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
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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
Not applicable. No validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For chemical synthesis uses, refer to the Reaction Conditions and Application notes provided in other sections, and consult the primary literature for substrate-specific procedures.
Biological Roles
Item-specific biological data: Not specified for this item.
General context (biochemistry/chemistry):
Aliphatic secondary amines like Ethyl(2‑methylbutyl)amine are protonatable bases (pKaH typically ~10.5–11.5), existing predominantly as ammonium cations under physiological pH. This leads to strong interactions with acidic biomolecules and membranes but also limits passive diffusion of the free base at neutral pH.
Such dialkylamines are not common endogenous metabolites in higher organisms; however, secondary amine functionality occurs widely in natural products and biomolecules (e.g., alkaloids, phospholipid headgroup derivatives) and in synthetic probes.
In biochemical assays, secondary amines can act as nucleophiles toward activated acyl donors (e.g., NHS esters), forming amide-linked conjugates. This chemistry underpins labeling/derivatization strategies in analytical workflows (e.g., tagging carboxylates), but specific application parameters must be optimized per system.
Protonated secondary amines can form ion pairs with anionic species (phosphates, carboxylates), influencing extraction/partitioning behavior in bioanalytical sample prep.
Caveats:
No biological activity or target specificity is claimed for this SKU; it is provided strictly for research and laboratory use (per Product Data: Research use only).
For any work involving biological matrices, confirm compatibility (cytotoxicity, protein reactivity) empirically and follow institutional safety protocols for amines (odor control, exposure limits).
Buffer Applications
Not typically used as a dedicated buffer component.
General notes (literature):
Secondary aliphatic amines have conjugate-acid pKa values in the ~10.5–11.5 range, which is outside most biological buffering regimes. While they can provide basic capacity in alkaline titrations, volatility, odor, and reactivity (e.g., acylation/sulfonylation with contaminants) limit their suitability as primary buffer components.
If a basic buffering system is required near pH 10–11, dedicated buffer systems such as CAPS (pKa ~10.4) or CHES (pKa ~9.3) are preferred for reproducibility, low volatility, and lower reactivity.
Practical alternatives:
For pH control in reactions employing Ethyl(2‑methylbutyl)amine, consider using it strictly as a stoichiometric/base reagent and rely on a separate, appropriate buffer (e.g., carbonate/bicarbonate or borate) to maintain pH, particularly in aqueous or biphasic systems.
Green Alternatives
Context: Ethyl(2‑methylbutyl)amine is a functional reagent rather than a solvent. “Greener alternatives” focus on reaction media and process design when employing this amine, or on alternative amines when functionally interchangeable.
Greener solvent/media choices (literature):
Replace chlorinated solvents (DCM) with ethyl acetate, 2‑MeTHF, CPME, or alcohols where compatible with reactivity and workup.
Employ aqueous or water-lean micellar systems (e.g., TPGS‑750‑M) for reductive amination or acylation to reduce VOC usage, acknowledging amine odor control and extraction considerations.
Use solid-supported reagents (resin-bound carbodiimides, polymeric sulfonyl chlorides) to ease purification and reduce solvent volume.
Alternative amine considerations:
If only basicity is required (non-nucleophilic base), consider greener, less odorous tertiary amines (e.g., N‑methylmorpholine) or carbonate bases—recognizing they are not nucleophilic replacements.
For nucleophilic amination where sterics are noncritical, lower-volatility cyclic secondary amines (e.g., piperidine, morpholine) may offer improved handling and lower VOC emissions at scale.
Small comparison (general):
Ethyl(2‑methylbutyl)amine: strong nucleophile/base; moderate volatility; notable odor; hydrophobic; good for sterically tuned acylations.
Morpholine: lower vapor pressure, water-miscible, oxygen-containing; often greener handling but different steric/electronic profile.
2‑MeTHF as medium: bio-based, higher boiling than THF, hydrophobic; frequently suitable for reductive amination and acylations involving secondary amines.
Trade-offs: Substituting the amine changes sterics/electronics and may alter selectivity and impurity profile; validate experimentally. Always assess PMI, E‑factor, and safety when choosing solvents and bases.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item.
General considerations (no therapeutic claims):
Role as intermediate/building block: Secondary amines such as Ethyl(2‑methylbutyl)amine are frequently used as starting materials for the synthesis of amide-, urea-, carbamate-, or tertiary amine–containing drug candidates and intermediates via acylation, sulfonylation, or reductive amination.
Salt formation strategy: The free base can be converted to pharmaceutically relevant salts (e.g., hydrochloride, sulfate, mesylate) to modulate crystallinity, hygroscopicity, and handling properties during process development. Selection is driven by stability and impurity profiles.
Process and analytical controls: For GMP contexts, typical controls include identification (IR/NMR/GC–MS), assay (GC), water (KF), residual solvents (ICH Q3C), elemental impurities (ICH Q3D), and control of nitrosamine risk (avoid nitrosating conditions during manufacture and storage; appropriate testing where relevant).
Work-up/Isolation: Formation of crystalline salts can simplify isolation and purification from complex reaction mixtures, followed by liberation of the free base if needed.
Note: This SKU is for research use only (Product Data). Any use in pharmaceutical manufacturing requires appropriate qualification, regulatory assessment, and supplier quality agreements.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet for any certified values (bp, density, refractive index, purity, stabilizers, etc.).
General/literature expectations for similar secondary C7 aliphatic amines (for context only):
Physical state/appearance: typically colorless to pale yellow, low-viscosity liquid with characteristic amine odor (literature, secondary alkylamines).
Boiling point: secondary C7 alkylamines often boil in the ~110–130 °C range at 1 atm (literature, analogous compounds). Branching can moderately reduce bp relative to straight-chain isomers.
Melting point: commonly below −50 °C (remain liquid well below 0 °C) (literature trend).
Density (20/25 °C): ~0.74–0.79 g/mL (literature range for C6–C8 secondary amines).
Refractive index (nD20): typically ~1.41–1.43 (literature, analogous secondary amines).
pKaH (conjugate acid): ~10.5–11.5 in water (literature, secondary alkylamines); free-base pKb ~3–3.5.
LogP (neutral base): expected moderate hydrophobicity, logP ~1.5–2.3 (literature estimates for C7 secondary amines); strong pH dependence due to protonation.
Solubility: free base has low–moderate water solubility that increases with branching but remains limited; salts (e.g., hydrochloride) are highly water-soluble. Miscible with many organic solvents (ethers, alcohols, hydrocarbons, chlorinated solvents) (literature).
Notes:
Actual values for this catalog item may differ; consult CoA/SDS for authoritative data.
Secondary amines show strong odor; trace impurities (e.g., water) can notably affect measured refractive index and density.
Quality and Grades
Item-specific grade/purity information: Not specified for this item; refer to CoA/Spec Sheet for certified assay, impurity profile, residual solvents, and stabilizers if any.
General guidance for amine reagent quality (context for selection):
Typical research grades include “reagent grade” (suitable for general synthesis), “anhydrous”/“dry” (controlled water content, often supplied over molecular sieves or with drying agents), and “HPLC grade” (low UV background—more relevant for solvents than reagents). For amines used in coupling chemistry or as intermediates for APIs, additional controls (water, amine value, color, peroxide, residual metals) may be important; verify via CoA.
Stabilizers: Some amines are offered with trace antioxidants or as acid salts to enhance shelf stability and reduce volatility/odor. Presence/absence of stabilizers affects reactivity (e.g., free-base vs. hydrochloride). For this item, stabilizers are not specified.
Analytical verification: titrimetric amine value, GC purity, water by Karl Fischer, residual solvents (GC), identity by NMR/IR/GC–MS. For chiral variants, enantiomeric ratio by chiral GC/HPLC (no stereospecific info provided for this item).
Suitability-by-application:
For acylation/sulfonylation, water and tertiary amine impurities can impact selectivity—prefer low water “anhydrous” lots.
For reductive amination, low aldehyde/ketone impurities and low peroxides (from solvents) reduce side reactions.
For salt formation, color and odor do not necessarily reflect purity—use analytical data.
Always defer to the specific CoA for E962273 when setting internal specifications.
Reaction and Applications
Expanded use-cases for Ethyl(2‑methylbutyl)amine as a secondary amine (literature/general):
N‑Acylation (Schotten–Baumann and related): Formation of secondary amides via reaction with acyl chlorides/anhydrides/activated esters. Common in intermediate synthesis; control base and temperature to suppress overacylation and minimize N→O acyl migration in mixed systems.
Reductive amination: Condensation with aldehydes/ketones to form iminium ions, followed by hydride reduction (NaBH3CN, NaBH(OAc)3, catalytic H2/Raney Ni or Pd/C) to furnish the corresponding tertiary amine. Solvent and pH (AcOH-buffered) are key.
Sulfonamide formation: Reaction with sulfonyl chlorides (e.g., TsCl, MsCl) in the presence of a base (Et3N, pyridine) yields N‑alkyl sulfonamides useful as protecting groups or pharmacophoric motifs.
Carbamate/urea/thiourea synthesis: With chloroformates (ROCOCl) to carbamates; with isocyanates or CDI-activated carbamates to ureas; with CS2/thiocarbonyl reagents to thioureas.
Alkylation/Quaternization: SN2 with primary alkyl halides or sulfates gives tertiary amines; excess alkylating agent yields quaternary ammonium salts. Control stoichiometry to limit overalkylation.
Michael addition: Nucleophilic addition to activated Michael acceptors (e.g., acrylates, maleimides) to form β‑amino derivatives.
Salt formation and phase-transfer roles: As a base, can form ammonium salts that serve as phase-transfer catalysts in some contexts (tertiary/quaternary more common).
Practical notes:
Drying improves selectivity in acylations; water favors hydrolysis of acylating agents.
The 2‑methylbutyl branch imparts steric hindrance that can modulate rates (slower SN2 vs straight-chain analogs) and improve selectivity in some acylations.
Avoid nitrosating conditions; secondary amines can form nitrosamines under acidic nitrite.
Reaction Conditions
General literature guidance for typical reactions of secondary alkylamines (parameters are illustrative, not item-specific specs):
N‑Acylation (to amides):
Reagents: acyl chloride or anhydride (1.0–1.2 eq), base (Et3N, DIPEA, Na2CO3, 1.5–2.5 eq).
Solvent: DCM, toluene, EtOAc, THF, MeCN.
Temperature/time: 0 °C to rt, 0.5–4 h (often exothermic on addition).
Workup: aqueous quench, wash, and crystallization or chromatography. Typical isolated yields: 70–95% with clean substrates.
Reductant: NaBH3CN (1.1–1.5 eq) in MeOH/EtOH with 0.5–1.0 eq AcOH at rt; or NaBH(OAc)3 in DCE/MeCN at rt.
Time: 1–16 h depending on substrate; typical yields 60–90%.
Sulfonylation (to sulfonamides):
Reagents: sulfonyl chloride (1.0–1.2 eq), base (Et3N or pyridine, 2.0 eq).
Solvent: DCM or MeCN; 0 °C to rt, 1–6 h. Yields commonly 70–95%.
Alkylation/Quaternization:
Electrophile: primary alkyl halide/sulfate (1.0–1.5 eq for tertiary amine; ≥2 eq for quaternary salt).
Solvent: MeCN, DMF, or acetone; 20–60 °C; time 2–24 h.
Use excess amine to limit overalkylation or protect with sulfonyl group to control selectivity.
Salt formation (HCl, TsOH):
Solvent: i‑Pr2O/Et2O/EtOAc/MTBE to precipitate; 0–25 °C.
Notes:
Moisture reduces rates in acylations and favors hydrolysis of acyl donors; dry conditions recommended.
The branched 2‑methylbutyl substituent can slightly retard sterically sensitive steps (e.g., SN2) relative to straight-chain analogs; adjust temperature/time accordingly.
Always verify conditions on small scale; actual performance will depend on substrate electronics/sterics.
Safety and Handling
Item-specific hazard data: Not specified for this item; refer to the product SDS for authoritative GHS classification, signal word, pictograms, and H‑statements.
General safety profile for aliphatic secondary amines (literature/analogous):
Likely GHS hazards: skin/eye irritation, respiratory irritation; may be harmful if swallowed; flammable liquid/combustible depending on flash point. Many lower alkylamines are corrosive to eyes/skin. Definitive classification must come from the SDS for this SKU.
Incompatibilities: strong oxidizers (risk of exotherm), strong acids (forms salts with heat and possible aerosols), acylating agents/acid chlorides/anhydrides (vigorous acylation), isocyanates/CO2 (carbamate/urea formation), nitrosating agents (risk of nitrosamine formation—avoid nitrite in acidic media), halogenating agents.
Peroxides: aliphatic amines are not classic peroxide formers; however, they can catalyze peroxide decomposition in ethers—use caution when combined with ether solvents.
PPE: safety glasses or goggles, lab coat, appropriate chemically resistant gloves (e.g., nitrile). Use in fume hood to control odor and vapors.
First aid (overview; follow SDS): eye/skin contact—immediately flush with water for ≥15 min, remove contaminated clothing; inhalation—move to fresh air; ingestion—rinse mouth, do not induce vomiting; seek medical attention in all cases of significant exposure.
Fire safety: expect vapors heavier than air; use CO2, dry chemical, or alcohol-resistant foam. Ground/bond during transfer if flammable.
Storage: tightly closed at room temperature (Product Data), away from acids/oxidizers. Minimize exposure to air/CO2 to limit salt/carbamate formation. Odorous—store in secondary containment.
Solvent Selection
Applicability: This product is a reactive reagent (secondary alkylamine), not a general-purpose solvent. Solvent selection here refers to media in which Ethyl(2‑methylbutyl)amine is typically dissolved or used.
General/literature guidance:
Polarity/ionization: As a neutral base, it is moderately nonpolar but becomes cationic in acidic media. Choice of solvent depends strongly on whether the free base or its salt is employed.
Miscibility profile: Free-base secondary alkylamines are usually miscible with common organics (ethers, alcohols, chlorinated solvents, hydrocarbons) and partially miscible with water. Protonated salts (e.g., HCl) are highly water soluble and less soluble in nonpolar solvents.
Typical solvent choices by transformation:
Acylation/sulfonylation/carbamoylation: dichloromethane, toluene, THF, EtOAc, MeCN; often with an auxiliary base (e.g., Et3N) if stoichiometry requires.
Reductive amination: MeOH, EtOH, i‑PrOH, DCE, THF, or MeCN; select based on hydride source (NaBH3CN, NaBH(OAc)3) and substrate solubility.
Alkylation (SN2) and quaternization: polar aprotic (DMF/DMSO/MeCN) to enhance rate; control temperature to reduce elimination/overalkylation.
Salt formation/crystallization: alcohol/ether/MTBE/EtOAc systems commonly used for precipitating amine salts.
Practical tips:
Drying: If water-sensitive coupling is planned, dry amine over KOH pellets or CaH2 and use dry solvents (molecular sieves).
Odor management: Conduct operations in a fume hood; choose higher-boiling, lower-volatility media where appropriate.
Greener media considerations: Where possible, replace chlorinated solvents with EtOAc, MeTHF, 2‑MeTHF, CPME, or alcohols, balancing rate/selectivity.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (per Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance for secondary alkylamines:
Container: Store tightly closed in compatible, sealed glass with PTFE-lined cap to minimize vapor loss and odor. Consider inert headspace (N2) for long-term storage to limit reaction with CO2 (carbamate formation) and atmospheric moisture.
Light/moisture sensitivity: Not strongly light-sensitive; avoid prolonged exposure to air and moisture, which can change assay (water uptake) and odor profile.
Stabilizers: Not specified for this item. If supplied as free base, consider keeping over KOH pellets in a desiccator cabinet to maintain dryness (do not store directly over reactive drying agents in the same bottle).
Freeze–thaw: Not applicable (liquid at ambient by analogy); if a salt form is prepared, avoid repeated freeze–thaw of aqueous stock solutions.
Preparation of solutions (general):
For moisture-sensitive couplings, prepare solutions in anhydrous solvents (e.g., DCM, THF, MeCN, EtOAc) under inert atmosphere. Verify concentration gravimetrically due to volatility.
For aqueous work: consider preparing acid salts (e.g., HCl) to enhance water solubility; neutralize in situ as required.
Regulatory note: For research use only (per Product Data). Always consult the SDS for this SKU prior to use.
Structure and Identity
Brief description: Ethyl(2-methylbutyl)amine is a branched, aliphatic secondary amine bearing one ethyl and one 2‑methylbutyl substituent on nitrogen (R–NH–R′).
Item-specific (from Product Data):
SKU: E962273
Product Name: Ethyl(2-methylbutyl)amine
CAS: 1038250-80-4
PubChem CID: 14525025
InChIKey: 394535 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity (general information, not item-specific spec):
Common structural class: secondary alkylamine (dialkylamine)
Expected molecular formula (by composition of substituents): C7H17N (literature/structure-based)
Approximate molecular weight: ~115.22 g/mol (literature, for C7H17N)
2D structural description (general chemistry):
Nitrogen center: sp3-hybridized amine nitrogen bearing one hydrogen and two alkyl groups.
One substituent is an ethyl group (–CH2–CH3); the other is a 2‑methylbutyl chain [–CH(CH3)–CH2–CH2–CH3], introducing branching adjacent to the nitrogen via a secondary carbon at C-2.
Functional groups: one secondary amine (–NH–). No additional heteroatoms, rings, or unsaturation.
Stereochemistry: As named, no defined stereocenter at nitrogen (inverts rapidly). The carbon at the 2‑position of the 2‑methylbutyl fragment is a potential stereocenter if the chain substitution is defined; the trivial name does not specify configuration, so material may be racemic unless otherwise stated (no stereochemical specification provided for this item).
Synthetic Utility
Functional group profile:
Secondary amine (R–NH–R′): strong, soft nucleophile; Brønsted base; readily forms amides, sulfonamides, carbamates, ureas, and tertiary amines.
Key transformations (literature/general):
Acylation with acid chlorides/anhydrides/activated esters to afford secondary amides. Steric bulk from the 2‑methylbutyl group can influence chemoselectivity (e.g., N‑ vs O‑acylation in multifunctional substrates).
Reductive amination with carbonyls to generate tertiary amines (NaBH3CN/AcOH in MeOH; NaBH(OAc)3 in DCE/MeCN/THF).
Alkylation (SN2) with primary alkyl halides/sulfates: forms tertiary amines; control overalkylation by using excess amine or phase-transfer conditions.
Sulfonylation with sulfonyl chlorides (e.g., TsCl, MsCl) to form sulfonamides, valuable as protecting groups or bioisosteres.
Carbamate and urea formation using chloroformates or isocyanates/CDI. Thiourea analogs via CS2 or isothiocyanates.
Formation of ammonium salts with acids—useful for isolation/crystallization and as intermediates for ion pairing and separations.
Coordination/borane complexes: amine–boranes (e.g., with BH3•THF) can be used in reductions and as protected amine forms.
Retrosynthetic value:
As a chiral-steric element (2‑methylbutyl), this amine can impart differentiation in diastereoselective steps when incorporated transiently (e.g., as a chiral auxiliary in some amide couplings—though not a classical auxiliary) or to modulate reactivity in N‑acyl intermediates.
Handling notes:
Drying over KOH or CaH2 prior to moisture-sensitive couplings. Avoid nitrosating agents; manage odor with closed systems.
Target Specificity
Not applicable. This product is a small-molecule aliphatic amine and is not an antibody, enzyme, or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies to this SKU.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
