(4-Ethyloctyl)(methyl)amine - ≥95% , CAS No.1272935-67-7

CAS: 1272935-67-7 Cat. No.: E1227716 PubChem CID: 62530824

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

• Sorrisos canónicos: CCCCC(CC)CCCNC
• IUPAC Name: 4-ethyl-N-methyloctan-1-amine
• InChIKey: NNFOFJTWZPEMHP-UHFFFAOYSA-N
• INCHI: 1S/C11H25N/c1-4-6-8-11(5-2)9-7-10-12-3/h11-12H,4-10H2,1-3H3
• SMILES isoméricas: CCCCC(CC)CCCNC
• PubChem CID: 62530824

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Amines
        • Level5 Secondary amines
          • Level6 Dialkylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Secondary amines
• Direct Parent: Dialkylamines
• Alternative Parents: Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Secondary aliphatic amine - Hydrocarbon derivative - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
• 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

Propriedades químicas e físicas

• Peso molecular: 171.320 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 171.199 Da
• Monoisotopic Mass: 171.199 Da
• Topological Polar Surface Area: 12.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 81.100
• 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 applications, refer to the Reaction Conditions and Synthetic Utility sections.

Biological Roles

• Item-specific: None provided. This product is intended for research use only.
• General/literature context for aliphatic amines
  • Primary/secondary aliphatic amines occur widely as metabolites, lipid headgroup precursors, and intermediates in biogenic amine pathways; however, the specific branched secondary amine (4‑ethyloctyl)(methyl)amine is not a known natural metabolite.
  • Protonated aliphatic amines interact strongly with acidic biomolecules (fatty acids, phosphates) and membranes, and quaternized derivatives are commonly used as cationic surfactants or lipid components in delivery systems. Any such uses must be evaluated for toxicity and are outside the scope of this product description.
  • In biochemical conjugation chemistry, hydrophobic secondary amines are sometimes introduced to modulate membrane association or alter partitioning coefficients of probes and small molecules.
• No clinical or therapeutic claims are made for this product; for formulation or biological testing, perform appropriate cytotoxicity and compatibility assessments.

Buffer Applications

• This compound is not a standard laboratory buffer. As a hydrophobic secondary amine, it is rarely used to prepare aqueous buffer systems.
• Literature guidance (if buffering is attempted)
  • Secondary aliphatic amines have conjugate-acid pKa values typically ~10.5–11.2, implying useful buffering capacity in the ~9.5–11.5 range when converted to partially neutralized ammonium salts.
  • Practical constraints: low intrinsic water solubility of the free base; prepare the hydrochloride (or other mineral-acid) salt to obtain aqueous solutions, then adjust pH with base. Expect surfactant-like behavior at higher concentrations, potential foaming, and adsorption losses.
  • Alternative buffers: For pH 9–11, consider established systems (CAPS, CHES, carbonate/bicarbonate, borate) with well-characterized properties and lower odor/volatility.
• Recommendation: Use standard buffer reagents; reserve this amine for synthetic transformations or surface-modification studies rather than routine buffering.

Green Alternatives

• Context: This product is a specific secondary amine building block; “greener alternative” typically concerns solvent choice and process design rather than replacing the amine itself.
• Greener process choices (literature guidance)
  • Solvent selection: prefer 2‑MeTHF, EtOAc, MeOH/EtOH, CPME over chlorinated solvents where compatible. Avoid DMF/DMAc/NMP if possible; MeCN is acceptable with proper recovery.
  • Coupling strategies: use water‑tolerant coupling (e.g., EDC/HOBt replacement with Oxyma/COMU to reduce hazardous byproducts) and minimize stoichiometric acid chlorides when feasible.
  • Energy and emissions: exploit room‑temperature couplings or flow quaternizations to limit thermal load; recover excess amine by vacuum stripping for reuse.
  • Waste minimization: form isolable salts (e.g., HCl) to enable crystallization rather than chromatographic purification.
• Comparison notes (qualitative)
  • Versus shorter, more volatile amines (e.g., methyl/ethyl amines): this C11 secondary amine tends to have lower vapor pressure and odor emissions, aiding exposure control.
  • Versus long-chain fatty amines: lower viscosity eases handling and can reduce need for diluents.
• Tradeoffs
  • Hydrophobic, branched amines may require less benign solvents for dissolution; plan for solvent recovery and aqueous waste treatment (amines elevate effluent COD and require pH adjustment).

Pharmaceutical Uses

• Item-specific: No pharmacopeial grade or excipient designation is provided for this item. For research use only.
• General/literature context (no therapeutic claims)
  • Aliphatic amines and their salts are widely used as intermediates in API synthesis (amide/urea/sulfonamide formation) and as building blocks for ionizable lipids, surfactants, and phase-transfer agents that can play roles in formulation development.
  • Quaternary ammonium derivatives derived from secondary amines serve as cationic surfactants, antimicrobial preservatives, or excipients in certain non-parenteral formulations; suitability requires rigorous safety and regulatory evaluation.
  • The branched, hydrophobic nature of (4‑ethyloctyl)(methyl)amine suggests it may be leveraged to tune lipophilicity and membrane interaction of small molecules or polymer conjugates in preclinical research.
• Compliance note: If considering use beyond bench research, verify impurity profiles, residual solvents, and elemental impurities per ICH Q3A/B and Q3D; no such specifications are provided for this catalog item.

Physical Properties

• Item-specific (from Product Data)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, refractive index, water content, metals: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed (general guidance; not specifications)
  • Physical state/odor: aliphatic secondary amines of this chain length are typically colorless to pale liquids with characteristic amine odor.
  • Boiling point: secondary C11 aliphatic amines commonly boil in the ~200–220 °C range (literature, compound-class estimate; confirm for this specific isomer).
  • Melting point: often below 0 °C for branched C11 amines (literature trend).
  • pKa (conjugate acid, aqueous, 25 °C): typically ~10.5–11.2 for unhindered secondary alkyl amines (literature).
  • LogP: expected high hydrophobicity; logP often ~4–6 for C11 secondary amines (literature class data).
  • Solubility: free base is sparingly soluble in water, but forms water‑soluble ammonium salts with mineral acids; miscible with many organic solvents (alcohols, ethers, hydrocarbons, chlorinated solvents) (literature).
  • Vapor pressure: low at ambient temperature relative to lower alkyl amines (literature trend).

Quality and Grades

• Item-specific (from Product Data)
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• Guidance for interpretation (general)
  • For amine reagents, “research grade” typically indicates suitability for synthetic use, with assay often reported by GC/GC–MS or NMR and limits for volatile bases/solvents and related alkylamines. Low water content may be important for moisture‑sensitive couplings or acylations.
  • If a high-purity or low-UV grade is required (e.g., for analytical derivatization), verify absorbance specifications and trace impurity profiles on the CoA. For preparative applications (amide couplings, quaternization), typical ≥95% assay is often adequate; chiral purity is not applicable here (no stereocenters expected).
  • Stabilizer implications: Unstabilized secondary amines are generally used neat. If supplied as an HCl (or other) salt for improved handling, note that neutralization will be required and added counterions may affect reactions and solubility.
  • Batch-to-batch: Review the CoA for assay method, residual solvents, water (Karl Fischer), and amine number (acid value titration) where applicable.

Reaction and Applications

• Functional class: secondary aliphatic amine (nucleophilic base; one N–H).
• Representative applications (literature; expandable to this substrate)
  • Amide synthesis: coupling with acid chlorides/anhydrides or via carbodiimide/HATU/EDC protocols to give N‑(4‑ethyloctyl)methylamides; imparts hydrophobicity/lipophilicity to targets (e.g., polymers, small molecules, linkers).
  • Urea/thiourea formation: reaction with isocyanates/isothiocyanates produces N‑substituted (thio)ureas—useful in H‑bonding organocatalysts or ligands.
  • Sulfonamide formation: reaction with sulfonyl chlorides under base to give N‑(4‑ethyloctyl)methylsulfonamides (common protecting/functional groups with tunable properties).
  • Reductive amination (to install this amine onto carbonyl substrates): condense the amine with an aldehyde/ketone and reduce the iminium (NaBH3CN, NaBH(OAc)3) to form tertiary amines.
  • N‑Alkylation/quaternization: alkyl halides or dialkyl sulfates convert the secondary amine to tertiary amines or quats—useful for phase-transfer catalysts or cationic surfactants.
  • Enamine formation: with carbonyls (esp. ketones) under dehydrating conditions; can be leveraged for α‑functionalization (though sterics of a branched C10 chain may slow rates).
• Practical tips
  • Dry the amine and solvents for moisture‑sensitive couplings; acid scavengers (Et3N, DIPEA) or non-nucleophilic bases (DBU) help control acylation.
  • For selective mono‑acylation, use controlled addition at 0–5 °C; monitor by TLC/GC.
  • Prepare/handle salts (e.g., HCl) to improve crystallinity and ease of purification when desired.

Reaction Conditions

General literature guidance for secondary aliphatic amines (adjust to substrate/scope):

• Amide coupling
  • Solvent: DCM, DMF, or MeCN (or green alternatives like 2‑MeTHF, EtOAc).
  • Reagents: acid chloride/anhydride with base (Et3N, DIPEA) or EDC/HOBt‑alternatives (Oxyma, COMU, HATU) with base.
  • Temperature/time: 0–25 °C, 1–16 h; monitor by TLC/LC–MS.
  • Typical outcomes: high conversions with minimal over‑acylation (no primary N present).
• Reductive amination (to make tertiary amines)
  • Carbonyl + this amine, pH ~5.5–6.5 (AcOH buffer), NaBH3CN or NaBH(OAc)3, MeOH/THF, 20–25 °C, 2–18 h. Alternatively, H2 (1–5 bar) with Pd/C in EtOH at rt–50 °C.
• N‑Alkylation / quaternization
  • Base: K2CO3/Cs2CO3 or NaH (for less reactive electrophiles) in MeCN/acetone/DMF; 20–60 °C. Quats often form cleanly with MeI/Me2SO4 or long‑chain alkyl halides; control exotherm and consider phase‑transfer catalysis in biphasic media.
• Formation of (thio)ureas and carbamates
  • Add to isocyanates/isothiocyanates/chloroformates in DCM/THF at 0–25 °C; reactions are typically rapid and exothermic.
• Workup tips
  • Aqueous acid wash removes excess amine; basify to recover if needed. Convert to HCl salt for crystallization. Dry organics thoroughly to prevent amine carryover.

Safety and Handling

• Item-specific hazard info (from Product Data)
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements / GHS class / pictograms: Not specified for this item; refer to SDS.
• General safety considerations for aliphatic secondary amines (literature/good practice)
  • Hazards: corrosive/irritating to skin, eyes, and respiratory tract; harmful if swallowed; may be harmful to aquatic organisms. Strong base; can cause chemical burns in concentrated form. Characteristic strong amine odor.
  • Incompatibilities: strong oxidizers (risk of exotherm/oxidation), acylating agents (react vigorously), acid halides/anhydrides (exothermic acylation), nitrosating agents (risk of N‑nitrosamine formation), and CO2 in air (can form carbamates on standing). Avoid copper and copper alloys; amines can attack certain non‑ferrous metals and elastomers.
  • PPE: lab coat, nitrile gloves (change regularly), splash goggles; use in fume hood. For bulk handling, consider face shield and apron.
  • First aid (overview; defer to SDS): eye contact—rinse with water for ≥15 min and seek medical attention; skin—remove contaminated clothing, wash with soap/water; inhalation—fresh air, monitor breathing; ingestion—rinse mouth, do not induce vomiting, seek medical attention.
  • Fire safety: combustible; use CO2, dry chemical, or foam. Amines can form dense vapors when heated—ensure ventilation.
  • Spill response: contain with inert absorbent, avoid release to environment; neutralize residues with dilute acid cautiously.
  • Storage notes: keep tightly closed under dry, inert atmosphere if possible to minimize oxidation and CO2 uptake; segregate from acids/oxidizers. Always consult the product SDS for authoritative guidance.

Solvent Selection

This product is a reactive amine reagent rather than a chromatography/processing solvent.

• General solubility/miscibility (literature)
  • The free base is hydrophobic and typically miscible with many organic solvents (ethers, alcohols, hydrocarbons, chlorinated solvents) but only sparingly soluble in water. Protonated salts (e.g., HCl) are water‑soluble.
• Choosing media for reactions involving this amine
  • N‑Acylation: polar aprotic solvents (DCM, THF, MeCN) or biphasic systems with aqueous base; control exotherm when adding acyl chloride/anhydride.
  • Reductive amination: protic (MeOH, EtOH) or aprotic (THF, toluene) with NaBH3CN/NaBH(OAc)3; buffer to pH ~5.5–6.5 to favor iminium formation.
  • Alkylation to tertiary amines: MeCN, DMF, or acetone with suitable base; avoid overalkylation if tertiary amine is not desired.
  • Quaternization: MeCN, toluene, or neat with alkyl halides/sulfates; manage heat release and viscosity.
• Comparison (literature perspective)
  • Versus shorter-chain amines (e.g., diethylamine): lower volatility/odor but reduced water miscibility.
  • Versus longer-chain amines: better handling (lower viscosity) and faster reaction kinetics due to less steric bulk, while retaining hydrophobic character useful for surfactant/lipid derivatives.

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 guidance for secondary aliphatic amines (literature/best practice)
  • Keep tightly closed in a dry place; exposure to air can lead to absorption of CO2 (carbamate formation) and moisture. For long-term storage, consider blanketing with inert gas (N2/Ar).
  • Segregate from acids and oxidizers. Store in amber glass or compatible HDPE; avoid copper/copper alloys.
  • If supplied as the free base: use as received; no reconstitution required. If provided as a salt (e.g., HCl), dissolve in appropriate solvent (MeOH, EtOH, water for salts) to the desired concentration; adjust pH as needed for reactions.
  • Freeze–thaw: generally not applicable; avoid freezing aqueous salt solutions to prevent concentration changes.
  • Stability check: Prior to moisture‑sensitive reactions, verify amine content by NMR or acid titration; distill under reduced pressure if higher purity is required.
• Research use only: As indicated by the supplier, this product is for research use only.

Structure and Identity

• Item-specific (from Product Data)
  • SKU: E1227716
  • Product name: (4-Ethyloctyl)(methyl)amine
  • CAS: 1272935-67-7
  • CID: 62530824
  • InChIKey: 242905 (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 (for context; not item specifications)
  • Likely composition based on the name: a secondary aliphatic amine bearing one methyl group and one branched C10 alkyl substituent (the “4-ethyloctyl” group). A reasonable constitutional assignment gives a formula around C11H25N (MW ≈ 171.33 g/mol), but confirm by CoA.
  • Structural features: one sp3-hybridized nitrogen (secondary amine, one N–H), a saturated, branched hydrocarbon chain (no rings, no heteroatoms other than N), no stereocenters expected for a simple 4-ethyl branching pattern.
  • 2D description: N center bonded to (i) a methyl substituent and (ii) a 10-carbon chain derived from octane bearing an ethyl branch at C4; remaining N valence is H (secondary amine).

Synthetic Utility

• Nucleophilicity/basicity: As a secondary aliphatic amine, it is a strong nucleophile and Brønsted base, enabling rapid acylation and N‑alkylation.
• Transformations (literature)
  • Amide formation: with activated carboxylic acids (acid chlorides, anhydrides) or coupling reagents (HATU, TBTU, EDC/Oxyma) to install a lipophilic, branched N‑substituent.
  • Urea/thiourea: addition to isocyanates/isothiocyanates for H‑bonding motifs.
  • Sulfonamides/carbamates: via sulfonyl chlorides or chloroformates under basic conditions.
  • Reductive amination: converts carbonyl compounds to tertiary amines bearing this hydrophobic substituent using NaBH3CN or NaBH(OAc)3; catalytic hydrogenation of imines is also effective.
  • N‑Alkylation and quaternization: SN2 with primary alkyl halides or dialkyl sulfates; affords tertiary amines or quaternary ammonium salts. Subsequent Hofmann elimination of quats can provide alkenes in synthesis sequences.
  • Enamine chemistry: formation from ketones enables α‑functionalization; steric hindrance from the branched chain can modulate selectivity.
• Retrosynthetic value: Serves as a handle to introduce a bulky, hydrophobic amine motif late-stage, enabling modulation of solubility, cLogP, and membrane association in probe or material design.
• Purification note: Converting crude products into ammonium salts (e.g., HCl) often aids crystallization and removal of unreacted amine.

Target Specificity

Not applicable. This product is a small-molecule amine reagent, not a biological targeting reagent or antibody. No antigen, epitope, clone, isotype, or species reactivity data are relevant.