This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
86.570 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Exact Mass
86.0659 Da
Monoisotopic Mass
86.0659 Da
Topological Polar Surface Area
26.000 Ų
Heavy Atom Count
4
Formal Charge
0
Complexity
2.800
Isotope Atom Count
5
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
2
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Application Protocols
Not applicable. No immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.
Practical guidance (general use):
For LC–MS internal standardization: Spike a known amount of Ethyl-d5-amine into samples/standards; use matched chromatography with the analyte and monitor M+5 channel. Optimize quantifier/qualifier ions based on the method.
For synthesis: See Reaction Conditions tab for representative procedures. Confirm isotopic retention by HRMS or 2H NMR when needed.
Biological Roles
Scope: Ethyl-d5-amine hydrochloride is an isotopically labeled analogue of ethylamine, intended for laboratory research. It is not used as a biomolecule or therapeutic.
General/literature context:
Ethylamine occurs in nature at low levels and participates in various biochemical transformations as a simple aliphatic amine. The deuterated analogue is chemically analogous but used as a tracer or internal standard.
Stable isotope labeling: The d5 label enables tracking by mass spectrometry in metabolic fate and derivatization studies, allowing differentiation from endogenous ethylamine or N-ethylated metabolites by a +5 Da mass shift.
Use cautions:
No medical or clinical claims are made. Any biological experiments using this reagent should be designed for research-only purposes with appropriate controls to account for potential isotope effects (usually minor for C–D bonds at non-reacting positions).
Buffer Applications
Not typically applicable. Ethyl-d₅-amine hydrochloride is not a standard buffering agent and lacks a defined buffering range in common biochemical buffer systems. While ammonium salts can influence pH, use established buffers (e.g., phosphate, HEPES, Tris) for pH control.
Practical note:
If included in aqueous solutions for analytical calibration or reactions, adjust pH separately with appropriate buffers or acids/bases; do not rely on this reagent for buffering capacity.
Green Alternatives
Context: This product is a small isotopically labeled amine salt, not a solvent. “Greener alternatives” considerations focus on how it is used rather than replacement of the molecule itself.
Prefer the hydrochloride salt over the free base to minimize VOC emissions and odor; this reduces occupational exposure and environmental release.
Use water or bio-based alcohols (ethanol) as reaction/media solvents when compatible (e.g., for in situ neutralization/acylation chemistry), minimizing reliance on chlorinated solvents.
For amide couplings, select coupling systems with improved EHS profiles (e.g., T3P in EtOAc/MeCN, EDCI with catalytic DMAP) and employ solvent recycling.
Where feasible, perform telescoped, base-mediated in situ free-base generation to avoid solvent-intensive pre-neutralization and solvent swaps.
Trade-offs:
Water-rich media can reduce rates/selectivity for some acylations and may require phase-transfer or surfactants.
The salt’s inorganic chloride content necessitates appropriate aqueous waste handling.
Not typically applicable:
There is no practical “green substitute” for the isotopic label itself when MS-based differentiation is required. Process optimization and solvent choice are the primary levers.
Pharmaceutical Uses
No therapeutic or clinical use is claimed. For research and development only.
General formulation/manufacturing context (literature):
Isotopically labeled small amines are commonly employed as internal standards in bioanalytical method development and validation (e.g., LC–MS/MS quantitation of related analytes).
In medicinal chemistry workflows, the d5 ethyl substituent can be introduced into candidate molecules (as N-ethyl-d5 analogues) to aid ADME studies and to support mass balance and metabolite tracking.
Regulatory note:
Pharmacopeial monographs for deuterated ethylamine salts are uncommon; verify all quality attributes by CoA/Spec and follow site-specific quality systems when using in regulated method development.
Physical Properties
Item-specific specifications:
Melting point, boiling point, density, refractive index, water/peroxide/metal limits, and UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
General/literature information (for context; not product specifications):
Physical state: Typically an ionic solid (ammonium chloride salt) at ambient conditions.
Volatility: Non-volatile; the hydrochloride salt form greatly reduces vapor pressure vs the free base.
Solubility profile: Highly soluble in water; freely soluble in polar protic solvents (e.g., methanol, ethanol). Sparingly soluble to insoluble in nonpolar solvents (e.g., hexanes, toluene). The free base (liberated in situ with base) is miscible with many organics.
Acid–base: Conjugate acid pKa (ethylammonium) ~10.6–10.8 (literature), indicating strong basicity of the amine free base. The hydrochloride salt forms acidic aqueous solutions due to NH3+/Cl−.
Hygroscopicity: Aliphatic amine hydrochlorides can be hygroscopic; minimize atmospheric moisture exposure for accurate weighing.
Deuterium considerations (literature):
Isotopic labeling increases average molar mass by ~5.03 Da vs the non-deuterated salt and can slightly alter physical constants (often within experimental uncertainty). Deuterium is bonded to carbon and is generally non-exchangeable under neutral conditions.
Quality and Grades
Item-specific grade/purity:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general):
Research-grade isotopically labeled amines are typically supplied with high isotopic enrichment (e.g., ≥98 atom % D on specified positions) and defined chemical purity. The precise enrichment pattern and residual protium content should be verified on the accompanying CoA.
Where applicable, additional specifications (water content by KF, residual solvents, GC/HPLC area %, and isotopic distribution by 1H/2H NMR or HRMS) are commonly provided in the CoA.
Impact of salt form: The hydrochloride salt often improves shelf stability and handling (reduced volatility, odor control) relative to the free base; trace inorganic chloride is inherent to the salt and not an impurity.
Recommendations:
For quantitative MS applications (internal standards), confirm isotopic purity and known impurity/isotopologue profiles on the CoA to evaluate potential isotopic overlap with analytes.
For synthesis, assess water content and residual acids (HCl) if moisture- or acid-sensitive reagents are involved; neutralize or base pre-treat if required.
Reaction and Applications
Use domains (literature/practice):
Isotopic internal standard: The +5 Da mass shift and matched chemistry to ethylamine-containing analytes make this reagent valuable for quantitative LC–MS/MS workflows and tracer studies.
Building block for labeled derivatives: Forms amides, ureas, thioureas, sulfonamides, carbamates, and imines, transferring the ethyl-d5 label to the product’s nitrogen substituent.
Representative transformations (literature):
Amide coupling: Reaction with acid chlorides or activated acids (HATU, EDCI, T3P) in DMF/MeCN with DIPEA to yield N-ethyl-d5 amides.
Sulfonylation/acylation: With sulfonyl chlorides or anhydrides under base to furnish N-ethyl-d5 sulfonamides/carbamates.
Reductive alkylation: Condensation with carbonyls to imines/schiff bases followed by hydride reduction to install the N-ethyl-d5 group under mild conditions.
Quaternization: Alkylation to quaternary ammonium salts; the ethyl-d5 substituent imparts a defined isotopic signature for MS tagging.
Isotopic integrity:
The five deuteriums are bound to carbon (CD3–CD2–) and are typically non-exchangeable. Retention is high across neutral to moderately basic/acidic conditions. Avoid prolonged metal-catalyzed hydrogenation or radical H/D scrambling conditions that could reduce D content.
Practical notes:
Use the HCl salt neat or generate the free base in situ with DIPEA/Et3N/Na2CO3. Control pH to drive acylations toward completion. For analytical standards, prepare stock solutions gravimetrically and verify isotopic distribution by HRMS or NMR.
Reaction Conditions
General literature guidance (not product specifications):
Amide formation (EDCI/HOBt or HATU): Dissolve carboxylic acid (1.0 equiv) and Ethyl-d5-amine·HCl (1.2–2.0 equiv) in DMF or MeCN; add base (2.0–3.0 equiv DIPEA) and coupling reagent (1.1–1.5 equiv). Stir 0–25 °C for 2–12 h. Typical isolated yields: 70–95% depending on substrate.
Acyl chloride route: DCM/DMF (0–25 °C), amine (as free base generated in situ with Et3N, 2–3 equiv). Add acyl chloride dropwise at 0 °C; warm to rt, 1–3 h. Quench and extract.
Sulfonamide formation: Sulfonyl chloride (1.0 equiv) in DCM or MeCN; add amine (1.5–2.0 equiv, generated in situ) and base (2–3 equiv). 0–25 °C, 1–6 h. Often near-quantitative by LC–MS.
Reductive amination: Carbonyl (1.0 equiv), amine·HCl (1.2–1.5 equiv), base (2–3 equiv), solvent MeOH/EtOH or MeCN; add NaBH3CN or NaBH(OAc)3 at 0–25 °C, 2–16 h. Control pH (5–6 for NaBH3CN in MeOH with AcOH). Yields commonly 60–90%.
Carbamate formation: Chloroformate (1.1 equiv) in DCM, amine (1.5 equiv) liberated with base, 0–25 °C.
Notes:
Liberate the free amine just-in-time to limit salt carryover; filter precipitated Et3N·HCl where applicable.
For LC–MS standards, prepare gravimetric stocks in MeOH/H2O (50:50) and store aliquots; verify mass shift (+5 Da) and absence of isotopic bleed by HRMS.
Avoid catalytic hydrogenation conditions that might induce H/D scrambling on aliphatic positions.
Safety and Handling
Authoritative safety classification:
GHS classification, signal word, H-statements, and pictograms: Not specified for this item; refer to the product SDS for definitive information.
General laboratory safety (literature/practice; not a substitute for SDS):
Likely hazards: Aliphatic amine salts can be irritants; solutions may be corrosive to eyes/skin. Avoid inhalation of dust and contact with skin and eyes.
Personal protective equipment: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood when handling powders/solutions that may release vapors or aerosols upon basification.
Handling notes: The hydrochloride salt is less volatile and easier to handle than the free base. If generating the free base in situ (e.g., by adding base), manage amine vapors in a hood.
Incompatibilities: Strong oxidizers; strong bases will liberate the free amine from the salt. Avoid contact with acylating/sulfonylating agents unless intended for reaction.
First aid overview: In case of skin/eye contact, rinse with water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always consult the SDS for full instructions.
Spill response: Avoid dust formation; sweep up solids carefully and place in appropriate waste. Neutralize aqueous residues as per institutional protocols.
Solvent Selection
Applicability: This product is a small, ionic, deuterium-labeled amine salt. Solvent selection is mainly relevant for its use in solution-phase synthesis or as an analytical standard.
General guidance (literature):
Polarity: As an ammonium chloride salt, it dissolves readily in polar protic solvents (water, methanol, ethanol). Solubility in polar aprotic solvents (DMF, DMSO) is also typically good. Poor solubility in nonpolar media (e.g., alkanes, ethers) is expected.
Working in organic synthesis: For acylations/sulfonylations and carbamate formation, dissolve the salt in MeOH, EtOH, MeCN, DMF, or DCM with a non-nucleophilic base (e.g., DIPEA, triethylamine) to liberate the free amine in situ.
Analytical use: For LC–MS internal standards, water/MeOH or water/ACN mixtures (0.1% formic acid if desired) are typical diluents. The deuterium label provides a +5 Da mass shift.
Comparison (qualitative):
Ethyl-d5-amine HCl vs free base: The HCl salt offers better handling (non-volatile, odor control) and aqueous solubility; the free base provides higher solubility in many organics but is more volatile/odorous. In situ basification balances both.
Tips:
If precipitation occurs in mixed solvents, increase the fraction of a polar protic component or add a small amount of water to DMF/DMSO to assist dissolution.
Avoid strong basic media if unintended reactions are possible; add base stoichiometrically to generate just enough free amine.
Storage and Reconstitution
Item-specific storage:
Storage Conditions: Room temperature (as provided). Protect from moisture by keeping the container tightly closed.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling (literature/practice):
Hygroscopic tendency is possible for amine hydrochlorides; minimize exposure to ambient humidity. If high precision is required, dry briefly under vacuum over P2O5 or in a desiccator before weighing (verify no decomposition for your application).
For solution preparation: Dissolve in water, methanol, ethanol, or DMF/DMSO as appropriate. For generating the free base, add a stoichiometric non-nucleophilic base (e.g., DIPEA) in situ.
Aliquoting: For analytical standards, prepare single-use aliquots to avoid multiple open/close cycles. Store sealed vials to limit isotopic exchange risks (generally minimal for carbon-bound deuterium).
Stability notes:
The hydrochloride salt is generally stable at ambient temperature away from moisture and light. Avoid prolonged exposure to strong bases/acids if the free base is not immediately consumed.
Research Use Note:
For research use only.
Structure and Identity
Brief description: Ethyl-d5-amine hydrochloride is the hydrochloride salt of a primary ethylamine in which the five carbon-bound hydrogens of the ethyl group are replaced by deuterium (2H). It serves as a stable isotopically labeled amine building block/internal standard.
Item-specific (from Product Data):
SKU: E474139
Product Name: Ethyl-d₅-amine hydrochloride
CAS: 284474-81-3
PubChem CID: 16213297
InChIKey: 428802 (as provided)
Storage Conditions: Room temperature
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity (informational):
Typical formula for the labeled salt: C2H3D5ClN (literature; isotopic composition explicitly includes D)
Approx. formula of the free base label: C2H2D5N (literature)
Representative labeled SMILES (free base, protonated salt shown): [2H]C([2H])([2H])C([2H])([2H])[NH3+].[Cl-] (literature)
Average molar mass (C2H3D5ClN): ~86.48 g/mol (calculated, literature)
Structural features (descriptive):
Functional group: primary aliphatic amine, present as the ammonium chloride salt (–NH3+ Cl−).
Isotopic labeling: five deuteriums distributed over the ethyl chain (CD3–CD2–), enabling mass-shifted derivatives (+5 Da vs protiated ethylamine HCl).
2D structure description: a two-carbon chain terminating in a protonated amino group; chloride counterion; no rings, no stereocenters.
Notes:
Exact SMILES/InChI for a specific labeled isotopomer may vary by deuterium placement convention; values above are representative (literature) and provided for reference only.
Synthetic Utility
Functional group and reactivity (literature):
Primary amine (as HCl salt) serves as a nucleophile after neutralization. It reacts readily with electrophiles: acyl chlorides/activated esters (amide formation), sulfonyl chlorides (sulfonamides), chloroformates (carbamates), and carbonyls (imines/enamines under dehydration).
Quaternization with alkyl halides affords ammonium salts bearing an ethyl-d5 substituent, useful for MS tagging.
Retrosynthetic value:
As a labeled ethylamine synthon, it enables direct installation of an N-ethyl-d5 group without late-stage hydrogen–deuterium exchange, providing robust isotopic fidelity.
Protecting group chemistry: The amine can be protected (e.g., Boc, Cbz) after liberation from the HCl salt, allowing orthogonal downstream manipulations while preserving the CD3–CD2 moiety.
Isotopic considerations:
Carbon-bound deuteriums are generally non-exchangeable in standard acylation/sulfonylation/reductive amination conditions, enabling reliable label retention through multistep sequences.
Operational tips:
For coupling: Pre-mix with base (e.g., 2–3 equiv DIPEA) in DMF/MeCN to form the free amine; add electrophile at 0–25 °C. For acid halides, maintain temperature control to manage exotherms.
Monitor reactions by LC–MS to confirm isotopic pattern retention (+5 Da isotopologue) and to quantify conversion without chromatographic ambiguity.
Target Specificity
Not applicable. This product is a small-molecule isotopically labeled amine salt, not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species specificity is relevant.
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