N-(4-Hydroxycyclohexyl)acetamide - Reagent grade

Cat. No.: N483951

QUALITÉ & PURETÉ Reagent Grade

Storage

Room temperature

Spécifications

Spécifications et pureté

Reagent grade

Conditions de stockage de stockage

Room temperature

Grade

Reagent Grade

Application Protocols

Not applicable. No antibody/assay protocols are associated with this small-molecule reagent. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

If preparing stock solutions for screening or biophysical experiments:

• Prepare concentrated stocks in DMSO (e.g., 10–100 mM) or ethanol under dry conditions.
• Filter sterilize if needed through 0.22 µm PTFE or PES.
• Store aliquots to minimize freeze–thaw and moisture uptake; document lot-specific solubility empirically.

Biological Roles

No specific biological function is assigned to N-(4-Hydroxycyclohexyl)acetamide. It is supplied for research use as an organic building block (Research Use Only; from Product Data).

General, non-clinical context (literature-based, not specific to this item):

• Amide- and alcohol-containing small molecules are prevalent in biochemical probes and as fragments in medicinal chemistry due to their balanced polarity and hydrogen-bonding capacity.
• The cyclohexyl group often serves as a lipophilic, conformationally restricted motif to modulate binding and pharmacokinetic properties in structure–activity relationship (SAR) studies.
• The 1,4-relationship between the amide tether and the hydroxyl on the ring can influence intramolecular hydrogen bonding and conformational preferences, which may be explored in physical-organic and computational studies.

No claims are made regarding biological activity, metabolism, or therapeutic application of this specific compound. It is intended strictly for laboratory research and synthetic use. For any biological testing, users should generate their own data packages (solubility in assay media, stability in buffer, serum stability, permeability, etc.) and follow institutional safety and compliance guidance.

Buffer Applications

This product is not a buffering agent and is not typically used to prepare biochemical buffers. It lacks a conjugate acid/base pair with a pKa in the physiological window suitable for buffering in water.

Practical guidance:

• If incorporating this compound into aqueous experiments, dissolve first in a suitable co-solvent (e.g., DMSO, ethanol) and then dilute into the desired buffer system (HEPES, phosphate, Tris, etc.) as appropriate for your assay.
• Assess solubility and stability in the target buffer empirically. Filtration through 0.22 µm membranes can help ensure homogeneity for biophysical studies.

Green Alternatives

While the compound itself is the target reagent/building block, greener choices can be made in its handling and transformations.

• Solvent optimization (greener substitutions):

  • Replace DMF/NMP with safer alternatives when feasible: dimethyl carbonate (DMC), propylene carbonate (PC), Cyrene, or aqueous ethanol for some coupling/derivatization steps.
  • Prefer ethanol or isopropanol over methanol; use water/EtOH mixtures for workups and crystallizations.
  • For oxidations of the secondary alcohol, consider catalytic TEMPO with bleach (NaOCl) in biphasic water/EtOAc under buffered conditions instead of chromium(VI) reagents.

• Reagent choices and conditions:

  • Esterifications: Use catalytic organocatalysis (DMAP) with less hazardous anhydrides; employ solvent-free or neat conditions where practicable.
  • Sulfonylations: Use greener bases (K2CO3) and solvents (EtOAc, MeTHF) instead of pyridine/DCM when compatible.
  • Oxidations: O2 or H2O2 with appropriate catalysts (e.g., Pd/C or Mn-catalyzed oxidations) as alternatives to hypervalent iodine or chromium reagents.

• Small comparison (illustrative):

  • Traditional: Swern oxidation (oxalyl chloride/DMSO; cryogenic; chlorinated byproducts).
  • Greener: TEMPO/NaOCl (aq), pH ~8–9, ambient temperature; minimal hazardous waste.

Trade-offs:

• Greener solvents may reduce solubility or change selectivity; reaction rates can be slower. Conduct small-scale screens to balance EHS profile with performance.
• Workup ease and recyclability (e.g., EtOAc, 2-MeTHF) can offset modest rate penalties, improving overall process greenness.

Pharmaceutical Uses

No pharmacopeial designation or excipient status is provided for this item. It is sold for research use only (from Product Data) and is not intended for human or veterinary use.

General formulation/manufacturing context (non-clinical, literature-based):

• As a small, polar organic building block, N-(4-Hydroxycyclohexyl)acetamide could serve as an intermediate in the synthesis of candidate APIs or advanced intermediates, where the cyclohexyl alcohol can be further elaborated (e.g., to carbamates, carbonates, ethers), and the amide can be retained or transformed.
• The dual H-bond donor/acceptor profile may make it a useful fragment in fragment-based drug discovery libraries; however, no claims are made about suitability, safety, or performance in pharmaceutical products.

If use is contemplated in regulated contexts, users should qualify material according to internal specifications (identity, purity, residual solvents, elemental impurities, microbial limits as applicable) and consult relevant pharmacopeial and regulatory guidance.

Physical Properties

Item-specific physicochemical specifications (mp, bp, density, water/peroxide/metal content, UV cutoff, etc.) are not provided in the Product Data for SKU N483951. Refer to the CoA/Spec Sheet for certified values.

General/literature and computed information for the neutral molecule (for guidance only):

• Molecular formula (calculated): C8H15NO2
• Molecular weight (calculated): ~157.21 g/mol
• Acid–base behavior (literature, qualitative):
  • Amide N–H is very weakly acidic in water; reported pKa in DMSO for simple amides ~17–20 (solvent dependent).
  • Secondary alcohol O–H has pKa typically ~16–18 in DMSO (significantly higher in water; essentially neutral at physiological pH).
• Polarity/H-bonding (literature, qualitative): Dual H-bond donor (N–H, O–H) and acceptor (C=O, O of OH) sites; expected to be moderately polar with significant aqueous miscibility when ion-paired or under H-bonding conditions.
• Solubility (literature, qualitative expectation):
  • Good solubility in polar organic solvents (DMSO, DMF, methanol, ethanol).
  • Limited to moderate solubility in water depending on temperature and ionic strength; salting-in by chaotropes may help.
  • Low solubility in nonpolar solvents (hexanes, toluene) without co-solvent.
• Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index, density, melting/boiling points, and logP: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific quality: Reagent Grade (from Product Data). Reagent Grade typically indicates suitability for general laboratory synthesis and analysis, with impurity limits appropriate for routine research use. It is not necessarily optimized for trace analysis, LC/GC, or biopharmaceutical applications unless otherwise stated.

• What Reagent Grade implies (general guidance):

  • Reasonable control of common impurities and residual solvents, but without ultra-low UV absorbance or sub-ppm metal specifications associated with HPLC/LCMS/trace-metal grades.
  • Suitable for most synthetic transformations, derivatizations, and as a building block/intermediate.

• Not provided for this item (consult CoA/Spec Sheet if needed):

  • Assay (purity %) by specific method
  • Water content (Karl Fischer)
  • Residual solvents and volatiles
  • UV cutoff/absorbance profile
  • Peroxide content (not typically applicable here)
  • Trace metal content
  • Stabilizers/additives

• Practical notes for use:

  • If employing this material in moisture-sensitive or catalytic reactions (e.g., coupling, metal-catalyzed oxidations), consider drying prior to use (vacuum over P2O5/sieves) and perform a small pilot to assess impact of residual moisture.
  • For chromatographic or bioanalytical contexts, verify UV/background and impurity profile with a reference lot before committing to scale.

Reaction and Applications

N-(4-Hydroxycyclohexyl)acetamide serves as a versatile bifunctional building block combining a secondary alcohol and a secondary amide. Typical research applications include:

• Orthogonal functionalization:
  • Alcohol derivatization: Esterification (acid chloride/anhydride, Steglich conditions with DCC/DMAP), sulfonylation (MsCl/TsCl), etherification (Williamson via alkoxide formation, though strong base is required and amide N–H must be considered), or carbonate formation.
  • Selective oxidation: Secondary alcohol → ketone (e.g., Dess–Martin periodinane, PCC, Swern, TEMPO/bleach under buffered conditions). The amide generally remains intact.
• Cyclization strategies:
  • Intramolecular substitution after conversion of the alcohol to a leaving group (e.g., OMs/OTs) can enable formation of bicyclic scaffolds if additional nucleophiles are introduced, exploiting the 1,4-disposition on the ring.
• Amide manipulations:
  • N-acyl unit can be retained as a hydrogen-bonding handle or transformed under forcing conditions (e.g., Hofmann/Lossen-type rearrangements require different precursors; direct amide activation possible with coupling reagents or electrophilic activators such as Tf2O/NEt3 followed by nucleophile capture).
  • Deprotection/swap of the acetyl group is possible via hydrolysis (acidic or basic; basic conditions can also induce acyl transfer in some contexts) to access the free amine on the cyclohexyl fragment.
• Conjugation chemistry:
  • After hydrolysis to the 4-hydroxycyclohexylamine, the alcohol can be orthogonally derivatized for linker installation, making this a useful intermediate toward diamine, amino-ether, or urea-bearing scaffolds.

Practical tips:

• Protect the alcohol (e.g., TBDMS/TBS, benzyl) when conditions risk undesired acylation/activation at O.
• For selective O- vs N-acylation/alkylation, exploit base choice, temperature, and reagent reactivity (amide N is far less nucleophilic than the alcohol).

Reaction Conditions

General literature guidance for typical transformations on N-(4-hydroxycyclohexyl)acetamide (optimize per lab scale; not item-specific):

• Alcohol esterification (Steglich): Carboxylic acid (1.1–1.5 eq), DCC (1.1–1.5 eq), DMAP (0.05–0.2 eq), solvent: DCM or DMF, 0 °C → rt, 2–18 h. Monitor by TLC/LC-MS. Filter DCU, work up, and purify.
• O-Sulfonylation: TsCl or MsCl (1.2–1.5 eq), base: pyridine or triethylamine (2–3 eq), solvent: DCM or MeCN, 0 °C → rt, 1–6 h. Alternatively K2CO3 in MeCN/acetone for greener base systems.
• Oxidation to ketone:
  • DMP (1.3 eq) in DCM, 0 °C → rt, 1–3 h; quench with aqueous Na2S2O3/NaHCO3.
  • TEMPO (0.05–0.1 eq), NaOCl (1.5–2 eq active), KBr (cat.), pH 8.6 buffer, 0–25 °C, 1–4 h; extract with EtOAc.
• Mitsunobu etherification: ROH substrate (1.0 eq), nucleophile (acidic; 1.2–2.0 eq), DIAD/DEAD (1.2–1.5 eq), PPh3 (1.2–1.5 eq), THF or THF/DMF, 0 °C → rt, 2–16 h. Note: consider amide N–H acidity; protection of the alcohol or amide may be required for chemoselectivity.
• Amide hydrolysis: Aqueous NaOH (1–5 M), reflux EtOH/H2O 2–12 h; or HCl (6 M) reflux. Workup to isolate 4-hydroxycyclohexylamine salts/bases; ensure compatibility with downstream steps.

Yields vary widely (40–90%) depending on reagent, scale, and protection strategy. Rigorous drying (where needed), inert atmosphere for moisture-sensitive reagents, and careful temperature control improve outcomes.

Safety and Handling

Authoritative safety classification (GHS) is not specified for this item in the Product Data. Always consult the product SDS for definitive hazard statements, pictograms, and response advice.

General safety guidance for amide/alcohol-containing organic solids (informational only):

• Likely hazards: Low volatility; dust may cause mechanical irritation to eyes/respiratory tract. Prolonged skin contact may cause irritation. Combustible organic solid; avoid ignition sources and dust accumulation.
• Handling/PPE: Use in a fume hood or well-ventilated area. Wear safety glasses or goggles, lab coat, and appropriate gloves (e.g., nitrile). Avoid inhalation of dust and contact with eyes/skin.
• Incompatibilities: Strong oxidizers (risk of exotherm/combustion). For derivatization steps, avoid strong dehydrating agents unless intended. Amide is generally stable to bases/acids, but the alcohol can be esterified/etherified under strongly acidic conditions.
• First aid (summary; follow SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap/water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Fire-fighting: Use water spray, CO2, dry chemical, or foam. Combustion may produce CO/CO2 and nitrogen oxides.
• Spill response: Avoid dust; sweep up and transfer to suitable container for disposal. Clean area with water/ethanol.
• Storage conditions (from Product Data): Store at room temperature. Keep container tightly closed, dry, and away from incompatible materials. Label: For research use only.

Solvent Selection

This compound is a moderately polar, hydrogen-bonding organic solid bearing both an amide and an alcohol.

• Polarity/HBD-HBA profile (literature, qualitative): Dual donor/acceptor functionality; engages in strong H-bonding with polar protic and aprotic solvents.

• Recommended solvent systems for dissolution and handling:

  • Strong polar aprotic: DMSO, DMF, NMP – excellent solubility, useful for stock solutions and coupling chemistry.
  • Polar protic: Methanol, ethanol, isopropanol – generally good solubility; convenient for recrystallization or workups.
  • Aqueous mixtures: Water/alcohol cosolvent systems can aid dissolution; pH has limited effect due to neutral functionality, but salts/urea can enhance solubility via H-bonding.
  • Nonpolar: Poorly soluble in toluene/hexanes; use as antisolvents for crystallization.

• When to choose alternatives:

  • If low toxicity/green metrics are priorities, prefer ethanol, isopropanol, or water/EtOH blends over DMF/DMSO.
  • For moisture-sensitive transformations on this substrate (e.g., conversion of the alcohol to a sulfonate), use dry acetonitrile, DCM, or THF for the reaction stage and switch to polar media for workup.

• Small comparison (general):

  • DMSO/DMF: Maximize solubility; harder to remove; higher boiling; less green.
  • EtOH/iPrOH: Good solvency; easy removal; greener; may participate in H-bonding affecting reactivity.
  • MeCN: Moderate solvency; volatile; good for coupling or activation steps with controlled water content.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at room temperature. Keep tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to heat and moisture.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and solution handling (general guidance):

• Solvents: DMSO, DMF, ethanol, or methanol typically afford concentrated stock solutions. Begin with 10–20 mg/mL trials and adjust based on clarity.
• Aqueous use: Dissolve first in a miscible organic solvent (e.g., DMSO or EtOH), then dilute into buffer with vigorous mixing to avoid precipitation. Final organic content of 0.5–5% v/v often balances solubility and assay compatibility.
• Filtration: For sensitive applications, pass solutions through a 0.22 µm membrane (PTFE for organic stocks; PES/nylon for aqueous-organic).
• Stability: Amide and secondary alcohol are generally stable at ambient conditions. Avoid strong acids/bases or oxidants unless intentional. Minimize exposure to light/air if long-term storage in solution is required.
• Aliquoting: For multi-use, prepare small aliquots to limit headspace and moisture uptake. Label with solvent, concentration, date, and lot ID.

Note: Item-specific specifications for appearance, water content, and solution stability are not provided; consult the CoA/Spec Sheet and SDS for authoritative guidance.

Research Use Only (from Product Data).

Structure and Identity

N-(4-Hydroxycyclohexyl)acetamide is a bifunctional small molecule containing a secondary amide and a secondary alcohol on a cyclohexane ring.

• Chemical identity (item-specific):

  • Product name: N-(4-Hydroxycyclohexyl)acetamide (SKU: N483951)
  • Grade: Reagent Grade (from Product Data)
  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • PubChem CID: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structure data (informational, not item-specific specs):

  • Molecular formula (calculated): C8H15NO2
  • Molecular weight (calculated): ~157.21 g/mol
  • SMILES (one possible representation, no stereochemistry implied): CC(=O)NC1CCC(O)CC1

• Structural features (descriptive):

  • One six-membered saturated ring (cyclohexane) bearing a hydroxyl group at the 4-position relative to the ring carbon attached to nitrogen (1,4-disubstitution pattern).
  • Secondary amide fragment: acetamide (CH3–CO–NH–) attached to ring carbon C1.
  • Secondary alcohol at C4 of the ring (–CHOH–), capable of hydrogen bonding and derivatization.
  • No defined stereocenter specified; the 4-hydroxylated cyclohexyl center can exist as axial/equatorial conformers; overall compound may form conformational isomers but no fixed stereochemistry is indicated.
  • Functional groups: amide (H-bond donor/acceptor), alcohol (H-bond donor/acceptor).

Synthetic Utility

Key functional groups and reactivity:

• Secondary alcohol (on a cyclohexyl ring): amenable to oxidation (→ ketone), esterification (→ O-acyl), sulfonylation (→ OMs/OTs), and substitution after activation (→ ethers, azides, halides via Mitsunobu or via sulfonates).
• Secondary amide (acetamide): robust under many conditions; hydrolyzable (acidic/basic); can be engaged in coupling after activation or transformed into other nitrogen functionalities via amide activation strategies.

Representative transformations (literature concepts):

• Oxidation to 4-oxo analogue: Dess–Martin periodinane or catalytic TEMPO/NaOCl (buffered) to afford the corresponding ketone while preserving the amide.
• Mitsunobu etherification: Alcohol → ether with acidic nucleophiles (e.g., carboxylic acids, phenols) using DIAD/DEAD and PPh3; consider amide N–H acidity and potential need for protection.
• O-Sulfonylation → intramolecular cyclization: Convert the alcohol to OTs/OMs, then engage nucleophiles (external or internal after amide deprotection/derivation) to build bicyclic motifs.
• Amide hydrolysis/deacetylation: Access 4-hydroxycyclohexylamine under basic/acidic conditions; subsequent urea/carbamate formation broadens scaffold diversity.
• Carbonate/carbamate formation: React the alcohol with chloroformates or CDI to introduce linkers and protecting groups.

Retrosynthetic value:

• Functions as a convergent node: ring functionalization at C4 can encode spatially separated polar and lipophilic domains; the amide can serve as a temporary protecting/activating handle for nitrogen, enabling stepwise diversification of the cyclohexyl core.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.