2-(4-bromophenoxy)-N,N-diethylethanamine - ≥95% , CAS No.1823-62-7

CAS: 1823-62-7 Cat. No.: B1073273 PubChem CID: 423953

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: CCN(CC)CCOC1=CC=C(C=C1)Br
• IUPAC Name: 2-(4-bromophenoxy)-N,N-diethylethanamine
• InChIKey: XKIFTEHOCFPRJE-UHFFFAOYSA-N
• INCHI: 1S/C12H18BrNO/c1-3-14(4-2)9-10-15-12-7-5-11(13)6-8-12/h5-8H,3-4,9-10H2,1-2H3
• Isomères SMILES: CCN(CC)CCOC1=CC=C(C=C1)Br
• CAS alternatif: 1823-62-7
• PubChem CID: 423953

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Bromobenzenes Alkyl aryl ethers Aryl bromides Trialkylamines Organopnictogen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Alkyl aryl ether - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Tertiary aliphatic amine - Tertiary amine - Ether - Organobromide - Organohalogen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a 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

Propriétés chimiques et physiques

• Poids moléculaire: 272.180 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 271.057 Da
• Monoisotopic Mass: 271.057 Da
• Topological Polar Surface Area: 12.500 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 154.000
• 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

No assay validation or bioanalytical protocols are specified for this item. It is a small-molecule intermediate; standard protocols depend on the intended synthetic or analytical use.

General lab-use examples (informational):

• Preparation of hydrochloride salt for handling:
  • Dissolve 1 equiv of the free base in anhydrous Et2O or MTBE (0.05–0.2 M) under inert atmosphere. Add 1.0–1.1 equiv of 2–4 M HCl in dioxane or ethanolic HCl dropwise at 0–25 °C. Stir 0.5–2 h, isolate precipitated salt by filtration, wash with cold ether, dry under vacuum.
• Quaternary ammonium formation (e.g., methylation):
  • Dissolve substrate in MeCN (0.1–0.5 M), add MeI (1.2–1.5 eq), stir at RT–40 °C until complete by TLC/LC–MS. Precipitate product with ether; filter and dry.
• Suzuki coupling example (Ar–Br to Ar–Ar):
  • Combine substrate (1.0 eq), aryl boronic acid (1.2 eq), Pd(PPh3)4 (3 mol%), K3PO4 (3.0 eq) in 1,4-dioxane/H2O (3:1, 0.1–0.3 M). Heat 90 °C for 6–12 h. Cool, extract, and purify by silica gel. If catalyst inhibition observed, pre-protonate the amine.

These examples are for research guidance only; adjust to your system and consult primary literature/SDS.

Biological Roles

Item-specific biological/biochemical annotations are not provided for this product and it is supplied strictly for research use only.

General context (literature/biochemistry):

• Structural class: tertiary aliphatic amine tethered to an aryl ether with a para-bromine substituent. Such motifs occur in medicinal chemistry as beta-aryloxy amine scaffolds, but this exact compound is not a known endogenous metabolite.
• Ionization: at physiological pH, tertiary amines are largely protonated (conjugate acid pKa for N,N-diethylamino moieties typically ~10–11), increasing aqueous compatibility of their salt forms and influencing membrane interactions and distribution in cell-based assays (research context only).
• Potential research utility: as a chemical probe precursor or intermediate to generate quaternary ammonium salts (cationic surfactant-like species) or to append diverse substituents onto the aryl ring via the bromo handle for SAR studies.
• Metabolic liabilities (general): tertiary amines are susceptible to N-dealkylation and N-oxidation by cytochrome P450s; aryl bromides can be sites for oxidative dehalogenation or conjugation after further functionalization (literature trends).

No claims are made regarding therapeutic activity, safety in vivo, or clinical use. All handling and experimentation should follow institutional biosafety and chemical safety practices.

Buffer Applications

This compound is not a standard buffering agent and is not typically used to prepare defined pH buffer systems.

Practical notes (general):

• As a tertiary amine, the free base can be protonated with mineral or organic acids to form salts (e.g., hydrochloride). These salts can be highly water-soluble but do not constitute classical buffer pairs with reliable pKa calibrations like TRIS or HEPES.
• For assays requiring controlled pH, use established buffers (e.g., phosphate, acetate, TRIS) and dissolve this compound (free base or salt) into the buffer or a miscible co-solvent as needed.

Recommendation: select buffer systems based on the biology/assay requirements and treat this material strictly as a solute or intermediate, not as a buffering component.

Green Alternatives

While the substance itself is a target/intermediate rather than a solvent, greener choices can be made for the processes employing it. Below are general, literature-based solvent replacements that maintain performance for common transformations on aryl bromides and tertiary amines.

Greener solvent options (general guidance):

• Replace DCM/chloroform with: ethyl acetate or methyl tert-butyl ether (extractions, dissolutions), and cyclopentyl methyl ether (CPME) for reactions.
• Replace THF/1,4-dioxane with: 2-methyltetrahydrofuran (2-MeTHF) or CPME (cross-coupling, nucleophilic substitutions). 2-MeTHF is bio-based, less volatile, and forms fewer peroxides than THF.
• Replace DMF/NMP with: propylene carbonate, dimethyl carbonate, or green alcohols (MeOH/EtOH/IPA) where feasible for quaternization and salt formation.
• Aqueous micellar catalysis: consider surfactant-enabled aqueous media for Suzuki couplings; can reduce organic solvent demand.

Trade-offs to consider:

• Solubility: the free base is less water-soluble; protonation may be required for aqueous or biphasic systems.
• Catalyst compatibility: some greener solvents (e.g., EtOAc) may require ligand/base tuning to match activity of dioxane/DMF.
• Workup: ethers like CPME promote clean phase splits but can carry peroxides—monitor and manage peroxides per SOP.

Summary table (general):

• Dioxane → 2-MeTHF/CPME (similar boiling range, improved safety)
• DCM → EtOAc/MTBE (reduced toxicity; similar volatility)
• DMF → MeOH/EtOH or propylene carbonate (lower hazard; adjust bases/temperatures accordingly)

Pharmaceutical Uses

No pharmacopeial grade or excipient use is specified for this item; it is supplied for research use only.

General context (literature/CMC):

• Role in discovery chemistry: tertiary aryl ether amines are common scaffolds/intermediates in medicinal chemistry campaigns. The para-bromo substituent offers a convergent handle for late-stage diversification (e.g., Suzuki, Buchwald–Hartwig) to build analog libraries.
• Salt selection (pre-formulation research): tertiary amines often form stable, crystalline salts (HCl, HBr, mesylate, tosylate). Such salts can improve handling, stability, and solubility for in vitro studies (non-clinical).
• Impurity considerations: amine-containing compounds may absorb CO2/H2O and develop surface films; quaternary ammonium byproducts may form during over-alkylation. Analytical monitoring by LC–MS and NMR is standard in CMC workflows.
• No claims are made regarding therapeutic indications, safety, or human/animal administration. Not intended for diagnostic or clinical use.

Physical Properties

Item-specific specifications (this product):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point, melting point, density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed properties (for context; not product specifications):

• Calculated molecular formula from the IUPAC name: C12H18BrNO (literature/computed).
• Calculated formula mass: ~272.19 g/mol (literature/computed).
• Physical state: many analogous tertiary aryl ether amines are colorless to pale yellow liquids or low-melting solids (general/literature; verify on CoA for this lot).
• Basicity: tertiary amine conjugate acid pKa typically ~10–11 (literature, tertiary N,N-diethylamino). Expect quantitative salt formation with mineral acids.
• Solubility profile (general):
  • Organic: expected to be freely soluble in chlorinated solvents (DCM, CHCl3), ethers (THF, MTBE), esters (EtOAc), aromatic solvents (toluene), and alcohols (MeOH–iPrOH).
  • Aqueous: free base low to moderate solubility at neutral pH; highly water-soluble as protonated salts (e.g., HCl).
• Partitioning: aryl bromide and ether increase hydrophobicity; tertiary amine provides pH-switchable polarity (general behavior).

Quality and Grades

Item-specific quality information:

• 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 common grades (general information to contextualize selection):

• Research grade: suitable for most synthetic and discovery workflows; typical assay by NMR/GC/LC but may have higher residual solvents or UV background.
• Puriss/Analytical grade: tight impurity profile; advantageous for kinetics or spectroscopic work where trace absorbers matter.
• HPLC grade (for solvents) / LC-MS grade (for solutions): minimized non-volatile residues and UV-absorbing impurities; relevant if using the compound as a standard or preparing analytical calibrants.
• Low-water/anhydrous variants: sometimes offered for amines to minimize CO2/H2O uptake; improves reproducibility in air/moisture-sensitive reactions.

What to verify on the CoA for this item:

• Assay or purity method (e.g., GC, HPLC, qNMR) and threshold.
• Residual solvent profile and identity.
• Water content (Karl Fischer) if relevant to your application.
• Identity confirmation (1H/13C NMR, MS).
• Handling notes (e.g., presence of acid scavengers or any stabilizer).

Reaction and Applications

As a bifunctional substrate, 2-(4-bromophenoxy)-N,N-diethylethanamine presents two orthogonal handles: an aryl bromide for cross-coupling and a tertiary amine for alkylation/salt formation. Typical research applications (literature/general):

• Cross-coupling at Ar–Br:

  • Suzuki–Miyaura to install aryl/alkenyl groups while retaining the phenoxy–alkyl–tertiary amine motif. Use Pd(0/II) catalysts with XPhos/SPhos or NHC ligands; bases such as K3PO4 or Cs2CO3 in toluene/dioxane/H2O.
  • Buchwald–Hartwig amination to convert Ar–Br to anilines/amides; consider transient protonation of the tertiary amine (e.g., as HBF4 salt) to reduce Pd coordination.
  • Sonogashira/Stille/Negishi feasible with standard conditions.

• Quaternization and PTC-like derivatives:

  • Alkylation with MeI, benzyl halides, or dialkyl sulfates to form quaternary ammonium salts—useful for phase-transfer catalysis studies or as ionic intermediates.

• Formation of acid salts:

  • Protonation (HCl, HBr, p-TsOH) affords crystalline salts for purification, storage, or biological assay feeds (research use only).

• Oxidation and downstream chemistry:

  • N-oxidation (m-CPBA) to the amine oxide; potential for Cope-type eliminations on tailored analogs.

Practical tips:

• Tertiary amines can poison Pd/Ni catalysts; pre-form the ammonium salt or add catalyst after base equilibration.
• Ether linkage is generally stable to bases and mild acids, facilitating harsh cross-coupling conditions on Ar–Br without cleaving Ar–O.
• Control pH during workup: switch between free base (organic-soluble) and salt (aqueous-soluble) for efficient purification.

Reaction Conditions

General literature guidance (representative, not product specifications):

• Suzuki–Miyaura coupling (Ar–Br):

  • Catalyst: Pd2(dba)3 (0.5–1 mol% Pd) with XPhos/SPhos (1–2 mol%) or Pd(PPh3)4 (2–3 mol%).
  • Base: K3PO4 (2–3 eq) or Cs2CO3.
  • Solvent: 1,4-dioxane/H2O (3:1), toluene/H2O, or 2-MeTHF/H2O.
  • Temperature/time: 70–100 °C, 4–16 h.
  • Note: Pre-protonate the tertiary amine (e.g., HBF4 salt) if catalyst inhibition is observed.

• Buchwald–Hartwig amination:

  • Catalyst/ligand: Pd2(dba)3 with BrettPhos or tBuBrettPhos (1–2 mol% Pd), NaOtBu or K3PO4 as base.
  • Solvent: toluene, CPME, or dioxane.
  • Temperature: 80–110 °C.

• Sonogashira coupling (if alkyne installation desired):

  • Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), Et3N or iPr2NH, in THF/MeCN/2-MeTHF, RT–60 °C.

• Quaternization (N-alkylation):

  • Alkyl halide (e.g., MeI, BnBr; 1.1–1.5 eq) in MeCN, acetone, or EtOH.
  • Temperature: 20–50 °C, 2–24 h.
  • Outcome: R4N+X− salts, often crystalline and water-soluble.

• Amine oxide formation:

  • Oxidant: m-CPBA (1.1–1.5 eq) in DCM at 0–25 °C; monitor to avoid over-oxidation.

Workup/purification tips:

• Exploit pH switching: extract free base into organic; crystallize salts from alcohol/ether.
• Remove palladium by scavengers (SiliaMetS, carbon) after couplings.

These conditions are broad guidelines derived from literature precedents on aryl bromides and tertiary amines.

Safety and Handling

Authoritative hazard classification for this specific item is not provided. Always consult the product SDS.

Item-specific safety data:

• Signal word, H-statements, GHS classes, pictograms: Not specified for this item; refer to SDS.
• Storage condition: Room temperature (per Product Data). Keep container tightly closed.

General safety guidance for tertiary aryl ether amines (informational, not a substitute for SDS):

• Likely hazards: may cause skin/eye irritation; harmful if swallowed; vapors may be irritating. Amines can be sensitizers in some cases.
• PPE: use chemical-resistant gloves (nitrile recommended), lab coat, and splash goggles. Handle in a fume hood.
• Incompatibilities: strong oxidizers; strong acids (forms salts, exotherm possible); acylating/alkylating agents; nitrosating agents; may react with CO2 from air to form carbamate films on prolonged exposure (common for amines).
• First aid overview:
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Inhalation: move to fresh air; obtain medical advice if symptoms persist.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: organic base likely combustible; use CO2, dry chemical, or foam. Cool containers with water spray.
• Spill response: absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains.

Always defer to the SDS and institutional protocols for definitive handling and disposal instructions.

Solvent Selection

This product is an organic tertiary amine/aryl ether intended as a building block or intermediate rather than a solvent. Solvent choice here addresses dissolution and reactivity support.

General solubility and polarity considerations (literature/general):

• Polarity class: moderately lipophilic free base with pH-switchable polarity (becomes hydrophilic upon protonation).
• Likely miscibility/solubility: high in DCM, chloroform, THF, EtOAc, MeCN, toluene, and alcohols (MeOH–iPrOH). Limited in water as free base; readily water-soluble as the hydrochloride (or other) salt.

Practical selection by operation:

• Nucleophilic substitutions, quaternization: MeCN, acetone, EtOH, or isopropanol are often excellent; polar aprotic media enhance rates with alkyl halides.
• Cross-couplings on the aryl bromide: anisole/toluene, 1,4-dioxane, or CPME/2-MeTHF with aqueous base; DME/THF also common. Convert amine to a non-coordinating salt (e.g., HBF4) if catalyst inhibition is observed.
• Salt formation/purification: dissolve in Et2O or MTBE, then add ethanolic HCl to precipitate the amine hydrochloride.
• Crystallization: if a solid salt is desired, alcohol/ether or alcohol/MTBE mixtures are typical for tertiary amine salts.

Comparison notes (general):

• DCM vs EtOAc: DCM provides rapid dissolution and easy removal; EtOAc is greener and compatible with salt-formation workflows.
• THF vs 2-MeTHF: 2-MeTHF offers improved safety/greenness with similar solubilizing power; better phase separation in workups.

Storage and Reconstitution

Item-specific storage/shipping:

• Storage condition: Room temperature (per Product Data).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General storage guidance for tertiary amines (informational):

• Container: store in tightly sealed amber glass to minimize light exposure and prevent air/moisture/CO2 ingress.
• Atmosphere: if long-term storage is anticipated, purge headspace with inert gas (N2/Ar); amines can slowly absorb CO2 and moisture.
• Segregation: keep away from strong acids, oxidizers, and acylating/alkylating agents.
• Stability: tertiary aryl ether amines are typically stable at ambient temperature; monitor for discoloration or precipitate (salt formation) over time.

Reconstitution/preparation of solutions (if needed):

• Stock solutions: prepare in dry DMSO, MeOH, MeCN, DCM, or 2-MeTHF at convenient concentrations (e.g., 10–100 mM) based on solubility and use-case. Filter through 0.2 µm PTFE if particulate is present.
• Aqueous use: convert to a salt (e.g., HCl) to enhance water solubility; adjust pH to maintain protonation.
• Freeze–thaw: not typically required; if freezing solutions, aliquot to avoid repeated freeze–thaw cycles.

Always refer to the certificate of analysis and SDS for product-specific stability and handling information.

Research Use Note: For research use only.

Structure and Identity

A para-brominated phenoxy ether bearing a flexible 2-(diethylamino)ethyl side chain; tertiary amine linked to the aryl ring via an ether spacer.

• SKU: B1073273
• Product name: 2-(4-bromophenoxy)-N,N-diethylethanamine
• CAS: 1823-62-7
• PubChem CID: 423953 (literature)
• InChIKey: 420222 (as provided in Product Data; full-length InChIKey not specified for this item; refer to CoA/Spec Sheet.)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet. Representative literature SMILES: Brc1ccc(cc1)OCCN(CC)CC (literature).
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. Computed (from name, literature): C12H18BrNO.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. Calculated (from computed formula): ~272.19 g/mol (literature/calculated).

Structural features (descriptive):

• Aromatic ring (para-bromophenyl) with a para bromine substituent relative to the phenoxy linkage.
• Aryl–oxygen–alkyl ether (phenoxy–CH2–CH2–) tether to a tertiary amine center.
• Tertiary amine substituents: two ethyl groups (N,N-diethyl) and one 2-hydroxy-equivalent alkyl chain via oxygen (as ether).
• No stereocenters; achiral, conformational flexibility in the ethoxy-amine chain.
• Functional groups: aryl bromide (for cross-coupling), aryl–alkyl ether (robust under many conditions), tertiary aliphatic amine (basic, nucleophilic; forms salts with acids).

Synthetic Utility

Key functional elements enable diverse transformations (literature/general):

• Aryl bromide (para to phenoxy):

  • Cross-coupling platform: Suzuki (Ar–B(OH)2), Buchwald–Hartwig (Ar–NR2), Sonogashira (Ar–C≡C–R), and carbonylation (Ar–C(O)R) to introduce wide-ranging functionality while preserving the phenoxy–alkyl–tertiary amine framework.
  • Halogen–metal exchange (with careful control) for ortho/para functionalization via lithium or magnesium reagents; protect or salt the amine to avoid deprotonation/coordination issues.

• Tertiary amine (N,N-diethyl):

  • Quaternization to generate ammonium salts (synthetic handles, PTCs, ionic liquids precursors).
  • N-oxidation (amine oxide) enabling Cope-type eliminations or polarity modulation.
  • Salt formation for purification/phase switching; facilitates selective extractions and crystallizations.

• Aryl–alkyl ether linkage:

  • Chemically robust under many coupling conditions; withstands strong bases (e.g., K3PO4, Cs2CO3) and moderate acids; can be cleaved only under forcing conditions (BBr3/AlCl3 for demethylation-type chemistry is not directly applicable to this secondary ether but Lewis-acidic conditions may disrupt at higher severity).

Retrosynthetic perspective:

• Disconnection to a 4-bromophenol (or 4-bromophenoxide) and 2-chloroethyl-diethylamine (or protected equivalents) via nucleophilic aromatic substitution or Williamson ether synthesis, followed by amine deprotection/alkylation as needed.

Target Specificity

Not applicable. This product is a small-molecule chemical and not an antibody, enzyme, or biological targeting reagent.

• Antigen/epitope, species reactivity, clone/isotype: Not applicable.
• No target-specific binding information is provided or implied for this item.