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
204.260 g/mol
XLogP3
4.600
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
204.115 Da
Monoisotopic Mass
204.115 Da
Topological Polar Surface Area
37.300 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
219.000
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
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Bewertungen
Kundenbewertungen
Application Protocols
No assay or kit protocols are provided for this small-molecule reagent.
Item-specific (Product Data): None specified.
General laboratory uses (literature/general):
Synthetic transformations as detailed in Reaction Conditions and Synthetic Utility.
Preparative guidance: dissolve in an appropriate organic solvent (e.g., DCM, EtOAc, MeCN, THF, alcohols) or convert to a soluble salt for aqueous-phase manipulations.
Analytical setup: characterize by 1H/13C NMR, IR (C=O ~1700 cm−1), LC–MS, and melting point where available.
For any specialized application (e.g., coupling to biomolecules), follow relevant standard operating procedures and validate conditions on small scale before scale-up.
Biological Roles
Item-specific (Product Data): None specified; this product is for research use only.
Literature/general context (no medical/clinical claims):
2-Cyclohexylbenzoic acid is a synthetic aromatic carboxylic acid with a bulky lipophilic ortho substituent. It is not a known natural metabolite.
Aromatic carboxylic acids in general may interact with lipid membranes and bind to serum proteins via hydrophobic and carboxylate interactions; such properties are often exploited in medicinal chemistry to modulate ADME, but they do not imply biological activity for this specific compound.
Carboxylates can act as weak inhibitors or ligands for certain enzymes in vitro through ionic and hydrophobic contacts; however, target-specific interactions for 2-cyclohexylbenzoic acid are not established in the literature.
In bioconjugation or materials biology, benzoic acid derivatives can serve as anchoring motifs after conversion to amides/esters with biomolecular handles (e.g., amine-containing peptides) using standard coupling chemistry.
Takeaway: treat this compound as a hydrophobic, weak acid handle rather than a defined bioactive molecule. For any biological testing, ensure appropriate controls and concentration–response characterization, and adhere to Research Use Only restrictions.
Buffer Applications
This compound is not a standard buffering agent.
Applicability:
As a weak aromatic acid, it can, in principle, participate in buffer systems around its pKa (typical benzoic-acid range ~4.2–4.6), but its low aqueous solubility and hydrophobicity make it impractical for conventional aqueous buffers.
If a benzoate buffer system is desired, sodium benzoate/benzoic acid is the typical pair used; 2-cyclohexyl substitution would further reduce water solubility and is not commonly employed.
Practical guidance:
For pH 4–5 buffers in biochemical work, consider acetate, citrate, or succinate systems instead.
For non-aqueous or mixed-solvent electrochemical/analytical methods, carboxylic acids can serve as proton donors, but validation is required; solubility ceilings will be limiting.
Therefore, buffer applications are generally not recommended for this item; see Reaction & Applications and Synthetic Utility for more relevant uses.
Green Alternatives
Greener choices relate chiefly to solvent and reagent selection during transformations of 2-cyclohexylbenzoic acid; the acid itself is a stable organic solid.
Prefer greener solvents when feasible:
Replace DCM/chloroform with ethyl acetate, 2-MeTHF, CPME, or toluene depending on solubility and process.
Use MeCN or EtOAc instead of DMF/NMP where coupling efficiency permits.
For workups, minimize halogenated waste; partition with EtOAc/MTBE before resorting to DCM.
Reagent choices (literature/general):
Steglich esterification (DCC/DMAP) can be substituted with EDC·HCl (water-soluble urea byproduct) in EtOAc or MeCN.
Use oxalyl chloride alternatives: Ghosez reagent or T3P/POCl3-free activation (e.g., T3P in EtOAc) to avoid SO2Cl2 residues.
Enzymatic esterifications in green solvents (2-MeTHF, ionic liquids, or solvent-free) may be viable for certain substrates.
Comparative snapshot (general):
DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; may require larger volumes due to solubility limits.
DMF vs MeCN: MeCN has lower boiling point and better environmental profile but can offer lower solubility for highly polar amide coupling partners.
THF vs 2-MeTHF: 2-MeTHF is bio-based, forms fewer peroxides and enables water-tolerant biphasic operations; note its odor and sometimes higher UV background.
Process intensification:
Consider solvent recycling, in-line scavenging of coupling byproducts, and telescoped one-pot activation/coupling to reduce solvent and reagent consumption.
All selections should be validated by small-scale trials to ensure performance criteria are met.
Pharmaceutical Uses
Item-specific (Product Data): None specified beyond Research Use Only.
Formulation/excipient context (general; no therapeutic claims):
2-Cyclohexylbenzoic acid is not a common pharmacopeial excipient. Aromatic benzoates/benzoic acid are used as preservatives in some contexts, but the ortho-cyclohexyl derivative is not standard for such use.
In medicinal chemistry, this scaffold may serve as an intermediate to prepare amides/esters for structure–activity relationship (SAR) exploration, leveraging the steric and lipophilic effects of the cyclohexyl group.
Prodrug or salt formation strategies could be explored in research to modulate solubility or permeability, yet these are investigational and fall under research-only usage.
Manufacturing considerations (general):
If used as an intermediate in GMP settings, control of residual solvents, identity (NMR/IR/HRMS), and purity (HPLC/GC) is essential. Trace metal and elemental impurities should be assessed if catalytic steps are involved.
No pharmacopeial monograph or excipient designation is implied for this product. It is supplied strictly for research and laboratory use.
Physical Properties
Item-specific (Product Data):
Appearance: 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.
Literature/general values (for reference; not specifications for this item):
Phase at ambient conditions: typically a crystalline solid for ortho-alkyl/alkylcyclohexyl benzoic acids.
Acid strength: aromatic carboxylic acid pKa commonly ~4.2–4.6; the ortho cyclohexyl (weakly donating, sterically bulky) often shifts pKa slightly upward relative to benzoic acid (pKa 4.20), e.g., estimated ~4.3–4.5 (literature ranges for similar ortho-alkylbenzoates).
Solubility profile: sparingly soluble in water (as the neutral acid); readily soluble in common organic solvents such as dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, THF, and alcohols; highly soluble in aqueous base as the benzoate salt.
Partitioning: expected lipophilic due to cyclohexyl group; logP for analogous o-alkylbenzoic acids is typically >2 (literature trend).
Boiling/melting: many benzoic acids decompose before boiling at 1 atm; melting points vary widely with substitution. A precise MP/BP for 2-cyclohexylbenzoic acid is not universally tabulated; consult CoA for this lot.
Spectroscopic identifiers: strong IR C=O stretch near ~1680–1710 cm−1 (carboxylic acid dimer), O–H broad band ~2500–3300 cm−1; aromatic C–H stretches ~3030 cm−1; characteristic 1H NMR signals for aromatic protons (δ ~7–8 ppm) and cyclohexyl aliphatic protons (δ ~1–2 ppm) (general guidance).
Note: All non-specified numeric properties above are literature expectations for closely related structures and are not item-specific specifications.
Quality and Grades
Item-specific (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.
Interpreting typical grades (general guidance):
Research/bioreagent grade: suitable for most synthetic and analytical workflows. If UV-sensitive chromatography is planned, low-UV or HPLC-grade solvents/reagents minimize background.
Purity reporting: for solid organic building blocks like benzoic acids, purity is commonly established by HPLC/GC area %, 1H NMR assay, or titration of acid content; residual solvents, water (Karl Fischer), and ash/metals may also be reported depending on application.
Trace metals/ions: if the compound is to be used in metal-catalyzed decarboxylative couplings or in sensitive organometallic steps, low metal content can be important. When relevant, request ICP data.
Implications for this item:
If amide coupling (medchem) or materials applications require tight impurity control, consult the lot-specific CoA for purity method, residual solvents, and water content. Absent a specified stabilizer, aromatic carboxylic acids are generally stable under ambient storage.
Documentation:
For regulatory or QA needs, request CoA, SDS, and Spec Sheet for the exact lot. Item-specific thresholds (UV cutoff, metals, peroxides, etc.) are Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
2-Cyclohexylbenzoic acid serves as a sterically encumbered, hydrophobic aromatic acid building block. The ortho-cyclohexyl group modulates sterics and lipophilicity, useful in medchem SAR and materials design.
Esterification (Fischer, Steglich) to generate ortho-cyclohexylbenzoate esters for protecting groups, prodrugs (research context), or polymerizable monomers.
Amide formation via carbodiimides (EDC/HOBt or DIC/HOAt), uronium reagents (HATU, TBTU), Mukaiyama salt, or mixed anhydrides to deliver o-cyclohexylbenzamides with increased lipophilicity/steric bulk.
Acid chloride formation (SOCl2, (COCl)2) followed by acylation of nucleophiles.
Rearrangements and homologations:
Curtius rearrangement (via acyl azide from DPPA) to access 2-cyclohexylbenzylamine derivatives after hydrolysis/trapping.
Schmidt or Hoffmann variants from suitable derivatives.
Photoredox/Ni dual catalysis of N-hydroxyphthalimide (NHPI) esters for C–C, C–N, or C–B bond formation, enabling aryl substitution without preformed halides.
Silver-mediated or copper-catalyzed decarboxylative halogenations (Hunsdiecker-type) to form 2-cyclohexylaryl halides.
Directing-group chemistry:
While –CO2H can direct certain ortho-functionalizations when converted to transient activating groups, the existing ortho substituent imposes steric control in electrophilic aromatic substitution on the ring (favoring meta to –CO2H relative to standard patterns).
Practical tips:
Ensure dryness for coupling reactions; acids can contain trace moisture. If needed, azeotropically dry or co-evaporate with toluene/MeCN.
Bulky ortho substituent may slow acylation; consider activating agents (HATU) and bases (DIPEA) and warming to 30–50 °C to drive to completion.
Monitor by LC–MS or 1H NMR; the downfield carboxylic OH (broad, δ 10–13 ppm) and carbonyl IR (~1700 cm−1) are convenient handles.
Reaction Conditions
General literature guidance for common transformations of 2-cyclohexylbenzoic acid (optimize per substrate; values are indicative, not item-specific specifications):
Esterification (Fischer):
Solvent/reagent: ROH (MeOH/EtOH/iPrOH), catalytic H2SO4 or p-TsOH.
Conditions: 50–80 °C (MeOH/EtOH) or reflux; Dean–Stark in toluene for higher-boiling alcohols; 4–16 h.
Notes: remove water to drive equilibrium; use molecular sieves or azeotrope.
Steglich/EDC esterification:
Solvent: DCM, EtOAc, or MeCN.
Reagents: DCC or EDC·HCl (1.1–1.5 eq), DMAP (0.1 eq).
Temp/time: 0 °C to rt, 2–16 h; monitor for urea byproducts.
Conditions: rt to 40 °C, 2–12 h; higher temp for hindered amines.
Acid chloride formation:
Reagents: SOCl2 (3–5 eq) with catalytic DMF.
Solvent: neat or DCM/toluene.
Conditions: 60–80 °C, 1–4 h; distill off volatiles, quench cautiously.
Curtius rearrangement:
Reagents: DPPA (1.2 eq), base (Et3N), toluene or PhMe/MeCN.
Conditions: 70–100 °C; trap isocyanate with alcohol/amine; 2–8 h.
Decarboxylative coupling (NHPI ester route):
Formation: DIC (1.1 eq) + NHPI (1.2 eq) in DCM.
Coupling: Ni catalyst (e.g., NiCl2·dppp 5–10 mol%), photocatalyst (Ir(ppy)3 1 mol%) under blue LEDs; partner varies (aryl bromide, amine, etc.).
Conditions: rt to 40 °C, 6–24 h, inert atmosphere.
Expected yields vary (40–90%) depending on substrate and sterics; the ortho-cyclohexyl group can modestly slow reactions, motivating slight reagent excess or mild heating.
Safety and Handling
Item-specific (Product Data):
GHS signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification and pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature (per Product Data).
General safety guidance for aromatic carboxylic acids (literature/general; not a substitute for SDS):
Likely hazards: may cause skin and eye irritation; dust may irritate the respiratory tract. Strongly acidic solutions can be corrosive to metals and tissue.
PPE: lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use dust control and local exhaust ventilation when handling powders.
Handling: avoid generating dust; use in a well-ventilated area or fume hood. Prevent contact with bases if not intended (neutralization generates heat). Avoid contact with oxidizers and strong reducing agents.
Incompatibilities: strong bases (forms benzoate salts and heat), strong oxidizers (possible exotherms), acid chlorinating agents (unless used deliberately under controlled conditions), reactive metals in acidic media.
First-aid overview: rinse skin/eyes with water for at least 15 minutes after exposure; remove contaminated clothing; move to fresh air if inhaled; seek medical attention if symptoms persist. If ingested, rinse mouth; do not induce vomiting unless advised by medical personnel.
Always consult the product’s SDS for definitive hazard classification, exposure limits, and emergency procedures.
Solvent Selection
This compound is a moderately lipophilic aromatic carboxylic acid; solvent choice depends on using it as a neutral acid versus its conjugate base.
Polarity/miscibility (general):
Neutral acid: soluble in medium-polarity organic solvents (DCM, chloroform, ethyl acetate, acetone, THF, MeCN) and in alcohols; sparingly soluble in water.
As benzoate salt: highly soluble in water and polar protic solvents.
Practical selection by task:
Esterification (Fischer): anhydrous alcohol (MeOH/EtOH/iPrOH) with catalytic mineral acid; toluene with Dean–Stark for water removal.
Amide coupling: polar aprotic media (DMF, DMAc, NMP, MeCN, DCM) depending on coupling system and substrate solubility.
Acid chloride formation: neat SOCl2 or oxalyl chloride; DCM/toluene as diluents if needed; add catalytic DMF for activation.
Purification: ethyl acetate/hexanes or DCM/MeOH systems often give good chromatographic control; recrystallization from EtOAc/hexanes or toluene/alcohol mixtures can be effective.
Comparison notes (general):
DCM vs EtOAc: DCM dissolves both aromatic acids and many byproducts but is chlorinated; EtOAc is greener and often adequate.
MeCN vs DMF: MeCN is easier to remove and has lower toxicity; DMF offers superior solubilization for polar amide couplings.
Tip: If aqueous workup stalls due to emulsions (common with lipophilic acids), salt the water phase (brine), add a small amount of iPrOH to the organic layer, or convert to the sodium benzoate and back-acidify after washing.
Storage and Reconstitution
Item-specific (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 storage guidance for aromatic carboxylic acids:
Store tightly closed in a dry, well-ventilated place at ambient temperature; protect from prolonged moisture exposure to prevent clumping and from strong light/heat.
If long-term storage is planned, consider desiccation and inert headspace (e.g., nitrogen) to minimize adventitious moisture uptake.
Reconstitution and use:
Solubility: readily dissolves in common organic solvents (e.g., DMSO, DMF, DCM, EtOAc, MeOH/EtOH, THF); sparingly soluble in water as the neutral acid but readily soluble in aqueous base as the benzoate salt.
Preparing stock solutions: for biochemical screening (research only), DMSO stocks of 10–100 mM are typical; filter (0.22 µm PTFE) if needed.
Freeze–thaw: solid form is robust; if preparing solutions, aliquot to avoid repeated freeze–thaw cycles that may concentrate water or promote hydrolysis of activated derivatives.
Stability notes:
The parent acid is generally stable; reactive derivatives (acid chlorides, NHS/NHPI esters) should be prepared fresh and used promptly.
Always refer to the product’s SDS and CoA/Spec Sheet for lot-specific handling and storage details.
Structure and Identity
Brief overview: 2-Cyclohexylbenzoic acid is an ortho-substituted benzoic acid bearing a saturated cyclohexyl group.
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.
Literature/computed identity (for reference only; not item-specific):
Typical molecular formula: C13H16O2 (benzoic acid core plus cyclohexyl substituent)
Typical molecular weight: ~204.26 g/mol
Representative SMILES: O=C(O)c1ccccc1C2CCCCC2 (depicts an ortho-cyclohexyl on the benzoic acid ring)
Functional groups and features: aromatic ring, carboxylic acid (–CO2H), bulky hydrophobic cyclohexyl at the 2-position (ortho) relative to –CO2H.
2D structural description (general):
A benzene ring bearing a carboxylic acid at position 1 and a cyclohexyl substituent at position 2 (adjacent). The –CO2H lies coplanar (approximately) with the aromatic ring; the cyclohexyl is a chair conformer extending out of plane, imparting steric bulk near the ortho region.
Stereochemistry: none (achiral), though conformational isomerism of the cyclohexyl ring is present.
Synthetic Utility
The molecule offers a versatile –CO2H handle on a sterically crowded, lipophilic aromatic ring, enabling diverse downstream transformations.
Key functional elements and reactivity (literature/general):
Carboxylic acid chemistry:
Convert to acid chloride (SOCl2 or (COCl)2) for acylations with alcohols, amines, or organometallics.
Form mixed anhydrides (pivaloyl chloride, isobutyl chloroformate) for milder couplings.
Uronium/carbodiimide-mediated amidations (HATU, TBTU, EDC/DIC+HOAt/DMAP) to make benzamides; the ortho cyclohexyl group can influence conformation and block undesired ortho reactions.
Carbon–carbon formation via decarboxylation:
Prepare NHPI (PINO) esters and engage in photoredox/Ni catalysis for aryl–aryl or aryl–heteroatom couplings, avoiding aryl halide synthesis.
Copper/silver-mediated decarboxylative halogenation/borylation to generate synthetically versatile aryl halides/boronates.
Rearrangements/homologations:
Curtius to isocyanate → ureas/carbamates/amines; Schmidt under strong acid; Lossen via activated hydroxamates.
Protecting group behavior:
The acid can serve transiently as a directing/anchoring group; subsequent decarboxylation removes it, offering a traceless handle in advanced syntheses.
Retrosynthetic value:
Starting from this acid allows rapid entry to o-cyclohexylbenzamides/esters, which are otherwise less accessible via direct electrophilic substitution due to the deactivating –CO2H. The cyclohexyl group’s steric footprint can tune receptor-binding pockets or polymer packing.
Analytical handles:
Strong IR C=O (~1700 cm−1), diagnostic 13C carbonyl at δ ~170–175 ppm; LC–MS typically shows M–H− at m/z ~203 (literature expectation for C13H16O2).
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or targeted biological reagent.
Item-specific (Product Data): No target, epitope, or isotype information is provided or applicable.
For biochemical studies, any observed interactions would be nonspecific physicochemical effects unless validated; see Biological Roles for general context.
Wir verwenden Cookies, um die ordnungsgemäße Funktion der Website sicherzustellen und, soweit zulässig, Ihr Nutzererlebnis zu verbessern. Sie können Ihre Einstellungen jederzeit unter „Einstellungen“ verwalten. Weitere Informationen finden Sie in unserer Cookie-Richtlinie.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
