This compound belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
89.140 g/mol
XLogP3
-0.400
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
89.0841 Da
Monoisotopic Mass
89.0841 Da
Topological Polar Surface Area
35.300 Ų
Heavy Atom Count
6
Formal Charge
0
Complexity
30.700
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
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
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Recensioni
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Application Protocols
No assay/application protocols are specified for this item in the Product Data. As a small-molecule reagent, it is typically used in standard organic synthesis workflows rather than immunoassays or staining protocols.
General usage guidance (chemistry focus):
For reductive amination: Combine carbonyl partner and (S)-2-methoxypropan-1-amine in anhydrous solvent, add mild acid, then reductant (e.g., NaBH(OAc)3) and stir at controlled temperature; work up and purify by chromatography or crystallization of a salt.
For amide coupling: Activate carboxylic acid with EDC/Oxyma or HATU in DMF/MeCN, add the amine and base at 0–25 °C; quench, extract, and purify.
For protection (Boc/CBz): Treat with Boc2O (or CBz–Cl) and base in DCM/THF; isolate protected amine for downstream steps.
Note: Adjust stoichiometry, temperature, and solvent to your substrate set. Confirm enantiomeric integrity of products derived from this chiral amine by chiral HPLC/GC. Always consult the product SDS for safe handling and the CoA for lot-specific quality details prior to use.
Biological Roles
This compound is a synthetic, chiral, aliphatic primary amine and is not known as a natural metabolite or cofactor. No specific biological roles are assigned to this item in the Product Data.
General context for small primary amines (literature/general):
Protonation/transport: In aqueous biological environments, primary amines are predominantly protonated (pKaH+ ~10–11), which alters membrane permeability and can facilitate salt-based solubilization.
Chemical handles: Primary amines serve as bioconjugation handles (e.g., acylation with NHS esters) in chemical biology; however, this item is offered for research chemistry and materials synthesis rather than as a bioconjugation standard.
Structure–property effects: The presence of a stereogenic center adjacent to an ether can influence binding topologies in exploratory structure–activity studies, but there are no target-specific claims for this product.
Caveats:
Any use in biological systems should be preceded by rigorous assessment of purity, counterion content, and cytotoxicity as applicable to the experimental design.
The product is for research use only and is not intended for diagnostic, therapeutic, or in vivo use.
Buffer Applications
This product is not a dedicated biological buffer. While primary amines are basic and can, in principle, contribute to buffering near their conjugate-acid pKa (~10–11, literature for aliphatic amines), (S)-2-methoxypropan-1-amine is not typically used as a standard buffer component.
Practical notes if used in pH control for research chemistry (not typical in biochemistry):
Aqueous compatibility: The free base can be dissolved in water and titrated with acid to prepare the corresponding ammonium salt, which will buffer weakly in the alkaline range. For reproducible biological work, prefer established buffers (e.g., Tris, CAPS, TAPS).
Ionic strength and compatibility: Non-volatile amine buffers are generally preferred for electrophoresis and enzyme assays; this compound is not recommended for such uses due to volatility and reactivity.
Recommendation: Use established buffering systems for biochemical applications and reserve this compound for synthetic transformations detailed in the Reaction & Applications and Synthetic Utility sections.
Green Alternatives
Greener use considerations for a small chiral primary amine focus on solvent and reagent choices rather than replacing the substrate itself.
Solvent selection (greener options):
Prefer 2-methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) over THF/Et2O for imine formation and reductive amination when solubility allows.
Use ethyl acetate or isopropanol/ethanol in place of chlorinated solvents (e.g., CH2Cl2) for acylations/reductive aminations where feasible.
For aqueous workups and salt formation, water/ethanol mixtures can reduce VOC emissions.
Reducing agents: Replace cyanoborohydride with BH3·THF alternatives, transfer hydrogenation (HCO2H/TEA, HCO2NH4), or H2/Pd when compatible, to avoid cyanide waste.
Coupling chemistry: Favor carbodiimide + Oxyma or enzymatic coupling approaches with safer profiles, and minimize HOBt use due to explosivity concerns.
Trade-offs (general):
2-MeTHF/CPME can exhibit lower polarity; solubility of the amine or intermediates may limit concentration, potentially requiring higher volumes.
Alcoholic media may lead to transalkylation or acetal/imine equilibria; control water content and time.
Transfer hydrogenation often requires elevated temperatures or specific catalysts, which may impact stereocenters.
Summary table (qualitative):
THF → 2-MeTHF: similar performance, improved sustainability; check solubility.
CH2Cl2 → EtOAc: greener but less polar; monitor reaction rates.
NaBH3CN → H2/Pd or BH3-based: eliminates cyanide; assess chemoselectivity.
Note: No item-specific “green grade” is declared. Optimize routes using the above greener levers while maintaining stereochemical integrity.
Pharmaceutical Uses
No pharmacopeial or excipient grade is specified for this item. It is not offered as a drug substance or excipient; rather, it is a research-use reagent.
Relevant roles in pharmaceutical R&D and manufacturing (literature/practice):
Chiral intermediate: Serves as a building block for synthesizing chiral secondary amines, amide-linked fragments, ureas/carbamates, and amino ethers, enabling rapid exploration of stereochemical space in medicinal chemistry.
Salt switch studies: As a basic amine, it can form diverse amine salts (e.g., HCl, mesylate, tartrate, fumarate) for property tuning (solubility, crystallinity) during intermediate handling (research context only).
Protecting group strategies: Conversion to Boc/CBz derivatives affords bench-stable intermediates amenable to scale-up and purification by crystallization.
Impurity standards/internal references: Potentially useful as a reference standard for analytical method development in routes where the amino ether motif appears (not item-certified; verify purity against internal specifications).
Compliance note:
This product is for research use only. For any use in GMP manufacturing or clinical development, independently qualify the material (identity, assay, ee, residual solvents, elemental impurities) and establish appropriate specifications and vendor oversight. No medical or clinical claims are made or implied.
Physical Properties
Item-specific measured specifications are not provided in the Product Data. Values below are literature/structure-informed guidance only and must not be construed as product specifications.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~89.14 g/mol (literature/structure-derived for C4H11NO)
Boiling point: Not specified for this item; literature for small aliphatic primary amines with similar MW suggests a low to moderate boiling point under atmospheric pressure.
Melting point: Not specified for this item; small aliphatic amines are typically liquids at room temperature (literature generalization).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
pKa (conjugate acid): Primary aliphatic amines typically show pKaH+ ~10–11 in water at 25 °C (literature, general class value).
LogP (octanol/water): Expected to be low due to basicity and hydrogen bonding capability; protonated form is water soluble (literature, qualitative trend for small primary amines). Not specified for this item; refer to CoA/Spec Sheet for any measured values.
Solubility: Primary amines of this size are generally miscible with many polar organic solvents and display appreciable water solubility, especially as salts (literature, general behavior). Item-specific solubility: Not specified for this item; refer to CoA/Spec Sheet.
Note: Actual properties may differ depending on enantiopurity, residual solvent, and water content. For quantitative method development, determine values experimentally under your conditions.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
In absence of a declared grade (e.g., AR, HPLC, ACS, anhydrous, enantiopure), rely on the Certificate of Analysis for assay, enantiomeric excess (ee), residual solvents, water content, and impurity profile.
For chiral amines, the enantiomeric purity (ee or er) is often critical. If not listed, confirm by chiral GC/HPLC before use in stereosensitive steps.
For applications in trace synthesis or catalysis, assess levels of metal contaminants and amine stabilizers if relevant; Not specified for this item—verify via CoA or by ICP/GC as needed.
If low UV background is required (e.g., LC mobile phase additive or detector baselines), ensure a low-UV grade or verify UV cutoff; Not specified for this item.
If water sensitivity is a concern, request or verify Karl Fischer moisture. Not specified for this item; refer to CoA/Spec Sheet.
Recommendations:
Upon receipt, document lot number, assay, ee, and water content. If your synthesis is stereodefined, run incoming QC (chiral HPLC, 1H/13C NMR, IR for N–H, O–CH3 signatures).
For GMP-relevant work, qualify the lot to internal specifications and retain samples. Ensure storage conditions match those stated: 2–8 °C, light-protected, under argon.
Reaction and Applications
(S)-2-Methoxypropan-1-amine is a chiral, nucleophilic primary amine that serves as a versatile building block and chiral handle.
Imine/Enamine chemistry: Forms imines (Schiff bases) with aldehydes/ketones; these can be reduced (reductive amination, e.g., NaBH3CN, NaBH(OAc)3, catalytic H2) to deliver secondary amines incorporating the chiral unit. The adjacent methoxy-bearing stereocenter can exert asymmetric induction in some cases.
Amide/Carbamate/Urea formation: Direct acylation with acid chlorides/anhydrides (base-assisted), coupling with carboxylic acids (EDC/HOBt, HATU, DIC/Oxyma), carbonylation or reaction with isocyanates (ureas) and chloroformates (carbamates) to furnish protected or functionalized derivatives.
Sulfonamide synthesis: Reaction with sulfonyl chlorides (e.g., TsCl, MsCl) affords sulfonamides that can be useful chiral auxiliaries or protecting groups.
N-alkylation (SN2): Alkyl halides/tosylates under basic conditions furnish secondary amines. Control over over-alkylation via stoichiometry or protection is recommended.
Chiral ligand/auxiliary precursor: The (S)-configured amino ether may be elaborated into oxazolidines or related heterocycles; the ether functionality is typically inert but can be manipulated (e.g., demethylation to amino alcohol under forcing conditions) to amino alcohols, precursors of chiral ligands.
Conjugation to electrophiles: Useful for preparing linkers or bifunctional intermediates where the methoxy-bearing stereocenter sets topology.
Practical notes:
Drying the free base over K2CO3 or by brief standing over molecular sieves (3Å/4Å) in aprotic solvent can improve reproducibility in imine/coupling steps.
Avoid excess heat/strong acids that may promote ether cleavage or racemization in harsh conditions.
Reaction Conditions
General conditions below are literature/practice guidance for small primary amines and are not product specifications. Optimize per substrate.
Reductive amination:
Solvent: MeOH, EtOH, i-PrOH, MeCN, or DMF (anhydrous).
Conditions: Mix carbonyl compound with amine (1.2–2.0 eq), add AcOH (0.2–0.5 eq) to drive imine formation; then add NaBH(OAc)3 at 0–25 °C, 2–16 h. Alternative: H2 (1–5 bar) with Pd/C in alcohol at RT–50 °C.
Notes: Control water; avoid strong acids that may cleave ether under forcing conditions.
Amide coupling:
Solvent: DMF, DCM, MeCN, 2-MeTHF.
Reagents: HATU or EDC·HCl/Oxyma with DIPEA/NEt3 at 0–25 °C, 1–12 h.
Notes: For acid-sensitive stereocenter, prefer milder reagents (EDC/Oxyma) and lower temperatures.
Sulfonamide formation:
Reagents: TsCl (1.05 eq), pyridine or NEt3 (2–3 eq) in DCM/MeCN, 0–25 °C, 1–6 h.
Carbamate/urea synthesis:
With Boc2O (1.1–1.5 eq) in THF/MeCN, base: NaHCO3/DIPEA, 0–25 °C.
With isocyanates (1.0–1.2 eq) in DCM/EtOAc, RT, 1–4 h.
N-alkylation (SN2):
Base: K2CO3 or NaHCO3 (mild) in MeCN/DMF; electrophile: primary halide/tosylate (1.0–1.5 eq); 25–60 °C, 2–16 h.
Notes: Limit over-alkylation via stoichiometry or temporary protection (Boc).
Epoxide opening:
Solvent: EtOH/MeOH or DMF, 25–60 °C, 2–12 h; yields β‑amino ethers/alcohols depending on epoxide.
Analytics and handling:
Monitor by TLC/UPLC-MS; derivatize amine for GC if needed (e.g., acylation).
Use anhydrous solvents and inert gas (argon) per Product Data to minimize water/CO2 uptake which can suppress nucleophilicity.
Safety and Handling
GHS hazard classification and pictograms are not provided in the Product Data for this specific item; consult the product SDS for authoritative information.
General safety considerations for small aliphatic primary amines (literature/practice):
Irritation/corrosivity: Primary amines can be irritating to skin, eyes, and respiratory tract; some exhibit corrosive behavior at high concentration. Avoid inhalation and contact.
Flammability: Low-MW amines may be flammable; keep away from ignition sources, use only in well-ventilated fume hoods.
Reactivity: Amines are basic and nucleophilic. They can react with acylating agents, strong oxidizers, acid chlorides/anhydrides, isocyanates, and carbonyls (forming imines/Schiff bases). They may absorb CO2 from air to form carbamate salts and water leading to protonation.
Handling and PPE:
Use in a fume hood. Wear safety glasses, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). For bulk handling, consider splash protection and an organic vapor respirator per SDS guidance.
Minimize exposure to air and moisture; this item is supplied argon charged and should be handled under inert atmosphere when feasible.
Storage and incompatibilities:
Per Product Data: Store at 2–8 °C, protected from light, under argon. Shipments are on wet ice.
Keep tightly sealed in compatible containers. Avoid oxidizers, strong acids (may form salts with heat release), acid chlorides/anhydrides, isocyanates, and carbonyl compounds without intentional control.
First aid (overview; follow SDS/protocols):
Eye/skin contact: Rinse with water for ≥15 min; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Solvent Selection
This product is a small, basic, chiral primary amine, not a bulk solvent. The following guidance pertains to dissolving and handling it as a reagent/solute.
Polarity and ionization: The free base is polar and hydrogen-bonding. It becomes highly water-soluble upon protonation (e.g., as HCl salt). For non-aqueous work, choose polar aprotic solvents or alcohols.
Common solvents (practical):
Polar aprotic: MeCN, DMF, DMSO, THF, 1,4-dioxane — promote nucleophilic reactivity and good solubility.
Protic: MeOH, EtOH, i-PrOH, water (as salt) — useful for imine formation/reductive amination (with control of water content).
Hydrocarbons: Limited solubility expected unless co-solvent used or as a salt pair with lipophilic counterions.
pH control: In aqueous systems, adjust to pH 10–11 to keep the free base (literature generality) or acidify to form soluble ammonium salts.
Dry media: For moisture-sensitive transformations (e.g., acylations, imine formation), use anhydrous solvents and handle under inert atmosphere to limit water and CO2 uptake.
Comparison (general):
Versus larger aliphatic amines, this compound typically shows higher polarity and better solubility in polar solvents, easing handling at modest concentrations (0.1–2 M).
For chiral applications, non-protic solvents (e.g., CH2Cl2, toluene, EtOAc) may be chosen to influence selectivity during auxiliary/catalyst interactions; confirm solubility beforehand.
Tip: Prepare stock solutions freshly; amine concentration in protic media can drift due to acid–base equilibria and CO2 absorption.
Storage and Reconstitution
Storage conditions (item-specific, from Product Data): Store at 2–8 °C, protected from light, argon charged.
Shipping: Supplied on wet ice to maintain cool conditions during transit.
Handling and preservation:
Keep container tightly closed. Purge the headspace with argon after each use to limit CO2 and moisture uptake, which can form ammonium salts/carbamates and alter reactivity.
Minimize exposure to air and light; use amber vials where possible.
If repeated access is required, consider preparing single-use aliquots under inert gas.
Reconstitution/stock solutions:
If supplied as a neat liquid/solid: dissolve to desired concentration in a dry, oxygen-free solvent such as MeCN, THF, DCM, DMF, or alcohols immediately before use. For aqueous work, adjust pH and/or prepare the corresponding ammonium salt.
Filter stock solutions through PTFE (for organics) or PVDF/nylon (for aqueous) syringe filters if particulate contamination is suspected.
Stability notes (general):
Avoid strong acids/bases and oxidants during storage. Prolonged exposure to acids may lead to ether cleavage; strong oxidants can degrade amines.
For long-term storage, maintain at 2–8 °C under argon as specified. If crystallization or phase changes occur, warm gently to ambient under inert gas and mix before dispensing.
Always consult the CoA/Spec Sheet for any lot-specific notes on appearance, water content, and stability.
Structure and Identity
A chiral, aliphatic primary amine bearing a methoxy substituent at the secondary (C2) position of propane.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (described):
Backbone: A three‑carbon chain (propan-1-amine) with the amino group at C1.
Substituents: A methoxy group (–OCH3) at the stereogenic C2 center, creating a secondary carbon bearing –OCH3 and –CH3 substituents, and a primary amino group (–CH2NH2) at C1.
Stereochemistry: Configured as (S) at C2; the methoxy-bearing center is the sole stereocenter.
Functional groups: One primary amine (basic, nucleophilic) and one aliphatic ether (methoxy, generally inert under neutral conditions).
2D structure in words:
From left to right: a terminal methyl group (CH3–), attached to a chiral carbon (–CH(–OCH3)–), followed by a methylene (–CH2–) terminating in a primary amine (–NH2). The methoxy substituent is bound to the chiral center via the ether oxygen, and the absolute configuration is S as designated by Cahn–Ingold–Prelog rules.
Aliphatic ether (–OCH3 at C2): Typically inert under neutral/basic conditions, providing electronic modulation and steric bias near the stereocenter. Under specific conditions, can be converted to an amino alcohol (e.g., demethylation) enabling ligand synthesis.
Stereocenter (S at C2): Offers chiral induction in neighboring reactions or serves as a stereodefined element in target molecules.
Key transformations (literature/practice):
Reductive amination: With aldehydes/ketones → chiral secondary amines; catalysts: NaBH(OAc)3 (mild, acetic acid additive) or H2/Raney Ni or Pd/C.
Amide coupling: With carboxylic acids (EDC·HCl/Oxyma, HATU, PyBOP) in DMF/MeCN; base: DIPEA/Et3N. Provides opportunities to install chiral amide fragments.
Urea/carbamate formation: Reaction with isocyanates or chloroformates to introduce protective or functional motifs.
Sulfonamides: With TsCl/MsCl in presence of base (e.g., pyridine, NEt3) for robust protecting/functional groups.
N-alkylation: SN2 with primary halides or epoxides (opening to β-amino ethers). Control double alkylation via protecting groups or excess amine.
Cyclizations: Formation of oxazolidines/oxazolines from carbonyl derivatives to lock stereochemistry for auxiliary use.
Utility considerations:
Maintain anhydrous conditions for imine/coupling steps; water suppresses imine formation and promotes salt formation.
Monitor for racemization under strong base/acid or elevated temperatures near the stereocenter.
The ether substituent can improve volatility/handleability vs analogous amino alcohols, aiding extractions and chromatography.
Target Specificity
Not applicable. This product is a small-molecule chiral amine and is not an antibody, enzyme, or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies. For target-directed studies, see the Synthetic Utility and Reaction & Applications sections for guidance on incorporating this amine into designed molecules.
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