3-Methoxy-2,5-dimethylaniline - ≥97% , CAS No.102440-04-0

CAS: 102440-04-0 Cat. No.: M963523 Formula: C₉H₁₃NO Peso molecolare: 151.2 PubChem CID: 53417558

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

• Sorrisi canonici: CC1=CC(=C(C(=C1)OC)C)N
• IUPAC Name: 3-methoxy-2,5-dimethylaniline
• InChIKey: YGMJHZBOUJHHLL-UHFFFAOYSA-N
• INCHI: 1S/C9H13NO/c1-6-4-8(10)7(2)9(5-6)11-3/h4-5H,10H2,1-3H3
• Isomeri SMILES: CC1=CC(=C(C(=C1)OC)C)N
• PubChem CID: 53417558
• Peso molecolare: 151.2

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers
      • Subclass Aminophenyl ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Aminophenyl ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Aminophenyl ethers
• Alternative Parents: Methoxyanilines p-Xylenes Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers Primary amines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminophenyl ether - Methoxyaniline - Phenoxy compound - Anisole - P-xylene - Xylene - Aniline or substituted anilines - Methoxybenzene - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Primary amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Amine - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.
• 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: 151.210 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 151.1 Da
• Monoisotopic Mass: 151.1 Da
• Topological Polar Surface Area: 35.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 127.000
• 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. No standardized bioassay protocols (WB, IHC, IF, FC, etc.) are associated with this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance.

Biological Roles

This product is a synthetic, non-natural, small aromatic amine. No biological role is assigned for this catalog item.

General biochemical context (literature-based, not specific to this item):

• Aromatic amines can interact with biological nucleophiles when protonated or metabolically activated; however, 3-methoxy-2,5-dimethylaniline is primarily used as a chemical building block in research chemistry, not as a biological reagent.
• Protonation state: At physiological pH, anilines are largely unprotonated (conjugate acid pKa typically ~5–6), resulting in low cationic fraction in neutral media and limited aqueous solubility unless converted to salts.
• Enzymatic transformation: Generic anilines may undergo oxidative metabolism (e.g., N-oxidation, O-demethylation, ring hydroxylation) in biological systems; these considerations are relevant only in toxicology/metabolism studies, not routine lab synthesis.

Research Use Only statement: Per Product Data, this material is for research use only and is not intended for diagnostic, therapeutic, or other clinical applications.

Buffer Applications

Not typically applicable. 3-Methoxy-2,5-dimethylaniline is not a buffering agent and is sparingly soluble in water as a free base. If aqueous handling is required, temporary conversion to its ammonium salt (e.g., HCl salt) can increase water solubility for extraction or crystallization purposes. For pH control in systems involving this compound, use an appropriate laboratory buffer (e.g., phosphate, acetate, citrate) independent of this reagent.

Green Alternatives

Opportunities to improve sustainability when working with this aryl amine focus on solvent and reagent choices rather than the substrate itself.

Greener solvent substitutions (general guidance):

• Replace DCM/chloroform with EtOAc, Me-THF (2-MeTHF), CPME, or toluene where kinetics and selectivity permit.
• Favor alcohols (EtOH, i-PrOH) or esters (EtOAc) for acylations/extractions when feasible.
• For Pd-catalyzed aminations, solvent systems like 2-MeTHF, CPME, or t-amyl alcohol have been demonstrated to work with modern ligands.

Comparison (illustrative):

• THF vs 2-MeTHF: 2-MeTHF is biorenewable, less miscible with water (easier workups), and exhibits lower peroxide propensity; THF remains broadly effective and is often required for highly polar reagents.
• Dioxane vs CPME: CPME shows better EHS profile and broader liquid range; dioxane is effective but flagged for regulatory concerns.

Reagent choices:

• Use organobases (K3PO4, K2CO3) over strong alkoxides where possible to reduce hazards.
• Employ catalytic acylations (e.g., DMAP at low loading) and greener acyl donors (isopropenyl acetate for transacylation) when compatible.

Waste minimization:

• Leverage acid–base toggling to recycle organic solvent and minimize chromatographic media.
• Monitor reactions by LC/UPLC to avoid overreaction and reduce byproducts.

Note: These are general best practices; optimize for your specific transformation.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is provided for this item; consult the CoA/Spec Sheet for any available quality statements. This product is for research use only.

General formulation/manufacturing relevance (literature-level):

• Synthetic intermediate: Substituted anilines are common precursors to APIs and agrochemicals via acylation (anilides), sulfonamide formation, urea/carbamate assembly, and metal-catalyzed C–N couplings.
• Salt formation: Temporary formation of anilinium salts (e.g., HCl, p-TsOH) can aid crystallization, purification, and handling, but such salts are typically intermediates rather than final dosage components.
• Analytical characterization: For process development, typical controls include residual solvents (GC), identity (NMR/HRMS), assay and impurities (HPLC/UPLC), and color index due to potential oxidative byproducts.

No therapeutic or clinical claims are made or implied for this product.

Physical Properties

Item-specific specifications (this batch):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for substituted anilines of this structure (informational only):

• Phase at ambient conditions: Typically a liquid or low-melting solid for dialkyl/methoxy anilines.
• Boiling point: Often in the 240–270 °C range for anisidine/dimethylaniline analogs (literature trends; check CoA for item-specific value).
• Melting point: Frequently near or below room temperature for similar isomers (literature trend).
• Density: Around 0.95–1.05 g/mL for comparable aryl amines (literature trend).
• Solubility: Low in water; high in common organic solvents (EtOAc, MeOH, EtOH, toluene, DCM, THF). Readily forms water-soluble ammonium salts under acidic conditions.
• pKa (conjugate acid, literature expectation): Anilinium conjugate acids typically pKa ~5–6; electron-donating substituents (OMe, Me) may shift basicity slightly higher than aniline.
• logP (literature expectation): Increased hydrophobicity vs aniline due to OMe/Me groups; often logP ~2–3 for comparable structures.
• Refractive index: Commonly nD 1.52–1.57 for related aryl amines (literature trend).

Notes:

• The above values are typical literature expectations for closely related structures, provided for planning only. They are not item-specific specifications. Always consult the CoA/Spec Sheet for exact values for SKU M963523.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and implications (general):

• Research grade vs high-purity: For synthetic applications (e.g., cross-coupling, peptide isostere synthesis, library building), higher purity minimizes side reactions and facilitates purification. If UV-transparent work (HPLC monitoring) is critical, materials screened for low non-volatile residues and low UV-absorbing impurities are preferred.
• Stabilizers: Not indicated for this item. Aromatic amines are generally shipped without stabilizers, but minimizing air/light exposure helps preserve color and purity.
• Trace metals/UV cutoff/water content: Not specified for this item; refer to CoA/Spec Sheet. If using in sensitive catalysis (e.g., Pd-catalyzed amination), consider pre-assaying or simple pretreatments (e.g., filtration through basic alumina if discolored) to remove trace oxidized species.
• Verification: For rigorous workflows, confirm identity by 1H/13C NMR and MS; check for aniline oxidation (imines/azo) by TLC/UPLC and UV/Vis (broad visible absorbance indicates aging/oxidation).

Reaction and Applications

This compound is a versatile electron-rich aniline suitable for numerous transformations and as a building block in discovery and materials chemistry.

Representative application families (general literature context):

• Cross-coupling (as amine partner): Buchwald–Hartwig amination with aryl halides/pseudohalides to form diarylamines. Electron-rich anilines often couple under milder conditions using Pd/XPhos, BrettPhos, or JohnPhos systems and strong bases (NaOtBu, Cs2CO3, K3PO4).
• N-Functionalization: Acylation (acid chlorides/anhydrides), sulfonylation (sulfonyl chlorides), carbamate/urea formation (chloroformates, isocyanates), reductive amination on the aniline nitrogen with activated carbonyls (after imine formation facilitators like Ti(OiPr)4 when needed).
• Electrophilic aromatic substitution (EAS): The –NH2 and –OMe groups strongly activate the ring; regioselectivity is biased to positions ortho/para to the dominant activators, though existing 2-/5-methyl groups impose steric control. Useful for nitration (mild conditions), sulfonation, halogenation, and Friedel–Crafts-type formylations (e.g., Vilsmeier–Haack), followed by further elaboration.
• Diazonium chemistry: Diazotization of the aniline (NaNO2/HX, 0–5 °C) enables Sandmeyer-type substitutions or azo coupling (dye/pigment precursors). Electron-rich rings can couple rapidly to activated phenols/anilines to form azo compounds.
• Protection strategies: Temporary masking of the aniline as acetanilide, Boc-, or Cbz-derivatives helps manage chemoselectivity in multi-step sequences.
• Materials/ligands: Anisidine/methyl-aniline cores appear in OLED emitters, photoinitiators, and donor–acceptor scaffolds; the 3-methoxy/2,5-dimethyl pattern modulates donor strength and sterics (general observation).

Practical tips:

• Maintain anhydrous conditions for metal-catalyzed couplings; basic pretreatment (e.g., pass through basic alumina) removes acidic traces.
• If discoloration occurs, short-path distillation under reduced pressure (if liquid) or recrystallization can restore quality; verify by NMR before use.

Reaction Conditions

General literature conditions for typical transformations involving electron-rich anilines (guidance only; optimize for your system):

• Buchwald–Hartwig amination (as amine partner):

  • Catalyst/ligand: Pd2(dba)3 (1–2 mol% Pd) with XPhos/BrettPhos (2–4 mol% ligand) or Pd-PEPPSI-type complexes.
  • Base: NaOtBu, KOtBu, Cs2CO3, or K3PO4 (2–3 equiv).
  • Solvent: Toluene, dioxane, CPME, 2-MeTHF, or t-BuOH.
  • Temp/time: 60–110 °C, 2–16 h depending on aryl halide electrophilicity (Ar–I/OTf > Ar–Br >> Ar–Cl).

• N-Acylation/sulfonylation:

  • Reagents: Acyl/sulfonyl chlorides (1.05–1.2 equiv) with Et3N or DIPEA (2–3 equiv) and catalytic DMAP (0.05–0.1 equiv) where appropriate.
  • Solvent: DCM, THF, or EtOAc.
  • Temp: 0–25 °C, 0.5–3 h.

• Diazotization/Sandmeyer:

  • Conditions: NaNO2 (1.1 equiv) in 2–4 M HCl at 0–5 °C, then CuX (X = Cl, Br, CN) or H3PO2 for deamination.
  • Caution: Control temperature to avoid decomposition; gas evolution possible.

• EAS (e.g., bromination):

  • Reagents: NBS or Br2 under mild conditions (0–25 °C) in AcOH, MeCN, or CHCl3; strong activation may require careful stoichiometry to avoid polysubstitution.

• DoM (if using protected anilide):

  • Base: s-BuLi (1.2–1.5 equiv) with TMEDA in hexanes/THF at −78 to −40 °C; quench with electrophile (e.g., DMF, I2, B(OMe)3).

Expected outcomes depend strongly on substrate/electrophile pair; perform small-scale scouting and monitor by TLC/LC-MS.

Safety and Handling

Regulatory/GHS status for this item:

• Signal word, H-statements, pictograms, GHS classification: Not specified for this item; refer to the SDS for SKU M963523.

General hazards and precautions for substituted anilines (informational, not a substitute for SDS):

• Hazards: Aromatic amines may be harmful if inhaled, ingested, or absorbed through skin; can cause skin/eye irritation and respiratory irritation. Some anilines undergo slow air oxidation and may discolor on exposure to air/light; oxidation products can enhance irritation.
• PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles. Handle in a fume hood to minimize inhalation exposure.
• Incompatibilities: Strong oxidizers (risk of exothermic oxidation), strong acids (salt formation; heat evolution on neutralization), acylating agents, and nitrosating agents (risk of N-nitrosamine formation under inappropriate conditions). Avoid prolonged exposure to air/light to limit oxidative darkening.
• First aid (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical advice if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Combustible organic liquid/solid. Use CO2, dry chemical, or foam. Combustion can produce NOx and CO/CO2.

Always consult and follow the product-specific SDS for definitive hazard information and emergency procedures.

Solvent Selection

Solubility/miscibility profile (general for substituted anilines):

• Polar organic solvents: Freely soluble in MeOH, EtOH, i-PrOH, acetone, acetonitrile, DMF, DMAc, DMSO.
• Moderately polar/aprotic: Soluble in THF, EtOAc, dioxane, MTBE.
• Nonpolar/aromatic: Soluble in toluene, xylenes, chlorinated solvents (DCM, chloroform).
• Water: Low solubility as the free base; high solubility as the protonated salt under acidic conditions (e.g., HCl, p-TsOH).

Choosing solvents for key operations:

• N-acylation/carbamoylation/urea formation: DCM, THF, or toluene at 0–25 °C with base (Et3N, DIPEA, pyridine). For greener options, EtOAc or 2-MeTHF often substitutes DCM/THF.
• Buchwald–Hartwig amination (as the amine partner): Toluene, dioxane, CPME, or t-BuOH frequently used with Pd catalysts and strong bases (NaOtBu, Cs2CO3).
• Electrophilic aromatic substitution (EAS): Acetic acid, nitromethane, or sulfonation media depending on electrophile.
• Workup: Acid–base extraction toggling between organic and aqueous phases enables efficient removal of inorganic salts and unreacted reagents.

Small comparison (general):

• THF vs 2-MeTHF: 2-MeTHF offers better phase separation and lower peroxide risk; THF provides broader solvation for polar reagents.
• DCM vs EtOAc: DCM gives rapid kinetics and easy cooling; EtOAc is greener and often adequate for acylations and extractions.

Storage and Reconstitution

• Storage conditions (item-specific from Product Data): Store at room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Form: Not specified for this item; refer to CoA/Spec Sheet. Typically provided as a neat liquid or low-melting solid for similar anilines.

General handling and preservation:

• Protect from air and light to minimize slow oxidation/discoloration; keep container tightly closed under inert gas if long-term storage is anticipated.
• Avoid contact with strong oxidizers and acids during storage.
• If solidifies on cold storage: Warm gently to ambient temperature to liquefy; mix thoroughly before use.
• No reconstitution is required for neat material. If preparing solutions, use dry, oxygen-free solvents for air/moisture-sensitive applications (e.g., metal-catalyzed couplings). Label solutions with solvent, concentration, and date; assess stability before reuse.

Disposal: Follow institutional and local regulations for disposal of aromatic amines; segregate from oxidizers and halogenated waste streams when required.

Structure and Identity

Brief overview: 3-Methoxy-2,5-dimethylaniline is a substituted aniline bearing one methoxy and two methyl substituents on the aromatic ring, making it an electron-rich, nucleophilic aryl amine useful as a building block.

• Item-specific identifiers (from Product Data)
  • CAS: 102440-04-0
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a nonstandard placeholder)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identity (general reference, not item-specific specs)
  • Molecular formula (literature): C9H13NO
  • Molecular weight (literature): ~151.21 g/mol
  • Common synonyms (literature): 3-Methoxy-2,5-dimethylbenzenamine; 3-Anisidino-2,5-dimethylbenzene (nomenclature variants)
• Structural features (general)
  • Core: An aniline (benzenamine) ring.
  • Substituents: NH2 at position 1; methoxy (–OCH3) at the 3-position; methyl groups at the 2- and 5-positions.
  • Functional groups: Primary aromatic amine, aryl ether (anisole-type methoxy), two alkyl substituents.
  • Electronic effects: Strongly ring-activating and ortho/para-directing groups (–NH2, –OMe, –Me) render the ring electron-rich and reactive toward electrophilic aromatic substitution.
  • 2D description in words: A six-membered aromatic ring bearing, clockwise from the aniline nitrogen, an ortho methyl, a meta methoxy, a para hydrogen, a meta methyl, and a remaining ring hydrogen, with the exocyclic –NH2 at C1.

Synthetic Utility

Key reactive elements:

• Primary aniline nitrogen (nucleophilic, basic): amenable to acylation, sulfonylation, carbamate/urea formation, Mitsunobu (with acids) in special cases, and Pd-catalyzed C–N cross-coupling (as amine partner).
• Electron-rich anisole-type aryl ether and two methyl substituents: Strongly activate the ring toward EAS; steric pattern (2- and 5-Me) biases incoming electrophiles and can protect ortho sites.

Useful transformations (general):

• N-Acylation to anilides that can direct subsequent metalation or be hydrolyzed later.
• Formation of diaryl- or aryl-alkyl ureas/carbamates (isocyanates, chloroformates), valuable in medicinal chemistry SAR.
• Diazotization/Sandmeyer sequences from the aniline to access aryl halides, cyano, hydroxy, or to perform azo coupling.
• Directed ortho-metalation (DoM) adjacent to methoxy or amide-protected anilide under strong base (e.g., s-BuLi/TMEDA), enabling installation of electrophiles with high regioselectivity.
• Oxidative couplings: Under Cu-catalysis or hypervalent iodine reagents, electron-rich anilines can undergo C–N or C–C couplings to build triarylamines or biaryls.

Protecting group strategy:

• Boc- or Cbz-protection tempers nucleophilicity/basicity and can steer selectivity in multi-functional settings; deprotection under standard acidic (Boc) or hydrogenolytic (Cbz) conditions.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies.