4-(Aminomethyl)octane - ≥95% , CAS No.857818-18-9

CAS: 857818-18-9 Cat. No.: A942025 Formula: C₉H₂₁N Peso molecolare: 143.270

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CCCCC(CCC)CN

IUPAC Name

2-propylhexan-1-amine

InChIKey

CUEUXLBCXLPVSU-UHFFFAOYSA-N

INCHI

1S/C9H21N/c1-3-5-7-9(8-10)6-4-2/h9H,3-8,10H2,1-2H3

Peso molecolare

143.270

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Amines
        • Level5 Primary amines
          • Level6 Monoalkylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Primary amines
• Direct Parent: Monoalkylamines
• Alternative Parents: Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydrocarbon derivative - Primary aliphatic amine - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic 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

Proprietà chimiche e fisiche

• Peso molecolare: 143.270 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 143.167 Da
• Monoisotopic Mass: 143.167 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 61.700
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic protocols, see the Reaction Conditions, Synthetic Utility, and Reaction & Applications sections.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.

• General biochemical context (no clinical claims)

  • 4-(Aminomethyl)octane is a simple primary aliphatic amine with a C9 hydrophobic chain. Such molecules are not endogenous metabolites but mimic features of fatty amines and lipidated amines, which can interact with membranes due to hydrophobic tails and cationic headgroups (when protonated).
  • In biochemical research, long-chain primary amines and their salts are used as building blocks for cationic lipids, ion-pairing reagents, and surface modifiers. Protonation state (pKaH ~10.4–10.8, literature) governs charge at physiological pH and thus influences binding to phospholipid bilayers and polyanionic biomolecules.
  • Derivatives (amides, quaternary ammonium salts) often display altered surfactancy and can serve as model compounds for studying membrane interactions or for preparing functionalized nanoparticles and delivery materials. The parent free base is primarily a synthetic intermediate rather than a biological reagent.

All uses are for research and laboratory experimentation only.

Buffer Applications

This compound is not a conventional biological buffer. Primary aliphatic amines have conjugate acid pKa values around 10.4–10.8 (literature), offering limited buffering near pH 10–11 in aqueous systems, but their low water solubility and odor make them impractical as buffer components.

• Practical notes
  • If an aqueous system is required, use the corresponding water-soluble ammonium salt (e.g., hydrochloride) and validate pH/pKa.
  • For non-aqueous titrations or as a basic additive (e.g., in HPLC mobile phases for specialized applications), volatile, well-characterized amines (e.g., triethylamine) are typically preferred.

For routine buffering needs, select established Good’s buffers or standard inorganic/organic buffering systems.

Green Alternatives

While the reagent itself is the desired nitrogen source, greener choices mainly concern solvent and reagent selection for transformations involving 4-(aminomethyl)octane.

• Greener solvent choices (literature guidance)

  • Replace chlorinated solvents (DCM) with bio-based ethers (2-MeTHF) or CPME for amide couplings and protections.
  • Prefer alcohols (EtOH, i-PrOH) or MeCN over DMF/NMP when compatible with coupling chemistry and workup.

• Reagent selection

  • Amide formation: Use carbodiimide chemistry with catalytic DMAP in greener solvents, or employ green coupling agents and coupling in EtOAc/2-MeTHF. Enzymatic amidation in organic media may be feasible for select substrates.
  • Reductive amination: NaBH(OAc)3 in toluene/EtOAc or catalytic hydrogenation (H2, Pd/C) in ethanol can reduce waste versus cyanoborohydride.

• Energy and waste minimization

  • Conduct reactions at ambient temperature/short times where possible; apply continuous flow for exothermic acylations.

• Comparison snapshot (general)

  • DCM vs 2-MeTHF: Similar solvating power for acylations; 2-MeTHF has higher boiling point, bio-based origin, better safety profile; trade-off is more challenging solvent removal and possible peroxide monitoring.
  • DMF/NMP vs MeCN/EtOH: MeCN/EtOH are easier to remove and often less hazardous; DMF/NMP offer higher polarity but carry reproductive-toxicity concerns.

Note: Choose greener approaches consistent with your target chemistry and regulatory constraints.

Pharmaceutical Uses

• Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

• General formulation/manufacturing context (no therapeutic claims)

  • Primary long-chain amines like 4-(aminomethyl)octane serve as intermediates to prepare:
    • Amide-linked lipophilic excipients (e.g., fatty amide derivatives) that can modulate solubility and permeability in research formulations.
    • Quaternary ammonium salts used as phase-transfer agents or cationic surfactants; such salts can aid emulsification and stabilization in nonclinical formulations and materials research.
    • Cationic lipid building blocks after further functionalization, explored in research for complexing polyanions (e.g., nucleic acids) in delivery material development.
  • Salt formation (e.g., HCl salt) improves handling, crystallinity, and aqueous compatibility, which can be advantageous for isolation and dosing in pre-formulation studies.

Note: No pharmacopeial monograph or clinical application is implied for this specific item. All uses are restricted to research and laboratory development.

Physical Properties

• Item-specific specifications

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

• Literature/computed (for closely related primary C9 aliphatic amines; for guidance only, not item specifications)

  • Molecular formula: C9H21N; Mr ≈ 143.27 g/mol
  • Physical state at RT: typically colorless to pale yellow liquid (amines may have characteristic amine odor)
  • Boiling point: typically ~200–210 °C at 1 atm (literature, nonylamine range; positional isomers similar)
  • Melting point: often below 0 °C (long-chain primary amines vary by isomer; many are liquids at RT)
  • Density (20–25 °C): ~0.79–0.83 g/mL (literature range for C9 primary amines)
  • Refractive index (nD20): ~1.42–1.44 (literature)
  • pKa (conjugate acid, pKaH): ~10.4–10.8 in water at 25 °C (typical primary alkyl amines)
  • LogP (octanol/water): expected moderately high (≈3–4), reflecting hydrophobic C9 chain; actual value depends on isomer
  • Solubility: low in water; miscible with nonpolar and many moderately polar organic solvents (e.g., hexanes, toluene, Et2O, THF, alcohols). Forms water-soluble ammonium salts with strong acids.

Notes: Values above are typical literature guidance for primary C9 aliphatic amines and may vary for this specific constitutional isomer. For exact specifications relevant to this SKU, refer to the product CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity information: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting typical grades (general guidance)

  • Research or laboratory grade: Suitable for most synthetic and development work; impurity profiles generally adequate for discovery chemistry.
  • Purity reporting: For amines, residual water, amine value (mg KOH/g), and GC area % are often used. Ultra-low metal content and UV cutoffs are less critical unless for catalysis or photochemical applications.
  • Stabilizers: Primary aliphatic amines typically do not require stabilizers; however, trace antioxidants or basicity modifiers are sometimes used in industry. If present, they will be listed on the CoA.

• What to check on receipt (best practices)

  • Verify GC purity, water content (Karl Fischer), and identity (1H NMR showing –CH2–NH2 and alkyl signals; IR N–H stretch ~3300 cm−1).
  • Inspect for discoloration or odor changes, which may indicate oxidation or contamination.

For application-critical specifications (e.g., metal content for cross-couplings, residual solvents), request the current CoA/Spec Sheet for SKU A942025.

Reaction and Applications

As a primary aliphatic amine, 4-(aminomethyl)octane is a versatile nucleophile/base for assembling nitrogen-containing molecules and materials.

• Typical transformations (literature/general)

  • Amide formation: Coupling to carboxylic acids (EDC·HCl, HATU, TBTU, PyBOP, DCC) or acylation with acid chlorides/anhydrides to give secondary amides bearing a hydrophobic C9 tail.
  • Ureas/carbamates/sulfonamides: Reaction with isocyanates or chloroformates; sulfonylation with sulfonyl chlorides (e.g., TsCl) under base.
  • Imine/enamine formation: Condensation with aldehydes/ketones; reductive amination with NaBH3CN/NaBH(OAc)3 or catalytic hydrogenation for secondary amines.
  • N-alkylation: SN2 alkylation with alkyl halides (risk of over-alkylation—use protecting groups or stoichiometry control). Borrowing-hydrogen catalysis affords monoalkylation selectivity with alcohols.
  • Cross-coupling (Buchwald–Hartwig, Chan–Lam): As an amine partner to aryl (pseudo)halides or boronic acids to build N-aryl secondary amines.
  • Michael/aza-Michael additions: To activated alkenes (acrylates, acrylonitrile) for β-alkylated amines.
  • Salt formation: Quaternization with alkyl halides to generate ammonium surfactant precursors.

• Use-cases

  • Hydrophobic linker/spacer in conjugates and materials (e.g., amide-linked lipophilic tails).
  • Intermediate for cationic lipids, phase-transfer agents, or surface-active species after quaternization.

• Practical tips

  • Drying: Amines can be dried over KOH pellets, CaH2, or molecular sieves; distill under reduced pressure if necessary.
  • Acid-sensitive: Avoid unintended exposure to acylating agents; neutralize acid residues before addition.
  • Odor control: Work in fume hood; cap promptly to minimize volatilization/odor.

All applications are for research and laboratory use only.

Reaction Conditions

General, literature-based guidance for primary aliphatic amines like 4-(aminomethyl)octane (optimize per substrate):

• Amide coupling

  • Solvent: DMF, MeCN, DCM, 2-MeTHF, or EtOAc.
  • Reagents: HATU or EDC·HCl (1.1–1.5 eq), amine (1.5–2.5 eq), base (DIPEA 2–3 eq).
  • Temperature/time: 0–25 °C, 1–16 h. Typical isolated yields: 70–95% for unhindered acids.

• Acyl chloride/anhydride acylation

  • Solvent: DCM, toluene, or 2-MeTHF; base: NEt3/DIPEA (2–3 eq).
  • Temperature: 0 °C to rt, slow addition to control exotherm; 1–3 h.

• Reductive amination

  • Solvent: MeOH/EtOH/i-PrOH or toluene/MeCN with 3Å MS.
  • Conditions: Carbonyl (1.0 eq), amine (1.2–2.0 eq), AcOH (0.2–0.5 eq) for imine formation, then NaBH(OAc)3 (1.2–1.5 eq) at rt, 2–18 h; or H2 (1–5 bar), Pd/C (5–10 wt%), EtOH, rt–50 °C.
  • Yields: 60–95% depending on sterics and chemoselectivity.

• N-alkylation (SN2)

  • Solvent: MeCN, DMF, DMSO; base: K2CO3, NaH, or Cs2CO3.
  • Electrophile: primary halides/tosylates; 0.5–1.0 eq for monoalkylation control.
  • Temperature: rt–60 °C; 2–24 h. Monitor for dialkylation.

• Boc protection

  • Reagents: Boc2O (1.1–1.5 eq), NEt3 (2 eq), DCM/2-MeTHF, 0 °C→rt, 1–3 h. Deprotect with TFA in DCM (0 °C→rt).

• Drying/handling

  • Dry amine over KOH pellets or CaH2; distill under reduced pressure if necessary. Store under inert atmosphere to limit CO2 uptake when working over extended periods.

All parameters are typical literature conditions; adjust to your substrate and scale.

Safety and Handling

• Item-specific hazard statements/classification

  • GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

• General safety profile for primary aliphatic amines (literature-based guidance; defer to SDS for this item)

  • Hazards: Irritating/corrosive to skin, eyes, and respiratory tract; may be harmful if swallowed. Combustible liquid; vapors may be irritating.
  • Reactivity: Bases; react exothermically with acids and acid chlorides/anhydrides; can react with oxidizers; may absorb CO2 from air to form ammonium carbamates on surfaces.
  • Peroxide risk: Not typically peroxide-forming.

• Handling

  • Use in a chemical fume hood. Avoid inhalation/skin contact. Employ appropriate PPE: lab coat, nitrile gloves, splash goggles. For larger-scale operations, consider face shield and butyl/laminated gloves.
  • Avoid contact with acids, acid halides, acylating agents, isocyanates, strong oxidizers, and carbonyl compounds unless intended.

• First aid (general)

  • Skin/eye contact: Immediate irrigation with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention.
  • Inhalation: Move to fresh air; monitor for respiratory irritation; medical evaluation as needed.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.

• Fire and spill

  • Firefighting: Alcohol-resistant foam, dry chemical, CO2. Cool containers with water spray.
  • Spill response: Absorb with inert material (vermiculite), avoid ignition sources, ventilate area, neutralize residues cautiously.

Always consult the SDS specific to SKU A942025 for authoritative guidance.

Solvent Selection

This product is a hydrophobic primary amine reagent, not a solvent.

• Polarity and miscibility (literature-based behavior of C9 aliphatic amines)

  • Poorly water-soluble in free-base form; forms water-soluble ammonium salts with strong acids (e.g., HCl, H2SO4).
  • Miscible or highly soluble in nonpolar and moderately polar organics (hexanes, toluene, diethyl ether, MTBE, CPME, THF, DCM, EtOAc, alcohols).

• Practical choices by transformation

  • Amide couplings: DMF, DMAc, NMP, MeCN, DCM, or green ethers (2-MeTHF/CPME). For acid chloride couplings, use aprotic solvent with base (Et3N, DIPEA) and low temperature.
  • Reductive amination: Alcohol solvents (MeOH/EtOH/i-PrOH) or toluene/MeCN with NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
  • N-alkylation (SN2): Polar aprotic (MeCN, DMF, DMSO) with base; phase-transfer in biphasic toluene or xylene can help less soluble electrophiles.
  • Protection (Boc, Cbz): DCM/2-MeTHF with base (NEt3) at 0–25 °C.

• When to choose alternatives

  • If water compatibility is needed, use the corresponding hydrochloride salt to increase aqueous solubility.
  • For greener processing, prefer 2-MeTHF/CPME or bioalcohols over chlorinated solvents where feasible.

Storage and Reconstitution

• Item-specific storage

  • Storage conditions: Room temperature (per Product Data). Keep container tightly closed.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General handling recommendations for primary aliphatic amines

  • Protect from strong acids, acid chlorides/anhydrides, and oxidizers.
  • Minimize exposure to air/CO2 to reduce formation of ammonium carbamate films; for long-term storage, consider an inert gas headspace and a desiccant.
  • If freezing is desired for long-term archiving, store in sealed amber glass at 2–8 °C or −20 °C; allow to warm to ambient before opening to prevent moisture ingress.

• Reconstitution

  • Supplied neat; no reconstitution required. If a solution is needed, prepare in a compatible anhydrous solvent (e.g., 2-MeTHF, toluene, THF, DCM, MeOH) under dry conditions.

• Stability/quality checks

  • Periodically verify identity/purity by GC or 1H NMR (look for expected alkyl/NH2 signals). Karl Fischer can assess adventitious water if critical.

• Research Use Note

  • For research use only.

Structure and Identity

Brief overview: 4-(Aminomethyl)octane is a saturated, linear C8 hydrocarbon bearing a primary aminomethyl substituent at the 4-position, giving a C9 primary aliphatic amine (a nonylamine constitutional isomer).

• Item-specific (from Product Data)

  • Product name: 4-(Aminomethyl)octane (SKU: A942025)
  • CAS: 857818-18-9
  • PubChem CID: 14416531
  • InChIKey: 53765 (as provided)
  • Storage: Room temperature
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/Literature structural identifiers and descriptors (general reference)

  • Molecular formula (literature): C9H21N
  • Relative molecular mass (Mr, literature): ~143.27 g/mol
  • Example canonical SMILES (literature): CCCCC(CN)CCC
  • Functional groups: Primary aliphatic amine (–CH2–NH2); fully saturated alkyl chain (no rings, no heteroatoms besides N)
  • Structural description (2D): An eight-carbon straight chain (octane). The central carbon (C4 by one numbering) bears a –CH2–NH2 substituent, yielding a primary amine one carbon removed from the backbone (aminomethyl). No stereocenters; constitutionally isomeric with nonylamine.

• Category context

  • Listed under: 生命科学 (Life Science) — research use only.

Synthetic Utility

• Functional handle

  • Primary aliphatic amine (–CH2–NH2) with strong nucleophilicity and basicity enables formation of amides, ureas, sulfonamides, carbamates, imines, and secondary/tertiary amines.

• Retrosynthetic value

  • Serves as a lipophilic nitrogen synthon. Incorporation via amide coupling onto carboxylic acid-bearing scaffolds introduces a C9 tail, tuning solubility and permeability. De novo installation via reductive amination onto carbonyl compounds offers flexibility in late-stage diversification.

• Named/representative reactions (literature)

  • Amide couplings: HATU/EDC/TBTU with DIPEA or collidine; acyl chloride/anhydride acylations at 0–25 °C.
  • Reductive amination: NaBH3CN/NaBH(OAc)3 or catalytic H2 (Pd/C, PtO2) with aldehydes/ketones.
  • Protecting groups: Boc (Boc2O, base), Cbz (Cbz–Cl), Fmoc (Fmoc–Cl) for orthogonal strategies.
  • N-arylation: Buchwald–Hartwig amination with aryl halides (Pd/XPhos/BrettPhos systems) to produce N-alkyl anilines.
  • Aza-Michael: Addition to acrylates/maleimides (often catalysis-free or base-catalyzed).
  • Alkylation: SN2 with alkyl halides (control over-alkylation by temporary protection or stoichiometry).

• Practical considerations

  • Use anhydrous conditions when required; dry over KOH/CaH2 or sieves.
  • Protonation state control is key: ensure free base for nucleophilic steps; convert to salt for purification/handling as needed.
  • The hydrophobic chain can cause phase separation; biphasic or micellar conditions may require surfactants or co-solvents.

Target Specificity

Not applicable. 4-(Aminomethyl)octane is a small-molecule primary amine, not a biological targeting reagent (e.g., antibody/ligand). No antigen, epitope, isotype, or species reactivity data apply to this product.