This compound belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.
External Descriptors
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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.
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Application Protocols
Not applicable. There are no immunoassay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) associated with this small-molecule reagent in the Product Data. For synthetic procedures, refer to the Reaction Conditions and Application notes provided in other sections.
Biological Roles
This product is a synthetic aromatic secondary amine intended for research and chemical manufacturing; it does not serve a canonical biological role.
General context (literature/general):
Aromatic amines can interact with biological systems via protonation (forming anilinium cations) and oxidative metabolism (e.g., N-oxidation, N-dealkylation, and ring hydroxylation) mediated by cytochrome P450 enzymes.
Secondary anilines may form salts with biological acids and can bind to proteins via hydrophobic and hydrogen-bonding interactions, but they are not endogenous metabolites.
In toxicological studies of related compounds, methemoglobinemia and sensitization have been observed; however, hazard classification for this specific item is not provided here and must be obtained from the SDS.
Use limitation: For research use only (per Product Data). No medical, diagnostic, or therapeutic applications are intended or supported.
Buffer Applications
N-Ethyl-m-toluidine is not a conventional buffering agent. As a hydrophobic secondary aromatic amine with a conjugate acid pKa near 5–5.5 (literature), it is not employed in standard biological or biochemical buffer systems.
Practical note: If protonated (e.g., as the hydrochloride), it can alter pH locally, but purpose-designed buffers (e.g., acetate, phosphate, Tris, HEPES) are preferred for controlled buffering capacity.
Refer instead to the Synthetic Utility and Reaction & Applications sections for relevant uses.
Green Alternatives
Selection of greener approaches depends on the role of N-ethyl-m-toluidine (reagent vs. intermediate).
Solvent choices (literature/general): Prefer bio-based or safer solvents when feasible for reactions involving this amine:
Replace DMF/DMAc/NMP with 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), tert-amyl alcohol, or propylene carbonate, considering catalyst compatibility.
Use toluene or anisole instead of chlorinated solvents when possible.
Catalysis and conditions:
Employ modern Pd catalysts/ligands enabling lower temperatures and lower catalyst loadings (reduces energy and metal footprint).
Consider copper catalysis with benign bases (K3PO4, carbonate) and green solvents (ethanol/2-MeTHF) where applicable.
Workup/waste minimization:
Favor aqueous acid–base extractions over silica-heavy chromatography for scale-up. Recover and recycle organic solvents via distillation.
Minimize amine oxidation by storing under inert gas (as supplied), reducing discard rate due to discoloration.
Illustrative comparison (general):
Traditional: Buchwald–Hartwig in toluene or dioxane, NaOtBu base, 100–110 °C.
Greener: Same coupling in 2-MeTHF or CPME with carbonate base at 60–90 °C using highly active ligands; or ethanol/water mixtures in micellar catalysis (where compatible).
Trade-offs: Greener solvents may alter amine basicity/catalyst solubility and affect selectivity; validate through small-scale screens before scale-up.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.
General/industrial context (literature/general):
Role: Used as an intermediate/building block in the synthesis of fine chemicals and potential active pharmaceutical ingredient (API) candidates where a meta-methyl-substituted anilide motif is required.
Operations: Frequently converted to amides, ureas, carbamates, or tertiary anilines to tune physicochemical properties (logP, pKa) during medicinal chemistry campaigns.
Salt formation: Secondary anilines form stable mineral acid salts (e.g., HCl), which can aid isolation and handling, but such salts are typically intermediates and not excipients.
Compliance note: For research use only (per Product Data). No clinical or therapeutic claims are made or implied.
Physical Properties
Note: Values below are literature/general references for N-ethyl-m-toluidine and are not item-specific specifications.
Appearance: Aromatic amines of this class are typically colorless to pale yellow liquids that may darken on air exposure (literature).
Boiling point: ~225–230 °C at 1 atm (literature for N-ethyl-3-methylaniline).
Melting point: Expected to be below 0 °C (liquid at ambient; literature indicates low/freezing below room temperature).
Density: ~0.94–0.97 g/mL at 20–25 °C (literature range for N-alkyl anilines with one ring methyl).
Refractive index (n20 D): ~1.53–1.55 (literature, typical for substituted anilines).
Vapor pressure: Low at 25 °C (literature: on the order of 10−3–10−2 kPa for similar anilines).
pKa (conjugate acid, pKaH): ~5.0–5.5 in water (literature for N-alkyl anilinium salts; basic, weaker than aliphatic amines due to resonance).
LogP (octanol/water): ~2.3–2.9 (literature estimate for secondary anilines with ring methyl).
Solubility: Sparingly soluble in water (literature: low g/L at 20–25 °C); miscible with common organic solvents (alcohols, ethers, esters, hydrocarbons, chlorinated solvents).
Item-specific numerical specifications (bp, mp, density, RI, water/peroxide/metal content, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on grades for aromatic amines (literature/general):
Technical grade: Suitable for bulk synthesis where trace impurities are tolerated. May contain higher levels of water, residual aniline/toluidine homologs, or oxidative byproducts.
Reagent/ACS grade: Meets common analytical specifications for laboratory synthesis; tighter control of non-volatile residue, color, and distillation range.
HPLC/spectrophotometric grade (if offered): Lower UV-absorbing impurities; suitable when the amine is used as a mobile-phase additive or where baseline stability is critical (less common for this class but sometimes specified for analytical work).
Low-water/anhydrous variants: Beneficial for moisture-sensitive reactions (e.g., acylations with acid chlorides, isocyanate chemistry, or metal-catalyzed couplings). Typically packaged under inert gas with molecular sieves or drying agents.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet. Many aromatic amines are supplied under inert atmosphere (as here) to limit oxidative darkening. If color develops over time, a simple distillation under reduced pressure or treatment over basic alumina can be used to restore quality for sensitive applications (evaluate by NMR/GC).
Always verify assay, water, and key impurity limits on the CoA for your specific lot before use in critical syntheses.
Reaction and Applications
N-Ethyl-m-toluidine serves as a versatile aryl secondary amine for C–N bond formation and downstream functionalization.
Coupling partner (literature/general):
Buchwald–Hartwig amination with aryl halides/pseudohalides to furnish tertiary anilines. Ligand choices (e.g., Xantphos, BrettPhos, tBuBrettPhos) and bases (NaOtBu, Cs2CO3) are common; aryl bromides/iodides react under milder conditions than chlorides.
Copper-catalyzed Ullmann–Goldberg aminations with aryl halides under elevated temperatures (CuI, diamine ligands).
Acylation and carbamoylation: Reacts with acid chlorides/anhydrides or chloroformates to give secondary amides/carbamates. Useful for installing protecting groups or modulating basicity and solubility.
Alkylation: Further N-alkylation (e.g., with alkyl halides) affords tertiary anilines; careful base choice (K2CO3, Cs2CO3) and solvent (acetonitrile, DMF) manage selectivity.
Electrophilic aromatic substitution (EAS): The N-ethylamino and meta-methyl groups are ortho/para-directing activators. For this meta isomer, ring substitution patterns favor positions ortho/para to each substituent; regioselectivity can be tuned via conditions and temporary N-acylation (to attenuate activation).
Oxidation chemistry: Susceptible to air/metal-catalyzed oxidation (color formation). Controlled oxidation can lead to imines/quinone imines, though overoxidation risks exist.
Applications: Intermediate in dyes, antioxidants, rubber chemicals, and fine chemical synthesis where a meta-methyl handle influences sterics/electronics of downstream transformations.
Practical tips: Dry and degas solvents; maintain inert atmosphere (argon per Product Data). For sensitive couplings, pre-form metal–ligand complexes and titrate base to avoid over-alkylation or decomposition.
Reaction Conditions
Representative literature conditions for common transformations involving N-ethyl-m-toluidine (general guidance; optimize per substrate):
Buchwald–Hartwig amination (formation of tertiary anilines):
Catalyst: Pd2(dba)3 (1–2 mol% Pd) with BrettPhos or Xantphos (2–4 mol%).
Base: NaOtBu or Cs2CO3 (2.0–2.5 equiv).
Solvent: Toluene, dioxane, CPME, or tert-amyl alcohol.
Temp/Time: 80–110 °C, 4–18 h. Aryl bromides/iodides react faster than chlorides. Typical isolated yields 70–95% for compatible partners.
Copper-catalyzed Ullmann–Goldberg amination:
Catalyst: CuI (5–10 mol%) with diamine ligand (e.g., N,N′-dimethylethylenediamine).
Base: K2CO3 or Cs2CO3 (2–3 equiv).
Solvent: DMSO, DMF, or greener alternatives (2-MeTHF) when compatible.
Temp/Time: 100–130 °C, 8–24 h.
N-Acylation to secondary amides:
Reagents: Acyl chloride (1.05–1.2 equiv) with Et3N or pyridine (2.0–2.5 equiv).
Solvent: DCM or THF, 0 °C → rt, 1–3 h; then aqueous workup. Often >80% yield.
Base: s-BuLi (1.1–1.5 equiv) with TMEDA, −78 to −40 °C in THF/Et2O, then electrophile quench.
Always exclude moisture/air for sensitive steps. Given Product Data indicates argon-charged storage, maintain inert conditions to minimize oxidation and color formation.
Safety and Handling
GHS classification (item-specific): Not specified for this item; refer to SDS.
Signal word / Hazard statements / Pictograms (item-specific): Not specified for this item; refer to SDS.
General safety information for secondary aromatic amines (literature/general):
Hazards: Harmful if swallowed, inhaled, or absorbed through skin; may cause skin/eye irritation and respiratory irritation. Many aromatic amines can cause methemoglobinemia; avoid exposure. Combustible liquid.
Chronic concerns: Aromatic amines may undergo nitrosation to form nitrosamines; avoid nitrosating conditions and strong oxidizers. Some may undergo air oxidation leading to darkening and potential sensitizers.
Handling: Work in a fume hood. Use appropriate PPE: lab coat, chemical-resistant gloves (nitrile or laminated film), splash goggles/face shield. Avoid inhalation of vapors/aerosols; prevent skin contact.
First aid (overview; consult SDS):
Inhalation: Move to fresh air; monitor for respiratory distress; seek medical attention.
Skin: Remove contaminated clothing; wash with soap and water; seek medical advice if irritation persists.
Eyes: Rinse cautiously with water for several minutes; remove contacts if present; seek medical attention.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Use dry chemical, CO2, or foam. Cool containers with water spray. Combustion may produce toxic nitrogen oxides.
Storage per Product Data: Store at room temperature, under inert gas (argon charged) to minimize air oxidation/discoloration. Shipments are via FedEx DG Service.
Solvent Selection
N-Ethyl-m-toluidine is typically used as a reagent/building block rather than a bulk solvent. Nevertheless, understanding its solvation behavior is useful when formulating reactions involving it.
Polarity class (general): Moderately polar, basic organic liquid; behaves as a hydrogen-bond base and donor (via N–H). Dielectric constant for analogous N-alkylanilines is in the low teens (literature), indicating modest polarity compared to alcohols.
Miscibility profile (literature/general):
Miscible with most organic solvents (THF, ethers, alcohols, esters, chlorinated solvents, aromatics, hydrocarbons).
Sparingly soluble in water due to hydrophobic ring and ethyl group; fully water-soluble upon protonation to its anilinium salt.
When choosing solvents for reactions using this amine:
Metal-catalyzed C–N coupling (Buchwald–Hartwig): Toluene, dioxane, CPME, or tert-amyl alcohol are common; polar aprotics like DMF/DMAc also work but are less green.
Acylation/carbamoylation: Use inert aprotic solvents (DCM, toluene, THF, acetonitrile). Control exotherm; ensure base scavenging of HCl.
Electrophilic aromatic substitution on the ring: Non-polar aromatics (toluene, xylene) or nitrobenzene/sulfolane for high-temperature regimes.
Comparison (literature/general):
Versus aliphatic amines: Lower basicity and nucleophilicity; better solubility in aromatics; less effective as standalone base.
Versus aniline: Slightly more lipophilic; reduced volatility; similar solubility but with higher bp and lower vapor pressure.
For purification, non-polar to mid-polar eluents (hexanes/EtOAc or toluene) typically provide good chromatographic separation; salts partition well into aqueous acid during workups.
Storage and Reconstitution
Storage conditions (Product Data): Store at room temperature, argon charged (under inert gas) to limit oxidative discoloration and degradation. Shipped via FedEx DG Service.
Container: Keep tightly closed in a compatible, dry, amber glass bottle to minimize light- and air-induced oxidation. Consider using PTFE-lined caps.
Handling: Purge headspace with argon or nitrogen after each use. Minimize exposure to air and moisture. If discoloration occurs, evaluate purity by GC/NMR; purification by short-path distillation under reduced pressure or passage through basic alumina may be used if appropriate.
Reconstitution: Not applicable; supplied as a neat liquid (no reconstitution required).
Stability: Aromatic secondary amines can slowly oxidize in air; inert-atmosphere storage, clean glassware, and avoidance of metal contaminants prolong shelf life.
Spill/containment: Absorb with inert material, collect for disposal, and wash area with detergent. Prevent entry into drains.
For definitive shelf-life, impurity limits, and any stabilizers, consult the lot-specific CoA/Spec Sheet and the SDS.
Structure and Identity
N-Ethyl-m-toluidine (also known as N-ethyl-3-methylaniline) is a secondary aromatic amine featuring an ethyl substituent on nitrogen and a meta-methyl group on the aniline ring.
Item-specific identifiers (from Product Data):
SKU: E140164
CAS: 102-27-2
CID: 7603
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (general reference values; not item-specific specs):
Example SMILES (literature): CCNc1cccc(C)c1 (secondary aniline with meta-CH3)
Structural features (general chemistry):
Functional groups: secondary aniline (Ar–NH–Et), methyl substituent at the 3-position of the ring relative to the anilide nitrogen.
Aromatic ring with two ortho/para-directing substituents (N-ethylamino and methyl). The N is sp3-hybridized; the ring is planar; the anilide lone pair conjugates weakly with the ring.
No stereocenters; achiral. 2D depiction: a benzene ring bearing CH3 at meta to the anilide nitrogen; nitrogen bound to one ethyl group and one ring carbon, with one N–H remaining.
Synthetic Utility
The molecule offers two principal reactive elements: a basic/nucleophilic secondary aniline nitrogen and an activated aromatic ring bearing a meta-methyl group.
Nitrogen-centered chemistry (literature/general):
N-acylation (acid chlorides/activated esters) → secondary amides; attenuates ring activation and improves chemoselectivity for EAS.
N-alkylation → tertiary anilines; control over mono-/dialkylation via base and solvent choice.
Reductive amination (as nucleophile toward aldehydes/ketones) to form tertiary anilines (with NaBH3CN/NaBH(OAc)3) when feasible.
Ring-functionalization:
EAS (nitration, halogenation, sulfonylation, Friedel–Crafts acylation) biased to positions ortho/para to N-ethylamino and methyl groups; temporary N-acylation often employed to moderate over-activation and improve regioselectivity.
Directed metalation: The anilide (after N-acylation or N-Boc protection) can undergo ortho-lithiation with s-BuLi/tmeda at low temperatures, enabling installation of electrophiles (D, halogens, carbonyl equivalents).
Cross-coupling as amine partner:
Buchwald–Hartwig and Ullmann–Goldberg couplings to form aryl–N(Et)(Ar′) tertiary anilines with high functional-group tolerance.
Derivatization of the methyl group:
Benzylic oxidation (e.g., SeO2, MnO2, or catalytic methods) to aldehyde/acid derivatives (meta-substituted), enabling further elaboration.
Strategic value: The meta-methyl substituent modulates sterics/electronics and provides a benzylic handle. The secondary aniline allows rapid access to amides/carbamates and late-stage diversification via C–N coupling.
Target Specificity
Not applicable. This product is a small-molecule aromatic amine, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined target claims). No antigen/epitope, species reactivity, clone, or isotype data are relevant.
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