3-Octylaniline - ≥98% , CAS No.118198-99-5

CAS: 118198-99-5 Cat. No.: O971036 Summenformel: C₁₄H₂₃N Molekulargewicht: 205.340

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: CCCCCCCCC1=CC(=CC=C1)N
• IUPAC Name: 3-octylaniline
• InChIKey: OBNZIMFKLILQCF-UHFFFAOYSA-N
• INCHI: 1S/C14H23N/c1-2-3-4-5-6-7-9-13-10-8-11-14(15)12-13/h8,10-12H,2-7,9,15H2,1H3
• Molekulargewicht: 205.340

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Aniline and substituted anilines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Aniline and substituted anilines
• Intermediate Tree Nodes: Not available
• Direct Parent: Aniline and substituted anilines
• Alternative Parents: Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aniline or substituted anilines - Organic nitrogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
• 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: 205.340 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 205.183 Da
• Monoisotopic Mass: 205.183 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 144.000
• 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 validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections.

Biological Roles

This product is a synthetic small-molecule building block. No specific biological role is assigned for this catalog item.

• General context (literature; not a claim for this item):

  • Aromatic amines can interact with biological membranes due to hydrophobic/π–π interactions; basic amines may be protonated under physiological pH, influencing partitioning.
  • Long-chain alkyl substitution (C8) increases lipophilicity and can enhance membrane association; however, many anilines show limited aqueous solubility and low bioavailability without formulation.

• Usage note: For research use only (as stated in Product Data). Not intended for human or veterinary use.

Buffer Applications

3-Octylaniline is not a buffering reagent. It is a hydrophobic aromatic amine with very low water solubility and is not used to prepare aqueous buffer systems.

• Practical note: If temporary aqueous handling is required, formation of water-soluble anilinium salts with strong acids (e.g., HCl) can aid extraction or pH-driven phase transfer, but this is not equivalent to buffer preparation.

Green Alternatives

Because 3-octylaniline is a target building block rather than a solvent, greener practice focuses on how it is used rather than replacing it outright.

• Greener solvent choices (literature guidance):

  • Prefer 2-MeTHF, CPME, toluene, or ethyl acetate over chlorinated solvents where feasible. Polar aprotics (DMF, NMP, DMAc) can often be replaced by propylene carbonate or Cyrene in certain couplings.
  • For extractions, minimize DCM/chloroform; use EtOAc or MTBE when compatible with partitioning and stability.

• Catalysis and conditions:

  • Use highly active Pd catalysts/ligands for Buchwald–Hartwig couplings to reduce catalyst loading and temperature.
  • Employ micellar catalysis (aqueous surfactant media) for some C–N couplings to reduce organic solvent usage (scope dependent; literature reports exist).

• Energy and waste reduction:

  • Consider continuous flow for exothermic acylations and diazotizations to improve heat transfer and reduce solvent volumes.
  • Implement solvent recycling and in-process crystallization (where applicable) to limit waste.

• Trade-offs:

  • Greener solvents may alter solubility of hydrophobic 3-octylaniline and bases/catalysts; yields can be sensitive to dielectric constant and ligand solubility. Pilot screens are recommended.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item.

• General formulation/building-block context (literature; not item-specific claims):

  • 3-Octylaniline may be used as a hydrophobic aniline fragment in medicinal chemistry research to adjust lipophilicity, permeability, and binding in exploratory structure–activity relationships (SAR).
  • Conversion to amides, ureas, or sulfonamides is common in lead optimization to modulate pKa and ADME properties.

• Compliance note: This product is supplied for research use only and is not intended for use in humans or for GMP manufacturing without appropriate qualification. Refer to CoA/Spec Sheet for any available quality attributes.

Physical Properties

• Item-specific (from Product Data):

  • Appearance: 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/general properties (not item-specific specifications):

  • Phase at ambient conditions: typically a viscous, hydrophobic liquid or low-melting solid for C8-alkyl anilines (literature).
  • Boiling point: high-boiling aromatic amines with C8 chains often distill >280–320 °C at 1 atm; substantially lower under vacuum (literature ranges, method-dependent).
  • Melting point: commonly below room temperature for many meta-alkyl anilines with long chains (literature trend).
  • Density: expected near 0.9–1.0 g/mL at 20–25 °C for long-chain anilines (literature trend).
  • Refractive index: aromatic amines typically n20 D ≈ 1.52–1.58 (literature range).
  • Solubility: very low in water; miscible with most organic solvents (e.g., toluene, dichloromethane, ethyl acetate, alcohols) (literature).
  • logP: long-chain alkyl anilines often exhibit logP ≈ 4–6 (literature, substitution-dependent).
  • Basicity: anilinium conjugate acid pKa typically ~4.5–5.5; electron-donating alkyl increases basicity modestly (literature).

Notes: Values above are general literature guidance for meta-octyl-substituted anilines and should not be construed as specifications for this catalog item.

Quality and Grades

• Item-specific (from Product Data):

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

• Guidance on interpreting grades (general):

  • Research-grade aromatic amines are typically supplied with assay (GC/1H NMR) and identity (GC-MS/LC-MS) confirmation; impurity profile may include residual starting aniline, positional isomers, and trace oxidized species.
  • If “anhydrous” or “inhibitor-free” is specified for anilines, it indicates tight water control and absence of stabilizers; neither is specified here.
  • For chromatography-sensitive work (e.g., UV detection), low-UV-absorbance solvents are relevant to solvents, not to this reagent; for reagents, low peroxide or metal content is sometimes noted—Not specified for this item; refer to CoA/Spec Sheet.

• What to check on receipt (best practice):

  • Appearance (colorless to pale yellow is typical; darkening may indicate oxidation).
  • Assay and isomer ratio if provided; residual solvents; water content (Karl Fischer) if moisture-sensitive applications are planned.
  • Stabilizers: Anilines are rarely stabilized, but vendors may recommend inert-atmosphere storage; verify in CoA if applicable.

Reaction and Applications

As a meta-alkylated aniline, 3-octylaniline serves as a hydrophobic amine building block in materials, dyes, and medicinal chemistry discovery.

• Representative transformations (literature):

  • Amide/urea/carbamate formation via acyl chlorides, isocyanates, or chloroformates to tune polarity and create linkers.
  • Sulfonamide synthesis for robust protecting/functional groups.
  • Buchwald–Hartwig C–N coupling as the nucleophilic amine partner with aryl/vinyl halides (Pd-catalyzed). Bulky octyl group can improve solubility in nonpolar media and modulate sterics.
  • Electrophilic aromatic substitution (on the aniline ring) is typically o/p-directing due to –NH2 activation; meta-octyl substituent influences regioselectivity and can provide steric bias.
  • Diazotization to anilinium diazonium salts (NaNO2/HCl, 0–5 °C) enabling azo coupling or Sandmeyer-type diversifications; long alkyl chain imparts amphiphilicity to azo dyes.

• Application spaces (literature):

  • Hydrophobic aniline fragments in ligand design for membranes/lipophilic targets.
  • Surfactant-like and soft-materials precursors where an aromatic headgroup with a long alkyl tail is desired.
  • Organic electronics/coatings: precursor to substituted anilides, azo pigments, and poly(arylene amine) segments.

• Practical tips:

  • Dry the amine and solvents for moisture-sensitive couplings; anilines can coordinate to metals—ligand choice/catalyst loading may need optimization.
  • Monitor for oxidative discoloration; passivate air exposure, and use antioxidants only if compatible with downstream steps (none are specified for this item).

Reaction Conditions

General literature guidance for reactions involving 3-octylaniline (optimize per substrate and scale):

• N-Acylation (to amides):

  • Solvent: DCM, THF, toluene, or pyridine.
  • Base: triethylamine, DIPEA, or pyridine.
  • Temperature: 0 °C (addition) to rt; 1–3 h typical. Monitor by TLC/LC-MS.

• Sulfonamide formation:

  • Reagents: sulfonyl chloride (1.0–1.2 equiv), base (2.0–3.0 equiv).
  • Solvent: DCM or acetonitrile; 0 °C to rt. Often complete within hours.

• Buchwald–Hartwig N-arylation (as amine partner):

  • Catalyst: Pd2(dba)3 (0.5–2 mol%) or Pd(OAc)2 (1–3 mol%).
  • Ligand: BINAP, XPhos, BrettPhos, tBuXPhos (2–6 mol%).
  • Base: NaOtBu, KOtBu, Cs2CO3 (2–3 equiv).
  • Solvent: toluene, dioxane, 2-MeTHF, or tAmOH.
  • Temperature: 80–110 °C; 4–24 h. Typical isolated yields for favorable pairs: 70–95% (literature).

• Diazotization/azo coupling:

  • Conditions: NaNO2 (1.05 equiv) in 2–4 M HCl at 0–5 °C; couple with activated aromatics/phenols under cold, buffered conditions.

• N-Alkylation:

  • Alkyl halide (1.1–1.5 equiv), base (K2CO3, Cs2CO3), solvent (acetonitrile, DMF), 25–60 °C; monitor to limit dialkylation.

Notes: These are non-item-specific literature conditions. Reaction performance depends on substrate electronics/sterics, purity, and mass transfer (long-chain substrates may require higher temperatures or co-solvents).

Safety and Handling

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature
  • GHS Classification / Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for alkyl anilines (literature; consult SDS for authoritative data):

  • Hazards: Aromatic amines can be harmful if swallowed, inhaled, or in contact with skin; may cause skin/eye irritation and can be absorbed dermally. Avoid aerosols and prolonged exposure.
  • PPE: Use appropriate gloves (e.g., nitrile), lab coat, and splash goggles. Handle in a fume hood to minimize inhalation.
  • Incompatibilities: Strong oxidizers; nitrosating agents; acylating/alkylating agents (uncontrolled reactions); avoid contact with acid chlorides without appropriate controls. Anilines can be slowly oxidized by air—minimize exposure to air/light for long-term storage.
  • First aid (overview):
    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Skin: Wash with soap and water; remove contaminated clothing.
    • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Fire: Combustible organic liquid/solid; use CO2, dry chemical, or foam. Thermal decomposition may release nitrogen oxides.
  • Spill response: Absorb with inert material; avoid release to the environment; dispose according to regulations.

Always consult the product’s SDS and your institutional EHS procedures for definitive hazard and handling information.

Solvent Selection

3-Octylaniline is a hydrophobic, weakly basic aromatic amine with very low water solubility.

• Polarity/miscibility (literature):

  • Miscible with nonpolar to moderately polar organics: hexanes, heptane, toluene, xylene, ether/THF, DCM, chloroform, ethyl acetate, alcohols.
  • Essentially insoluble in water and most aqueous buffers at neutral/basic pH; forms soluble anilinium salts in strong mineral acids (e.g., HCl) for extraction purposes.

• Practical choices by task:

  • Synthesis and coupling: DMF, DMAc, NMP, toluene, dioxane, or 2-MeTHF are common for Buchwald–Hartwig amination where 3-octylaniline is the amine nucleophile.
  • Acylation/sulfonylation: DCM, THF, toluene, or pyridine as solvent/base; control temperature to manage exotherms.
  • Salt formation/extraction: Dissolve product in ether/DCM and extract into aqueous acid to form the anilinium salt; back-extract with base to regenerate the free amine.

• Comparison notes (literature):

  • Toluene vs. xylene: xylene allows higher temperatures without pressure; toluene offers lower viscosity and easier removal.
  • DMF/NMP vs. 2-MeTHF: polar aprotics dissolve catalysts/bases well but have higher EHS burdens; 2-MeTHF is a greener, water-tolerant alternative for some couplings.

• Analytical prep:

  • For GC, derivatization (e.g., acylation) may aid volatility and peak shape.
  • For HPLC, reversed-phase methods (C18) with high organic content (ACN/MeOH) and UV detection near 230–280 nm are typical for anilines.

Storage and Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General best practices for anilines (literature; not item-specific requirements):

  • Store tightly sealed under dry, inert atmosphere if possible to minimize oxidative discoloration.
  • Protect from prolonged light and air; consider amber glass.
  • If material solidifies at low temperature, gently warm to ambient and homogenize before use; avoid localized overheating.
  • For weighing/dispensing, minimize headspace and reseal promptly. If long-term storage is anticipated, aliquot to reduce repeated air exposure.

• Reconstitution: Not applicable—supplied neat. If needed, dissolve in a compatible anhydrous organic solvent (e.g., toluene, DCM, THF, 2-MeTHF) just prior to use.

• Research Use Note: For research use only (as provided).

Structure and Identity

Brief description: 3-Octylaniline is a hydrophobic, meta-alkylated aniline (primary aromatic amine) bearing a straight-chain n-octyl group at the 3-position of the aniline ring.

• Item-specific (from Product Data):

  • Product Name: 3-Octylaniline
  • CAS: 118198-99-5
  • SKU: O971036
  • InChIKey: 253576 (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 (general identity data, not item-specific specs):

  • Typical molecular formula for 3-octylaniline: C14H23N (literature)
  • Approximate molecular weight: ~205.35 g/mol (literature)
  • Example (canonical) SMILES: CCCCCCCCC1=CC(=CC=C1)N (one of several equivalent representations; literature)
  • Functional groups: primary aniline (–NH2), hydrophobic n-octyl substituent at the meta (3-) position.
  • Structural features: monosubstituted aniline core with a second, meta-positioned linear C8 chain; no stereocenters; planar aromatic ring with a basic aniline nitrogen weakly conjugated to the ring.

• 2D structure in words: A benzene ring carrying an –NH2 at position 1 (aniline) and a linear n-octyl chain at position 3 (meta to –NH2).

Synthetic Utility

Key reactive site: the primary aniline nitrogen (nucleophilic, weak base). The aromatic ring is strongly activated o/p by –NH2; the meta n-octyl substituent provides steric and electronic modulation.

• Transformations (literature):

  • N-Acylation/sulfonylation/carbamoylation to give amides, sulfonamides, and carbamates—robust handles for further chemistry or property tuning.
  • N-Arylation (Buchwald–Hartwig) with aryl halides/triflates to access diarylamines; ligand choice (e.g., BrettPhos, XPhos, RuPhos) helps with hindered partners.
  • Formation of diazonium salts enabling azo coupling (dyes/pigments) or Sandmeyer reactions, expanding substitution patterns.
  • N-Alkylation to secondary/tertiary anilines; employ mild bases and phase-transfer catalysts to limit over-alkylation.
  • Electrophilic aromatic substitution: nitration, halogenation, and Friedel–Crafts acylation predominantly at ortho/para to –NH2; meta-octyl alters steric approach and regioisomer ratios.

• Retrosynthetic value:

  • Serves as a lipophilic aniline synthon to introduce long-chain hydrophobicity without additional heteroatoms.
  • Useful in constructing amphiphilic architectures (e.g., anilide headgroup + C8 tail) for materials and surface-active molecules.

• Practical considerations:

  • Protect –NH2 if undesired during ring functionalization (e.g., acetanilide strategy).
  • Control oxidation/discoloration by limiting air/light exposure; purify under inert atmosphere when feasible.

Target Specificity

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