This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
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
232.320 g/mol
XLogP3
2.700
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
232.158 Da
Monoisotopic Mass
232.158 Da
Topological Polar Surface Area
55.100 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
261.000
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
No validated biological application protocols (e.g., WB, IHC, IF, FC) are provided for this item. As a small-molecule building block, usage protocols are reaction‑ and project‑specific.
General lab guidance:
For stock solutions in screening assays, dissolve in anhydrous DMSO (e.g., 10–50 mM), filter (0.22 μm PTFE), and aliquot to minimize freeze–thaw cycles.
For synthetic use, confirm identity/purity by NMR and LC‑MS prior to multi‑gram preparations. Record water content (KF) if moisture‑sensitive transformations are planned.
Refer to your project’s SOPs and this product’s CoA/SDS for any specific handling or preparation instructions.
Biological Roles
This product is supplied strictly for research use; no clinical or diagnostic claims are made.
General context (biochemistry/chemoinformatics; not item-specific claims):
Aryl amide scaffolds, especially anilides with additional amino substituents, are prevalent motifs in enzyme ligands and protein–protein interaction probes due to their ability to serve as both H‑bond donors/acceptors and to engage in aromatic stacking.
The para‑amino group can modulate basicity and electronic properties of the ring, impacting binding interactions in discovery screening campaigns and enabling facile salt formation for assay solubilization.
The cyclohexylcarboxamide fragment provides a lipophilic contact surface while retaining a polar carbonyl vector; such balance is commonly explored in SAR for permeability and solubility tuning.
For biochemical assays, the free aniline allows conjugation to reporter tags (e.g., isothiocyanates, NHS esters) to build tool compounds, while the intact amide can anchor the fragment within H‑bond networks.
Any specific biological activity of N-(4-amino-2-methylphenyl)cyclohexanecarboxamide is not established here; consult primary literature if exploring target engagement. Ensure appropriate counterscreens for anilines (potential redox activity/assay interference) and maintain strict RUO handling.
Buffer Applications
Not typically applicable. N-(4-Amino-2-methylphenyl)cyclohexanecarboxamide is an organic building block rather than a buffering agent.
Practical notes:
If dissolution in aqueous buffers is required for assays, form anilinium salts by adding a stoichiometric acid (e.g., HCl, citrate) to improve aqueous solubility; confirm pH compatibility with your system.
Use co‑solvents such as DMSO (prepare concentrated stocks, e.g., 10–50 mM) and dilute into buffer with vigorous mixing to avoid precipitation.
No validated buffer recipes or pH ranges are specified for this item.
Green Alternatives
Greener use of this amide building block focuses on solvent and reagent choices, since the substrate is fixed.
Preferable solvents (when compatible):
2‑MeTHF and CPME as drop‑in alternatives to THF/DCM for many extractions and some couplings; improved safety and renewability.
Ethyl acetate or i‑PrOAc instead of DCM/CHCl3 for chromatography and workups.
Water/ethanol co‑solvent systems for diazotization/azo coupling, when pH control permits.
Coupling reagents and bases:
T3P (propanephosphonic anhydride) in EtOAc/2‑MeTHF can replace carbodiimides, reducing urea byproducts and improving EHS profile.
Enzymatic amidation (where applicable to downstream targets) or use of CDI for carbamate/urea formation to minimize hazardous byproducts.
Workup and purification:
Crystallization or trituration in green solvents (EtOAc/heptane, IPAc/heptane) to reduce silica waste.
Aqueous acid/base extractions to form/release anilinium salts, enabling phase‑switch purification without halogenated solvents.
Comparison snapshot (general):
DCM vs EtOAc: DCM offers higher solubility but is chlorinated and volatile; EtOAc is biodegradable, lower toxicity, often adequate for this substrate.
DMF/DMAc vs NBP/PC (N‑butylpyrrolidone/propylene carbonate): NBP/PC are higher‑boiling, less regulated alternatives; ensure compatibility with reagents and removal strategy.
Note: Verify solubility/kinetics before scaling; minor adjustments (temperature, concentration) often bridge performance gaps when switching to greener media.
Pharmaceutical Uses
For research use only. No pharmaceutical or clinical use is claimed for this product.
Salt formation: The para‑aniline can be protonated to give stable anilinium salts (e.g., HCl, mesylate) that may enhance crystallinity and aqueous handling during screening or pre‑formulation studies.
Solid form: Anilide amides often crystallize well; polymorph screening in different solvent systems (alcohols/esters/aromatics) can be used to optimize isolation and stability of intermediates in process R&D.
Impurity control: Track oxidative byproducts of anilines (azobenzenes, quinone imines) in stability studies; store under ambient but dry, away from strong oxidants.
Analytical methods: HPLC with UV detection (amide/aromatic chromophore), LC‑MS (ESI+), and NMR provide robust ID and purity checks for library synthesis and nonclinical studies.
There is no pharmacopeial monograph or excipient role indicated for this item in the provided data.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Expected/literature-informed characteristics for analogous anilide amides (informational, not item specs):
Physical state: typically a crystalline solid for comparable secondary aryl amides bearing cyclohexanecarbonyl groups.
Polarity: moderately polar due to one secondary amide (H‑bond donor/acceptor) and one aniline amino group (H‑bond donor/acceptor), with hydrophobic cyclohexyl and tolyl segments.
Solubility profile (qualitative):
Likely low in water at neutral pH; increased aqueous solubility upon protonation of the aniline (e.g., in acidic media) forming ammonium salts.
Good solubility expected in polar aprotic organic solvents (DMF, DMSO, NMP) and chlorinated solvents (DCM, chloroform); variable in ethyl acetate and alcohols depending on temperature.
Acid–base behavior: aromatic p‑amino group is weakly basic (conjugate acid pKa for para‑substituted anilines commonly ~4–6, literature); amide is nonbasic and weakly acidic at N–H (typical pKa of amide N–H ~15–18 in DMSO, literature).
Partitioning: overall amphiphilic but favoring organic phase; logP for similar cyclohexanecarboxanilides often in the moderate range (literature), dependent on ionization state.
Thermal behavior: aromatic amides commonly show higher melting points due to strong intermolecular H‑bonding; exact MP/BP for this item is not available here.
Note: For authoritative numeric values (mp, bp, density, refractive index, UV cutoffs, trace impurities), consult the product’s CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance):
Research/biochemistry grade emphasizes low residual solvents and identifiable impurity profiles suited for biological assays (non-clinical).
Synthetic grade (if provided) focuses on assay purity suitable for most organic transformations; trace metals and UV cutoffs are usually not controlled as tightly as HPLC/LC‑MS grades.
HPLC/LC‑MS grade solids (when available) are optimized for low baseline noise and fluorescence/UV impurities.
Verification and documentation:
For amide building blocks, quality is typically supported by 1H/13C NMR, HRMS/ESI, IR (amide C=O), and HPLC/GC purity.
If salt content or residual water is relevant (e.g., hygroscopic materials), Karl Fischer and LOD may be reported. For this item, such parameters are not specified.
Stabilizers/additives: None specified. If stabilizers are used for aniline-containing compounds, they are typically antioxidants; consult CoA if listed.
Practical note: For reactions sensitive to trace aniline oxidation products, consider pre-washing or brief silica plug before use, and verify purity by HPLC/LC‑MS.
Reaction and Applications
As a bifunctional building block, N-(4-amino-2-methylphenyl)cyclohexanecarboxamide offers orthogonal reactivity at the aniline (para‑NH2) and the secondary amide (CONH–) sites.
Transformations centered on the para‑aniline:
Electrophilic acylation/carbamoylation/sulfonylation at the aniline nitrogen to access ureas, carbamates, and sulfonamides.
Diazotization (Ar–NH2 → Ar–N2+) enabling azo coupling to phenols/anilines for dye intermediates (under cold, acidic conditions; mindful of stability and safety of diazonium salts).
Palladium‑catalyzed Buchwald–Hartwig N‑arylation using the aniline as nucleophile to install aryl/heteroaryl groups (ligand/catalyst tuned for anilines; bases such as NaOtBu or Cs2CO3 in toluene/1,4‑dioxane/PhMe or polar aprotics).
EDC/HATU/T3P-mediated coupling to activated acids/carboxylates for amide extension at the aniline nitrogen.
Transformations at the secondary amide:
N‑acyl activation is more challenging; amide N–H can be deprotonated (strong base) for N‑alkylation or converted to imides/carbamates with appropriate reagents.
Carbonyl functionalization: reduction to the corresponding amine (e.g., via borane, LiAlH4) to access cyclohexylmethyl aniline derivatives.
Hydrolysis (harsh acid/base, reflux) to regenerate cyclohexanecarboxylic acid and the aniline derivative.
Orthogonal strategies:
Protect aniline as acyl/sulfonyl/urea to manipulate the amide moiety.
Employ chemoselective conditions to functionalize the aniline without affecting the amide (e.g., mild acylations, Pd‑catalyzed couplings at aryl halides introduced subsequently).
Use cases: Preparation of ligand fragments, dye/azo intermediates, medicinal chemistry analog libraries (non-clinical), and materials monomers where H‑bonding is desirable.
Reaction Conditions
The following are general literature-style conditions for transformations of anilides and anilines; they are guidance only and not item-specific specifications.
Amide formation (synthesis of this compound):
Cyclohexanecarboxylic acid (1.0 eq), 4‑amino‑2‑methylaniline (1.0–1.2 eq), coupling agent (e.g., HATU 1.1 eq or EDC·HCl 1.2 eq with HOBt/oxyma), base (DIPEA 2–3 eq), solvent (DMF/DMAc), 0–25 °C to room temperature, 2–16 h. Typical isolated yields for analogous anilides: 60–90% (literature).
Aniline acylation/sulfonylation:
Acyl chloride/sulfonyl chloride (1.05–1.2 eq), base (pyridine or Et3N 2 eq), DCM or toluene, 0 °C → rt, 1–4 h; monitor by TLC/HPLC.
Diazotization/azo coupling (for the para‑aniline):
NaNO2 (1.1 eq) in 2–6 M HCl at 0–5 °C to form diazonium; couple with activated aromatic partner in mildly alkaline buffer (pH 8–10) or phenols under cold conditions. Safety: avoid isolation of dry diazonium salts; perform in situ.
Amide reduction to amine:
BH3·THF (3–6 eq) in THF, reflux 4–16 h; or LiAlH4 (2–4 eq) in THF/Et2O at 0 °C → reflux. Quench cautiously; yields for simple anilides often 60–85%.
N‑Alkylation at amide N–H:
Strong base (NaH, 1.1–1.5 eq) in DMF/THF at 0–25 °C, then alkyl halide (1.2–2 eq), 2–8 h. Compete with O‑alkylation/hydrolysis; conditions require optimization.
Purification:
Normal‑phase silica, DCM/MeOH or DCM/EtOAc with 0.1–1% Et3N; or reverse‑phase C18 with water/MeCN + 0.1% formic acid for ionizable derivatives.
Always validate conditions on small scale; adjust stoichiometry, temperature, and base according to reactivity of the chosen electrophile/nucleophile.
Safety and Handling
GHS/CLP: Not specified in Product Data; defer to the official SDS for hazard classification, pictograms, signal word, and H‑statements.
General hazards for analogous anilide solids (informational, not item-specific):
May cause irritation to skin, eyes, and respiratory tract upon dust generation or contact.
Aromatic amines can be sensitizers or harmful if absorbed; avoid exposure to the free base and dust.
Recommended PPE and controls:
Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to control dust and vapors during reactions.
Avoid inhalation of dust; if powder handling is required, use local exhaust or respirator per institutional policy.
First aid (overview; follow SDS):
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical attention for persistent irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities and reactivity (general):
Strong oxidizers (anilines may be oxidized); strong acids/bases under forcing conditions (hydrolysis of amide in strong acid/base, high temperature); acyl/alkylating agents (may react at aniline nitrogen).
Stability: Aromatic amides are generally stable under ambient conditions. Protect from prolonged light/air exposure if performing sensitive assays involving the aniline moiety.
Waste: Dispose according to local regulations for organic laboratory chemicals.
Always consult the SDS for definitive and up-to-date safety guidance.
Solvent Selection
Compound type: moderately polar aryl–alkyl secondary amide with an additional aniline –NH2. Exhibits both H‑bond donor and acceptor behavior, but remains largely organic-soluble.
Practical solvent choices (general guidance):
Polar aprotic: DMSO, DMF, NMP — excellent for dissolving at room temperature; ideal for coupling, acylation, and SNAr steps involving the aniline.
Chlorinated: DCM, CHCl3 — good solubility; useful for workups and chromatography. Mind safety/green considerations.
Esters/alcohols: EtOAc, i‑PrOAc, MeOH, EtOH — variable solubility; can aid in recrystallization or salt formation with acids.
Hydrocarbons: Toluene, heptane — limited solubility at ambient; may be used hot for crystallization or slurry purification.
Aqueous media: Low solubility at neutral pH; solubility increases in acidic water via anilinium salt formation (e.g., with HCl, TFA).
Selection scenarios:
Reaction setup (couplings/functionalizations): DMF/DMAc/NMP commonly chosen for base‑promoted steps on the aniline; DCM or THF for acyl chloride formation or carbamate/urea derivatization.
Purification: Normal‑phase silica using DCM/MeOH or DCM/EtOAc gradients with a small percentage of base (e.g., 0.1–1% NEt3) to avoid tailing of amines; reverse phase if needed for higher polarity derivatives.
Dielectric constants/refractive indices: Not specified for this item; consult chosen solvent data to model dissolution and chromatographic behavior.
Storage and Reconstitution
Storage (item-specific from Product Data): Room temperature.
Container: Store tightly closed in a dry, well‑ventilated place. Use amber glass if prolonged light exposure is anticipated (anilines can slowly oxidize).
Inert atmosphere: Not required for basic storage; optional nitrogen/argon blanket can be used for long‑term stability studies.
Moisture sensitivity: Amides are generally not hygroscopic, but keep desiccated to maintain consistent assay concentrations and to prevent hydrolysis under harsh conditions.
Reconstitution/preparation:
For synthetic use: dissolve in dry DMF, DMSO, DCM, or methanol as needed. Warm gently (30–40 °C) and sonicate to aid dissolution; avoid overheating.
For bioassay stocks: prepare concentrated DMSO solutions (e.g., 10–50 mM). If aqueous delivery is required, dilute into buffer while vortexing; slight acidity can enhance solubility via anilinium formation. Filter sterilize through 0.22 μm if sterility is essential.
Freeze–thaw: Solid material tolerates ambient cycling; for solutions, aliquot to avoid repeated freeze–thaw that may promote degradation.
Stability monitoring: Periodically check by HPLC/LC‑MS for oxidative byproducts (e.g., color change, new peaks). Discard if significant degradation is observed.
Note: If any item-specific limits (water, metals, UV cutoff) are required, they are not specified for this item; refer to the CoA/Spec Sheet.
Structure and Identity
Brief: N-(4-Amino-2-methylphenyl)cyclohexanecarboxamide is an anilide bearing a cyclohexanecarbonyl group; it combines a secondary amide with an aniline para-amino and ortho-methyl substituents.
Core functional groups: secondary amide (–CONH–), aniline para‑amino (–NH2) on the aryl ring, ortho‑methyl on the aryl ring, cyclohexyl acyl fragment (cyclohexanecarbonyl).
2D structure (verbal): a cyclohexyl–CO–CONH– linkage connects the cyclohexanecarbonyl to an aniline ring. The amide nitrogen is bound to the aryl ring at its 1‑position; the ring bears a methyl at the 2‑position (ortho to the amide linkage) and a primary amino at the 4‑position (para to the amide linkage).
Stereochemistry: none (achiral as drawn; cyclohexyl ring can adopt chair conformations).
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
InChI: Not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional group set: secondary amide (CONH–) linking a cyclohexanecarbonyl and a substituted aniline (2‑Me, 4‑NH2). This arrangement provides orthogonal handles for derivatization and fragment growth.
Retrosynthetic value:
Disconnection at the amide gives cyclohexanecarbonyl chloride (or activated acid) and 4‑amino‑2‑methylaniline (o‑toluidine, para‑amino substituted) as precursors.
Protect‑functionalize strategy: temporarily protect the para‑aniline (e.g., Boc, Cbz, sulfonamide) to permit selective transformations at the amide (e.g., N‑alkylation at CONH, carbonyl activation, reductions).
Amide manipulation: BH3·THF or LiAlH4 reduction → benzylic-type anilines with cyclohexylmethyl linkage; CDI or phosgene equivalents → imidates/carbamates.
Cross-coupling after installing aryl halides on the ring (via diazotization–halogenation or electrophilic substitution), followed by Suzuki/Buchwald steps to diversify the aryl domain.
Materials/assembly:
The amide N–H and carbonyl can promote supramolecular assembly (H‑bonding), aiding in cocrystal or polymer additive studies.
Purification advantages:
Strong UV chromophore from the aryl amide facilitates HPLC monitoring; basic modifiers (0.1–1% Et3N) in normal‑phase chromatography reduce streaking of amines.
Overall, it serves as a robust, modular intermediate for constructing ureas, sulfonamides, azo dyes, and reduced amine derivatives spanning discovery chemistry to materials exploration.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, enzyme, or probe with defined target specificity). No antigen/epitope, clone, isotype, or species reactivity information is provided or expected for this item.
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