4-[(4-Methylcyclohexyl)amino]cyclohexan-1-ol - ≥98% , CAS No.1152964-08-3

CAS: 1152964-08-3 Cat. No.: M935364 Formula: C₁₃H₂₅NO Peso molecolare: 211.340 Numero EC: 113-085-5

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

CC1CCC(CC1)NC2CCC(CC2)O

IUPAC Name

4-[(4-methylcyclohexyl)amino]cyclohexan-1-ol

InChIKey

MTMTYFVAPKIEOQ-UHFFFAOYSA-N

INCHI

1S/C13H25NO/c1-10-2-4-11(5-3-10)14-12-6-8-13(15)9-7-12/h10-15H,2-9H2,1H3

Peso molecolare

211.340

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Alcohols and polyols
        • Level5 Secondary alcohols
          • Level6 Cyclohexanols

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Secondary alcohols
• Direct Parent: Cyclohexanols
• Alternative Parents: Cyclohexylamines Cyclic alcohols and derivatives Dialkylamines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexylamine - Cyclohexanol - Cyclic alcohol - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring.
• 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: 211.340 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 211.194 Da
• Monoisotopic Mass: 211.194 Da
• Topological Polar Surface Area: 32.299 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 179.000
• 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 biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, see the Reaction & Applications and Reaction Conditions sections for general laboratory guidance.

Biological Roles

No biological function is assigned to this catalog reagent. It is supplied for research use as a synthetic building block.

• General biochemical considerations (literature context)
  • Aliphatic amino alcohols can engage in hydrogen bonding and protonation equilibria (pKaH typically ~10–11 for secondary cyclohexylamines), enabling interactions with acidic biomolecules or membranes in assay settings.
  • The amphiphilic nature (cationic amine, polar alcohol, hydrophobic rings) can influence permeability and solubility characteristics in medicinal chemistry campaigns when used as a fragment or side chain.
  • Formation of stable ammonium salts with mineral or organic acids can improve aqueous handling in biochemical assays.

No clinical or therapeutic claims are made. For any biological testing, characterize the salt form, purity, and stereochemical composition as these can affect assay outcomes.

Buffer Applications

This compound is not a standard buffering reagent and is not typically used to prepare defined pH buffer systems.

• General note (literature)
  • Secondary amines have conjugate acid pKa values often in the 10–11 range, meaning ammonium salts of this compound would buffer weakly near basic pH. However, lack of defined composition and potential hydrophobicity make it unsuitable as a primary buffer component.

For robust, well-characterized buffers, use established systems (Tris, HEPES, MOPS, phosphate). If the reagent must be present during an assay, prepare the desired buffer separately and add the compound as a solute or as a defined salt.

Green Alternatives

This SKU is a discrete reagent/building block rather than a process solvent. “Greener alternatives” therefore focus on reaction media and coupling strategies used with it.

• Greener solvent choices (literature guidance)
  • Prefer EtOAc, 2‑MeTHF, CPME, MeOH/EtOH over chlorinated solvents when compatible with selectivity and workup.
  • For amide formations, acetonitrile or 2‑MeTHF can often substitute for DMF/CH2Cl2.
• Greener coupling methodologies
  • Use carbodiimide-free couplings (e.g., CDI, EDC·HCl in water/EtOAc biphasic systems) to reduce urea waste from DCC.
  • Enzymatic acylations in organic media can provide selectivity for O‑ vs N‑acylation under milder conditions.
• Energy and waste minimization
  • Run at ambient temperature/short times where possible; telescope protection–acylation–deprotection steps to reduce solvent exchanges.

Comparison snapshot (general)

• Conventional: CH2Cl2 or DMF with DCC/HOBt for acylations → chlorinated waste and urea byproducts.
• Greener: 2‑MeTHF or EtOAc with EDCI (or acid anhydrides) and catalytic DMAP → easier workup, lower hazard profile.

Note: Selection must be validated for your specific transformation; this section provides general options rather than item-specific prescriptions.

Pharmaceutical Uses

• Intended use
  • For research use only; not for human or veterinary use.
• Role in pharmaceutical R&D (general)
  • Serves as a versatile intermediate/building block to explore structure–activity relationships (SAR) where a bulky, conformationally restricted, basic side chain is desired.
  • The amino alcohol motif can be derivatized to amides, carbamates, and ureas, enabling rapid library synthesis for lead optimization.
  • Salt formation (e.g., HCl, mesylate) can improve crystallinity for solid-state studies and facilitate purification.
• Excipient status
  • No pharmacopeial excipient status is indicated for this specific item. Not specified for this item; refer to CoA/Spec Sheet.

All pharmaceutical-related work should treat this reagent strictly as a synthetic intermediate within GMP-governed processes as applicable; consult internal quality systems for specifications.

Physical Properties

• Item-specific specifications
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (See computed value under Structure & Identity.)
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (See computed value under Structure & Identity.)
• Literature/computed expectations for this scaffold (for planning only; not item specifications)
  • Phase at RT: Often low-melting solid or viscous liquid for aliphatic amino alcohols of this size.
  • Solubility: Typically soluble in polar organic solvents (alcohols, DMSO, DMF) and partially soluble in moderately polar solvents (EtOAc, CH2Cl2); limited solubility in hydrocarbons; forms salts soluble in water/alcohols.
  • Basicity: Secondary cyclohexylamines commonly have pKaH ~10–11 (literature, scaffold-based expectation).
  • Polarity/proticity: Bifunctional; can engage in both H‑bond donation (N–H, O–H) and acceptance (N, O), giving relatively high polarity versus purely hydrocarbon frameworks.
  • LogP: Secondary cyclohexylamines with one OH and one methylcyclohexyl substituent are expected to be moderately lipophilic (qualitative, literature trend).

For authoritative physical constants (bp, mp, density, refractive index, UV cutoff), refer to the item’s CoA/Spec Sheet; values are not specified in the current Product Data.

Quality and Grades

• Item-specific quality
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting typical grades (general guidance)
  • Research/biochemistry grade: emphasizes low residual metals/impurities that could interfere with biological assays.
  • Synthetic grade: suitable for organic synthesis; impurity profile prioritized for reaction reliability. If offered as “98%+” or similar, minor diastereomeric content may be present unless stereochemistry is specified.
  • HPLC grade (when applicable to liquids/solvents): low UV absorbance, filtration; less relevant for a reagent-building block except for chromatography applications.
• Impurity considerations for amino alcohols (general)
  • Potential impurities include starting amines/alcohol isomers, residual solvents, and trace water. Water content and amine titration can materially affect coupling efficiency and salt formation outcomes.

Always verify actual assay, residual solvent, and water limits on the provided CoA for SKU M935364 before regulated or quantitative use.

Reaction and Applications

• Representative applications in synthesis (general, consistent with functional groups present)
  • Amide/urethane/urea libraries: the secondary amine can be acylated (acid chlorides/anhydrides), carbamylated (chloroformates), or reacted with isocyanates to furnish ureas—useful for SAR exploration in medicinal chemistry.
  • Carbamate protection: convert the amine to Boc/CBz carbamates to direct chemoselectivity toward the alcohol.
  • O‑Derivatization: the secondary alcohol can be esterified (DCC/DMAP, EDCI) or converted to mesylate/tosylate, enabling further substitution or intramolecular cyclizations.
  • N‑Oxylation/oxidation: selective oxidation to hydroxylamine or N‑oxide is uncommon for secondary aliphatic amines but can be considered for probe synthesis.
  • Ligand/scaffold: the amino alcohol motif can chelate metals or engage in hydrogen-bond networks; occasionally employed as chiral auxiliaries when stereochemistry is set, or as polar linkers in bifunctional molecules.
• Chemoselectivity notes
  • Competing N- vs O‑acylation: control with protecting groups, reagent stoichiometry, and base; DMAP promotes O‑acylation, while acid chlorides + base favor N‑acylation.
  • Steric environment: both nucleophiles are secondary and on cyclohexyl frameworks; steric hindrance may slow acylation—use activated coupling or catalytic promoters.
• Practical tips
  • Drying: remove water (azeotrope with toluene or co-evaporate with acetonitrile). Free amines can be dried over K2CO3/Na2SO4 after organic extraction.
  • Salt formation: HCl, HBr, or mesylate salts can improve crystallinity and handling; verify stoichiometry by titration/NMR.

Reaction Conditions

The following are general literature conditions appropriate for aliphatic secondary amino alcohols; confirm on small scale with this specific substrate.

• N‑Acylation (amide)
  • Reagents: acid chloride (1.1–1.5 eq), base (DIPEA or Et3N, 2–3 eq), solvent CH2Cl2 or 2‑MeTHF.
  • Conditions: 0–25 °C, 0.5–4 h. Monitor for O‑acylation; suppress with base and low temperature.
• Carbamate/Urethane formation
  • Reagents: Boc2O (1.1–1.5 eq) or alkyl chloroformate, catalytic DMAP; solvent THF/CH2Cl2.
  • Conditions: 0–25 °C, 1–6 h; typical isolated yields 70–90% (literature, substrate dependent).
• Urea formation
  • Reagents: isocyanate (1.0–1.2 eq); solvent CH2Cl2/THF; add amine at 0–5 °C, warm to rt.
  • Conditions: 1–3 h; often near-quantitative conversion by LC.
• O‑Mesylation/Tosylation
  • Reagents: MsCl/TsCl (1.2–1.5 eq), base (Et3N, 2–3 eq), catalytic DMAP; CH2Cl2.
  • Conditions: 0 °C to rt, 1–2 h; follow by SN2 displacement if desired.
• Reductive amination (on related carbonyl precursors)
  • Reagents: NaBH(OAc)3 (3–4 eq), AcOH (0.5 eq), MeCN/THF; rt, 2–16 h.

Note: Water sensitivity varies by transformation; maintain anhydrous conditions for acylations/sulfonylations. These conditions are general references, not specifications for this SKU.

Safety and Handling

• Item-specific hazard information
  • Signal word: Not specified for this item; refer to SDS.
  • GHS classification: Not specified for this item; refer to SDS.
  • H-statements/Pictograms: Not specified for this item; refer to SDS.
• General safety considerations for aliphatic secondary amino alcohols (literature/good practice)
  • Likely to be irritating to skin, eyes, and respiratory tract; avoid inhalation of vapors/aerosols and contact with skin/eyes.
  • PPE: lab coat, nitrile gloves, splash goggles; handle in a fume hood.
  • Incompatibilities: strong oxidizers; acyl halides, anhydrides, isocyanates (vigorous acylation/urea formation); strong mineral acids (salt formation, exotherm); CO2 absorption by free amine can form carbamates on standing.
  • Reactivity notes: both –OH and –NH– are nucleophilic; may react with activated carbonyls; can catalyze base-sensitive reactions; avoid unintended contact with acid chlorides/anhydrides.
  • First aid (overview; defer to SDS): rinse skin/eyes with water for ≥15 min; remove contaminated clothing; if inhaled, move to fresh air; if ingested, rinse mouth—seek medical attention.
  • Fire safety: organic combustible; use CO2, dry chemical, or foam. Combustion may release NOx/COx.

Always consult the SDS for this specific SKU for definitive hazard classification and response guidance.

Solvent Selection

This compound is a polar, bifunctional organic base/nucleophile. Solvent choice depends on whether you target O‑ or N‑reactivity and downstream isolation.

• Miscibility and polarity (general/literature expectations)
  • Good solubility: methanol, ethanol, isopropanol, acetone, DMSO, DMF, DMAc.
  • Moderate solubility: acetonitrile, ethyl acetate, dichloromethane.
  • Limited solubility: alkanes, toluene (can improve by heating or forming salts for aqueous work-up).
• Choosing solvents by transformation
  • Acylation/carbamate formation: CH2Cl2, THF, EtOAc, or MeCN; include a base (e.g., DIPEA) when using activated carbonyls.
  • Urea synthesis with isocyanates: anhydrous CH2Cl2/THF; avoid protic solvents that can compete.
  • Sulfonylation (tosylation/mesylation) of the OH: pyridine or CH2Cl2 with a hindered base; low temperature improves selectivity.
  • Reductive amination (on related substrates): protic alcohols or MeCN with NaBH(OAc)3/Et3N.
• Workup/isolation tips
  • Free base often extracts into organic phase at basic pH; convert to hydrochloride or other salts to crystallize or to enhance aqueous handling.
  • For chromatographic purification, add a small % of NH4OH or Et3N to silica eluent to prevent streaking/retention of basic amines.

Confirm actual solubility and handling on a small scale; defer to the CoA for any item-specific solubility notes if provided.

Storage and Reconstitution

• Item-specific storage
  • Storage conditions: Room temperature (as provided in Product Data).
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• General handling/stability for amino alcohols
  • Store tightly closed under dry, inert atmosphere if possible to minimize moisture uptake and CO2 interaction with the free amine (carbamate formation on prolonged exposure).
  • Protect from strong oxidants and reactive acylating agents during storage.
  • If needed, prepare a stable salt (e.g., HCl salt) for long-term storage; verify via NMR/elemental analysis.
• Reconstitution/solution prep
  • Solid or viscous liquids can be dissolved in dry alcohols (MeOH/EtOH/iPrOH), DMSO, DMF, or CH2Cl2 as appropriate for the intended use.
  • Prepare stock solutions freshly or store aliquots at 2–8 °C under inert gas to limit degradation; avoid repeated freeze–thaw cycles for solutions.

Always consult the CoA/SDS for any additional, item-specific storage cautions or incompatibilities for SKU M935364.

Structure and Identity

A bifunctional aliphatic building block combining a secondary amine and a secondary alcohol on two cyclohexyl frameworks.

• Item-specific identifiers (Product Data)
  • CAS: 1152964-08-3
  • CID: 24131540
  • InChIKey: 228098 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Composition (computed/literature)
  • Suggested molecular formula: C13H25NO (computed from name; for reference only)
  • Approx. molecular weight: ~211.35 g/mol (computed)
• Nomenclature and structural features (general description)
  • Name indicates a cyclohexan-1-ol ring bearing, at the 4-position, a secondary amino substituent linked to a 4‑methylcyclohexyl group.
  • Functional groups: secondary amine (–NH–) bridging two alicyclic carbons; secondary alcohol (–CHOH–) on a cyclohexyl ring.
  • Ring systems: two saturated six-membered (cyclohexyl) rings; one is 4‑methyl‑substituted.
  • Stereochemistry: not specified; the substituted cyclohexanol and the aminated stereocenter(s) on the rings can give rise to cis/trans relationships and potentially diastereomeric mixtures unless otherwise stated (general consideration; not item-specific).
  • 2D description: HO–C*(cyclohexyl) at C1, and at C4 of that ring a –NH– linker to a 4‑methylcyclohexyl group.

Note: Where exact identifiers (SMILES, full standardized InChIKey) are required for informatics, consult the CoA/Spec Sheet for this SKU.

Synthetic Utility

• Functional group leverage
  • Secondary amine: nucleophilic, basic; readily forms amides (acid chlorides/anhydrides, EDCI-mediated couplings), ureas (isocyanates/carbonyldiimidazole), and alkylated products (careful to avoid over-alkylation).
  • Secondary alcohol: allows esterification, carbonate formation, and activation (MsCl/TsCl) for substitution; intramolecular cyclizations possible when paired with suitable electrophiles.
• Selectivity/control
  • Protecting group strategy: Boc or Cbz on nitrogen to direct O‑acylation; silyl or carbonate protection on oxygen to direct N‑acylation.
  • Sterics: the cyclohexyl environments often impart selectivity in mixed acylation or alkylation scenarios, aiding regio-/chemoselection.
• Retrosynthetic value
  • Acts as a handle to append a constrained, lipophilic, basic moiety to scaffolds (e.g., peptidomimetics, PROTAC-like linkers) while offering an auxiliary OH for further diversification or conjugation.
• Purification/characterization tips
  • Free base may tail on silica; add 0.5–2% Et3N/NH4OH to eluents. Monitor by dual staining (ninhydrin for amine, KMnO4 for alcohol) or LC-MS in ESI+ mode (readily protonates).
  • Diastereomeric mixtures may arise; employ crystallization of salts or chiral SFC if stereochemical control is required.

Target Specificity

Not applicable. This product is a small-molecule reagent/building block and is not an antibody, enzyme, or affinity ligand. No target specificity data are provided for this item.