N-(2-Methoxyethyl)-2-propanamine - Reagent grade

Cat. No.: N483989

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Specifiche e purezza

Reagent grade

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Reagent Grade

Application Protocols

No assay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule reagent in the Product Data.

• General lab use examples (non-validated, literature-based):
  • Amide formation protocol: dissolve carboxylic acid (1.0 equiv) and this amine (1.1–2.0 equiv) in DCM; cool 0 °C; add HATU (1.1 equiv) and DIPEA (2–3 equiv); stir at 0–25 °C until completion by TLC/LC–MS; work up with sat. NaHCO3.
  • Reductive amination: combine carbonyl compound, this amine (1.5–2.0 equiv), AcOH (0.3–1.0 equiv) in MeOH; add NaBH3CN (1.5–2.0 equiv) portionwise; stir at 20–30 °C; quench with NaHCO3 and extract.

These are illustrative starting points only; optimize for your system. For validated, application-specific protocols, consult the primary literature.

Biological Roles

This compound is provided strictly for research use and is not intended for biological administration. No specific biological role is assigned to this item in the Product Data.

• General context (literature; not item-specific claims):

  • Small aliphatic secondary amines are common motifs in biomolecular ligands and intermediates; they exist predominantly as protonated ammonium species at physiological pH (pKaH typically ~10–11).
  • Ether-containing side chains can increase aqueous solubility and modulate membrane permeability when such amines are embedded within larger scaffolds.
  • Secondary amines can form nitrosamines in the presence of nitrosating agents; laboratories handling nitrite-containing matrices should avoid co-exposure.

• Typical laboratory uses with biological interfaces:

  • As a building block to derivatize carboxylates (forming amides) or to install tertiary amines via reductive amination in probe/small-molecule libraries.
  • Formation of water-soluble ammonium salts (e.g., hydrochloride) to assist in bioconjugation workflows or analytical method development.

No pharmacological, toxicological, or clinical performance is implied. For any work involving biological systems, ensure appropriate institutional approvals and hazard assessments are in place.

Buffer Applications

Not typically used as a defined biological buffer component. While secondary amines can exhibit buffering action around the pKa of their conjugate acids (~10–11 for simple aliphatic secondary amines, literature), this compound is not a standard buffer reagent and lacks validated buffer recipes.

• If a basic environment is required in synthesis or sample prep:
  • Consider conventional buffer systems with established pKa/pH ranges and spec sheets (e.g., Tris, CAPS, carbonate/bicarbonate) rather than bespoke amines.
  • For organic media, non-nucleophilic organic bases (e.g., DIPEA) or tertiary amines may be preferred to avoid side reactions.

For analytical or biological buffering, choose reagents with documented buffer capacity, ionic strength parameters, and compatibility data. Refer to the literature and your method’s validation requirements.

Green Alternatives

While this product is a reagent, greener thinking applies to the solvents and reagents chosen for its reactions and workups.

• Greener solvent choices (literature guidance):

  • Replace chlorinated solvents (DCM, chloroform) with 2-MeTHF, CPME, EtOAc, or toluene where feasible for acylations and carbamylations.
  • For reductive amination, EtOH or i-PrOH often substitute well for MeOH or MeCN; aqueous ethanol mixtures can work with NaBH3CN or NaBH(OAc)3 under controlled pH.
  • For SN2 alkylations, consider green(er) polar aprotics like propylene carbonate or Cyrene in place of DMF/DMSO where compatibility allows.

• Reagent and process considerations:

  • Use solid coupling reagents with safer profiles (e.g., COMU vs HATU) and minimize excesses.
  • Favor catalytic hydrogenation (H2/Pd) for imine reduction when compatible, reducing cyanoborohydride waste.
  • Isolate as a crystalline salt (e.g., fumarate) to avoid solvent-intensive distillation of volatile free base.

• Comparison snapshot (general):

  • DCM vs EtOAc/2-MeTHF: EtOAc/2-MeTHF reduce halogenated waste; may require temperature or base adjustments for equal performance.
  • DMF vs CPME/propylene carbonate: greener options can lower worker exposure and waste persistence; viscosity and solubility may change workup profiles.

Note: Selection must be validated for the specific substrate set; small aliphatic amines are generally compatible with many bio-derived solvents but may show different partitioning during quench/workup.

Pharmaceutical Uses

No pharmaceutical excipient or pharmacopeial status is provided in the Product Data for this item. It is supplied for research use only.

• General, non-clinical context (literature):
  • As a small secondary amine, it may serve as a synthetic intermediate to prepare amide, carbamate, urea, sulfonamide, or tertiary amine functionalities within drug discovery programs.
  • Formation of crystalline salts (e.g., hydrochloride, mesylate, fumarate) can improve handling and enable solid-form studies during lead optimization.
  • The ether-containing side chain can modulate solubility and basicity when this motif is incorporated into larger structures.

No therapeutic claims are made. If materials produced with this reagent are intended for further development, ensure that starting-material quality, impurity profiles (e.g., nitrosamine risk assessment), and residual solvent limits are addressed under appropriate quality systems.

Physical Properties

• Item-specific specifications (from Product Data):

  • 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 properties for the named structure (reference only; not item-specific):

  • Molecular formula: C6H15NO (computed from the named structure)
  • Molecular weight: ~117.19 g/mol (computed)
  • Phase at ambient: expected liquid for small aliphatic secondary amines with C6 backbone (literature/analogy)
  • Basicity: conjugate acid pKa typically ~10–11 for secondary aliphatic amines (literature, general range)
  • Hydrogen-bonding: H-bond donor (1 N–H) and acceptor (N, O)
  • Polarity/solubility: often fully miscible or highly soluble in water for low-mass dialkylamines bearing an ether; readily miscible with polar organic solvents (alcohols, ketones, esters) and many nonpolar organics (literature/analogy)

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

  • Boiling point, melting point
  • Density, refractive index
  • Vapor pressure, flash point
  • Water content, UV cutoff

Practical note (general): Secondary amines may absorb CO2 and moisture from air and can show apparent mass changes or pH drift upon prolonged exposure. Always rely on the product’s CoA for release values and on the SDS for safe handling-related physicochemical parameters.

Quality and Grades

• Item-specific grade (from Product Data):

  • Grade/Purity: Reagent Grade

• What Reagent Grade generally indicates (general guidance; not a specific specification for this lot):

  • Suitable for routine synthetic and preparative laboratory use where high chemical purity is required but where specialized attributes (e.g., ultra-low metallic content, low UV absorbance for HPLC, or GC-resolved solvent backgrounds) are not mandated.
  • Typical expectations: assay consistent with stated identity, controlled levels of common impurities and residual solvents, packaged to minimize contamination and atmospheric uptake for amines.

• Implications for this amine:

  • Secondary amines can form trace nitrosamines if exposed to nitrosating agents; reputable Reagent Grade control avoids such contamination pathways in manufacture, but storage/handling remains critical.
  • Ether-containing side chains can reduce odor intensity relative to simple dialkylamines but do not eliminate volatility; seals and liners should be compatible with amines (avoid acidic or cellulose-based liners prone to reaction/adsorption).

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

  • Exact purity/assay, water content, residual solvents, stabilizers/inhibitors (if any), metal ion limits, UV cutoffs.

For regulated analyses (e.g., trace quantitation, LC-UV baselines), consider verifying suitability with a small trial and consult the lot-specific CoA.

Reaction and Applications

As a secondary amine bearing an ether side chain, N-(2-methoxyethyl)-2-propanamine is a versatile nucleophile/base for small-molecule synthesis and materials modification.

• Representative application families (literature/general):

  • Acylation to secondary/tertiary amides using acid chlorides or activated carboxylic acids (EDC/HOBt, HATU, DIC/DMAP). The isopropyl-2-methoxyethyl amide motif can modulate polarity and basicity in target molecules.
  • Alkylation to the corresponding tertiary amine via SN2 electrophiles (benzyl, alkyl halides, epoxides). Control over-dialkylation by stoichiometry and order of addition.
  • Reductive amination onto carbonyls (aldehydes/ketones) to construct tertiary amines; use NaBH3CN or NaBH(OAc)3 in alcoholic or aprotic solvents under mildly acidic conditions.
  • Sulfonylation and carbamylation to access sulfonamides and carbamates (e.g., with sulfonyl chlorides or chloroformates) for protecting-group strategies or property tuning.
  • Urea/thiourea formation with CDI, isocyanates, or isothiocyanates; useful for hydrogen-bonding motifs in medicinal chemistry.
  • Salt formation (HCl, fumarate, oxalate) to improve crystallinity, stability, and handling of this otherwise volatile base.

• Practical considerations:

  • Secondary amines may undergo nitrosation; rigorously exclude nitrite/nitrosating conditions.
  • The ether moiety is generally inert but can engage in intramolecular H-bonding in salts, sometimes affecting crystallization.
  • For scale-up, meter the amine into electrophile at controlled temperature to manage exotherms; verify heat release by DSC or calorimetry when possible.

These uses expand on the compound’s role as a polar, sterically differentiated amine nucleophile.

Reaction Conditions

General literature guidance for secondary aliphatic amines; adjust to your substrate and consult primary references.

• Acylation to amides:

  • Solvent: DCM, THF, EtOAc, or toluene. Temperature: 0–25 °C (ice bath start recommended). Base: DIPEA or Et3N (2–3 equiv) when using acid chlorides. Time: 0.5–4 h typical. Workup: aqueous bicarbonate then brine; silica gel purification (avoid acidic silica if base-sensitive).

• Coupling with carboxylic acids (peptide-type):

  • Reagents: EDC·HCl/HOBt or HATU/DIPEA; Solvent: DMF, DCM, or 2-MeTHF; Temp: 0–25 °C; Time: 1–16 h; Monitor for over-acylation or O→N acyl transfer side products.

• Reductive amination (to tertiary amines):

  • Solvent: MeOH, EtOH, or MeCN; Additives: 1–2 equiv AcOH; Reductant: NaBH3CN (1.5–2 equiv) or NaBH(OAc)3 (2–3 equiv); Temp: 20–30 °C; Time: 2–18 h. Alternative: H2 (1–5 bar) with Pd/C in EtOH for imines stable in situ.

• Alkylation (SN2):

  • Solvent: MeCN, acetone, or DMF; Base: K2CO3/Na2CO3 or DIPEA; Electrophile: primary halides, benzyl halides, epoxides; Temp: 25–60 °C; Time: 2–24 h. Control quaternization by limiting electrophile and slow addition.

• Sulfonylation/carbamylation:

  • Solvent: DCM or THF; Base: Et3N/DIPEA; Temp: 0–25 °C; Time: 0.5–4 h. Quench carefully; salts may precipitate.

• Expected yields:

  • Well-optimized acylations/reductive aminations often 70–95% (literature). Actual outcomes depend on substrate/electrophile.

Note: None of these constitute item-specific specifications. Validate on small scale and observe appropriate safety controls.

Safety and Handling

• Item-specific hazard details (from Product Data):

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

• General safety profile for small aliphatic secondary amines (literature/guidance; not item-specific):

  • Typical hazards: flammable liquid/vapor (varies by flash point), corrosive/irritant to skin, eyes, and respiratory tract; harmful if inhaled. Strong ammonia-/amine-like odor.
  • Incompatibilities: strong oxidizers; acids (exothermic salt formation); acylating agents, acid chlorides/anhydrides, isocyanates (vigorous reactions); nitrosating agents (risk of nitrosamine formation). Can absorb CO2 forming carbamates on surfaces/caps.
  • PPE: lab coat, safety glasses/goggles, nitrile gloves; use in fume hood to control vapors/odor and avoid inhalation.
  • First aid (overview; follow SDS): move to fresh air for inhalation; rinse skin/eyes with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
  • Fire fighting: alcohol-resistant foam, dry chemical, CO2. Cool containers with water spray.

• Handling/storage (Product Data + best practice):

  • Storage Conditions: Room temperature (per Product Data). Keep tightly closed, in a well-ventilated place. Protect from moisture/CO2 ingress; consider inert gas blanket for long-term storage.
  • Avoid prolonged exposure of opened containers; wipe threads and recap promptly.

Always consult the Aladdin SDS for SKU N483989 for authoritative hazard classification and response measures.

Solvent Selection

This product is a reactive amine building block rather than a process solvent. Solvent choice should optimize its nucleophilicity/basicity, manage exotherms of salt formation, and ensure complete dissolution of both reagents.

• Polarity/miscibility (literature/analogy):

  • Typically highly soluble to fully miscible in polar organics (MeOH, EtOH, acetone, MeCN, EtOAc) and many ethers (THF, MTBE, 2-MeTHF). Often miscible with water due to combined amine and ether functionalities.

• Choosing media by transformation:

  • Acylations (acid chlorides/anhydrides): use aprotic solvents (DCM, THF, EtOAc, toluene). Add base (e.g., DIPEA, Na2CO3) if the amine is used as limiting reagent to control HCl.
  • Carbamate/urea formation (with chloroformates/isocyanates): DCM, THF, or CPME; maintain cooling for exotherms.
  • Reductive amination (as nucleophile): MeOH, EtOH, i-PrOH, or MeCN with NaBH3CN/NaBH(OAc)3; buffer with AcOH/TFA as needed.
  • Alkylation to tertiary amine: polar aprotic solvents (MeCN, DMF, DMSO) improve SN2 rates; include non-nucleophilic base.

• Practical tips:

  • Dry, oxygen/acid-free media improve reaction cleanliness; secondary amines can form salts with adventitious acids/CO2 that reduce free-base nucleophilicity.
  • For workups, partition as free base (basify) or isolate as a crystalline salt (e.g., HCl) for stability/handling.

• Not specified for this item: any role as chromatography-grade solvent or UV transparency attributes; refer to CoA if such use is contemplated.

Storage and Reconstitution

• Item-specific storage (from Product Data):

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

• General handling guidance for small aliphatic secondary amines (literature/best practice):

  • Store tightly sealed in the original container to minimize uptake of CO2/moisture and prevent oxidative discoloration. If storing for extended periods, consider an inert gas blanket (N2/Ar).
  • Keep away from acids, oxidizers, and sources of ignition. Use in a fume hood to manage vapors/odor.
  • If supplied as a free base and volatility is a concern, preparing a portion as an acid addition salt (e.g., HCl salt) can aid weighing and storage; regenerate free base as needed.

• Reconstitution: Not applicable—this product is expected to be supplied neat as a liquid (or as otherwise indicated on the label). If solidified by low-temperature exposure, gently warm to ambient and mix thoroughly before use.

Always consult the container label and the lot-specific CoA for any additional storage or stabilization notes applicable to SKU N483989.

Structure and Identity

Secondary aliphatic amine bearing an isopropyl group and a 2-methoxyethyl substituent (ether-containing side chain). The nitrogen is secondary (one N–H) and sp3-hybridized; no stereocenters present.

• Item-specific identifiers (from Product Data):

  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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 identity (for reference; not item-specific):

  • Preferred name (IUPAC-style): N-(2-methoxyethyl)propan-2-amine (secondary amine)
  • Structural features: (CH3)2CH–NH–CH2–CH2–O–CH3 (isopropyl on N; ether-terminated 2-carbon chain)
  • Functional groups: secondary amine (basic, nucleophilic), ether (polar, H-bond acceptor)
  • Molecular formula (computed from structure above): C6H15NO (literature)
  • Approximate molecular weight: ~117.19 g/mol (literature)
  • Example SMILES (literature): CC(C)NCCOC

• 2D description in words:

  • Central nitrogen bound to an isopropyl fragment [(CH3)2CH–], a two-carbon chain ending in a methoxy group [–CH2–CH2–O–CH3], and one N–H. The molecule is flexible, acyclic, and overall polar due to the amine and ether oxygen.

Note: The above “literature/computed” details are provided for context. For item-specific identifiers and release specifications, consult the Aladdin CoA/Spec Sheet for SKU N483989.

Synthetic Utility

Key reactive site: the secondary amine nitrogen. The ether side chain is typically inert under many conditions, providing polarity without competing nucleophilicity.

• Transformations (literature/general):

  • Acylation: With acid chlorides/anhydrides or activated esters to form N-acyl derivatives. Use base scavenging (DIPEA, Et3N) to neutralize HX; maintain 0–25 °C to control exotherm.
  • Sulfonylation: Reaction with sulfonyl chlorides affords sulfonamides; often in DCM or acetonitrile with base.
  • Alkylation: SN2 alkylation to tertiary amines using haloalkanes, benzyl halides, or epoxides. Control over-alkylation and quaternization with stoichiometry/slow addition.
  • Reductive amination: Condensation with carbonyls followed by reduction (NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation) to access tertiary amines.
  • Carbamate/urea formation: With chloroformates (carbamates) or isocyanates/CDI (ureas); useful for protection or property tuning.
  • Salt formation: HCl or other mineral/organic acids to give crystalline ammonium salts suited to isolation/purification.

• Orthogonality and selectivity:

  • The ether oxygen is non-basic and a poor nucleophile; it typically survives acylation/alkylation at nitrogen.
  • N–H permits further derivatization; careful base choice avoids competing O-alkylation of the ether (rare under typical conditions).

• Handling tips:

  • Minimize exposure to acidic vapors/CO2 to preserve free-base reactivity.
  • For volatile losses, trap on acidified silica or pre-form a salt, then regenerate free base as needed.

Target Specificity

Not applicable. This product is a small-molecule amine, not a biological targeting reagent (e.g., antibody, ligand with defined biological target in the Product Data). No antigen, epitope, or species specificity is assigned.