3-Cyclohexaneamidobenzoic acid - ≥95% , CAS No.180991-55-3

CAS: 180991-55-3 Cat. No.: C1345864 Formula: C₁₄H₁₇NO₃ Peso molecolare: 247.29 Numero EC: 874-056-7

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1CCC(CC1)C(=O)NC2=CC=CC(=C2)C(=O)O

IUPAC Name

3-(cyclohexanecarbonylamino)benzoic acid

InChIKey

UKYBHQDUVKBFFX-UHFFFAOYSA-N

INCHI

1S/C14H17NO3/c16-13(10-5-2-1-3-6-10)15-12-8-4-7-11(9-12)14(17)18/h4,7-10H,1-3,5-6H2,(H,15,16)(H,17,18)

Peso molecolare

247.29

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Acylaminobenzoic acid and derivatives
• Alternative Parents: Benzoic acids Anilides N-arylamides Benzoyl derivatives Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Acylaminobenzoic acid or derivatives - Benzoic acid - Anilide - Benzoyl - N-arylamide - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
• 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: 247.290 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 247.121 Da
• Monoisotopic Mass: 247.121 Da
• Topological Polar Surface Area: 66.400 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 310.000
• 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

No vendor-validated bioassay or analytical protocols are provided for this specific item.

General laboratory usage notes (literature/practice-based):

• Stock solutions: Prepare in DMSO (e.g., 10–100 mM) or DMF; filter (0.22 μm PTFE) if needed. Record exact concentration gravimetrically.
• Coupling screens: Use small-scale (0.05–0.2 mmol) arrays with HATU/EDC/T3P; monitor by LC-MS. Quench with aqueous acid/base depending on chemistry.
• Crystallization trials: Explore EtOH/EtOAc, iPrOH/EtOAc, or MeOH/water antisolvent systems for solid‑form screening.

For any regulated or validated workflows, create a method SOP and capture lot-specific details from the CoA.

Biological Roles

This product is supplied strictly for research use. No biological roles are assigned for this catalog item.

General context (literature/general):

• Chemical class: Aromatic carboxylic acid bearing a secondary amide with a cyclohexyl substituent. Such motifs are common in small‑molecule probe development due to their H‑bonding capabilities (amide) and tunable ionization (carboxylate vs. acid).
• Biochemical behavior: The amide is typically metabolically stable relative to esters; the carboxylic acid can exist as an anion at physiological pH, influencing permeability and protein binding. These are broad chemical tendencies and not specific to this item.

No claims are made regarding biological activity, targets, ADME, or clinical utility for this specific substance.

Buffer Applications

This compound is not typically used as a laboratory buffer.

• Rationale: Although it contains a carboxylic acid (general pKa for benzoic acids ~4–5, literature), the presence of a neutral amide and hydrophobic framework limits its practicality as a defined buffer component. Classic buffer systems (acetate, citrate, phosphate, Tris, HEPES) provide superior buffering capacity and solubility.
• If pH modulation is required during reactions, use standard buffer salts; this compound may be converted to its sodium/potassium carboxylate for solubility studies but not as a primary buffer.

Green Alternatives

While the substance itself is a solid building block, greener choices often center on solvent and coupling reagent selection.

Greener choices (literature/general):

• Solvents: Prefer 2‑MeTHF, Cyrene, CPME, EtOAc, or ethanol over DMF/DMAc/NMP where feasible (e.g., in esterifications or when using reactive acid chlorides). For amide couplings, EtOAc or 2‑MeTHF with T3P or CDI can be effective.
• Coupling reagents: Consider T3P (50% in EtOAc), CDI, or DMTMM as lower‑hazard alternatives to HATU/HBTU (which generate guanidinium byproducts and can pose safety risks).
• Energy efficiency: Use room‑temperature couplings and solvent recycling when possible; crystallization‑induced purification over chromatographic separations lowers solvent usage.

Small comparison (general):

• DMF/DMAc/NMP: excellent solubility; regulatory scrutiny and higher toxicity.
• 2‑MeTHF/EtOAc: renewable/low toxicity; may need longer reaction times or higher equivalents.
• T3P/CDI: simpler workups (water-soluble byproducts); may be less effective with severely hindered amines.

Recommendation:

• Begin with 2‑MeTHF or EtOAc and T3P (or CDI) for amidation/esterification screens. If solubility limits progress, escalate to DMF or DMSO, documenting solvent selection rationale for green metrics.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. It is offered for research use only.

General formulation/manufacturing context (literature/general):

• Role in discovery chemistry: Carboxylic acid–amide scaffolds are frequently explored in medicinal chemistry campaigns to modulate potency, polarity, and metabolic stability. This material can function as a building block/intermediate, not as a finished drug or excipient.
• Salt/ester switching: Transient esterification of the acid or formation of sodium/potassium salts may be used to adjust solubility for pre-formulation studies of derived compounds.

No therapeutic or clinical claims are made for this product.

Physical Properties

Item-specific physico-chemical specifications (mp, bp, density, UV cutoff, water/peroxide/metal content) were not provided for SKU C1345864.

• Item-specific values:
  • Melting point, boiling point, density, refractive index, UV cutoff, elemental limits: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility and behavior (literature/general expectations for aromatic carboxamide–carboxylic acids):
  • Solubility (qualitative): Typically sparingly soluble in water at neutral pH; increased solubility in polar aprotic organic solvents (e.g., DMSO, DMF, NMP) and in alcohols upon warming. Forms water‑soluble salts under basic conditions (e.g., Na+/K+ carboxylate).
  • Acid–base: Contains one carboxylic acid (typical pKa ~4–5, literature general for benzoic acids) and a neutral amide (non-basic under normal conditions).
  • LogP (trend): Aromatic ring + cyclohexyl group increase hydrophobicity; ionization of the acid markedly lowers logD at basic pH (literature/general trend).
  • Solid state: Amide and acid functionalities favor hydrogen-bonding; crystalline solids are typical for similar structures (literature/general).

Note: For exact numerical values relevant to method validation or regulatory dossiers, consult the product CoA/SDS or measure under your specific conditions.

Quality and Grades

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

Guidance and context (general):

• Analytical/AR grade typically ensures low inorganic residues and suitability for general analytical work.
• Synthesis/reagent grade is suitable for routine organic synthesis; purity is commonly >95% by HPLC/GC/NMR (varies by supplier/spec).
• High-purity/HPLC grade places additional emphasis on low UV background and low volatile/UV-active impurities, useful for chromatographic method development.
• Pharmacopoeial grades (USP/EP/JPC) define specific identification, assay, and impurity limits for compendial materials; this compound is a research chemical and may not have monographs.

Stabilizers/Additives:

• No stabilizer information provided for this item. If trace inhibitors or residual coupling reagents are a concern for your application (e.g., medicinal chemistry SAR or materials synthesis), request the lot-specific CoA including analytical method (HPLC area %, NMR, water by KF, residual solvents per ICH Q3C) and impurity profile.

Recommendation:

• For moisture/acid-sensitive downstream chemistry, consider verifying water content (KF) and residual solvents on the specific lot. If using for quantitative studies, confirm assay/area %, and check for possible isomeric or oligomeric impurities associated with amide formation.

Reaction and Applications

3-Cyclohexaneamidobenzoic acid serves as a versatile bifunctional building block combining an aromatic carboxylic acid with a cyclohexyl-bearing amide. This makes it useful in fragment linking, linker exploration, and late-stage diversification.

Representative application families (literature/general):

• Amide-linked scaffold in SAR: The cyclohexyl amide imparts lipophilicity and conformational bias; the benzoic acid can be coupled to amines (EDC/HOBt, HATU, T3P) to furnish diamides or peptidomimetic motifs.
• Esterification and pro-moiety exploration: Conversion of the benzoic acid to methyl/ethyl esters (Fischer esterification or via acid chloride) enables protecting-group strategies and solubility tuning.
• Acid chloride/anhydride formation: Activation with SOCl2 or oxalyl chloride (with catalytic DMF) affords the acid chloride for rapid acyl transfer to nucleophiles.
• Decarboxylative methods (advanced): Emerging decarboxylative cross-couplings (e.g., redox-active esters from the acid) allow C–C bond formation to diversify the aromatic ring side chain without halogen preinstallation.
• Directed aromatic substitution (conceptual): Both –CO2H and –CONH– groups are deactivating and meta-directing; electrophilic substitution, if needed, generally requires forcing conditions.
• Salt screening/materials: Carboxylate salts (Na+/K+) can be prepared for solubility studies or crystallographic investigations.

Practical tips:

• For coupling on the acid, ensure thorough drying (azeotrope or vac-dry) to maximize activation efficiency. Add a base (DIPEA/TEA) and maintain 0–25 °C as needed to control O→N acyl transfer and minimize epimerization in chiral partners.

Reaction Conditions

General conditions (literature guidance) relevant to this scaffold:

• Amide formation at the benzoic acid:
  • HATU (1.1–1.5 equiv), DIPEA (2–4 equiv), DMF, 0–25 °C, 1–12 h. Monitor by LC-MS/HPLC. Workup by aqueous quench and extraction or reverse‑phase purification.
  • EDC•HCl (1.2–1.5 equiv) + HOBt/HOAt (0.1–1.0 equiv) or Oxyma, DIPEA, DMF/CH2Cl2, 0–25 °C. Reduced urea byproducts versus carbodiimide alone.
  • T3P (50% in EtOAc, 1.2–2.0 equiv), iPr2NEt, EtOAc/2‑MeTHF, rt–50 °C, 1–6 h. Greener profile; easy aqueous workup.
• Esterification of the benzoic acid:
  • Fischer: ROH (excess), catalytic H2SO4 or p‑TsOH, reflux, Dean–Stark if needed; hours to overnight.
  • Acid chloride route: SOCl2 (2–4 equiv, cat. DMF), CH2Cl2 or toluene, reflux 1–3 h → add ROH/amine with base at 0–25 °C.
• Redox-active ester formation/photoredox coupling:
  • DIC (1.1 equiv), NHP (1.1 equiv), DMAP (cat.), CH2Cl2, rt, 2–4 h → Ni/photoredox conditions with aryl/alkyl partners under blue LEDs (see current literature for catalysts and ligands).
• Purification tips:
  • Strong silica interactions due to acid/amide; include 0.1–1% AcOH or Et3N in eluents, or switch to reverse‑phase C18 with volatile modifiers.

All conditions are literature/general guidelines; optimize for your substrate set and scale.

Safety and Handling

Safety details specific to this catalog item (GHS, pictograms) are not provided here. Always review the product SDS before use.

• Item-specific hazard data:
  • Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.
• General safety guidance for aromatic carboxylic acids and amides (literature/general):
  • Irritation: Carboxylic acids can cause skin/eye irritation; avoid inhalation of dusts.
  • PPE: Laboratory coat, nitrile gloves, safety goggles; handle powders in a fume hood or with local exhaust.
  • First aid (overview): Inhalation — move to fresh air; Skin — wash with soap/water; Eyes — rinse cautiously with water for several minutes; Ingestion — rinse mouth. Seek medical attention if symptoms persist. Follow SDS instructions.
  • Incompatibilities: Strong bases (forms salts), strong oxidizers, strong reducing agents, and acyl activation reagents may react vigorously. Avoid contact with acid chlorides or dehydrating agents unless intended.
  • Thermal/combustion: Organic solids may burn; combustion may produce CO/CO2 and nitrogen oxides.
• Handling tips:
  • Minimize moisture uptake when planning coupling reactions; store desiccated if high-precision synthesis is needed.
  • Use dust control practices; weigh in a draft-free environment.

Definitive hazard classification and exposure controls must be taken from the SDS for this specific lot.

Solvent Selection

As a moderately polar, multifunctional organic solid (aromatic carboxylic acid + amide), solvent choice hinges on target operation (dissolution, coupling, crystallization, or purification).

• Dissolution (general):
  • Recommended: DMSO, DMF, DMAc, NMP — excellent solvents at ambient temperature.
  • Conditional: Methanol, ethanol, isopropanol — may require warming/sonication; avoid high base content unless salt formation is intended.
  • Aqueous media: Poor at neutral pH; solubility improves substantially in basic aqueous solutions (carboxylate salt formation). Limited in acidic water.
• Workup and isolation:
  • For coupling reactions in DMF/DMAc, aqueous basic washes can extract residual acids; acidify to re-precipitate the product (if target is neutral form).
  • Crystallization often feasible from alcohols or mixed alcohol/ester systems (e.g., EtOH/EtOAc) due to hydrogen-bonding lattice formation.
• Purification:
  • Reverse-phase HPLC: Ionizable acid aids retention control with pH modifiers (e.g., 0.1% formic acid or ammonium bicarbonate for LC-MS).
  • Normal-phase chromatography may be challenging due to strong silica interactions; add 0.1–1% acetic acid/triethylamine or use EtOAc/MeOH modifiers.
• Comparison (general):
  • DMSO/DMF provide maximum solubility; EtOAc/MeOH blends aid crystallization and cleanup. Water (basic) is best for salt formation and extractions.

Storage and Reconstitution

• Item-specific storage and shipping:
  • Storage conditions: Room temperature (as provided).
  • Shipped in: Normal conditions.
• Stability considerations (general):
  • Aromatic carboxylic acid–amide scaffolds are typically stable at ambient temperature when kept dry and protected from prolonged light/heat. Avoid strong acids/bases unless intended for reaction.
• Reconstitution/solubilization (general):
  • Organic: Dissolve in DMSO, DMF, or EtOH. Typical lab stocks: 10–100 mM in dry DMSO; store aliquots at 2–8 °C or −20 °C to minimize freeze–thaw, if needed for analytical work.
  • Aqueous: Limited solubility at neutral pH; dissolve by adjusting to basic pH (e.g., 0.01–0.1 M NaOH) to form the carboxylate, then back‑titrate if necessary.
• Packaging and handling:
  • Keep container tightly closed. Use desiccant if operating in humid environments to maintain consistent mass during weighing.
• Research Use Note:
  • For research use only. Not for human or veterinary use.

For lot-specific stability, purity, and assay, refer to the CoA/Spec Sheet and SDS.

Structure and Identity

A bifunctional aromatic carboxylic acid bearing a cyclohexane‑derived amide at the meta (3‑) position, useful as a heterobifunctional building block in synthesis.

• Item-specific registry:
  • SKU: C1345864
  • Product name: 3-Cyclohexaneamidobenzoic acid
  • CAS: 180991-55-3
  • PubChem CID: 1133567
  • InChIKey: 362550 (as provided; format appears abbreviated — verify on CoA/SDS)
• Structure descriptors (item-specific):
  • 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 interpretation from the name; literature/general):
  • Core: Benzene ring substituted at the 1-position by a carboxylic acid (–CO2H) and at the 3-position by an amide function.
  • Amide substituent: The amide is bound to a cyclohexyl/cyclohexane-derived moiety (–CONH–C6H11 or –CO–NH–C6H11, depending on naming convention). Overall, it is an aromatic carboxylic acid bearing a cyclohexylcarbamoyl-type substituent at the meta position.
  • Functional groups: Aromatic ring, carboxylic acid, and secondary amide. No stereocenters expected (cyclohexane is achiral in its parent form).
  • 2D description in words: A benzoic acid ring with meta amide linkage to a saturated six‑membered cycloalkyl ring; both acid and amide are electron-withdrawing relative to the ring.

Synthetic Utility

Key synthetic features (literature/general):

• Bifunctionality: The benzoic acid provides a handle for further acylation (to amides/esters/acid chlorides), while the cyclohexane‑derived amide offers H‑bonding and conformational constraint.
• Retrosynthesis: Accessible from 3‑aminobenzoic acid via acylation with a cyclohexane‑derived acyl species (e.g., cyclohexanecarbonyl chloride) or via coupling of 3‑aminobenzoic acid with cyclohexyl isocyanate/activated derivatives, depending on the exact amide orientation.
• Protecting-group logic: Convert the acid to a methyl/benzyl ester to enable selective manipulations at the amide; hydrogenolysis or saponification restores the acid.
• Activation tactics: SOCl2/oxalyl chloride (cat. DMF) to acid chloride; EDC•HCl/HOBt or HATU/DIPEA for coupling to amines; CDI or T3P for greener amidations.
• Diversification: Formation of redox-active esters (e.g., N‑hydroxyphthalimide esters) from the acid permits decarboxylative couplings (C–C, C–N) under photoredox or Ni catalysis.
• Aromatic transformations: Both –CO2H and –CONH– are deactivating/meta‑directing; electrophilic substitutions are disfavored and may need strong conditions. Directed metalation is challenging without additional directing groups.

Target Specificity

Not applicable. This product is a small-molecule research chemical, not a biological reagent (e.g., antibody, enzyme, or probe with defined biomolecular target specificity). No target, epitope, clone, isotype, or species reactivity information applies.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

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

The CAS Number is 180991-55-3, the molecular formula is C14H17NO3, and the molecular weight is 247.29 g/mol. InChIKey UKYBHQDUVKBFFX-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.