This compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
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. No tested immunoassay applications (WB, IHC, IF, FC) or dilution guidelines are relevant to this small-molecule reagent. For synthetic or materials applications, refer to the Reaction & Applications and Reaction Conditions sections for practical guidance.
Biological Roles
No endogenous biological role is established for 4-dimethylaminophenethylamine; it is a synthetic aromatic diamine used as a chemical building block.
General considerations (literature):
The molecule features a protonatable primary amine (strong base) and a weaker tertiary anilino nitrogen. Under physiological pH, the primary amine will be largely protonated, increasing aqueous solubility; the anilino NMe2 contributes electron donation and potential charge-transfer interactions with aromatic biomolecules or membranes.
The phenethylamine scaffold is common in bioactive ligands; however, activity is highly substituent-dependent. No claims are made for any biological activity of this specific compound in vivo or in vitro in a therapeutic context.
As a cationic handle, it can be used to prepare conjugates (e.g., with carboxylate-bearing biomolecules) or to introduce positive charge into polymers/surfaces for research in delivery, imaging, or materials, subject to appropriate safety and regulatory constraints.
Primary aliphatic amines can undergo oxidative deamination or N-acetylation in biological systems; tertiary anilines may be susceptible to N-oxidation. These are general pathways and not item-specific assurances of fate or safety.
This product is supplied strictly for research use only. No medical, diagnostic, or clinical use is intended or implied.
Buffer Applications
This compound is not a standard buffering reagent. While it contains basic functional groups, it is not used to prepare defined pH buffer systems in analytical biochemistry.
Not typically applicable: Established laboratory buffers (Tris, HEPES, phosphate, acetate) provide well-characterized pKa values and minimal reactivity. In contrast, 4-dimethylaminophenethylamine is a reactive nucleophile that can interfere with biomolecules and assays.
Practical note: If used in biological formulations (e.g., as a cationic additive or conjugation handle), maintain buffering with conventional systems and keep the amine in salt form to control pH. For buffering needs, select a dedicated buffer with a pKa near the target pH rather than relying on this amine.
Green Alternatives
Greener considerations largely involve solvent/reagent choices and salt handling; the amine itself is a fixed substrate. Below are practical substitutions aligned with green chemistry principles.
Solvent swaps (literature guidance):
Replace dichloromethane with 2-MeTHF, CPME, or EtOAc for acylations and extractions where feasible.
Favor ethanol or isopropanol for reductive amination instead of MeOH (toxicity) or DCE (halogenated), when compatible with the carbonyl substrate.
Use MeCN judiciously; where high polarity is needed, consider propylene carbonate or dimethyl carbonate (if reactivity tolerates).
Reagents:
Reductive amination: Prefer NaBH(OAc)3 in AcOH/EtOH or catalytic hydrogenation (H2/Pd) over NaBH3CN to avoid cyanide waste, when chemoselectivity permits.
Amide formation: Use EDCI/HOBt alternatives such as CDI or greener uronium salts; aqueous micellar catalysis (TPGS-750-M) can enable couplings in water, reducing organic solvent use.
Workup/waste minimization:
Isolate as a crystalline salt (e.g., HCl) to avoid solvent-intensive distillations of the free base.
Employ solvent recovery and base washes with carbonate/bicarbonate rather than strong bases to minimize hazard.
Comparison (qualitative):
DCM vs 2-MeTHF: 2-MeTHF is biorenewable, higher boiling (complicates removal) but often supports similar acylations; DCM has higher volatility and halogenated-waste concerns.
MeOH vs EtOH: EtOH is less toxic and renewable at scale, but may be less reactive in some reductions; adjust catalyst/loading accordingly.
Always validate greener substitutions on small scale to confirm selectivity and kinetics.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item. It is offered for research and development only.
Formulation role (general, literature): The primary amine can be derivatized to amides, ureas, or carbamates, serving as an intermediate in API discovery chemistry. The para-dimethylamino group can modulate electronic properties of aromatic systems, often exploited in lead optimization and materials for imaging.
Salt forms: Converting the free base to a mineral acid salt (e.g., hydrochloride) enhances crystallinity, aqueous solubility, and handling; choice of counterion affects hygroscopicity and processability. Item-specific salt form is Not specified for this item; refer to CoA/Spec Sheet.
Manufacturing considerations (general):
For GMP contexts, define residual solvent limits, related substances, enantiomeric excess (not applicable here), and polymorph/salt form. None are specified for this research-grade listing.
Avoid reactive excipients that may form adducts with primary amines (e.g., reducing sugars under certain conditions).
No therapeutic claims are made. Any use in pharmaceutical development should be preceded by full characterization (identity, purity profile), toxicology assessment, and adherence to applicable regulatory frameworks.
Physical Properties
Item-specific physico-chemical specifications were not provided. Where helpful, general/literature values for closely related structures are noted for planning purposes; verify experimentally and consult the CoA/SDS for this item.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Aromatic phenethylamine bases typically boil >200 °C at 1 atm; literature, class trend.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Free-base phenethylamines are often liquids at ambient conditions; literature, class trend.)
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Vapor pressure: Not specified for this item; refer to CoA/Spec Sheet (expected very low at RT; literature, class trend).
Solubility (literature, qualitative):
Miscible with polar organic solvents (alcohols, acetone, DMF, DMSO).
Moderately soluble in less polar solvents (EtOAc, toluene) as free base; solubility increases in protic media via H-bonding.
Water solubility: moderate for free base; high as protonated salts (e.g., HCl). Actual value not specified for this item; refer to CoA/Spec Sheet.
Acid–base properties (literature, qualitative):
Primary aliphatic amine conjugate acid pKaH typically ~9.5–10.5.
Tertiary anilinium (para-dimethylamino) pKaH typically ~5–6 (significantly weaker base).
Partitioning (literature, qualitative): bifunctional; logP increases with deprotonation; protonation yields water-soluble ammonium salts. Numerical logP not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
For coupling chemistry and building-block use, researchers often prefer ≥95% GC/LC purity to minimize side reactions (amide/urea formation, reductive amination). If your application is spectroscopic or kinetic, consider HPLC-grade materials or recrystallization/distillation under reduced pressure immediately prior to use.
UV cutoffs, metal content, water, and residual solvents can impact sensitive catalysis (e.g., Pd-catalyzed couplings on the ring) and analytical assays. These parameters are Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: None indicated for this item; refer to CoA/Spec Sheet. If supplied as a free base, trace inhibitors are uncommon; salts (e.g., HCl) typically require no stabilizer and offer improved shelf life and handling.
Identity/assay methods recommended (general best practice):
Identity by 1H/13C NMR (diagnostic NMe2 singlet near 2.9–3.1 ppm; benzylic CH2 ~2.7–3.0 ppm; CH2–NH2 ~2.8–3.1 ppm; aromatic AA′BB′ pattern), IR (broad N–H ~3300 cm−1, aromatic C–H, tertiary amine C–N), and MS (M+H+ ~165, literature).
Purity by GC or LC with ELSD/UV (the para-NMe2 group gives strong UV response around 254–280 nm).
If a salt form is required for weighing accuracy and reduced volatility, request/specify the hydrochloride or other mineral acid salt during ordering when available.
Reaction and Applications
As a para-donor-substituted phenethylamine, 4-dimethylaminophenethylamine is a versatile building block combining a strongly nucleophilic primary amine with an electron-rich anilino donor on the ring.
Key application families (literature):
Amide/urea/sulfonamide synthesis: The terminal –NH2 couples readily with acyl chlorides, activated esters, carbodiimide systems (DCC/HOBt, EDCI/HOBt), and sulfonyl chlorides to give functionalized linkers and conjugates. The NMe2 group survives many acylation and sulfonylation conditions.
Reductive amination/alkylation: Formation of imines/iminium ions with aldehydes/ketones followed by reduction (NaBH3CN, NaBH(OAc)3) to furnish secondary/tertiary phenethylamines. Useful in library synthesis of cationic ligands, dyes, and materials.
Electrophilic aromatic substitution (EAS): The para NMe2 group strongly activates the ring; ortho positions relative to NMe2 undergo formylation (Vilsmeier–Haack), halogenation, or sulfonation under mild conditions, enabling subsequent elaboration while preserving the ethylamine chain.
Quaternization of the anilino NMe2: Alkylating agents (e.g., MeI, MeOTf) generate aryltrimethylammonium salts, valuable for phase-transfer or as precursors to zwitterionic materials and cationic dyes (push–pull motifs).
Protecting-group chemistry: The primary amine is readily protected (Boc, Cbz, Fmoc) to orthogonally manipulate ring chemistry (e.g., ortho-formylation) without side reactions at the side-chain amine.
Materials and sensing: The NMe2 donor confers strong ICT (intramolecular charge transfer) characteristics when conjugated; the side-chain amine serves as a handle for surface immobilization or polymer conjugation (literature use-cases).
Practical tips:
Use stoichiometric base during acylations to neutralize HCl/acid coproducts.
If both nitrogens are reactive under conditions (e.g., strong alkylation), deploy protecting groups to control selectivity.
For EAS on the ring, maintain the primary amine as a salt (e.g., HCl) to reduce side reactions and increase chemoselectivity.
Reaction Conditions
General literature conditions for common transformations of 4-dimethylaminophenethylamine are summarized below. Optimize for your substrate set and scale.
Amide formation (side-chain –NH2):
Conditions: Acid chloride (1.05–1.2 eq), base (2.0–3.0 eq Et3N or DIPEA), solvent DCM or THF, 0 °C to RT, 1–4 h. Alternatively, EDCI/HOBt (1.1–1.5 eq each) in DMF/DCM with DIPEA at RT to 40 °C, 2–12 h.
Notes: Keep water <0.1% for carbodiimide methods. Monitor by TLC/LC–MS; quench into saturated NH4Cl, extract.
Reductive amination:
Conditions: Carbonyl (1.0 eq), amine (1.2–2.0 eq), AcOH (0.5–1.0 eq) in MeOH/EtOH/MeCN; add NaBH(OAc)3 (1.5–2.5 eq) at RT, 2–16 h. For ketones, warm to 40–60 °C or use NaBH3CN with pH 5–6.
Notes: Avoid strong acid; protonates amine and suppresses imine formation. Work up with basified brine.
Sulfonamide formation:
Conditions: Sulfonyl chloride (1.05–1.2 eq), base (2–3 eq pyridine or Et3N), DCM or MeCN, 0 °C to RT, 1–3 h.
Vilsmeier–Haack formylation (ring ortho to NMe2):
Conditions: POCl3 (2–3 eq) added to DMF (10–20 eq) at 0 °C, then substrate; heat 60–90 °C, 2–6 h. Quench onto ice, neutralize, extract.
Notes: Keep side-chain amine as HCl salt to minimize side reactions.
Quaternization of NMe2:
Conditions: MeI or MeOTf (2–5 eq) in MeCN or acetone, RT to reflux, 2–24 h, giving aryltrimethylammonium salt.
Protection of side-chain amine:
Boc protection: Boc2O (1.1–1.5 eq), DIPEA (2–3 eq), DCM/THF, 0 °C to RT, 1–3 h.
Expected yields (literature, typical): 60–90% for clean acylations/sulfonylations; 50–85% for reductive aminations depending on sterics; 40–70% for Vilsmeier formylation after workup. Always confirm on small scale.
Safety and Handling
Safety information specific to this catalog item was not provided; consult the SDS for authoritative guidance. The following are general precautions for aromatic/aliphatic amine bases of this class.
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
Likely hazards (general, literature): Corrosive/irritating to skin, eyes, and respiratory tract; harmful if swallowed; may cause sensitization in susceptible individuals. Amines can be harmful to aquatic organisms.
PPE: Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Use in a fume hood to avoid inhalation of vapors or aerosols.
Handling notes:
Avoid contact with acids unless forming a controlled salt; exotherms can occur during neutralization.
Amines can absorb CO2 and moisture; keep containers tightly closed; purge headspace with inert gas if long-term storage is expected.
Avoid oxidizers and acylating/alkylating agents unless intended; violent reactions possible.
First aid (overview; defer to SDS):
Skin/eye contact: Immediately flush with water for ≥15 min; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire response: Amines are combustible; use dry chemical, CO2, alcohol-resistant foam. Combustion may produce NOx.
Spill response: Absorb with inert material, avoid acid/base neutralization on skin; ventilate area; dispose per local regulations.
Solvent Selection
This compound is a bifunctional base (primary aliphatic amine + tertiary anilino). Solvent choice depends strongly on whether it is used as a nucleophile (free base) or in salt form.
Polarity/miscibility (literature, qualitative):
Free base: Miscible with polar organics (MeOH, EtOH, iPrOH, acetone, acetonitrile, DMF, DMSO); moderate solubility in EtOAc and toluene; limited in hexanes.
Salt forms (e.g., HCl): Freely water-soluble; also soluble in MeOH/EtOH and aqueous-organic mixtures.
Selection guidelines:
Nucleophilic substitutions/acylations: Use dry, aprotic media (DCM, THF, DMF, MeCN) with a hindered base (DIPEA, Et3N) to control protonation state.
Reductive amination: MeOH, EtOH, or DCE/MeCN with AcOH; reduction with NaBH3CN or NaBH(OAc)3.
Carbodiimide couplings: DCM/DMF or DMF with DIPEA or NMM; consider in-situ salt formation for solubility.
Electrophilic aromatic substitution on the ring: Often performed in polar aprotic media or POCl3/DMF (Vilsmeier) depending on transformation.
Comparison (general):
DCM vs MeCN: DCM maximizes basic amine reactivity and minimizes ion pairing; MeCN provides higher polarity for charged intermediates and is easier to remove than DMF.
Alcohols: Good for reductive amination; may lead to transesterification side reactivity in acylations.
Drying: If water-sensitive reagents are used, pre-dry the amine (co-evaporate with toluene, store over K2CO3, or distill under reduced pressure) to minimize adventitious water.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance/physical form: Not specified for this item; refer to CoA/Spec Sheet.
Best practices (general):
Free-base amines can absorb CO2/H2O; store tightly sealed under inert gas if possible. Use amber glass to minimize potential light-induced discoloration of anilines.
If supplied as a salt (e.g., HCl), store desiccated to avoid deliquescence; salts offer improved long-term stability.
Avoid contact with strong oxidizers and acids/bases during storage.
Reconstitution/dissolution (general guidance):
Organic media: Dissolves readily in MeOH, EtOH, DMSO, DMF, and MeCN. For moisture-sensitive reactions, pre-dry solvents and the amine (co-evaporate with toluene or dry over K2CO3, then filter).
Aqueous work: Prepare as an acid salt to enhance water solubility; adjust pH cautiously as exotherms may occur during neutralization.
Freeze–thaw: Not typically required for this item. If preparing stock solutions (e.g., in DMSO), store aliquots at −20 °C to avoid repeated freeze–thaw cycles.
Always consult the product’s CoA/Spec Sheet and SDS for item-specific handling, storage stability, and any recommended stabilizers. Research use only.
Structure and Identity
4-Dimethylaminophenethylamine is a bifunctional aromatic diamine comprising a para-dimethylamino substituent on a phenyl ring and a two-carbon tether terminating in a primary amine.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C10H16N2 (literature)
Molecular weight: ~164.24 g/mol (literature)
Structural features (descriptive, literature):
Aromatic ring: monosubstituted benzene bearing a strongly electron-donating para N,N-dimethylamino group.
Side chain: –CH2–CH2–NH2 (phenethylamine) at the para position relative to NMe2.
Functional groups: one tertiary anilino nitrogen (–NMe2, weakly basic) and one aliphatic primary amine (–NH2, strongly basic/nucleophilic).
Stereochemistry: achiral; no stereocenters.
2D structure in words (literature): A benzene ring with para substituents: at C-1 the N,N-dimethylamino group (–N(CH3)2), and at C-4 a two-carbon chain ending in a primary amine (–CH2–CH2–NH2). The electron-donating NMe2 activates the ring (o/p-directing), with ortho positions relative to NMe2 most activated for electrophilic aromatic substitution.
Synthetic Utility
4-Dimethylaminophenethylamine unites an electron-rich anilino donor with a benzylic primary amine, enabling orthogonal transformations on the ring and side chain.
Transformations centered on the side-chain amine (literature):
Acylations to amides/carbamates using acyl chlorides, anhydrides, activated esters (DIC/HOAt, EDCI/NHS). Control chemoselectivity via protection of the side-chain amine (Boc, Cbz, Fmoc) when alkylating the ring nitrogen or performing strong electrophilic steps.
Reductive amination with aldehydes/ketones (NaBH(OAc)3, NaBH3CN, or H2/Pd) to access secondary/tertiary amines; subsequent quaternization furnishes permanent cations.
N-alkylation and sulfonylation to generate structure–activity libraries.
Transformations centered on the ring (literature):
Vilsmeier–Haack formylation at ortho to NMe2, giving o-formyl intermediates; subsequent Knoevenagel condensations can introduce push–pull chromophores.
Electrophilic halogenation/iodination under mild conditions due to strong activation by NMe2; facilitates cross-coupling (Suzuki, Sonogashira) after converting to aryl halides.
Quaternization of the NMe2 (MeI/MeOTf) to aryltrimethylammonium salts, enabling SNAr or cross-coupling via C–N activation strategies.
Orthogonality and strategy:
Use protonation (convert to HCl salt) to suppress side-chain nucleophilicity during ring functionalization.
For selective modification of the side-chain amine, mask the anilino N via quaternization or maintain as free base; the tertiary aniline is relatively unreactive toward acylation.
Overall, this scaffold serves as a versatile donor–acceptor platform and a convenient handle for conjugation to acids, isocyanates, sulfonyl reagents, and surfaces.
Target Specificity
Not applicable. This product is a small-molecule amine, not an antibody or biologic. No antigen, epitope, species reactivity, clone, or isotype information applies.
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