2-Bromo-N,N-dimethylethylamine hydrobromide - ≥95% , CAS No.2862-39-7

CAS: 2862-39-7 Cat. No.: B183437 Summenformel: C₄H₁₀BrN.BrH Molekulargewicht: 232.9 EG-Nummer: 220-680-4 PubChem CID: 45791347

GRADE & PURITY ≥95%

Synonyms

AM84884 | Ethanamine, 2-bromo-N,N-dimethyl-, hydrobromide | Ethanamine, 2-bromo-N,N-dimethyl-, hydrobromide (1:1) | GS-4522 | M0735 | A876676 | Dimethylaminoethyl bromide hydrobromide | SCHEMBL28116 | 2-Bromo-N,N-dimethylethan-1-amine--hydrogen bromide (1

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyme

AM84884 | Ethanamine, 2-bromo-N,N-dimethyl-, hydrobromide | Ethanamine, 2-bromo-N,N-dimethyl-, hydrobromide (1:1) | GS-4522 | M0735 | A876676 | Dimethylaminoethyl bromide hydrobromide | SCHEMBL28116 | 2-Bromo-N,N-dimethylethan-1-amine--hydrogen bromide (1

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥95%

Namen und Kennungen

• Pubchem Sid: 488201254
• Kanonisches Lächeln: CN(C)CCBr.Br
• IUPAC Name: 2-bromo-N,N-dimethylethanamine;hydrobromide
• InChIKey: MFRUVSDIZTZFFL-UHFFFAOYSA-N
• INCHI: 1S/C4H10BrN.BrH/c1-6(2)4-3-5;/h3-4H2,1-2H3;1H
• Isomere SMILES: CN(C)CCBr.Br
• PubChem CID: 45791347
• Molekulargewicht: 232.9

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Klasse Organonitrogen compounds
      • Subclass Amines
        • Ebene5 Tertiary amines
          • Ebene6 Trialkylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Klasse: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Tertiary amines
• Direct Parent: Trialkylamines
• Alternative Parents: Organopnictogen compounds Organobromides Organic bromide salts Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Tertiary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Organic bromide salt - Organic salt - Organobromide - Organohalogen compound - Alkyl halide - Alkyl bromide - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 232.940 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 232.924 Da
• Monoisotopic Mass: 230.926 Da
• Topological Polar Surface Area: 3.200 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 28.700
• 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: 2

XLogP3

Referenzen

1. Jingjing Guo, Ailian Wang, Wenxi Ji, Taoyi Zhang, Haolin Tang, Haining Zhang.  (2021)  Protic ionic liquid-grafted polybenzimidazole as proton conducting catalyst binder for high-temperature proton exchange membrane fuel cells.  POLYMER TESTING,      [PMID:] [10.1016/j.polymertesting.2021.107066]

2. Zena Chen, Zhihang Liao, Fangning Du, Xiang Che, Likun Wang, Wei Shi, Changmin Yu, Naidi Yang.  (2025)  One-Step Facile Synthesis of a Cationic Photosensitizer with Electrostatic Anchoring of Bacteria for Photodynamic Therapy of MRSA-Infected Wounds.  ACS Applied Materials & Interfaces,      [PMID:41448952] [10.1021/acsami.5c18942]

Application Protocols

No biological assay protocols (WB, IHC, IF, FC) are applicable to this chemical reagent.

• Practical lab protocol sketch (chemical use; general)
  • To install a 2-dimethylaminoethyl group on a phenol: Dissolve phenol (1.0 eq) and K2CO3 (2.5 eq) in MeCN (0.2 M). Add 2-bromo-N,N-dimethylethylamine·HBr (1.3 eq). Stir at 40 °C for 6 h. Monitor by LC/MS. Filter off salts, concentrate, partition between water and EtOAc, basify aqueous layer to pH ~10, extract, dry, and purify by flash chromatography.

This sketch is illustrative and not an item-specific validated protocol; optimize per substrate and consult the SDS before use.

Biological Roles

This product is a synthetic organic reagent rather than a biomolecule. It is not typically discussed in the context of endogenous biological roles.

• General notes (contextual, not product-specific claims)
  • Tertiary amines and their salts are common motifs in biomolecule ligands and ion-exchange materials; introducing a dimethylaminoethyl side chain can modulate cationic character and pKa of target molecules.
  • Quaternization of tertiary amines derived from this reagent can produce permanently cationic groups useful in bioconjugation supports and nucleic acid-binding polymers.

No clinical or therapeutic claims are made. For research use only.

Buffer Applications

Not a buffering reagent. As a tertiary amine hydrobromide, it does not serve as a standard biochemical buffer system.

• Practical note
  • If used in aqueous synthesis or polymer modification, maintain controlled pH (typically 7–10) with a separate buffering system (e.g., carbonate or phosphate) to manage the ammonium/amine equilibrium and suppress side reactions.

For dedicated buffering, select established buffers (e.g., Tris, HEPES, phosphate) appropriate to your pH window.

Green Alternatives

• Solvent greening (general recommendations)

  • Prefer acetonitrile, acetone, or ethanol over DMF/DMSO when feasible; these offer easier removal, lower toxicity classifications, and better life-cycle metrics while still supporting SN2 chemistry with bromides.
  • Employ water or water–ethanol mixtures with phase-transfer catalysts (e.g., TBAB alternatives from biorenewable sources) to perform O-/S-alkylations under milder, more sustainable conditions.

• Reagent/leaving-group considerations

  • Bromide is effective but generates Br– waste. In some programs, switching to mesylate/tosylate analogs of 2-dimethylaminoethanol (prepared in situ) can reduce halogenated waste; trade-off is often reduced reactivity compared to bromide.
  • If downstream quaternization is planned, directly using 2-dimethylaminoethyl chloride hydrochloride or the corresponding mesylate in MeCN can be greener than DMF-based bromide processes, depending on EHS assessments.

• Energy and process intensification

  • Microwave or flow SN2 in MeCN/EtOH can shorten reaction times and reduce solvent volumes.
  • Solid-supported bases (K2CO3 on silica) enable solvent minimization and facile filtration.

• Comparison snapshot (general)

  • 2-Bromo DMAE·HBr vs 2-chloro DMAE·HCl: Cl– option reduces bromide waste but may require higher temperature or iodide activation.
  • DMF vs MeCN: DMF often faster but less green; MeCN is more manageable in scale-up and waste treatment.

Balance greener choices with safety and performance; validate on small scale before process adoption.

Pharmaceutical Uses

This material is offered for research and process development only and is not intended for human or veterinary use.

• Formulation/manufacturing context (general)
  • Tertiary amine haloalkyl salts like this can be intermediates for synthesizing cationic excipient analogs (e.g., ion-exchange resins, permeation enhancers) and API side chains bearing dimethylaminoethyl groups.
  • The hydrobromide counterion may be exchanged (salt metathesis) to HCl, sulfate, or organic acid salts as required for downstream processing.

No claims are made regarding pharmacopoeial status, GMP suitability, or therapeutic applications for this SKU. Refer to your quality unit for qualification strategy if used in regulated development.

Physical Properties

• Item-specific specs for this catalog entry

  • 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 physicochemical data (indicative; not item specifications)

  • Molecular formula (hydrobromide): C4H11Br2N (literature)
  • Formula weight: ~232.95 g/mol (calculated from literature formula)
  • Physical state: Typically a crystalline, hygroscopic salt (literature, typical for dialkylaminoethyl hydrobromides)
  • Solubility: Expected to be freely soluble in water, methanol, ethanol; soluble in polar aprotic solvents such as acetonitrile and DMF (literature/analogy)
  • Partitioning: Cationic salt; logP is not typically meaningful for the hydrobromide form; distribution depends on pH/ion-pairing (general note)
  • pKa: The conjugate acid of a tertiary amine typically has pKa ~9–10 in water (literature, general range for dimethylammonium); exact value for this salt not verified.
  • Hygroscopicity: Amine hydrobromide salts are often hygroscopic; store tightly closed and desiccated (general guidance).

Note: Exact BP/MP, density, refractive index, UV cutoff, water/peroxide/metal content are Not specified for this item; refer to CoA/Spec Sheet and SDS for authoritative data.

Quality and Grades

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

• Interpreting common grades for similar salts (general guidance)

  • Research grade: Suitable for most synthetic applications; impurity profile focuses on residual solvents, inorganic halides, and related amine/haloamine species.
  • High-purity or low-water grades: Beneficial for moisture-sensitive SN2 reactions and polymer functionalizations; controlled water limits reduce competing hydrolysis.
  • Stabilizers: Not typically required for this type of salt; absence/presence of stabilizers should be verified on the CoA. If present, stabilizers can affect downstream quaternization/polymerization and should be removed during workup.

• Quality considerations specific to this chemistry

  • Key impurities: 2-hydroxyethyl dimethylamine salts (from hydrolysis), unreacted dimethylamine salts, and over-brominated species. Inorganic bromide content and residual water can influence reaction rates and selectivity.
  • Analytical control: Titrimetric halide, Karl Fischer for water, 1H/13C NMR (D2O), IC for bromide, and LC/MS for related substances are commonly used (general practice).

Consult the Aladdin CoA/Spec Sheet for this SKU (B183437) for the definitive grade, assay, and impurity limits.

Reaction and Applications

As a β-bromoethyl tertiary ammonium salt, this reagent is a convenient electrophile for installing a 2-dimethylaminoethyl fragment onto nucleophiles via SN2 displacement of bromide.

• Typical transformations (literature/general)

  • O-alkylation: Phenols and carboxylates → aryl/alkyl 2-dimethylaminoethyl ethers/esters (base: K2CO3/Cs2CO3; solvent: MeCN/DMF).
  • S-alkylation: Thiols/thiolates → thioethers bearing dimethylaminoethyl side chains (often rapid at ambient temperature).
  • N-alkylation: Primary/secondary amines → tertiary amines with pendant dimethylaminoethyl group; control stoichiometry to avoid multiple alkylations.
  • Polymer/solid support modification: Introduces cationic tertiary amine functionality for ion-exchange resins, membranes, and flocculants (followed by quaternization if desired).
  • Intramolecular aziridinium chemistry: Under strong base, transient aziridinium formation can occur; nucleophiles can open the ring regioselectively (useful for selectivity tuning).

• Practical notes

  • Base choice: Mild inorganic bases (K2CO3, Na2CO3) minimize elimination and over-alkylation; stronger bases may generate free amine and side reactions.
  • Counterion effects: Bromide is a good leaving group; in some cases, in situ halide exchange (e.g., to iodide via NaI, Finkelstein) can enhance rates.
  • Workup: Products may form ammonium salts; basify and extract into organic solvent, or isolate as acid salts as required.
  • Monitoring: TLC may be challenging for ionic species; HPLC or LC/MS is preferred. 1H NMR (D2O/CD3OD) cleanly shows disappearance of –CH2–CH2–Br signals.

• Representative contexts

  • Synthesis of cationic surfactant precursors, ligand scaffolds, functional monomers, and small-molecule building blocks containing a DMAE appendage.

Reaction Conditions

General guidance from literature/analogous systems (optimize per substrate):

• O-/S-alkylation

  • Substrate: Phenols/thiols (1.0 eq)
  • Reagent: 2-Bromo-N,N-dimethylethylamine·HBr (1.2–1.5 eq)
  • Base: K2CO3 or Cs2CO3 (2.0–3.0 eq)
  • Solvent: MeCN or DMF (0.1–0.5 M)
  • Temperature: 25–60 °C
  • Time: 2–16 h
  • Notes: Add base first to generate phenolate/thiolate; bromide is displaced SN2. Monitor by LC/MS.

• N-alkylation of amines

  • Base: K2CO3 or DIPEA (2.0 eq)
  • Solvent: MeCN, DMF
  • Temperature: 25–50 °C
  • Caution: Control stoichiometry to limit multiple alkylations; consider protecting groups if selectivity is critical.

• Halide activation (optional)

  • Add NaI (1.5 eq) in MeCN (Finkelstein conditions) to enhance leaving-group ability; typically accelerates sluggish substrates.

• Workup

  • Dilute with water, basify to liberate free tertiary amine products, extract with EtOAc/MTBE. Alternatively, isolate as acid salts by adding HCl/AcOH in IPA and precipitating.

• Typical outcomes

  • Clean SN2 with inversion at electrophilic carbon (primary center). Yields are substrate-dependent; 60–90% commonly reported for unhindered nucleophiles (literature, general range).

Safety and Handling

• Item-specific hazard fields

  • GHS Classification, Signal Word, H-Statements, Pictograms: Not specified for this item; refer to SDS.

• General safety considerations for haloalkyl ammonium hydrobromides (literature/industry practice)

  • Hazards: Alkyl bromides are electrophilic and may be harmful if inhaled, swallowed, or in contact with skin. Hydrobromide salts may be corrosive/irritant, especially to eyes and mucosa. This compound can alkylate nucleophiles; handle as a potential sensitizer/irritant.
  • PPE: Use lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles. Handle in a fume hood.
  • Incompatibilities: Strong bases (may liberate free amine and HBr; exotherm possible), strong oxidizers, strong nucleophiles without temperature control (risk of vigorous SN2). Avoid contact with reactive metals in presence of moisture/acids (H2 evolution possible).
  • Peroxide formation: Not applicable (no ether functionality), but product can slowly decompose to liberate HBr under harsh conditions; avoid prolonged heating.
  • First aid (overview; defer to SDS):
    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Skin contact: Remove contaminated clothing; rinse with water for ≥15 min.
    • Eye contact: Rinse cautiously with water for ≥15 min; seek medical attention.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Fire response: Use CO2, dry chemical, or alcohol-resistant foam. Emits HBr, NOx, and brominated vapors on thermal decomposition.

Always consult the product SDS for definitive hazard, exposure limits, and spill/cleanup guidance.

Solvent Selection

This salt is polar and typically handled in polar protic or polar aprotic media. Choice of solvent depends on whether you need it dissolved as the ammonium salt or engaged in an SN2 reaction to transfer the 2-dimethylaminoethyl group.

• Miscibility/solubility profile (literature/general)

  • Water, methanol, ethanol: High solubility; useful for salt handling, ion-exchange, and aqueous-phase transformations.
  • Acetonitrile, DMF, DMSO: Good solubility; favored for SN2 alkylations of phenols, thiols, and amines with a mild inorganic base.
  • Acetone, IPA: Often workable for phase-transfer or precipitation-driven protocols.

• Selection tips

  • For efficient SN2 on the –CH2–CH2–Br moiety, a polar aprotic solvent (MeCN, DMF) with K2CO3, Cs2CO3, or NaHCO3 often boosts rates while keeping the amine protonated initially to minimize side reactions. After alkylation, neutralize to free the tertiary amine on product.
  • For aqueous operations (e.g., ion-exchange, polymer modification), buffer ionic strength to control activity; avoid high pH that may promote elimination or hydrolysis.
  • Avoid strong nucleophiles in highly basic alcoholic media if competing intramolecular aziridinium formation or over-alkylation is a concern.

• Comparison snapshot (general)

  • MeCN vs DMF: MeCN is lower boiling and easier to remove; DMF often gives faster SN2 but is harder to dry/remove.
  • Water/alcohols: Preferred for handling, quenching, and salt metathesis; less ideal for rate-demanding SN2 unless using phase-transfer catalysis.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place.
  • Shipped in: Normal conditions (per Product Data).

• General handling for amine hydrobromide salts

  • Hygroscopic tendency is common; keep container tightly sealed. Consider desiccant storage to maintain material integrity.
  • Avoid prolonged exposure to strong bases or elevated temperatures; these can promote decomposition or side reactions.

• Solution preparation (general guidance)

  • Aqueous stocks: Dissolve to the desired concentration in deionized water; filter if needed. Adjust pH cautiously if free amine is required downstream.
  • Organic stocks: Readily dissolves in MeOH, EtOH, or MeCN. For SN2 uses, include an appropriate base (e.g., K2CO3) in situ rather than pre-neutralizing the salt to limit side reactions.
  • Storage of solutions: Prefer freshly prepared solutions. If storage is necessary, refrigerate aqueous solutions and use within a few days; assess stability by LC before critical applications.

Refer to the product CoA and SDS for limits on moisture, stability, and any special precautions specific to this SKU.

Structure and Identity

A bifunctional haloalkylammonium salt featuring a β-bromoethyl chain attached to a dimethylammonium center; the counterion is bromide. The molecule contains both a covalent C–Br (alkyl bromide) and a protonated tertiary amine (ammonium), making it a potent SN2 alkylating electrophile.

• Item-specific (from Product Data)

  • Product name: 2-Bromo-N,N-dimethylethylamine hydrobromide
  • CAS: 2862-39-7
  • InChIKey: 217912 (as provided)
  • Storage: Room temperature
  • Shipped: Normal
  • Research use: For research use only

• Literature/computed identifiers and features (for reference; not item specifications)

  • Expected molecular formula (salt): C4H11Br2N (literature)
  • Calculated molecular weight (formula above): ~232.95 g/mol (literature)
  • Canonical SMILES (salt, one representation): [Br-].CN+CCBr (literature)
  • Functional groups: tertiary ammonium, primary alkyl bromide (2-bromoethyl)
  • Structural description (2D): A dimethylammonium center [N+(CH3)2H] bonded to –CH2–CH2–Br; overall charge balanced by Br–.
  • Key reactivity elements: β-haloethyl fragment enables SN2 displacement; the tertiary amine is present as an ammonium, typically liberated by base during workup.

• Stereochemistry

  • None (acyclic, no stereocenters).

Synthetic Utility

• Functional group leverage

  • Primary alkyl bromide (–CH2–CH2–Br): High SN2 reactivity to append a 2-dimethylaminoethyl unit to O, N, S, and C nucleophiles.
  • Protonated tertiary amine: Facilitates handling as a non-volatile salt; can be neutralized post-reaction to reveal the free tertiary amine in products.

• Retrosynthetic value

  • Serves as a lynchpin for introducing basic side chains that can be further diversified (quaternization to ammonium, acylation on the tertiary amine after deprotonation, or conversion to betaine/zwitterions).
  • Enables rapid access to DMAE-substituted ethers, thioethers, amides, ureas, carbamates, and heterocycles via intramolecular cyclizations (e.g., aziridinium opening strategies).

• Named/related methodologies (literature)

  • Williamson-type O-alkylation (under phase-transfer or in MeCN/DMF with carbonate base).
  • Menshutkin quaternization (downstream on tertiary amines derived from the reagent).
  • Finkelstein activation (NaI) to transiently increase leaving-group ability where needed.

• Process notes

  • Counterion exchange (to iodide, tosylate, or BF4–) can modulate reactivity/solubility for specific substrates.
  • Ionic nature aids in scavenging excess reagent by aqueous washes; adjust pH during workup to partition products efficiently.

Target Specificity

Not an antibody, enzyme, or biological targeting reagent. No target specificity information applies to this small-molecule building block.

For intended chemical selectivity, see Reaction & Applications and Synthetic Utility tabs.

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How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.