Cyclohexanecarboxylic acid, 4-formyl-2-methoxyphenyl ester , CAS No.588674-77-5

CAS: 588674-77-5 Cat. No.: C1051275 PubChem CID: 4504529

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

COC1=C(C=CC(=C1)C=O)OC(=O)C2CCCCC2

IUPAC Name

(4-formyl-2-methoxyphenyl) cyclohexanecarboxylate

InChIKey

YCEBTYIAJWTZQH-UHFFFAOYSA-N

INCHI

1S/C15H18O4/c1-18-14-9-11(10-16)7-8-13(14)19-15(17)12-5-3-2-4-6-12/h7-10,12H,2-6H2,1H3

Isomeri SMILES

COC1=C(C=CC(=C1)C=O)OC(=O)C2CCCCC2

CAS alternativo

588674-77-5

PubChem CID

4504529

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol esters

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol esters
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol esters
• Alternative Parents: Phenoxy compounds Methoxybenzenes Benzoyl derivatives Benzaldehydes Anisoles Alkyl aryl ethers Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenol ester - Phenoxy compound - Anisole - Benzaldehyde - Methoxybenzene - Phenol ether - Benzoyl - Alkyl aryl ether - Aryl-aldehyde - Monocyclic benzene moiety - Carboxylic acid ester - Ether - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carbonyl group - Organooxygen compound - Aldehyde - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 262.300 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 262.121 Da
• Monoisotopic Mass: 262.121 Da
• Topological Polar Surface Area: 52.600 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 309.000
• 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 (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For chemical use, see Reaction & Applications, Synthetic Utility, and Reaction Conditions for general guidance.

Biological Roles

This product is a synthetic small-molecule building block. No biological role or pathway participation is provided in the Product Data.

• Item-specific: None specified; For research use only.

• General notes (not product-specific; for context only):

  • Aryl esters with aldehyde substituents are common intermediates in discovery chemistry but are not typical biometabolites.
  • In biological systems, esters can undergo hydrolysis by esterases; however, this compound is not intended for biological administration or diagnostic use.

All work should be confined to research laboratory settings; no clinical or in vivo claims are implied.

Buffer Applications

Not typically applicable. This compound is a hydrophobic aryl ester and is not used as a pH buffer or electrophoresis reagent. For practical guidance, see Reaction & Applications, Synthetic Utility, and Solvent Selection sections for relevant use-cases.

Green Alternatives

Greener practice focuses on solvent and reagent selection, since the substrate is a neutral aryl ester with an aldehyde.

• Preferable solvents (literature, green chemistry guides):

  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
  • For polar aprotic needs, consider dimethyl carbonate (DMC), propylene carbonate (PC), or Cyrene in place of DMF/DMAc when compatible.

• Energy and protection economy:

  • Use chemoselective reagents to avoid protection of the aldehyde (e.g., mild Wittig variants, organocatalytic reductive amination).
  • Employ flow hydrogenation or transfer hydrogenation for reductions.

• Catalyst choices:

  • Organocatalysts (DMAP, N-heterocyclic catalysts) for acyl transfer can reduce metal waste.
  • If cross-coupling of the aryl ester is pursued, nickel catalysts at low loadings and greener solvents (2-MeTHF, toluene) are reported.

• Comparison snapshot (general):

  • DCM vs 2-MeTHF: similar solvating power for many aldehyde reactions; 2-MeTHF is bio-based with higher boiling point aiding separation.
  • THF vs CPME: CPME offers wider liquid range and lower peroxide formation tendency.

Note: Assess solvent substitution against reaction performance and downstream EHS constraints. Item-specific green metrics (E-factor, PMI, solvent UV-cutoff) are not specified for this item; refer to CoA/Spec Sheet or conduct internal assessment.

Pharmaceutical Uses

No pharmacopeial or excipient information is provided for this item.

• Item-specific: Grade/purity and any compendial status are not specified; refer to CoA/Spec Sheet.

• Context (general, non-clinical):

  • Aryl aldehyde esters are sometimes leveraged as synthetic intermediates during API route exploration or impurity standard preparation, but they are not themselves drug products or approved excipients.
  • Process chemists may use such intermediates to adjust lipophilicity or as masked carboxyl functions during multistep synthesis.

This product is supplied strictly for research use only.

Physical Properties

Item-specific specifications are not provided in the Product Data.

• 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 expectations for this scaffold (for planning only; not product specifications):

  • Physical state: small aryl ester with a cyclohexyl group; typically a crystalline solid or viscous oil depending on purity and crystallinity (literature, analogous compounds).
  • Solubility: expected good solubility in common organic solvents (DCM, THF, EtOAc, toluene, MeCN) and poor solubility in water (literature, aryl esters/aliphatic esters).
  • Polarity/logP: aryl ester with cyclohexyl substituent is typically lipophilic with moderate-to-high logP (literature, analogous structures).
  • UV characteristics: conjugated aryl aldehyde typically shows strong absorbance in near-UV (around 250–330 nm) due to aryl–CHO chromophore (literature). Exact cutoff/ε: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting/boiling points, density, refractive index, pKa/logD: Not specified for this item; refer to CoA/Spec Sheet.

Always confirm working values using the item’s CoA/Spec Sheet or measure in-house for method development.

Quality and Grades

• Item-specific (from Product Data):

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance):

  • Research grade: suitable for most synthetic and discovery workflows; impurity profiles vary by lot.
  • ≥95–99% purity (if specified on CoA): supports use as a building block without extensive pre-purification; verify by NMR/LC.
  • HPLC grade/low UV absorbance (typically for solvents): not applicable to this solid/solute unless UV specs are listed.

• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. For aldehyde-containing compounds, vendors sometimes avoid stabilizers to prevent side reactions. If inhibitor removal is necessary, perform a quick silica plug or recrystallization and confirm identity by NMR.

• What to verify upon receipt (best practice):

  • Appearance, assay/purity, and identity by 1H NMR (diagnostic aldehyde singlet ~9.5–10.0 ppm, literature) and MS.
  • Residual solvents, water content, and specific limits: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

This building block unites two orthogonal handles: an electrophilic aryl aldehyde and an aryl ester derived from cyclohexanecarboxylic acid. This enables stepwise diversification.

• Transformations at the aldehyde (literature):

  • Wittig/Horner–Wadsworth–Emmons olefinations to styrenyl or substituted alkenes.
  • Reductions to benzyl alcohols (NaBH4/CeCl3, DIBAL, catalytic hydrogenation) or tobenzhydrol derivatives after further elaboration.
  • Reductive aminations with amines to furnish benzylamines (NaBH3CN, BH3·THF), taking care to suppress ester aminolysis or transesterification.
  • Acetal protection (e.g., ethylene glycol, p-TsOH) to mask the aldehyde during subsequent acyl-transfer steps.

• Transformations at the ester (literature):

  • Transesterification (ROH, base or acid catalysis); DMAP catalysis for milder conditions to preserve the aldehyde.
  • Aminolysis to amides under nucleophilic catalysis (DMAP, HOBt) or with activating agents (e.g., BTFFH, CDI) if direct aminolysis is sluggish.
  • Hydrolysis to regenerate cyclohexanecarboxylic acid (controlled acidic/basic conditions; protect aldehyde if necessary).
  • Nickel-catalyzed cross-coupling of aryl esters (decarbonylative or acylative pathways) to forge C–C bonds, enabling late-stage diversification of the anisyl fragment.

• Divergent synthesis strategies:

  • Protect–manipulate–deprotect sequences centered on the aldehyde (acetal) allow independent tuning of the acyl component.
  • Orthogonal one-pot sequences are possible with chemoselective reagents (e.g., hydrosilylation–acylation cascades under Lewis acid catalysis; literature).

• Use cases:

  • Intermediates for fragrance, agrochemical, and materials motifs where cyclohexyl and anisyl elements are valued (research context only).

Reaction Conditions

General literature guidance for related functional groups; confirm on small scale for this specific substrate. Values are indicative, not specifications.

• Wittig/HWE olefination (on the aryl aldehyde):

  • Solvent: THF, toluene, or CH2Cl2; 0 to reflux depending on ylide stability.
  • Base: n-BuLi/NaHMDS for stabilized ylides; DBU/NaH for HWE.
  • Typical time: 1–16 h; E/Z selectivity governed by ylide type and conditions.

• Reductive amination:

  • Solvent: MeOH, EtOH, or MeCN with molecular sieves.
  • Reductant: NaBH3CN or BH3·THF; 0–25 °C, 1–6 h.
  • Note: Competing ester aminolysis can occur; use mild conditions and short exposure.

• Ester transesterification/aminolysis:

  • Catalyst: DMAP (5–20 mol%) or TBD; alcohol or amine nucleophile (1.5–5.0 equiv).
  • Solvent: THF/MeCN/EtOAc; 25–60 °C, 2–18 h.
  • Protect aldehyde as acetal for basic or high-temperature protocols.

• Hydrolysis to acid:

  • Acidic: aq. HCl or p-TsOH in MeOH/THF, 25–50 °C.
  • Basic: Na2CO3/NaOH in MeOH/H2O; monitor to avoid Cannizzaro-type issues in strong base.

• Ni-catalyzed C–O activation of aryl esters (literature):

  • Catalyst: Ni(cod)2 (2–10 mol%) with appropriate ligand (e.g., dppf) and base (e.g., Zn, Mn).
  • Coupling partner: organoboron/organozinc; solvent: toluene/dioxane; 80–120 °C, 6–24 h.

Always monitor by TLC/LC–MS; quench conditions should preserve the aldehyde if unprotected.

Safety and Handling

Safety information in the Product Data is incomplete; consult the SDS for authoritative guidance. Handle under good laboratory practices.

• Item-specific (from Product Data):

  • Storage conditions: Room temperature.
  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.

• General hazards for related structures (informational; not product-specific):

  • Aryl aldehydes can be irritants and sensitizers; avoid inhalation, ingestion, and skin/eye contact.
  • Esters and aldehydes are combustible organic compounds; keep away from ignition sources.

• PPE and engineering controls (best practice):

  • Use nitrile gloves, lab coat, and chemical splash goggles.
  • Work in a fume hood to avoid exposure to vapors and to manage potential odor from aldehydes.

• Handling tips:

  • Minimize exposure to strong bases/acids if the aldehyde must be preserved (base can induce aldol-type reactions; acid can catalyze acetalization).
  • Avoid prolonged exposure to air/light if aldehyde oxidation is a concern; keep containers tightly closed.

• Incompatibilities (general): strong oxidizers (risk of oxidation of aldehyde), strong bases (transesterification; aldol with adventitious carbonyls), strong acids (acetal formation; ester hydrolysis).

• First aid (overview; see SDS):

  • Eye/skin contact: Rinse with water for at least 15 minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air.
  • Ingestion: Rinse mouth; seek medical attention.

Always defer to the product SDS for exact hazard and response language.

Solvent Selection

This compound is a neutral, lipophilic aryl ester with an aryl aldehyde and methoxy substituent. It typically dissolves in common organic solvents and is poorly soluble in water (literature, analogous compounds).

• Polarity/miscibility (general, literature):

  • Good: DCM, chloroform, EtOAc, THF, toluene, MeCN, acetone, DMF/DMSO.
  • Poor: water, very polar protic solvents without co-solvent.

• Selecting solvents by task:

  • Chromatography: Begin with hexane/EtOAc or toluene/EtOAc gradients; aldehyde chromophore aids UV detection at 254–300 nm.
  • Carbonyl transformations (e.g., Wittig/olefination on the aldehyde): THF, toluene, or CH2Cl2 depending on base/nucleophile.
  • Transesterification/aminolysis (acyl transfer): use polar aprotic media (THF, MeCN, DMF) with catalysts like DMAP or base; monitor to avoid aldehyde side-reactions.
  • Metal-catalyzed ester activation/cross-coupling: toluene, dioxane, or DMAc are common choices in Ni-catalyzed ester couplings (literature).

• Practical tips:

  • If the aldehyde is sensitive, minimize protic solvents and prolonged basic conditions.
  • For aqueous workups, saturated NaHCO3 and brine washes are gentle; avoid strong base if the aldehyde must remain intact.

• Comparison (general):

  • Versus more polar aryl acids/amides, this ester offers better solubility in nonpolar media; versus acid chlorides, it is milder and more stable to storage.

Storage and Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• General handling recommendations for aryl aldehyde esters (informational; not product-specific):

  • Store in a tightly sealed amber vial under dry air or inert gas to limit oxidation/polymerization of the aldehyde.
  • If long-term storage is planned, refrigeration (2–8 °C) can further slow degradation; allow to warm sealed and dry before opening to prevent moisture condensation. Follow Product Data primary instruction (room temperature) unless internal stability data suggest otherwise.
  • Avoid prolonged exposure to light and moisture; consider adding a desiccant pack in secondary containment.

• Reconstitution/dispensing:

  • Prepare stock solutions in anhydrous solvents such as DCM, THF, toluene, EtOAc, MeCN, or DMSO, depending on application (literature, analogous compounds).
  • Filter solutions through a PTFE syringe filter before sensitive reactions.
  • For weighed solids, quickly cap after use; purge headspace with inert gas if available.

Refer to the CoA/Spec Sheet and SDS for any lot-specific stability notes, impurity profiles, or additional storage cautions.

Structure and Identity

Brief overview: Cyclohexanecarboxylic acid, 4-formyl-2-methoxyphenyl ester is an aryl ester featuring an aldehyde (–CHO) and methoxy (–OCH3) on the phenyl ring, esterified with cyclohexanecarboxylic acid. This places a nucleophilically sensitive aldehyde orthogonal to an acyl–oxygen bond poised for acyl transfer or cross-coupling chemistry.

• Item-specific (from Product Data):

  • CAS: 588674-77-5
  • CID: 4504529
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product data string provided is incomplete.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general description):

  • Core: substituted anisyl fragment (phenyl bearing 2-methoxy and 4-formyl substituents) connected via an O–C(O) linkage to a cyclohexyl carbonyl (cyclohexanecarboxylate).
  • Functional groups: aryl aldehyde (electrophilic), aryl methyl ether (electron-donating), aryl ester (acyl–oxygen, susceptible to transesterification/aminolysis under activation).
  • 2D topology (verbal): a benzene ring with methoxy at ortho (2-position) and formyl at para (4-position) relative to the phenoxy oxygen; that oxygen bridges to a carbonyl attached to a cyclohexyl ring.
  • Stereochemistry: none expected (no stereocenters in the described scaffold).

Synthetic Utility

Key reactivity stems from two orthogonal functional groups:

• Aldehyde handle:

  • Electrophilic center compatible with C=C construction (Wittig/HWE), nucleophilic additions (organometallics under carefully controlled conditions to avoid ester reaction), and reductive amination.
  • Easily protected as acetals for orthogonal manipulations of the ester moiety.

• Aryl ester handle:

  • Amenable to transesterification and aminolysis under nucleophilic catalysis (DMAP) or activation (e.g., CDI-mediated conversion to mixed anhydrides followed by amines).
  • Entry to carboxylic acid by hydrolysis; subsequent coupling to diverse amines/alcohols.
  • Potential substrate for Ni-catalyzed C–O activation enabling cross-coupling (decarbonylative or acylative) to install C(sp2)–C bonds on the anisyl ring (literature).

• Orthogonality and selectivity:

  • Protect aldehyde during strong basic or nucleophilic ester chemistry to prevent undesired aldol, Cannizzaro (in strong base), or imine formation.
  • Conversely, retain ester under conditions tailored to aldehyde transformations (neutral to mildly acidic, non-nucleophilic solvents).

• Retrosynthetic value:

  • Serves as a convergent junction between a cyclohexyl carboxyl fragment and a 2-methoxy-4-formyl phenyl fragment; each can be diversified independently for library synthesis and SAR exploration.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone information is relevant or provided in the Product Data.