4-(Methanesulfonylmethyl)cyclohexan-1-amine - ≥95% , CAS No.1315498-93-1

CAS: 1315498-93-1 Cat. No.: M980245 Summenformel: C₈H₁₇NO₂S Molekulargewicht: 191.290

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: CS(=O)(=O)CC1CCC(CC1)N
• IUPAC Name: 4-(methylsulfonylmethyl)cyclohexan-1-amine
• InChIKey: ISVAEECBNYJRAX-UHFFFAOYSA-N
• INCHI: 1S/C8H17NO2S/c1-12(10,11)6-7-2-4-8(9)5-3-7/h7-8H,2-6,9H2,1H3
• Molekulargewicht: 191.290

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Klasse Organonitrogen compounds
      • Subclass Cyclohexylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Klasse: Organonitrogen compounds
• Subclass: Cyclohexylamines
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclohexylamines
• Alternative Parents: Sulfones Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexylamine - Sulfonyl - Sulfone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Organosulfur compound - Primary aliphatic amine - Amine - Aliphatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as cyclohexylamines. These are organic compounds containing a cyclohexylamine moiety, which consist of a cyclohexane ring attached to an amine group.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 191.290 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.098 Da
• Monoisotopic Mass: 191.098 Da
• Topological Polar Surface Area: 68.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 222.000
• 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 as standardized bioassay protocols. This item is a synthetic intermediate rather than an assay reagent. For practical laboratory use, see the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for procedure-style guidance on coupling, reductive amination, and α-sulfonyl functionalization.

Biological Roles

This compound is a synthetic organic building block without established endogenous biological roles.

• General considerations (literature)

  • Primary aliphatic amines can interact with biological macromolecules via ionic and hydrogen-bonding interactions; therefore, handle with normal precautions for bioactive amines.
  • The sulfone group is metabolically robust and often used in medicinal chemistry to modulate polarity, conformation, and metabolic stability of drug-like molecules; however, no specific biological function is attributed to this particular structure.

• Use context

  • Intended for research and laboratory synthesis only (per Product Data: Research Use Only). Not for human or animal therapeutic or diagnostic use.

No organismal pathway or receptor specificity is known for this exact compound based on the provided information.

Buffer Applications

Not typically applicable. 4-(Methanesulfonylmethyl)cyclohexan-1-amine is a synthetic building block, not a dedicated buffering agent. While its conjugate acid possesses basicity typical of primary aliphatic amines (literature pKa ~10–11), it is not used to formulate laboratory buffers. For relevant usage, see Reaction & Applications and Synthetic Utility.

Green Alternatives

This product is a solid/liquid building block, not a process solvent. “Greener” considerations therefore focus on solvent and reagent choices when using it.

• Greener solvent choices (literature/general)

  • Prefer 2-MeTHF, CPME, or toluene over THF/Et2O for strong-base steps (better safety/peroxide profile, often recyclable).
  • For amide couplings, ethanol or MeCN can replace DMF/NMP where feasible; water/MeCN biphasic protocols with water-soluble coupling agents may be applicable.
  • For chromatography, consider reverse-phase or crystallization/salt-formation to minimize solvent use.

• Reagent alternatives

  • Couplings: T3P (in EtOAc or 2-MeTHF) is a lower-toxicity alternative to HATU/BTU reagents and simplifies workup.
  • Reductive amination: hydrogenation (H2/Pd) or sodium triacetoxyborohydride in MeOH/EtOAc can reduce reliance on cyanoborohydride or DMF.

• Small comparison (literature)

  • THF vs 2-MeTHF: similar performance in base-mediated α-sulfonyl deprotonations; 2-MeTHF offers higher boiling point and better sustainability index.
  • DMF/NMP vs MeCN/EtOAc: MeCN/EtOAc are easier to remove, have better EHS profiles, but may reduce solubility; test concentration and temperature.

• Waste minimization

  • Use in-flow base-mediated functionalizations can reduce solvent volumes; in situ salt formation of the amine can aid crystallization and product isolation, reducing chromatography.

Pharmaceutical Uses

• Item-specific status

  • No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet if needed.

• General context (non-clinical)

  • This material can serve as an intermediate in the synthesis of amine-rich, saturated scaffolds used during medicinal chemistry campaigns. The sulfone enhances polarity and can act as a temporary activating group for C–C bond construction.
  • Possible roles in process chemistry include: intermediate for API candidates, handle for late-stage diversification, or precursor to salts for improved isolation.

• Compliance note

  • For research use only. Not formulated as a GMP-grade excipient or API. Any use in pharmaceutical development should be supported by appropriate qualification (identity/purity, residual solvents, elemental impurities) based on project requirements.

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 weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (informational; not product specifications)

  • Approx. formula and MW: C8H17NO2S, ~191.30 g/mol (computed from name)
  • Acid–base: primary aliphatic amine with typical conjugate acid pKa ~10–11 (literature, general for cyclohexylamines). The methylene α to the sulfone (–CH2–SO2–) is significantly acidified (pKa in DMSO commonly high 20s to low 30s for alkyl sulfones; literature generality), enabling deprotonation with strong bases.
  • Polarity/solubility (qualitative, literature): expected good solubility in polar aprotic solvents (DMF, DMSO, acetonitrile) and alcohols; free base typically sparingly soluble to moderately soluble in water, while protonated salts (e.g., HCl) are water-soluble.
  • Volatility: low (non-volatile solid or high-boiling oil anticipated for this MW and functionality; literature expectation).

• Refractive index, density, melting/boiling point, UV cutoff, residual water/peroxide/metal content

  • Not specified for this item; refer to CoA/Spec Sheet.

Note: Use the item’s CoA for definitive material-specific physical data; the above values are general literature expectations for analogous structures.

Quality and Grades

• Item-specific quality information

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades (general)

  • Research-grade building blocks are typically provided at assay >95% by NMR/LC unless otherwise noted; HPLC or LC–MS traces are commonly used to confirm purity. For trace metal, residual solvent, or water content, refer to the specific CoA; these are item-specific and not inferred.
  • If chromatography-grade material is required (e.g., low UV background), request UV cut-off and absorbance profile; not specified for this item.

• CoA and batch control

  • Each lot may exhibit small variations (e.g., polymorph, residual solvent). Verify identity by NMR/HRMS as needed for sensitive applications. For salt content vs free base, confirm with CoA.

• What this means for users

  • For coupling chemistry or medicinal chemistry SAR, verify amine content (titration) and residual water when using moisture-sensitive coupling reagents. If performing base-sensitive α-sulfonyl deprotonations, confirm absence of protic impurities.

Reaction and Applications

This reagent is a versatile bifunctional building block combining a nucleophilic primary amine with an α-activating sulfone.

• Transformations via the amine (literature/general)

  • Amide/urea/carbamate formation using acid chlorides, anhydrides, activated esters, or coupling reagents (HATU, EDCI, T3P). Protecting groups (Boc, Cbz, Fmoc) can be introduced to orthogonally mask the amine during sulfone chemistry.
  • Reductive amination: the amine can be introduced into more elaborate frameworks via condensation of the corresponding ketones/aldehydes followed by reduction (e.g., NaBH3CN, BH3·THF).
  • N-alkylation: under basic conditions with alkyl halides (consider competing C-alkylation at the α-sulfonyl position; protect or control conditions accordingly).

• Transformations via the sulfone (literature/general)

  • α-Deprotonation/alkylation: the methylene adjacent to –SO2– is significantly acidified; strong, non-nucleophilic bases (LDA, LiHMDS, NaHMDS; −78 to 0 °C) generate the carbanion, enabling C–C bond formation with alkyl halides, epoxides, or carbonyl electrophiles (via alkylation or aldol-type additions).
  • Elimination chemistry: subsequent manipulations can unveil alkenes (e.g., via β-elimination after α-functionalization) or serve as a handle for Julia-type olefination variants when converted to appropriate arylsulfone derivatives.
  • Oxidation state: the sulfone is already fully oxidized; it is robust under many conditions, aiding stepwise elaboration.

• Applications

  • Useful intermediate for assembling saturated amine-rich scaffolds in medicinal chemistry and fragment-to-lead programs.
  • Entry to diversity-oriented libraries via orthogonal chemistry at N and at the α-sulfonyl carbon.

Practical tip: Sequence planning is key—protect the amine to avoid N- vs C-alkylation ambiguity during α-sulfonyl deprotonations.

Reaction Conditions

• Amide coupling (literature guidance)

  • Typical: carboxylic acid (1.0 eq), this amine (1.1–1.5 eq), HATU or EDC·HCl (1.1–1.5 eq), base DIPEA (2–3 eq) in DMF or MeCN, 0–25 °C, 1–16 h. Workup via aqueous quench and extraction; purify by chromatography or crystallization.
  • Alternative green protocol: T3P (50% in EtOAc) with DIPEA in EtOAc or 2-MeTHF, rt to 50 °C.

• Reductive amination (literature)

  • Carbonyl (1.0 eq), amine (1.2–2.0 eq), AcOH (0.2 eq) in MeOH/THF; reduce with NaBH3CN (1.2 eq) at 0–25 °C, 2–12 h, or use NaBH(OAc)3 in DCE/MeCN. Catalytic hydrogenation (H2, Pd/C, 1–5 bar) is a cyanide-free option.

• α-Deprotonation/alkylation at the sulfone (literature)

  • Base: LDA, LiHMDS, or NaHMDS (1.1–1.5 eq) in anhydrous THF, toluene, or 2-MeTHF, −78 to 0 °C.
  • Electrophiles: primary alkyl bromides/iodides, benzyl halides; epoxides (to give β-hydroxysulfones); aldehydes/ketones (followed by trapping).
  • Quench: careful, at low temperature with NH4Cl(aq); protect amine (e.g., Boc) beforehand to prevent N-alkylation.

• Representative outcomes (qualitative)

  • Amide couplings: typically good yields (70–95%) under standard conditions when sterics permit.
  • α-Alkylations: moderate to high yields depending on electrophile and base; competing N-alkylation minimized by protection and temperature control.

All parameters above are general literature guidance for analogous substrates; optimize for your specific system.

Safety and Handling

• Item-specific hazard data

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

• General safety considerations (literature/good practice; not a substitute for SDS)

  • Primary aliphatic amines can be corrosive/irritant to skin, eyes, and respiratory tract; avoid inhalation and contact. Sulfone functionality is generally of low acute reactivity, but the molecule remains an organic base.
  • PPE: lab coat, chemical-resistant gloves (e.g., nitrile), safety goggles; handle in a fume hood.
  • Incompatibilities: strong oxidizers (may over-oxidize organic substrates), acylating/alkylating agents (uncontrolled reactions with the amine), and strong acids/bases without appropriate controls. For strong base-mediated chemistry (e.g., deprotonation α to sulfone), rigorously exclude moisture.
  • First aid (overview):
    • Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention as needed.
    • Inhalation: move to fresh air; support breathing; obtain medical attention.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
  • Fire: use CO2, dry chemical, or foam; product expected to be combustible organic.

Always consult the Aladdin SDS for authoritative hazard classification, exposure limits, and spill/accident response.

Solvent Selection

• Polarity and miscibility (literature/general)

  • As a bifunctional, moderately polar molecule (amine + sulfone), the free base typically dissolves well in polar aprotic media (DMF, DMSO, NMP, acetonitrile) and alcohols (MeOH, EtOH). Water solubility is limited in the free base but increases markedly upon formation of mineral-acid salts (e.g., HCl, H2SO4).
  • For chromatographic purification, normal-phase silica with polar eluents (DCM/MeOH with base additive like 0.5–1% Et3N) or reverse-phase C18 with aqueous acetonitrile are commonly effective.

• Choosing solvents by task

  • Amide coupling (acylation of amine): DMF, DCM, or MeCN are typical. Add base (DIPEA) and coupling reagent (HATU/EDC).
  • α-Deprotonation/alkylation at the sulfone-bearing methylene: use anhydrous THF, MTBE, toluene, or DME with strong, non-nucleophilic bases (LDA, NaHMDS, LiHMDS) under inert atmosphere.
  • Salt formation/crystallization: IPA/Et2O or EtOAc/hexanes systems often assist salt precipitation.

• Quick comparison (literature)

  • DMSO: maximal solubility; high boiling; harder to remove.
  • DMF/NMP: good solubility; compatible with peptide-type couplings; consider workup and safety.
  • MeCN: moderate solubility; easy removal; lower basicity environment.
  • Alcohols: facilitate salt formation/protonation equilibria; may compete in acylation if not controlled.

Note: Verify actual solubility for your lot experimentally; no item-specific solubility is specified.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (per Product Data). Protect from moisture and strong acids/bases. Keep container tightly closed.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Stability considerations (general)

  • Primary amines can adsorb CO2/H2O from air and may form salts over long exposure; store under inert gas if prolonged storage is expected. The sulfone group is typically robust to oxidation; avoid strong reducing agents unless intended.

• Reconstitution/dissolution (general)

  • Readily dissolves in polar aprotic solvents (DMF, DMSO, MeCN) and alcohols. For aqueous work, prepare as an acid salt (e.g., dissolve in minimal IPA and add HCl in dioxane) to enhance water solubility.
  • For moisture-sensitive transformations (e.g., α-deprotonation), dry the material under vacuum and dissolve in anhydrous, oxygen-free solvent; handle under inert atmosphere.

• Freeze–thaw guidance

  • Not typically applicable unless stored as a solution. For solution storage, use dry, oxygen-impermeable vials; aliquot to avoid multiple freeze–thaw cycles.

Always consult the CoA/SDS for batch-specific stability and handling recommendations.

Structure and Identity

Brief description: 4-(Methanesulfonylmethyl)cyclohexan-1-amine is a bifunctional aliphatic building block bearing a primary amine on a cyclohexane ring and a methanesulfonylmethyl substituent at the 4-position.

• Item-specific (from Product Data)

  • CAS: 1315498-93-1
  • CID: 58345904
  • InChIKey: 149643 (as provided)
  • 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 (non-spec; informational)

  • Expected molecular formula (parsed from name): C8H17NO2S
  • Approximate molecular weight: ~191.30 g/mol
  • Functional groups: primary aliphatic amine (–NH2), sulfone (–SO2–) within a –CH2–SO2–CH3 side chain, saturated cyclohexane ring.
  • Structural features: cyclohexan-1-amine core with a trans/relative stereochemistry not specified (achiral as drawn unless ring substitution imposes conformational preference). The –CH2–SO2–CH3 substituent is attached at C4 of the ring via the methylene carbon; the sulfone bears a terminal methyl group.

• 2D structure in words

  • Six-membered saturated ring bearing –NH2 at carbon 1 and a –CH2–SO2–CH3 substituent at carbon 4. The sulfone is tetrahedral at sulfur with two S=O bonds; the amine is primary and nucleophilic.

Synthetic Utility

• Functional group handles

  • Primary amine (nucleophile; can be protected as Boc/Fmoc/Cbz). Useful for amide, sulfonamide, urea, carbamate formation, and N-alkylation or reductive amination.
  • α-Sulfonyl methylene (–CH2–SO2–CH3) is activated toward deprotonation, enabling construction of C–C bonds adjacent to sulfur; post-functionalization can remove or transform the sulfone.

• Named/related strategies (literature)

  • Julia-type olefination pathways after converting to appropriate arylsulfone derivatives.
  • Ramberg–Bäcklund (from α-halo sulfones) to form alkenes—requires additional functionalization.
  • Auxiliary-like behavior: the sulfone can act as a traceless activating group for α-carbon elaboration followed by reductive removal (e.g., with Mg/Amalgam or SmI2 in some systems), though conditions must be tailored.

• Retrosynthetic value

  • Separates N-functionality from C(α)-reactivity, allowing orthogonal sequence control: protect N, elaborate α to the sulfone, then deprotect/couple at N. Alternatively, first derivatize N to install directing or solubilizing groups before C–C bond formations at the α position.

• Purification/handling tips

  • Add 0.5–1% Et3N to silica eluents to suppress streaking of the basic amine.
  • Consider isolating as a crystalline hydrochloride or p-toluenesulfonate salt for improved handling and stability when appropriate.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined target, or probe). No antigen, epitope, clone, or species reactivity information is provided or relevant.