters/diamides for incorporation into aromatic polyesters or amide‑containing materials.
Linker strategy: acid chloride enables selective acylation of nucleophiles under Schotten–Baumann or nonaqueous conditions when base‑sensitive groups are present.
Practical notes
For peptide‑like couplings, HATU/EDC with catalytic DMAP in DMF or DCM often gives high conversions; monitor for O→N acyl migration in polyfunctional partners.
To avoid aryl‑O cleavage, refrain from strong Lewis acids (e.g., BBr3) unless ether deprotection is intended.
Target Specificity
Not applicable. This product is a small‑molecule research chemical (aromatic carboxylic acid), not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype data apply.
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