4-Methylquinolin-3-amine - ≥95% , CAS No.50878-90-5

CAS: 50878-90-5 Cat. No.: M709155 Formula: C₁₀H₁₀N₂ Peso molecolare: 158.2 Numero EC: 859-947-0 PubChem CID: 4348180

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CC1=C(C=NC2=CC=CC=C12)N

IUPAC Name

4-methylquinolin-3-amine

InChIKey

HANMWNJJOSJZHD-UHFFFAOYSA-N

INCHI

1S/C10H10N2/c1-7-8-4-2-3-5-10(8)12-6-9(7)11/h2-6H,11H2,1H3

Isomeri SMILES

CC1=C(C=NC2=CC=CC=C12)N

PubChem CID

4348180

Peso molecolare

158.2

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Quinolines and derivatives
      • Subclass Aminoquinolines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Quinolines and derivatives
• Subclass: Aminoquinolines and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Aminoquinolines and derivatives
• Alternative Parents: Methylpyridines Aminopyridines and derivatives Benzenoids Heteroaromatic compounds Azacyclic compounds Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aminoquinoline - Methylpyridine - Aminopyridine - Benzenoid - Pyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 158.200 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• 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: 158.000
• 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

Application Protocols

Not applicable as standardized bioassay protocols (e.g., WB, IHC, IF, FC) are for biological reagents. For this small-molecule building block:

• General handling: Weigh quickly to minimize exposure to ambient moisture; dissolve in dry organic solvent (e.g., DMSO, DMF, MeCN) or convert to an acid salt for aqueous work.
• Typical stock solutions: 10–100 mM in anhydrous DMSO for screening chemistry; filter if needed (PTFE, 0.2 µm) to remove particulates.

Refer to individual synthetic procedures in the Reaction Conditions section for use-case-specific steps.

Biological Roles

Item-specific biological data are not provided. In general, 4-methylquinolin-3-amine is a synthetic heteroaromatic amine and is not a known endogenous metabolite.

• Quinoline motif (general context): The quinoline core is prevalent in research ligands and probe molecules due to its planar, π-rich structure and ability to engage in π–π stacking and hydrogen bonding. The ring nitrogen can act as a weak base and metal ligand, often influencing binding modes in biochemical studies.
• Primary amine handle: Facilitates conjugation to biomolecules (e.g., via NHS-esters to form amide linkages) for probe or affinity reagent development. The amine’s basicity enables salt formation for improved aqueous handling during bioconjugation workflows.
• Photophysical note (general): Quinoline derivatives can exhibit UV absorption and, in some cases, fluorescence; substitution patterns determine quantum yield and emission maxima. No item-specific photophysical constants are provided here.

This product is supplied strictly for research use only and should not be used for diagnostic or therapeutic purposes.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare biological buffers. The primary amine can form salts with acids, but defined buffer systems (e.g., phosphate, Tris, HEPES) are preferred for pH control.

• If dissolution into aqueous media is needed for assays, prepare an acid salt (e.g., HCl) in a compatible buffer, or dissolve first in DMSO then dilute into the assay buffer, monitoring final DMSO content.
• For buffer selection and pH stability, refer instead to the Solvent Selection and Storage sections.

Green Alternatives

While the compound itself is a target scaffold, greener strategies focus on solvent and reagent selection during its use and derivatization.

• Prefer greener solvents where feasible:

  • Replace DMF/DMSO with Cyrene, propylene carbonate, ethanol, or 2-MeTHF when solubility and reaction scope permit.
  • Swap dichloromethane with EtOAc or 2-MeTHF for acylations/sulfonylations; consider aqueous micellar media (e.g., TPGS-750-M) for couplings.

• Greener bases/reagents:

  • Use K2CO3 or NaHCO3 instead of stronger bases where compatible.
  • Employ organocatalytic or copper-catalyzed aminations under milder conditions to reduce Pd loadings.

• Process-intensification options:

  • Continuous flow for hazardous steps (e.g., diazotization) to improve safety and minimize waste.

• Comparative snapshot (general):

  • Conventional vs greener choices
    • DMF → Cyrene/PC (biobased, lower toxicity; higher viscosity trade-off)
    • DCM → EtOAc/2-MeTHF (renewable sources; different polarity may affect rates/selectivity)
    • Toluene/dioxane → CPME/2-MeTHF (better worker exposure profiles; peroxide management still required for ethers)

All substitutions should be validated at small scale; yields and selectivity can shift with solvent polarity and hydrogen-bonding properties.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item. 4-Methylquinolin-3-amine is generally used as a synthetic intermediate/building block in pharmaceutical research.

• Typical roles (general, non-clinical):
  • Starting material for amide, urea, sulfonamide, and N-aryl derivatives in medicinal chemistry campaigns.
  • Ligand precursor in coordination chemistry supporting catalyst or probe development.
• Regulatory note: Not intended for human or veterinary use. For research use only. Any application in GMP or clinical manufacturing would require independent qualification and specification setting beyond the scope of this catalog entry.

Physical Properties

Item-specific numerical specifications are not provided in the Product Data. The following are general/literature expectations for the named structure; verify against the CoA/Spec Sheet for this specific lot before use.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Aromatic amines of this type are commonly crystalline solids; literature description may vary.)
• Molecular weight (literature): ~158.20 g/mol for C10H10N2
• Melting point (literature, if reported for analogous 3-aminoquinolines): often in the 80–160 °C range; exact value for 4-methylquinolin-3-amine not confirmed here.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• pKa (qualitative, literature): Primary anilines typically have conjugate acid pKa around 4–6; the quinoline ring nitrogen is weaker basicity than pyridine. Exact pKa values for this specific substitution pattern are not provided here.
• Solubility (general): Expected to be sparingly soluble in nonpolar hydrocarbons; soluble in polar organics (DMSO, DMF, alcohols) and in dilute mineral acids as the ammonium salt.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• UV-Vis: Quinoline chromophore absorbs in the near-UV; precise λmax and cutoff not specified for this item.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• What grade implies (general guidance):
  • Research or technical grade materials are suitable for synthetic and exploratory work where trace-level impurities are acceptable.
  • Higher-purity or assay-defined materials (e.g., 98–99%) are preferred for structure–activity studies or when downstream purification is limited.
  • Low-residual-solvent and low-UV grades are relevant only if the compound is used as an analytical standard or optical probe.
• Stabilizers/inhibitors: None specified for this item; most aromatic amines do not require stabilizers under normal storage.
• Lot-specific documentation: For assay, impurity profile, residual solvents, elemental analysis, and chromatographic purity, consult the Certificate of Analysis (CoA) and specification sheet. These documents supersede generalized expectations.
• Fit-for-use notes: If planning metal-catalyzed couplings or late-stage functionalization, consider pre-screening for trace metals and halogens (ICP/MS, ion chromatography) and perform a drying step if moisture-sensitive downstream chemistry is anticipated.

Reaction and Applications

As a 3-amino-4-methylquinoline, this compound is a versatile heteroaromatic building block. The primary amine engages in classical aniline chemistry, while the quinoline ring provides additional coordination and directing effects.

• Derivatization of the amine:
  • Acylation and carbamoylation to access amides and ureas (e.g., with acid chlorides, anhydrides, chloroformates; base such as Et3N or pyridine). Sulfonylation with sulfonyl chlorides affords sulfonamides useful as stable handles.
  • N-Alkylation via SN2 with alkyl halides or via reductive amination with aldehydes/ketones (NaBH3CN, NaBH(OAc)3). Protecting groups (Boc, Cbz, Fmoc) are readily introduced for orthogonal synthesis.
• Cross-coupling as amine nucleophile:
  • Buchwald–Hartwig amination with aryl/vinyl halides/triflates using Pd catalysts and ligands (e.g., XPhos, BrettPhos) to build diarylamines on nitrogen.
• Diazonium chemistry and further ring functionalization:
  • Although the amine is on a heteroaromatic ring, diazotization (NaNO2/HX, 0–5 °C) can enable Sandmeyer-type transformations to diversify the 3-position (literature-dependent feasibility and yields vary for quinolinyl amines).
• Directed metalation/coordination:
  • The quinoline N can chelate metals, aiding C–H activation or ortho-selective transformations under transition-metal catalysis.
• Applications (general):
  • Scaffold in medicinal chemistry campaigns, materials and fluorescence probes derivatization (quinoline chromophore), and ligand design. No medical/clinical claims; for research and synthesis only.
• Practical tips:
  • Maintain anhydrous conditions when required (e.g., acyl chloride couplings). For silica chromatography, add 0.1–1% Et3N to prevent tailing of basic products. Prepare hydrochloride or tosylate salts to enhance aqueous handling when needed.

Reaction Conditions

The following are general, literature-style conditions for common transformations of primary aromatic amines and quinoline derivatives. They are provided as guidance; optimize for your substrate and scale.

• Acylation (amide formation):
  • Reagents: acyl chloride (1.1–1.5 eq) or mixed anhydride; base Et3N or pyridine (2–3 eq).
  • Solvent: DCM, THF, EtOAc, or MeCN.
  • Temperature/time: 0 °C to rt, 0.5–4 h; often quantitative to high yields after workup.
• Sulfonylation (sulfonamide):
  • Reagents: RSO2Cl (1.1–1.5 eq), base (Et3N, DIPEA) 2–3 eq.
  • Solvent: DCM or 2-MeTHF; 0 °C to rt, 1–3 h.
• Reductive amination:
  • Carbonyl (1.1–2 eq), NaBH(OAc)3 (2–3 eq) in DCE or MeOH/THF with AcOH (cat.).
  • rt to 40 °C, 2–16 h; monitor by LC/MS.
• N-Alkylation (SN2):
  • Alkyl halide (1.2–2 eq), K2CO3/Cs2CO3 (2–3 eq) in DMF or MeCN.
  • 40–80 °C, 4–24 h; minimize overalkylation by stoichiometry and base choice.
• Buchwald–Hartwig N-arylation:
  • Pd2(dba)3 (1–2 mol%) or Pd(OAc)2 (1–3 mol%) with XPhos/BrettPhos (2–6 mol%), base NaOtBu or Cs2CO3.
  • Solvent: toluene, dioxane, or CPME; 80–110 °C, 6–24 h.
• Diazotization (substrate-dependent for heteroaromatics):
  • NaNO2 (1.1 eq) in HCl (2–4 M) at 0–5 °C to form diazonium; trap with CuX for Sandmeyer variants.

Note: The quinoline nitrogen can coordinate catalysts; ligand/base choices may need adjustment to maintain activity. Conduct small-scale screens to tune conditions.

Safety and Handling

Always consult the product SDS for authoritative safety information. No item-specific GHS details are provided in the Product Data; the following are general precautions for aromatic amines and heteroaromatic bases.

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
• Likely hazards (general): May cause skin and eye irritation; dust may be harmful if inhaled. Aromatic amines can be harmful if swallowed. Avoid formation of dust and contact with skin/eyes.
• PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a well-ventilated fume hood.
• Handling: Avoid breathing dust; prevent contact with oxidizers and strong acids/bases unless forming salts intentionally. When preparing acid salts for solubility, control exotherm and pH.
• First aid (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Spill/cleanup: Avoid dust generation; sweep up and collect in suitable container; ventilate area. Dispose according to local regulations.
• Stability: Aromatic amines are generally stable under ambient conditions; protect from strong oxidants and excessive heat. No special inhibitor noted for this item.
• For research use only (per Product Data).

Solvent Selection

4-Methylquinolin-3-amine is a heteroaromatic primary amine with dual basic sites (aniline N and ring N) and an extended π-system. This profile guides solubility and reactivity.

• Polarity/miscibility (general):
  • Expected to dissolve well in polar aprotic solvents (DMSO, DMF, NMP) and moderately in polar protic solvents (MeOH, EtOH).
  • Limited solubility in nonpolar hydrocarbons (hexanes, toluene) unless warmed or converted to a salt.
  • Readily soluble as acid salts in aqueous media; free base has low water solubility.
• Choosing solvents by task:
  • Reaction medium for acylation/sulfonylation: dichloromethane, THF, MeCN, or pyridine/Et3N as base; for greener options consider EtOAc or 2-MeTHF.
  • N-alkylation (SN2): DMF/MeCN with inorganic base (K2CO3/Cs2CO3) or DMSO with milder bases.
  • Metal-catalyzed arylation (as nucleophile): dioxane, toluene, or CPME with a base (NaOtBu) under Buchwald–Hartwig conditions.
  • Purification: Normal-phase silica may retain basic amines; add a few percent Et3N to eluents or use basic alumina/reverse-phase.
• Comparison (general):
  • DMSO/DMF: highest solvating power for polar substrates; harder to remove.
  • MeCN/EtOAc: easier workup, good balance for many electrophilic reactions.
  • Alcohols: useful for reductive amination or salt formation, but may compete in acylations.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Container: Store in a tightly closed container, preferably amber glass to minimize photodegradation of aromatic systems.
• Atmosphere: Keep dry; a desiccator or dry cabinet is recommended if frequent opening is expected. Inert gas backfill is optional but beneficial for long-term stability.
• Stability: Aromatic amines are generally stable under ambient conditions; avoid prolonged exposure to light, air, and strong oxidants.
• Reconstitution and use:
  • Prepare stock solutions in dry DMSO, DMF, MeCN, or alcohols. For aqueous applications, form a soluble acid salt (e.g., HCl) or dissolve in DMSO then dilute into buffer while monitoring final cosolvent content.
  • Working solutions should be used promptly or stored at 2–8 °C for short periods; freeze at −20 °C for longer storage if solvent permits. Avoid repeated freeze–thaw; aliquot when practical.
• Specifications such as water content, residual solvents, or assay are Not specified for this item; refer to CoA/Spec Sheet.
• Research Use Note: For research use only.

Structure and Identity

4-Methylquinolin-3-amine is a nitrogen-containing polycyclic aromatic (quinoline) bearing an aniline-like primary amine at the 3-position and a methyl substituent at the 4-position.

• Item-specific identifiers (from Product Data):

  • CAS: 50878-90-5
  • CID: 4348180
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Provided value appears incomplete.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/typical identity data (for the named structure; provided for context):

  • Molecular formula (literature): C10H10N2
  • Molecular weight (literature): ~158.20 g/mol
  • Core scaffold: quinoline (fused benzene–pyridine) with N in the pyridine ring
  • Functional groups: primary aromatic amine (–NH2) at C-3; methyl at C-4
  • Aromaticity: fully conjugated bicyclic system; amine lone pair conjugated with the ring (anilide character)

• 2D structural description (general): The molecule consists of a benzene ring fused to a pyridine ring (quinoline). The ring nitrogen is part of the pyridine moiety. The C-3 position (on the benzopyridyl framework, adjacent to the ring nitrogen across the ring junction) bears a primary amine, while the adjacent C-4 position bears a methyl substituent. No stereocenters are present; the compound is achiral.

Synthetic Utility

Key reactive elements and how they enable synthesis:

• Primary aniline-like amine (at C-3):
  • Electrophile capture: acylation, sulfonylation, carbamoylation to give amides/sulfonamides/ureas (robust handles for SAR and stability).
  • N-alkylation and N-arylation: build secondary/tertiary amines via SN2 or Buchwald–Hartwig coupling; protect (Boc/Cbz) for orthogonality.
  • Reductive amination: install diverse alkyl groups under mild conditions with NaBH(OAc)3 or NaBH3CN.
• Quinoline ring nitrogen:
  • Acts as a weak base/ligand, enabling directed metalation/C–H activation and coordination to transition metals (e.g., Pd, Cu) to steer regioselectivity.
• Ring functionalization options (literature, general):
  • Electrophilic substitution is deactivated by the ring N; however, activated conditions (e.g., nitration/sulfonation) or metalation can provide access to further substitution.
  • Diazonium pathways at the 3-amino substituent may enable Sandmeyer-type diversification (scope can be substrate-dependent for heteroaromatics).
• Retrosynthetic value:
  • Serves as a convergent node: amine derivatization late in synthesis, while the 4-methyl group tunes lipophilicity and sterics without additional reactivity.

Practical note: For chromatographic purification of basic products, modify eluents with 0.1–1% triethylamine or use basic alumina to minimize tailing.

Target Specificity

Not applicable. This product is a small-molecule heteroaromatic amine, not an antibody, enzyme, or affinity reagent. No antigen/epitope or species reactivity information applies.