This compound belongs to the class of organic compounds known as quinolines and derivatives. These are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
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
158.200 g/mol
XLogP3
1.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
158.084 Da
Monoisotopic Mass
158.084 Da
Topological Polar Surface Area
38.900 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
147.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
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
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No item-specific, validated application protocols are provided for this small-molecule reagent.
General laboratory usage examples:
Stock solutions: Dissolve the free base in dry DMSO, DMF, MeOH, or MeCN to 10–100 mM; filter (0.22 µm) if needed. For aqueous assays, pre-form an HCl salt or acidify to pH ~6 to enhance solubility.
Coupling sequence (example): To a solution of carboxylic acid (1.0 equiv) and HATU (1.1 equiv) in DMF, add DIPEA (3 equiv) and this amine (1.2 equiv) at 0–25 °C; stir 2–12 h; quench and purify by acid–base extraction or chromatography.
Reductive amination (example): Combine aldehyde (1.2 equiv) and this amine (1.0 equiv) in MeOH with AcOH (0.5 equiv), stir 30–60 min, then add NaBH(OAc)3 (2.0 equiv); stir 2–16 h; work up and purify.
These examples are for guidance only and are not product-specific validations. Adjust conditions based on substrate reactivity and safety considerations.
Biological Roles
No item-specific biological data are provided. The following context is general for quinoline-containing benzylamines used in research chemistry.
Quinoline motif: The quinoline ring is a privileged heteroaromatic scaffold in chemical biology due to its planarity, π-stacking capability, and ring nitrogen that can participate in hydrogen bonding or metal coordination. These properties are often leveraged in probe and ligand design.
Primary amine handle: The –CH2NH2 group enables rapid diversification into amides, sulfonamides, ureas, and carbamates, allowing systematic SAR exploration when assembling libraries for target binding studies. Protonation state control (pH-dependent) modulates cell permeability and aqueous solubility in assay buffers.
Metal binding: After derivatization, bidentate donors incorporating the quinoline nitrogen can chelate transition metals, useful in metalloenzyme probe design and fluorescence quenchers/sensors (general literature context).
Fluorescence/UV: Quinoline chromophores often show strong UV absorption and, in some derivatives, environment-sensitive fluorescence, which can be exploited in reporter designs after conjugation.
Important: No claims are made regarding biological efficacy, safety, or therapeutic use. This product is supplied strictly for research and laboratory use, as stated in the product data.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare classical buffer systems. As a primary amine, it can be protonated and dissolved in buffered aqueous media for assays or conjugations, but it does not define a stable buffer pair with a broad, standardized pH range.
Practical guidance (general):
To dissolve the free base in aqueous systems, adjust to mildly acidic pH (e.g., pH 5.5–6.5) or pre-form a water-soluble salt (e.g., HCl). Use co-solvents (10–30% MeCN, DMF, or DMSO) if needed.
Avoid strongly basic buffers when unprotected; the amine may undergo unwanted reactions with carbonyl-containing buffer components.
For pH-controlled reactions or bioconjugation, refer instead to the Solvent Selection and Reaction Conditions sections for solvent/buffer choices.
Green Alternatives
Greener choices concern primarily solvent and coupling reagent selection, as the substrate is fixed.
Prefer greener solvents where feasible:
Replace DMF/NMP with MeCN, MeOH/EtOH, 2-MeTHF, CPME, or water/MeOH cosolvent systems when solubility allows.
For extractions, EtOAc and MTBE are often preferable to DCM/CHCl3; heptane over hexane for lower toxicity.
Coupling/reductive amination reagents:
Use water-tolerant coupling systems (e.g., EDC/Oxyma or DMTMM) to avoid hazardous uronium salts and minimize racemization (if chiral partners are present).
For reductive amination, NaBH(OAc)3 in acetic acid/MeOH or catalytic hydrogenation (H2/Pd) can be greener than cyanoborohydride, balancing safety against over-reduction risk.
Small comparison (general):
DMF vs. MeCN/2-MeTHF: DMF offers superior solubility but is reproductive-toxic; MeCN/2-MeTHF are lower hazard and easier to remove, though sometimes less solvating for salts.
DCM vs. EtOAc/CPME: DCM is volatile and problematic for worker exposure; EtOAc/CPME provide good solvency with better environmental profiles but may alter reaction rates.
Workup/waste minimization:
Plan protection/deprotection sequences to avoid phosgene surrogates when possible (e.g., use Boc anhydride instead of triphosgene).
Concentrate on telescoped processes (in situ salt formation, in-line scavengers) to reduce solvent usage.
Note: Always validate greener substitutions on small scale to ensure comparable yields/selectivities.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation grade is specified for this item.
Not specified for this item; refer to CoA/Spec Sheet.
General context for research and process chemistry:
Quinoline-containing benzylamines like quinolin-3-ylmethanamine are often used as intermediates in the synthesis of more elaborate small molecules. The primary amine can be converted into amides, ureas, and sulfonamides that serve as advanced intermediates during route scouting.
Salt selection studies: Protonatable amines are amenable to salt screening (e.g., HCl, HBr, mesylate, sulfate) to optimize crystallinity, solubility, and stability for handling in research-scale process development. Such experiments are strictly non-clinical at this stage.
Analytical development: Strong UV absorbance of quinoline facilitates HPLC/UPLC method development with UV detection; stability-indicating methods often monitor oxidative degradants (e.g., N-oxides) and dimerization products.
Important: This product is for research use only and is not intended for human or veterinary use, clinical diagnostics, or as a drug substance/excipient.
Physical Properties
Item-specific specifications are not provided. The following are general expectations for this scaffold; confirm with the CoA/SDS for this lot.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting/Boiling Point: Not specified for this item; refer to CoA/Spec Sheet. (Arylbenzylamines are often crystalline solids with moderate melting points; literature values vary with salt form.)
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable unless liquid; not specified.
Solubility (general guidance, literature):
Free base: typically soluble in polar organics (DMSO, DMF, MeOH, EtOH, acetonitrile) and partially in moderately polar solvents (EtOAc, DCM).
Water: low-to-moderate as free base; high as protonated salts (e.g., HCl salt).
pKa (literature, qualitative): primary aliphatic amine conjugate acid typically pKa ~9–10; quinoline ring nitrogen pKaH ~4–5. Exact values depend on substitution and medium.
LogP/logD (literature, qualitative): heteroaromatic benzylamines are moderately lipophilic in free-base form; logD decreases sharply under acidic conditions due to protonation and increased aqueous solubility.
Practical notes (general):
Protonation markedly increases water solubility; preparation of hydrochloride salts is common for handling and purification.
Hygroscopicity may occur for some salt forms; the free base can absorb CO2 over time. Store under desiccation per product data.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical quality attributes for this class of product:
Research/analytical grade materials for heteroaromatic amines commonly specify high assay (e.g., >97–99%) with defined impurity thresholds (residual solvents, related aromatics, oxidized species). Absent item-specific values, verify acceptance criteria on the CoA for your lot.
Stabilizers: None indicated for this item. Primary amines generally do not require stabilizers; however, exclusion of moisture/CO2 minimizes salt/carbamate formation and discoloration. Product data already specifies desiccated, protected-from-light storage.
UV profile: Not specified for this item; refer to CoA/Spec Sheet. Quinoline chromophores typically exhibit strong UV absorption (200–350 nm), which is relevant for HPLC detection; low-UV grades may be beneficial for chromatographic solvents, but are not applicable here.
Residual metals, water, peroxides, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
What the grade means in practice (general):
For coupling chemistry (amide/sulfonamide/urea formation), low water content and low aldehydic impurities reduce side reactions (Schiff base formation, over-acylation). Drying (e.g., azeotrope, vacuum) and in situ base selection can mitigate residual acidity. Confirm moisture and assay on the CoA prior to sensitive transformations.
Reaction and Applications
This heteroaromatic benzylamine is a versatile building block and ligand precursor.
Derivatization of the primary amine:
Amide synthesis with carboxylic acids/acid chlorides (EDC/HOBt, HATU, CDI; or acyl chlorides with base). Practical tip: preform amine salt with weak acid to modulate reactivity if overacylation is an issue.
Ureas/carbamates: phosgene surrogates (triphosgene, CDI) or isocyanates/chloroformates; Boc/Cbz/Fmoc protection for orthogonal strategies.
Sulfonamides: reaction with sulfonyl chlorides in DCM/MeCN and base (TEA/DIPEA).
Reductive alkylation: formation of imines with aldehydes/ketones followed by NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
Benzylic functionalization:
Oxidation to the corresponding aldehyde/acid (e.g., via Dess–Martin or TEMPO-mediated sequences post-protection) enables access to 3-quinoline acyl derivatives.
Directed lithiation or halogenation strategies allow further ring elaboration at positions 2, 4, 5, or 8, though the benzylic amine may require protection.
Coordination/ligand uses:
The quinoline nitrogen plus an appended donor (after derivatization of –CH2NH2) can furnish bidentate ligands for late-transition-metal complexes.
Practical tips:
Protect the amine (Boc/Cbz) before electrophilic aromatic substitution or strong-base conditions to avoid side reactions.
The quinoline ring is electron-deficient; nucleophilic aromatic substitution is facilitated at suitably activated positions.
Reaction Conditions
General, literature-based guidance; optimize for your specific substrates. No item-specific method validation is implied.
Amide coupling (to carboxylic acids):
Solvent: DMF, NMP, DCM, or MeCN; 0.05–0.2 M.
Reagents: HATU/EDC·HCl (with Oxyma or HOAt), DIPEA or TEA base (2–4 equiv).
Temperature: 0 °C to rt; 1–16 h. Typical isolated yields: 70–95% for unhindered acids (literature ranges).
Sulfonamide formation:
Solvent: DCM or MeCN; base: DIPEA (2–3 equiv).
Temperature: 0 °C to rt; 1–4 h. Monitor for over-sulfonylation if excess sulfonyl chloride is used.
Reductive amination:
Formation: mix amine and carbonyl (1.0–1.5 equiv) with AcOH or Ti(OiPr)4 (catalytic) as activator in MeOH/MeCN.
Reduction: NaBH(OAc)3 (2–3 equiv) at rt, 2–18 h; or H2 (1–3 bar) with 5–10% Pd/C in EtOH/AcOH at rt–40 °C.
N-protection (Boc):
Boc2O (1.2–1.5 equiv), base (NaHCO3 or TEA), dioxane/water or THF; 0 °C to rt, 1–3 h.
Quinoline N-oxidation:
m-CPBA (1.1–1.5 equiv) in DCM at 0 °C to rt, 1–3 h. Protect the benzylic amine to avoid over-oxidation.
Workup tips:
Free-base amines may streak on silica; convert to salts (HCl in dioxane) for crystallization, or use basic-modified silica (1–2% NEt3) during chromatography.
For aqueous workups, avoid strong base washes that can emulsify protonated amines; instead, do acid–base partitioning to toggle solubility.
Safety and Handling
Hazard classifications for this specific item are not provided; consult the Aladdin SDS for definitive information.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
Likely hazards (general for primary amines/quinoline derivatives): skin/eye irritation, respiratory irritation; may be harmful if swallowed; strong odor; can form salts with acids; may cause sensitization in predisposed individuals.
Storage (product data):
Store at 2–8 °C
Protect from light
Desiccated
Shipped on wet ice
Incompatibilities (general): strong oxidizers, acid chlorides/anhydrides, carbonyl-activating reagents (unprotected amine will react), and strong acids/bases that may lead to degradation. Avoid CO2 exposure for the free base to prevent carbamate/acid salt formation.
Handling/PPE: use in a fume hood with appropriate PPE (lab coat, safety glasses, nitrile gloves). Avoid inhalation and contact. Keep containers tightly closed under dry inert headspace if possible.
First aid (overview; defer to SDS):
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms develop.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste: collect amine-containing waste in compatible, labeled containers. Neutralize/reactivity toward acylating agents should be considered before disposal, per institutional and regulatory guidance.
Solvent Selection
Quinolin-3-ylmethanamine is a moderately basic heteroaromatic benzylamine. Solvent choice depends on whether the free base or a protonated salt is used and on target transformation.
Polarity/miscibility (general):
Highly soluble in polar aprotics (DMSO, DMF, NMP) and protics (MeOH, EtOH, iPrOH).
Moderately soluble in MeCN, EtOAc, DCM; limited in hexanes/MTBE unless as salt-pairs or with cosolvent.
Aqueous solubility increases drastically upon acidification (e.g., as HCl salt).
Typical selections by application:
Amide couplings: DMF, NMP, DCM/DMF mixtures; protic alcohols possible with carbodiimides/urate reagents.
Reductive amination: MeOH, EtOH, iPrOH, or MeCN with water as needed; choose solvent compatible with chosen hydride (NaBH3CN/NaBH(OAc)3).
N-protection (Boc, Cbz, Fmoc): Dioxane, THF, DCM, or MeCN; add base (TEA/DIPEA).
Salt formation/purification: IPA/Et2O or EtOAc/hexanes antisolvent crystallizations for hydrochloride or other mineral-acid salts.
Comparison notes:
DMSO/DMF maximize solubility but complicate workup; MeOH/EtOH are greener and simplify isolation for small-scale.
For bioconjugation contexts, aqueous buffers at pH 6–7.5 with miscible organics (10–30% MeCN or DMF) can keep the free base in solution; adjust pH to control protonation.
Drying: If needed, dry amine solutions over basic desiccants (K2CO3, molecular sieves) to avoid salt formation; avoid acidic desiccants (silica gel) which can retain/protonate the amine.
Storage and Reconstitution
Storage (product data): Store at 2–8 °C, protected from light, under desiccation. Shipped on wet ice.
Container: Use amber, airtight containers to minimize light exposure and moisture/CO2 ingress. Purge headspace with inert gas if storing the free base for extended periods.
Stability: Item-specific stability data are not provided; monitor by HPLC/LC–MS for long-term studies. Avoid prolonged exposure to air and light which may promote discoloration or oxidative byproducts (e.g., N-oxides) in quinoline derivatives.
Reconstitution/solution preparation (general):
Prepare stock solutions in dry DMSO, DMF, MeOH, EtOH, or MeCN. Typical concentrations: 10–100 mM depending on solubility and intended use.
For aqueous work: form a water-soluble salt (e.g., dissolve in minimal HCl(aq) then dilute with buffer) or co-solubilize with 10–30% water-miscible organic solvent. Adjust pH to maintain protonation if high aqueous solubility is required.
Filter sterilize (0.22 µm) for cell-free biochemical assays if necessary.
Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw and atmospheric exposure. Store solutions at −20 °C (or lower) protected from light; bring to rt before opening to minimize condensation.
Specifications such as water content, assay, residual solvents, and exact shelf life: Not specified for this item; refer to CoA/Spec Sheet.
Research use only, as noted in the product data.
Structure and Identity
Quinolin-3-ylmethanamine is a heteroaromatic benzylamine bearing a quinoline ring substituted at the 3-position by a methanamine (–CH2NH2) side chain. The scaffold combines an electron-deficient quinoline nucleus (fused benzopyridine) with a primary aliphatic amine.
Fused bicyclic aromatic system (benzannulated pyridine = quinoline)
Primary aliphatic amine (–CH2NH2) at C-3 of quinoline
One ring nitrogen (sp2) in the pyridine portion; one exocyclic primary amine nitrogen (sp3)
No defined stereocenters; achiral
2D description in words: a quinoline ring (benzene fused to pyridine) with a benzylic –CH2NH2 substituent at the carbon adjacent to the pyridine nitrogen across the ring (position 3).
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
Notes:
The benzylic methanamine enhances nucleophilicity/basicity relative to anilines and enables broad derivatization (amide, urea, sulfonamide formation) while the quinoline ring can engage in π–π interactions and metal coordination through its ring nitrogen.
Synthetic Utility
Key functional elements—an electron-deficient quinoline ring and a benzylic primary amine—make quinolin-3-ylmethanamine a strategic synthon.
Primary amine reactivity:
Amidation with acids/acid derivatives; rapid library build via HATU/EDC/DMTMM-mediated couplings.
Urea/carbamate formation to introduce hydrogen-bond donors/acceptors and tune basicity/lipophilicity.
Sulfonamidation to enhance metabolic stability and polarity.
Reductive amination to install secondary/tertiary amines without over-acylation risk.
Quinoline ring as handle:
N-oxide strategy: temporary activation of the ring (via m-CPBA) for regioselective substitution, then reduction back to quinoline (e.g., PCl3, Zn/AcOH).
Directed metallation/electrophile trapping at positions 2/4/5/8 depending on directing groups and protecting strategies.
Protecting group tactics:
Boc for base-stable sequences (removed with TFA); Cbz for hydrogenolysis routes; Fmoc for base-labile deprotection in parallel synthesis.
Conjugation chemistry:
The benzylic amine enables attachment to linkers/spacers (PEGylated NHS esters, isothiocyanates) to give probes, resin-bound ligands, or metal-chelating ligands incorporating quinoline.
Retrosynthetic value:
As a linchpin, it can back-track either to quinoline-3-carboxaldehyde (via reductive amination) or to 3-(halomethyl)quinoline (via substitution), providing multiple disconnections for route development.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological macromolecule or antibody. No antigen/epitope or species specificity is relevant. For target engagement in research assays, see Biological Roles and Synthetic Utility for general scaffold behavior.
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.
