2-(3-methylphenyl)-2-morpholin-4-ylethanamine - Reagent grade

Cat. No.: M482504

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

사양 및 순도

Reagent grade

보관 조건

Room temperature

등급

Reagent Grade

Application Protocols

Not applicable. No antibody/assay-specific protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for general procedural guidance. Always adapt conditions to your substrate and consult primary literature where precision is critical.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to literature if the compound appears in a biological context. Aladdin supplies this material strictly for research use only.
• General context (for amines of this class; not a claim of activity)
  • Polyfunctional basic amines often act as cationic species at physiological pH and can interact with acidic biomolecules (e.g., carboxylates, phosphates) by ionic pairing or hydrogen bonding.
  • Morpholine-containing motifs are common polarity-tuning groups in medicinal chemistry scaffolds; they enhance aqueous solubility and can modulate pKa and ADME properties. The presence of both a tertiary amine (morpholine) and a benzylic primary amine suggests potential for salt formation and transporter interactions in model systems, but no specific biological role is established for this compound.
  • Aromatic substituents (e.g., 3-methylphenyl) add hydrophobic surface area that can influence membrane affinity; the overall balance of polar and nonpolar features is often exploited in probe design.
• Use limitations
  • No pharmacological, toxicological, or clinical profile is provided here. Do not use in vivo or for diagnostic purposes. For any bioassay, establish handling, dosing, and deactivation protocols specific to your system.

Buffer Applications

This compound is not a standard buffering agent and is not commonly used to prepare defined pH buffer systems.

• Practical notes (general)
  • As a polyamine, it can accept protons and thus contribute to buffering capacity locally, but it lacks a well-characterized, narrow pKa window and standardized recipes required for reproducible buffer systems.
  • For buffer preparation in the pH 6–8 range, consider dedicated buffers such as HEPES, MOPS, Tris, or phosphate. For basic ranges, borate or carbonate systems are preferred. If your application involves pH manipulation during extractions or crystallizations of this compound, use standard acids/bases and validated buffer systems; do not rely on this reagent itself as a buffer.

Green Alternatives

While this product is a reagent/building block (not a bulk solvent), greener choices can be made in reactions and workups involving it.

• Greener solvent swaps (general guidance)
  • Replace DCM with EtOAc or 2-MeTHF for acylations and extractions where feasible.
  • Use ethanol or isopropanol as media for reductive amination instead of MeOH or halogenated solvents.
  • Favor CPME or 2-MeTHF over THF when prolonged reflux or peroxide concerns are relevant.
• Greener reagents/bases
  • Prefer NaBH(OAc)3 over NaBH3CN to avoid cyanide; or catalytic hydrogenation where compatible.
  • Use organic carbonates (K2CO3, Cs2CO3) or aqueous NaHCO3 in biphasic systems rather than strong, hazardous bases when selectivity allows.
  • For couplings to carboxylic acids, employ uronium/phosphonium reagents with greener profiles (e.g., COMU) and minimize DMF by switching to MeCN/EtOAc mixtures.
• Process-intensification
  • Perform salt formation to crystallize and avoid chromatographic silica waste.
  • Employ aqueous workups that exploit differential protonation (pH-swing extractions) to minimize solvent usage.
• Trade-offs
  • Greener solvents may alter selectivity or rates; conduct small-scale screens. Some alternatives (2-MeTHF, CPME) have different miscibility profiles that affect phase splits and crystallizations. All points above are general, literature-based considerations for amine chemistry and are not item-specific specifications.

Pharmaceutical Uses

• Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet. This product is supplied for research use only and is not intended for human or veterinary use.
• General considerations for this structural class (non-clinical)
  • Aromatic, morpholine-bearing amines are widely used as synthetic intermediates or side-chain components in discovery chemistry. They are often converted to pharmaceutically acceptable salts (e.g., HCl, mesylate, tosylate) to improve handling and stability.
  • Salt screening and polymorph studies can be valuable for library compounds featuring multiple basic sites; counterion choice affects hygroscopicity, solubility, and crystallinity.
  • In formulation research settings, tertiary amines can impact pH of vehicles; compatibility with excipients (e.g., avoidance of aldehyde-containing excipients that can form imines) should be assessed.
• Manufacturing research notes
  • For scale-up as an intermediate, control of residual solvents and amine content is critical; quench and purge strategies for acylation/alkylation steps should be validated. No therapeutic or clinical claims are made or implied for this item.

Physical Properties

• Item-specific specifications (measured):
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point, melting point, density, refractive index, solubility, pKa, logP: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general expectations for similar structures (for planning only; not item specifications)
  • Polyfunctional aromatic aliphatic diamines with morpholine rings are typically viscous oils or low-melting solids; they are hygroscopic bases that form crystalline salts (e.g., HCl, TsOH) with sharply higher melting points (literature, general for related morpholinyl-arylethylamines).
  • Free-base amines are usually miscible with polar organic solvents (MeOH, EtOH, acetone, MeCN) and moderately soluble in less polar solvents when warmed; protonated salts are water-soluble (literature, general behavior of tertiary/primary amines).
  • Basicity: tertiary morpholine N pKb ~5.5–6.0; primary benzylic-type amines often have conjugate acid pKa ~9–10 (literature, typical ranges for morpholine and benzylic primary amines). These values are provided for context only. Notes: Use the product’s CoA for definitive, item-specific values. When precise physical constants matter (e.g., process design, purification), generate a salt and measure directly under your lab conditions.

Quality and Grades

• Supplied grade for this item
  • Grade/Purity: Reagent Grade (item-specific). No numerical purity, stabilizers, or metal/anion limits are specified for this SKU; refer to CoA/Spec Sheet for release criteria.
• What Reagent Grade typically implies (general guidance)
  • Suitable for routine synthetic and analytical laboratory use. Impurity profiles are controlled to support general research applications but are not necessarily optimized for trace analysis, LC/UV transparency, or GMP manufacturing.
  • Reagent Grade small-molecule amines typically meet identity by NMR/IR/HRMS and assay by GC/LC; residual solvents and water may be reported on CoA.
• Practical implications for this compound class
  • As a polyamine, trace water/CO2 uptake can influence assay and titration; where critical, dry under vacuum and standardize by acid titration or quantitative NMR.
  • For chromatography-sensitive work, consider preparing a defined salt (e.g., HCl) to sharpen melting point and reduce tailing, or purify as the free base via flash chromatography using basic modifiers (e.g., 0.1–1% Et3N) depending on your workflow.
• Documentation
  • For exact specifications, analytical methods, and lot-specific results, consult the Aladdin CoA and Specification Sheet for SKU M482504.

Reaction and Applications

• Role in synthesis (general for this scaffold)
  • Versatile diamine building block featuring a benzylic primary amine and a tertiary morpholine. It can serve as a handle to introduce polar, basic functionality into ligands, linkers, and discovery compounds.
• Representative transformations (literature/general)
  • Selective N-acylation or N-sulfonylation of the primary amine to furnish amides/sulfonamides; morpholine tertiary N remains largely unreactive to acylation under standard conditions.
  • Reductive amination at the primary amine to access secondary amines while retaining the morpholine functionality; use NaBH3CN/NaBH(OAc)3 in alcohols with AcOH buffer.
  • Urea/carbamate formation (e.g., CDI or triphosgene for ureas with isocyanates/isothiocyanates).
  • Quaternization of the morpholine nitrogen (MeI/MeOTf) to tune solubility and generate ionic derivatives (applies to many morpholine-containing amines).
  • Salt screening (HCl, HBr, methanesulfonate, p-toluenesulfonate) for crystallinity and purification.
• Selectivity/orthogonality
  • Primary vs tertiary amine reactivity allows orthogonal protection: Boc or Cbz on the primary amine; tertiary morpholine does not accept acyl protecting groups but can be quaternized if needed.
• Use cases (non-clinical)
  • Commonly leveraged in medicinal chemistry workflows as a basic side chain; useful in generating libraries via amide coupling, SNAr onto activated aromatics (via the primary amine), or as a nucleophile in Mitsunobu-avoidant strategies using activated esters. Note: No specific manufacturer application text was provided beyond “For research use only.” The above reflects general synthetic use patterns for analogous morpholinyl-arylethylamines.

Reaction Conditions

General, literature-informed guidance for amine manipulations relevant to this scaffold (not item-specific specifications):

• N-Acylation of the primary amine
  • Conditions: acyl chloride (1.1–1.5 eq) or HATU/EDC with carboxylic acid (1.1–1.5 eq); base DIPEA (2–3 eq) or Na2CO3 (aq) in DCM, DMF, THF, or MeCN; 0–25 °C; 0.5–4 h. Typical isolated yields: 70–95% in small-molecule systems.
• N-Sulfonylation
  • Conditions: sulfonyl chloride (1.1–1.5 eq), base (pyridine, TEA), solvent DCM or MeCN; 0–25 °C; 1–3 h. Work up with aqueous bicarbonate; 65–90% yields common.
• Reductive amination (at the primary amine)
  • Conditions: carbonyl compound (1.0–1.5 eq), AcOH (0.2–0.5 eq), NaBH3CN (1.2–2.0 eq) or NaBH(OAc)3 (2–3 eq) in MeOH, EtOH, or i-PrOH; 20–40 °C; 2–16 h. Alternatively, Ti(OiPr)4-assisted imine formation in THF, then NaBH4.
• Boc protection
  • Conditions: Boc2O (1.1–1.5 eq), base (TEA/NaHCO3), DCM or MeCN; 0–25 °C; 1–3 h. Deprotect with TFA/DCM at 0–25 °C.
• Quaternization of the morpholine nitrogen (if desired)
  • Conditions: MeI or MeOTf (2–3 eq) in MeCN or acetone; 0–25 °C; 2–24 h; generates ammonium salts that are water-soluble.
• Chromatography and workup
  • Include 0.1–1% Et3N in silica eluents to mitigate tailing. For salt toggling, extract free base into organic at basic pH and protonated form into water at acidic pH (pH 2–3 with HCl). Note: Optimize equivalents and temperatures for your substrate; monitor by LC/MS or TLC with basic modifiers.

Safety and Handling

• GHS information for this specific item
  • Signal Word: Not specified for this item; refer to SDS.
  • Hazard Statements (H-): Not specified for this item; refer to SDS.
  • Pictograms / Classification: Not specified for this item; refer to SDS.
• General hazards for polyamine reagents (literature/experience-based)
  • Amines can be corrosive/irritating to skin, eyes, and respiratory tract; some may cause sensitization. Aromatic/aliphatic amines may be harmful if swallowed. Avoid inhalation of vapors and aerosols.
  • Amines may react with acid chlorides, anhydrides, strong oxidizers, and CO2 (to form carbamates/ureas on surfaces). Keep away from strong oxidizing agents and nitrosating conditions (risk of nitrosamine formation).
• Handling & PPE (good laboratory practice)
  • Use in a fume hood. Wear safety glasses or goggles, lab coat, and appropriate chemical-resistant gloves (nitrile typically suitable; verify compatibility).
  • Avoid contact with acids/bases unless intended; cap promptly to minimize CO2 uptake and moisture.
• First aid (overview; defer to SDS)
  • Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; seek medical advice if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; get medical attention.
• Fire & stability
  • Combustible organic base; use CO2, dry chemical, or foam to extinguish. Ethers in morpholine are not typical peroxide formers under storage, but avoid prolonged exposure to air/UV in solvents that do form peroxides.

Solvent Selection

This SKU is a basic, polyfunctional amine (aromatic benzylic primary amine plus a tertiary morpholine). Solvent choice affects reactivity, protonation state, and workup.

• Polarity/miscibility (general behavior)
  • Free base: typically miscible with polar organics (MeOH, EtOH, acetone, MeCN, DMF, DMSO); moderate solubility in EtOAc/THF; limited in alkanes.
  • Protonated salts: high water solubility; miscible with alcohol–water mixtures; reduced solubility in nonpolar solvents.
• Selection by task
  • N-acylation/sulfonylation: DCM, THF, or MeCN with a non-nucleophilic base (DIPEA, Na2CO3). Add 0.1–1% Et3N in chromatography solvents to suppress streaking.
  • Reductive amination/alkylation (on the primary amine): MeOH, i-PrOH, or EtOH buffered with AcOH (then NaBH3CN/NaBH(OAc)3). DCM/MeCN for imine formation when water-sensitive.
  • N-protection (Boc, Cbz): DCM/MeCN with DIPEA or aqueous NaHCO3 biphasic systems.
  • Salt formation/crystallization: IPA/Et2O/MTBE antisolvent systems for HCl or p-TsOH salts.
• Comparison/alternatives (general)
  • For greener profiles, swap DCM with EtOAc or 2-MeTHF; replace DMF with MeCN or CPME where feasible.
• Practical tips
  • Control acid equivalents to avoid undesired protonation of both amines when selective reactivity is needed. Dry solvents improve reproducibility for acylations and imine chemistry.

Storage and Reconstitution

• Storage (item-specific)
  • Storage Conditions: Room temperature (per Product Data). Protect from moisture and CO2 to minimize formation of ammonium salts/carbamates on exposure to air. Keep container tightly closed.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• General handling for polyamines
  • If long-term storage is planned, consider storing as a defined salt (e.g., HCl) in a desiccator to improve stability and handling. Free bases may gradually absorb water/CO2.
  • Before critical use, especially in stoichiometric applications, dry under vacuum (e.g., 25–40 °C, high vacuum, several hours) and assay if needed.
• Reconstitution
  • Not applicable: supplied neat. If preparing stock solutions, use dry polar solvents (MeOH, MeCN, DMSO) and store aliquots in sealed vials under inert gas at 2–8 °C for medium-term stability, or at −20 °C for extended periods. Allow solutions to reach room temperature before opening to avoid condensation.
• Stability notes
  • Avoid prolonged exposure to strong oxidizers and nitrosating agents. For salts, store in airtight containers to prevent deliquescence. Always refer to the product’s SDS and CoA for authoritative guidance on safe handling and storage.

Structure and Identity

• Item-specific identifiers
  • 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.
• Name-based structural features (interpretation of the chemical name; general information)
  • The compound name “2-(3-methylphenyl)-2-morpholin-4-ylethanamine” indicates an ethanamine backbone bearing two substituents at the 2-position: a 3-methylphenyl (meta-tolyl) group and a morpholin-4-yl moiety (connected via the ring nitrogen of morpholine).
  • Functional groups: one primary amine (–CH2–NH2 or –CH(NH2)– depending on exact substitution pattern implied by the name) and one tertiary amine embedded in the morpholine ring; one aromatic ring (3-methylphenyl); one ether oxygen within the morpholine ring.
  • Heterocycles: morpholine (six-membered, saturated, containing O and tertiary N).
  • Likely exists as a basic, polyfunctional amine capable of forming ammonium salts with mineral or organic acids.
• 2D structural description (general)
  • A single aromatic ring (meta-tolyl) attached to a substituted ethyl fragment; the same carbon also bears the morpholinyl group, giving a β,β-disubstituted ethanamine framework with an additional tertiary amine site. No stereochemical descriptors are given; the 2-substituted center may be stereogenic if all substituents are distinct, but configuration is not specified for this item.

Synthetic Utility

• Functional group leverage
  • Primary amine: highly nucleophilic center for amide/sulfonamide formation, reductive amination, and coupling chemistry (HATU/EDC/COMU). Can be selectively protected (Boc, Cbz, Fmoc) to enable downstream transformations.
  • Morpholine tertiary amine: provides basicity and polarity; can be quaternized to install a permanent positive charge; typically inert to acylation but participates in alkylation under strong conditions.
  • Aromatic (3-methylphenyl): offers a handle for π–π interactions in ligands; can undergo electrophilic substitution on the ring (subject to directing effects of the substituents) or serve as a spectroscopic tag.
• Orthogonal strategies
  • Differentiate the two nitrogen centers via acid–base manipulation: transiently protonate one site to drive selective reactions at the other.
  • Protect the primary amine for transformations that might otherwise lead to over-alkylation or imine formation; leave morpholine unprotected for solubility benefits.
• Library synthesis applications
  • Rapid generation of amide/sulfonamide arrays, ureas/carbamates, and secondary amines via reductive amination. The scaffold’s dual basic sites facilitate aqueous workups (pH swing) and salt-based purifications.
• Retrosynthetic value
  • Serves as a convergent node linking aryl fragments to polar amine motifs, enabling modular assembly of ligand-like scaffolds and tool compounds in SAR campaigns.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (e.g., antibody, ligand with validated target specificity). No antigen, epitope, clone, isotype, or species-reactivity information is provided or implied for SKU M482504.