3-Cyclopropylcyclohexan-1-amine - ≥95% , CAS No.1334146-49-4

CAS: 1334146-49-4 Cat. No.: C963611 分子式: C₉H₁₇N 分子量: 139.240

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

仕様と純度

≥95%

保管条件

Room temperature

純度

≥95%

名前と識別子

• カノニカル・スマイル: C1CC(CC(C1)N)C2CC2
• IUPAC Name: 3-cyclopropylcyclohexan-1-amine
• InChIKey: HMQZOXXSWCKCAS-UHFFFAOYSA-N
• INCHI: 1S/C9H17N/c10-9-3-1-2-8(6-9)7-4-5-7/h7-9H,1-6,10H2
• 分子量: 139.240

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• 分類: Organonitrogen compounds
• Subclass: Cyclohexylamines
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclohexylamines
• Alternative Parents: Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexylamine - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary aliphatic amine - Amine - Aliphatic homomonocyclic compound
• 説明: 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

化学的性質と物理的性質

• 分子量: 139.240 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 139.136 Da
• Monoisotopic Mass: 139.136 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 118.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• 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

No item-specific, validated application protocols are provided for this SKU. Typical uses are in organic synthesis as described under Reaction & Applications and Synthetic Utility.

For method development, consider including:

• Small-scale test reactions (0.1–0.2 mmol) to assess solubility and reactivity.
• Control experiments varying base, solvent, and temperature to optimize selectivity.
• If salt forms are prepared (e.g., HCl salt), document stoichiometry and workup procedures for reproducibility.

Refer to institutional SOPs and primary literature for detailed, reaction-specific protocols.

Biological Roles

This product is supplied strictly for research use. There are no biological roles or functions specified for this item.

General context for saturated aliphatic amines in chemical biology/medicinal chemistry (literature-based):

• Privileged motif: Cyclohexyl- and cyclopropyl-containing amines are frequently used to modulate lipophilicity, basicity, and conformational constraint in small-molecule libraries, often improving membrane permeability and metabolic stability.
• Protonation state in physiology: Primary aliphatic amines are predominantly protonated (as ammonium) near neutral pH (pKaH ~10–11), influencing distribution and target engagement in biochemical assays.
• Derivatization handle: The –NH2 group enables formation of amides, sulfonamides, carbamates, and ureas commonly found in bioactive scaffolds.

No cellular pathways, receptors, enzymes, or transporters are specifically associated with 3-cyclopropylcyclohexan-1-amine itself. Do not infer therapeutic or diagnostic utility from the information provided here.

Buffer Applications

Not typically used as a laboratory buffer component. Primary aliphatic amines have conjugate-acid pKa values around 10–11 and could, in principle, buffer in the alkaline range; however, this compound lacks the water solubility, low UV absorbance profile, and regulatory acceptance typical of standard buffers (e.g., Tris, CAPS, carbonate).

Recommendation: Use established buffering systems for pH control. Employ this amine as a reactive building block rather than as a buffer.

Green Alternatives

Greener choices focus on solvent selection and coupling methodologies, as the amine itself is the targeted building block.

• Solvent substitutions (literature/general):
  • Replace chlorinated solvents (DCM, CHCl3) with EtOAc or 2-MeTHF where solubility allows.
  • Prefer MeOH/EtOH over isopropanol or higher alcohols when feasible due to lower environmental impact.
  • Use anisole, cyclopentyl methyl ether (CPME), or 2-MeTHF as greener ethers versus THF/diethyl ether (better stability, reduced peroxide risk for CPME).
• Coupling reagents and activation:
  • Consider EDC·HCl + Oxyma or DMTMM as alternatives to benzotriazole-based reagents (HATU/HBTU), reducing energetic byproducts.
  • Explore enzymatic amidation or flow reductive amination to limit waste and improve safety.
• Workup and purification:
  • Favor salt toggling (acid/base extractions) over silica-intensive chromatography to reduce solvent use.
  • Implement telescoped steps (e.g., in situ imine formation then reduction) to minimize intermediate isolations.

Illustrative comparison (general):

• THF vs 2-MeTHF: similar performance; 2-MeTHF is bio-derived, more hydrophobic, higher bp aiding recovery.
• DCM vs EtOAc: EtOAc is less toxic and biodegradable; DCM offers higher solubility but worse environmental profile.

Adopt green metrics (E-factor, PMI) and solvent selection guides (ACS, GSK) during route design with this amine.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; it is for research use only.

General formulation/synthesis context (literature-based):

• Intermediate/building block: Frequently, saturated primary amines are incorporated into active pharmaceutical ingredient (API) candidates via amide, sulfonamide, carbamate, or urea linkages.
• Salt forms: For handling and crystallization studies, forming hydrochloride, mesylate, or sulfate salts may improve stability, hygroscopicity, and solid-state properties. Salt selection is typically guided by pKa, solubility, and crystallinity screens.
• Impurity control: Residual amines can impart odor and reactivity; rigorous purge during API workups is standard. Monitoring by GC or LC–MS is common.

This information is provided for process-development perspective only; no therapeutic or clinical claims are implied.

Physical Properties

Item-specific physical specifications (exact BP, MP, density, refractive index, UV cutoff) are not provided for this SKU. Refer to the CoA/Spec Sheet for authoritative values.

Literature/computed expectations for a saturated C9 primary amine with a cyclohexyl core and cyclopropyl substituent (provided for planning only):

• State/appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: see Structure & Identity (literature/computed)
• Molecular weight: see Structure & Identity (literature/computed)
• Boiling point: Not specified for this item; primary aliphatic amines of similar carbon count often boil in the ~170–220 °C range (literature, general trend). Do not use as specification.
• Melting point: Not specified for this item; many low-polarity primary amines are liquids or low-melting solids near ambient temperature (literature, general trend).
• Density (20–25 °C): Not specified for this item; typical liquid aliphatic amines are ~0.80–0.90 g/mL (literature, general trend).
• pKa (conjugate acid, pKaH): Typically ~10–11 for unhindered primary aliphatic amines; cyclohexylamine is ~10.6 (literature). Substitution may shift slightly.
• LogP (neutral base): Likely in the moderate hydrophobic range due to bicyclic hydrocarbon skeleton; not specified for this item.
• Solubility:
  • Water: Limited to moderate as the free base; markedly increased upon protonation to water-soluble ammonium salts (literature, general behavior).
  • Organic solvents: Expected to be miscible or highly soluble in alcohols, ethers, chlorinated solvents, and hydrocarbons (literature, general behavior).

Use these literature/computed notes only for preliminary method development; confirm critical parameters experimentally or via the product’s CoA.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Primary amines are generally supplied neat without stabilizers unless otherwise indicated.
• Analytical controls (general expectations): For research-grade aliphatic amines, identity is commonly supported by NMR and MS, with GC/HPLC purity reporting. Water content (e.g., Karl Fischer), residual solvents, and inorganic/metallic impurities may be included in a detailed CoA where applicable. Item-specific limits are not specified for this product.
• What the grade implies: In the absence of a declared “HPLC,” “anhydrous,” or “pharmacopeial” grade, users should assume standard research-use quality suitable for synthetic, screening, and method-development applications, not for clinical or GMP manufacturing.
• UV cutoff/low-UV suitability: Not specified for this item; if using as a mobile-phase additive or analyte near UV detection limits, evaluate baseline effects experimentally.

For critical applications (e.g., asymmetric synthesis, medicinal chemistry SAR campaigns), request and review the CoA/Spec Sheet for exact purity, diastereomeric composition (if controlled), water content, and any residual solvent or metal data.

Reaction and Applications

As a sterically defined, saturated primary amine, 3-cyclopropylcyclohexan-1-amine is a versatile building block for medicinal and materials chemistry where a conformationally constrained, lipophilic amine is desired.

Representative application families (literature/general):

• Amide formation: Coupling with carboxylic acids using HATU/HBTU/EDC·HCl or acid chlorides/anhydrides to furnish secondary amides. The cyclopropyl–cyclohexyl framework enhances metabolic stability and lipophilicity in drug discovery motifs.
• Sulfonamide/Carbamate/Urea synthesis: Reaction with sulfonyl chlorides (e.g., TsCl), chloroformates/Boc2O, or isocyanates/activated carbonates.
• Reductive amination: Condense with aldehydes/ketones to form imines/iminium ions, then reduce (NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation) to install diversified N-alkyl analogs.
• Alkylation (SN2) and N-arylation: N-alkylation under phase-transfer or polar aprotic conditions; Buchwald–Hartwig or Ullmann-type N-arylation on aryl halides (where base-tolerant conditions are selected).
• Salt formation/crystallization: Formation of HCl, mesylate, or other salts for purification, handling, and property tuning.

Practical tips:

• Base strength: pKaH ~10–11; ensure appropriate base/acid stoichiometry in couplings to control protonation state.
• Protection strategies: Boc, Cbz, or Fmoc protection facilitate multistep sequences; Boc removal under TFA; Cbz by hydrogenolysis.
• Diastereomeric considerations: As a 1,3-disubstituted cyclohexane, cis/trans mixtures may occur; chromatographic separation or salt resolution may be needed if a single diastereomer is required.

These are general synthetic applications; tailor conditions to substrate electronics and sterics.

Reaction Conditions

Typical conditions for common transformations of primary aliphatic amines (literature/general guidance; optimize per substrate):

• Amide coupling:

  • Reagents: HATU or EDC·HCl/Oxyma; base: DIPEA (2–3 equiv).
  • Solvent: DMF, NMP, or DCM.
  • Temp/time: 0–25 °C, 1–16 h.
  • Notes: Control protonation; pre-cool for acid chlorides to minimize overacylation; monitor by LC–MS.

• Acyl chloride acylation:

  • Base: TEA or pyridine (2–3 equiv).
  • Solvent: DCM or THF.
  • Temp: 0–25 °C.
  • Quench: Aqueous bicarbonate; extract and wash acid to remove base salts.

• Sulfonamide formation (TsCl):

  • Base: TEA or NaHCO3.
  • Solvent: DCM, MeCN, or THF.
  • Catalyst: DMAP (0–10 mol%) as needed.

• Reductive amination:

  • Step 1: Carbonyl + amine in MeOH/EtOH/THF with 3Å MS or slight acid (AcOH) to drive imine.
  • Step 2: NaBH3CN (pH 5–6, AcOH buffer) or NaBH(OAc)3 (neat AcOH/DCM/MeCN) at 0–25 °C, 1–18 h; alternatively H2 (1–5 bar), Pd/C in EtOH.

• Boc protection:

  • Reagents: Boc2O (1.1–1.5 equiv), base: TEA/NaHCO3.
  • Solvent: DCM/THF.
  • Temp: 0–25 °C.

• Buchwald–Hartwig N-arylation:

  • Catalyst: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%); Ligand: BINAP/XPhos/BrettPhos.
  • Base: NaOtBu or Cs2CO3.
  • Solvent: Toluene/dioxane.
  • Temp: 80–110 °C.

Expected yields vary widely by substrate; confirm by small-scale screening. Manage cis/trans diastereomer issues by monitoring and, if needed, separating isomers after transformation.

Safety and Handling

GHS classification, signal word, pictograms, and H-statements are not specified for this item. Always consult the product SDS for authoritative safety information.

General safety considerations for aliphatic primary amines (literature-based guidance):

• Hazards: May be corrosive/irritating to skin, eyes, and respiratory tract; vapors can be irritating. Amines can be harmful if swallowed or inhaled. Sensitization is uncommon but possible.
• PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Employ a fume hood to minimize inhalation exposure.
• Handling:
  • Avoid contact with acids without control—exothermic neutralization can occur.
  • Amines can absorb CO2 and moisture from air; keep containers tightly closed.
  • Avoid contact with oxidizing agents and acid chlorides without appropriate controls.
• First aid (overview; consult SDS):
  • Skin/eye contact: Immediate decontamination with copious water for at least 15 minutes; remove contaminated clothing; seek medical advice.
  • Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention.
• Spill response: Absorb small spills with inert material (vermiculite, dry sand). For larger releases, ventilate area and follow institutional spill procedures.
• Fire safety: Many amines are combustible; use appropriate extinguishing media (CO2, dry chemical, foam). Fire may produce nitrogen oxides.

These are general amine handling principles; defer to the SDS and institutional safety protocols for this specific product.

Solvent Selection

This compound is a hydrophobic primary amine with moderate basicity and nucleophilicity.

• Polarity class (general): Moderately polar, proton-accepting/proton-donating (via –NH2). Basic nitrogen favors hydrogen bonding with protic solvents and coordination in polar aprotics.
• Miscibility profile (literature/general):
  • High solubility in alcohols (MeOH, EtOH, i-PrOH), ethers (THF, MTBE), chlorinated solvents (DCM, chloroform), and many hydrocarbons (toluene, heptane).
  • Limited to moderate solubility in water as the free base; readily water-soluble as ammonium salts (e.g., hydrochloride).
• When to choose protic vs aprotic:
  • Protic (MeOH/EtOH): Favor salt formation, reductive amination, or SN1-type solvolysis; convenient workups.
  • Aprotic (DCM/THF/DMF/MeCN): Preferred for acylations, sulfonylations, and peptide-type couplings (HATU/EDC), minimizing side reactions and improving reagent solubility.
• Acidic media: The amine will be protonated and water-soluble; useful for extractions and salt isolation but suppresses nucleophilicity.
• Basic media: Free base is more nucleophilic and hydrophobic; useful for alkylation and acylation reactions.

Comparison (literature/general):

• THF vs 2-MeTHF: 2-MeTHF offers greener profile and higher hydrophobicity; both dissolve aliphatic amines well.
• DCM vs EtOAc: DCM provides better solubility for many reagents but is less green; EtOAc can suffice for extractions and some couplings.

Confirm solubility and solvent compatibility experimentally for your specific transformation.

Storage and Reconstitution

• Storage conditions (from Product Data): 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.
• Container/closure: Store in a tightly sealed container to limit moisture and CO2 uptake. Glass with PTFE-lined cap is recommended for amines.
• Inert atmosphere: Optional but beneficial for long-term stability, particularly if frequent opening is expected.
• Light sensitivity: Not typically light-sensitive; store away from direct sunlight as good practice.
• Reconstitution/Use:
  • Use as supplied (neat). To prepare solutions, select dry, compatible solvents (e.g., DCM, THF, MeOH, EtOH, MeCN) based on the intended application.
  • For aqueous work, prepare acidic solutions to form the ammonium salt and enhance water solubility; adjust pH carefully.
• Freeze–thaw guidance: Not applicable to neat liquids/solids; if stored as a solution, avoid repeated freeze–thaw cycles and prepare single-use aliquots.
• Stability notes: Avoid strong oxidants. Minimize prolonged exposure to air to reduce odor development and CO2 uptake.

Always refer to the product’s CoA/Spec Sheet and SDS for item-specific handling and stability details. For research use only.

Structure and Identity

Overview: 3-Cyclopropylcyclohexan-1-amine is a saturated, aliphatic primary amine bearing a cyclopropyl substituent at the 3-position of a cyclohexane ring and an amino group at the 1-position. As a 1,3-disubstituted cyclohexane, mixtures of cis/trans diastereomers are possible in the absence of stereochemical control.

• Molecular formula (literature/computed): C9H19N (free base considered as C9H19N; neutral parent often represented as C9H17N depending on hydrogen counting conventions; typical empirical formula for the free amine is C9H19N)
• Molecular weight (literature/computed): ~141.26 g/mol for C9H19N; ~139.24–141.26 g/mol range reported depending on exact empirical representation. Not specified for this item; refer to CoA/Spec Sheet for the definitive value.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• CAS: 1334146-49-4
• CID: 54594791 (PubChem, for reference)
• Key functional group: Primary aliphatic amine (–NH2)
• Structural features:
  • Six-membered cyclohexane ring with a primary amine at C1 (cyclohexan-1-amine scaffold)
  • Cyclopropyl substituent at C3 (compact, highly strained C3 ring contributing to lipophilicity and conformational constraint)
  • Potential for cis/trans diastereomerism about the ring; conformational equilibria between chair conformers affect axial/equatorial orientation of substituents.
• 2D description in words: A cyclohexane chair bearing –NH2 at C1 and a cyclopropyl group at C3; other ring positions are unsubstituted hydrocarbon carbons.

Synthetic Utility

Key reactivity arises from the primary amine on a conformationally constrained, hydrophobic scaffold.

• Nucleophilic reactions:
  • Acylation/Amide formation: With acyl chlorides, anhydrides, or activated esters (HATU/EDC). Use base (DIPEA, TEA) in aprotic solvent to maintain the free base.
  • Sulfonylation: Reaction with sulfonyl chlorides (e.g., TsCl, MsCl) to afford sulfonamides—often excellent leaving groups or pharmacophores.
  • Carbamate/Urea formation: Via chloroformates (Boc2O) or isocyanates; CDI or triphosgene protocols enable urea linkages.
• Reductive amination: Straightforward installation of N-alkyl substituents after imine formation with aldehydes/ketones; reduction with NaBH3CN/NaBH(OAc)3 or catalytic hydrogenation.
• Protection/deprotection: Boc, Cbz, or Fmoc protection supports multi-step sequences and regioselective transformations.
• Metal-mediated N-arylation: Buchwald–Hartwig coupling with aryl halides under Pd catalysis; Cu-catalyzed Ullmann variants also applicable.
• Resolution/Isomer control: If a single cis/trans diastereomer around the cyclohexane ring is required, leverage crystallization of diastereomeric salts or chromatographic separation; downstream transformations can preserve or invert relative stereochemistry depending on conditions.

The cyclopropyl substituent introduces ring strain and steric bias that can influence transition-state geometry, sometimes enhancing selectivity or altering reaction rates compared to linear alkyl amines.

Target Specificity

Not applicable. This product is a small-molecule amine building block, not a biological macromolecule or affinity reagent. No target, epitope, clone, or species reactivity is specified for this item.