4-(2-(2-Bromo-5-chlorophenoxy)ethyl)morpholine - ≥95% , CAS No.1255574-55-0

CAS: 1255574-55-0 Cat. No.: B1349099 Formula: C₁₂H₁₅NO₂ClBr Molecular Weight: 320.61 PubChem CID: 53217042

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1COCCN1CCOC2=C(C=CC(=C2)Cl)Br

IUPAC Name

4-[2-(2-bromo-5-chlorophenoxy)ethyl]morpholine

InChIKey

QPTYRKYUGKVPKH-UHFFFAOYSA-N

INCHI

1S/C12H15BrClNO2/c13-11-2-1-10(14)9-12(11)17-8-5-15-3-6-16-7-4-15/h1-2,9H,3-8H2

Isomeric SMILES

C1COCCN1CCOC2=C(C=CC(=C2)Cl)Br

PubChem CID

53217042

Molecular Weight

320.61

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Chlorobenzenes Bromobenzenes Alkyl aryl ethers Morpholines Aryl chlorides Aryl bromides Trialkylamines Oxacyclic compounds Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organochlorides Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Alkyl aryl ether - Bromobenzene - Chlorobenzene - Halobenzene - Aryl bromide - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Oxazinane - Morpholine - Tertiary aliphatic amine - Tertiary amine - Oxacycle - Azacycle - Organoheterocyclic compound - Dialkyl ether - Ether - Organopnictogen compound - Organic oxygen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organohalogen compound - Organobromide - Organochloride - Aromatic heteromonocyclic 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

Chemical and Physical Properties

• Molecular Weight: 320.610 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 318.997 Da
• Monoisotopic Mass: 318.997 Da
• Topological Polar Surface Area: 21.700 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 227.000
• 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 application protocols are specified for this catalog item.

Guidance for typical small-molecule handling (general):

• Preparation of screening stocks: dissolve in anhydrous DMSO to 10–50 mM; vortex/sonicate as needed; sterile-filter if required by workflow.
• Cross-coupling setup: pre-dry glassware, degas solvents (sparge or vacuum/N2 cycles), and stage ligands/bases appropriate to aryl bromide/chloride activation.

For any biological assay or analytical method, develop and validate protocols specific to your system. Refer to the CoA/SDS for any lot-specific precautions.

Biological Roles

This product is a synthetic organic building block and is not a biological molecule. No endogenous biological role is associated with 4-(2-(2-bromo-5-chlorophenoxy)ethyl)morpholine.

General context (literature/general):

• The morpholine motif is widely used in medicinal chemistry to modulate basicity, polarity, and solubility, but such usage reflects design strategy rather than inherent biological function.
• Halogenated phenoxy scaffolds are common in SAR exploration for tuning potency and metabolic stability; any biological effects are target- and substitution-specific and cannot be generalized to this compound.

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

Buffer Applications

Not typically applicable. This compound is not a buffering reagent and does not define a reproducible conjugate acid/base pair over a defined pH range for buffer preparation.

Practical note:

• If aqueous handling is required, the morpholine nitrogen can be protonated to form a water-soluble salt (e.g., HCl salt) that may be dissolved in standard laboratory buffers, but the compound itself does not act as a buffer.

Green Alternatives

While the substance itself is the target building block, greener choices can be made around its use—particularly in solvent/catalyst selection and sequence design.

Greener process considerations (literature/general):

• Replace high-boiling polar aprotics (NMP/DMF) with 2-MeTHF, CPME, or aqueous micellar media where compatible.
• Favor ethanol/water or 1,4-dioxane/water (with attention to dioxane’s regulatory status) for Suzuki couplings; explore acetate or carbonate bases over hydroxides.
• Use palladium on reusable supports or nickel catalysis for aryl bromide activation when feasible; reduce precious metal loadings with highly active ligand systems (e.g., XPhos, SPhos, BrettPhos).
• For amide/sulfonamide formation at morpholine N, employ greener coupling reagents (e.g., CDI, EDC·HCl) and avoid excessive chlorinated solvent use; DCM can often be replaced by EtOAc or Me-THF.

Illustrative comparison (general):

• Conventional: DMF, Pd(PPh3)4, toluene, high temperature.
• Greener alternative: 2-MeTHF or CPME with aqueous base, Pd/C or Pd–NHC at ≤0.5 mol%, or micellar catalysis (TPGS-750-M) in water at 40–70 C.

Trade-offs:

• Solubility and rate may decrease in greener media; ligand optimization and phase-transfer strategies can compensate.
• Workup may be simplified (safer solvents, easier removal) but precipitation or emulsions can occur—optimize salt forms and anti-solvents accordingly.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item.

General context (literature/general):

• In drug discovery, morpholine-containing aryl ethers are frequently employed as intermediates or reference compounds during hit-to-lead and lead optimization campaigns.
• Any use would be as a synthetic intermediate or screening compound rather than a formulated pharmaceutical ingredient.

Regulatory note:

• Not specified for pharmacopeial grade. For research use only. Consult CoA if considering use in regulated development chemistry (e.g., impurity standards or process intermediates).

Physical Properties

Item-specific physico-chemical constants are not provided in the Product Data. The following notes are general expectations based on structure; they are NOT item specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (computed from name; literature/computed): ~320.61 g/mol (C12H15BrClNO2).
• Molecular formula (computed; literature/computed): C12H15BrClNO2.
• Boiling point / melting point: Not specified for this item; refer to CoA/Spec Sheet. For similar aryl–morpholine ethers, melting points vary widely; liquid/semi-solid behavior is possible (literature trends).
• Density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general guidance, literature expectation):
  • Organic: expected to be soluble in polar aprotic media (DMSO, DMF, NMP) and moderately soluble in chlorinated solvents (DCM, CHCl3) and MeOH/EtOH.
  • Aqueous: limited solubility in neutral water; solubility increases upon protonation (e.g., as HCl salt).
• pKa (qualitative, literature expectation): secondary amine of morpholine typically pKaH ~7–8.5; actual value depends on substitution. Not specified for this item; verify experimentally if critical.
• LogP (qualitative): presence of Br/Cl aryl increases lipophilicity; morpholine decreases it. Anticipate moderate logP; not specified for this item.

Always confirm critical parameters (mp, bp, solubility limits, water content, UV cutoff) with the item’s CoA/Spec Sheet before method development.

Quality & Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance (general):

• When grade/purity is unspecified, the Certificate of Analysis (CoA) is the controlling document for assay, impurity profile, and any stabilizers/residual solvents. Request and review lot-specific CoA before regulated or quantitative work.
• Typical quality attributes relevant for this scaffold:
  • Identity: confirmed by 1H/13C NMR and mass spectrometry; aryl-halide isotopic patterns (Br/Cl) provide diagnostic MS signatures.
  • Purity: HPLC/UPLC area % and/or qNMR. For cross-coupling precursors, low levels of hydrolysis (phenol) and dehalogenated aryl impurities are desirable.
  • Residual solvents/reagents: Not specified for this item; refer to CoA/Spec Sheet.
  • Water content: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: None indicated in Product Data. If present in a given lot, they will be listed on the CoA.

Practical notes for users:

• If employing Pd-catalyzed couplings, assess halide integrity by LC–MS prior to scale-up.
• For bioassay use, consider converting to a defined salt (e.g., HCl) for improved consistency if free base variability impacts solubility; coordinate with QA as this is not part of the supplied specification.

Reaction & Applications

Designed as a versatile halogenated aryl ether bearing a morpholine handle, this building block supports rapid library synthesis and late-stage diversification.

Key application families (literature/general):

• Cross-coupling on the aryl bromide/chloride:
  • Suzuki–Miyaura: install aryl/heteroaryl/alkenyl substituents at Br (preferred) and, under more forcing conditions, at Cl. Typical bases: K2CO3, Cs2CO3; solvents: dioxane/H2O, toluene, CPME.
  • Buchwald–Hartwig amination: amination at the aryl bromide with Pd/XPhos or BrettPhos systems; the aryl chloride may also react with stronger catalysts/ligands.
  • Sonogashira/Negishi/Stille: enable alkyne/vinyl/alkyl installations from the aryl bromide.
• N-functionalization of morpholine:
  • Acylation/sulfonylation/carbamoylation to tune basicity and polarity (e.g., ureas, amides, sulfonamides).
  • Alkylation or quaternization (e.g., MeI) to generate permanently charged analogs (for SAR or solubility tuning).
• SNAr (limited): the 2-bromo-5-chloro substitution pattern is deactivating toward SNAr; cross-coupling routes are generally preferred over nucleophilic aromatic substitution unless additional activating groups are introduced.

Practical notes:

• Orthogonal reactivity: exploit Ar–Br first for selectivity, leaving Ar–Cl for second-stage coupling.
• Protecting-group strategy: the free morpholine N can chelate Pd and affect catalysis; transient protonation (HX), Boc protection, or using ligand sets tolerant to amine donors can improve outcomes.
• Workup: monitor for hydrolysis to the corresponding phenol; minimize prolonged basic aqueous exposure and high-temperature aqueous phases.

Use cases: medicinal chemistry lead elaboration, linker installation, and bifunctional probe synthesis where a polar tertiary amine surrogate (morpholine) is desired.

Reaction Conditions

The following conditions are general literature guidance for scaffolds of this type and are NOT item specifications. Optimize per substrate and scale.

• Suzuki–Miyaura coupling (at Ar–Br):

  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI (0.5–1 mol%).
  • Ligand: XPhos/SPhos (if using Pd2(dba)3 1–2 mol%).
  • Base: K2CO3 or Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (4:1) or 2-MeTHF/H2O.
  • Temp/time: 60–90 C, 2–12 h.
  • Notes: Maintain amine as HCl salt or add acid scavenger to mitigate catalyst binding by free amine.

• Buchwald–Hartwig amination (at Ar–Br, then Ar–Cl if needed):

  • Catalyst: Pd2(dba)3 (1–2 mol%) with BrettPhos or RuPhos (2–4 mol%).
  • Base: NaOtBu or Cs2CO3 (2–3 equiv).
  • Solvent: toluene, xylene, or tBuOH/PhMe.
  • Temp/time: 80–110 C, 4–16 h.
  • Notes: Boc-protect morpholine N if it competes as a ligand; alternatively, use robust ligand sets tolerant to amines.

• N-acylation/sulfonylation of morpholine:

  • Reagents: acyl chlorides/anhydrides or sulfonyl chlorides (1.1–1.5 equiv) with Et3N/DIPEA (2–3 equiv).
  • Solvent: DCM, THF, or MeCN.
  • Temp/time: 0 C to rt, 0.5–4 h.

• Stock solutions for screening:

  • DMSO at 10–50 mM; filter through 0.2 µm PTFE.

Yields vary widely (40–90%) depending on partners/ligands. Monitor by LC–MS; confirm halide integrity prior to second-stage couplings.

Safety & Handling

Hazard classification details are not provided in the Product Data for this specific item. Treat as a halogenated aryl ether containing a secondary amine.

• GHS information (per Product Data):
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

General safety guidance (literature/general):

• Likely hazards: skin/eye irritation, respiratory irritation; harmful if swallowed or inhaled. Avoid aerosol formation.
• PPE: lab coat, safety glasses or goggles, appropriate chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood.
• Handling: avoid contact with strong oxidizers; strong bases/acids may cause degradation or salt formation; avoid prolonged exposure to elevated temperatures.
• Incompatibilities: strong oxidizing agents; electrophilic halogenating agents; may undergo undesired reactions with strong nucleophiles at aryl halides under forcing conditions.
• First aid (overview; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Fire safety: treat as combustible organic solid/liquid; use CO2, dry chemical, or foam. Combustion may release HCl/HBr and nitrogen oxides—firefighters should wear SCBA.

Always consult the product’s SDS for authoritative, up-to-date hazard and response information.

Solvent Selection

This compound is a moderately lipophilic aryl ether with a basic morpholine nitrogen. Solvent choice depends on whether you need the free base or its protonated form.

General miscibility and polarity (literature/experience-based guidance):

• Polar aprotic solvents (DMSO, DMF, NMP): typically provide high solubility and are preferred for stock solutions and for Pd-catalyzed couplings.
• Chlorinated solvents (DCM, CHCl3): moderate solubility and good for extraction and normal-phase chromatography.
• Alcohols (MeOH, EtOH, i-PrOH): solubility variable; can aid crystallization or salt formation.
• Hydrocarbons/ethers (toluene, THF, CPME): useful as reaction media in cross-coupling and SNAr when combined with a polar co-solvent.
• Aqueous systems: free base has limited water solubility; protonated salts (e.g., HCl) show improved aqueous solubility.

Selection tips:

• Cross-coupling at Ar–Br/Cl: 1,4-dioxane/H2O, toluene, or CPME/EtOH/H2O under Pd catalysis; DME or THF for lower boiling profiles.
• N-acylation/sulfonylation at morpholine N: use DCM, MeCN, or THF with organic base (DIPEA, Et3N); avoid strongly protic media that can quench acid chlorides/anhydrides.
• Purification: normal-phase silica using DCM/MeOH or hexanes/EtOAc; add 0.1–1% Et3N if tailing occurs due to basicity.

Note: Specific solubility limits and UV cutoffs are not specified for this item; confirm experimentally or consult the CoA/Spec Sheet.

Storage & Reconstitution

• Storage conditions (per Product Data): Room temperature.
• Shipping (per Product Data): Shipped under normal conditions.

General storage guidance (small molecules):

• Keep tightly closed in the original container, protected from moisture and prolonged light exposure.
• If long-term storage is anticipated, consider an inert atmosphere (N2/Ar) after opening, especially if frequent heating or exposure to bases is expected during use.
• Avoid storing near strong oxidizers or acids.

Reconstitution and working solutions (general guidance; not item specifications):

• Solvents: DMSO, DMF, or MeOH typically provide robust dissolution; for aqueous applications, prepare acid salts (e.g., HCl salt) or dilute DMSO stocks into buffered media.
• Stock concentration: 10–50 mM in anhydrous DMSO for screening; verify clarity and stability over time.
• Filtration: if required, use 0.20–0.45 µm PTFE syringe filters.
• Freeze–thaw: if preparing aliquots in DMSO, minimize freeze–thaw cycles by aliquoting single-use volumes.

Item-specific specifications (water content, appearance, purity, stabilizers) are Not specified for this item; refer to CoA/Spec Sheet. For research use only.

Structure & Identity

A halogenated phenoxyethyl–substituted morpholine designed as a multifunctional aryl-halide building block and polar heterocycle handle.

• SKU: B1349099
• Product name: 4-(2-(2-Bromo-5-chlorophenoxy)ethyl)morpholine
• CAS: 1255574-55-0 (per Product Data)
• PubChem CID: 53217042 (per Product Data)
• InChIKey (per Product Data): 303293
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural description (derived from the chemical name; literature/interpretation):

• Core ring: morpholine (six-membered, oxygen and secondary amine opposite; saturated heterocycle).
• Substitution: at the 4-position of morpholine via a –CH2–CH2–O– linkage to a 2-bromo-5-chlorophenyl ring (phenoxy ether).
• Functional groups: secondary amine (–NH–), cyclic ether (morpholine O), aryl ether (phenoxy), aryl bromide, and aryl chloride.
• Topology in words (2D): morpholine ring bearing at C-4 a two-carbon tether terminating in an ether oxygen bonded to a 1,2,4,5-tetrasubstituted benzene where positions 2 and 5 carry Br and Cl, respectively, and the phenoxy oxygen occupies one ring position.

Computed/literature identifiers (computed from the name; not item specifications):

• Molecular formula (computed): C12H15BrClNO2
• Molecular weight (computed): ~320.61 g/mol

Notes:

• Where discrepancies arise, item-specific identifiers and exact structure should be confirmed against the Certificate of Analysis (CoA) and SDS.

Synthetic Utility

Functional group ensemble and reactivity (literature/general):

• Aryl halides (Br, Cl): orthogonal handles for Pd/Ni-catalyzed couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Negishi, Stille). The aryl bromide is typically more reactive; aryl chloride can be addressed with stronger ligand systems.
• Secondary amine (morpholine N): nucleophilic; acylation, sulfonylation, carbamoylation, and alkylation produce diverse analogs. Protonation affords crystalline salts to aid purification/handling.
• Aryl ether (phenoxy): generally inert under many conditions, conferring stability; can participate in directed metalation strategies on the ring under specialized conditions.
• Ether linker (–CH2–CH2–O–): flexible spacer that can be varied in length or functionalized via oxidation (e.g., to aldehyde/acid) after appropriate protection.

Retrosynthetic value:

• Enables late-stage introduction of the morpholine–oxyethyl fragment onto elaborated aryl frameworks (or vice versa), streamlining library enumeration with two orthogonal diversification nodes (Ar–Br/Cl and N–H).

Practical tactics:

• Sequence planning: couple at Ar–Br first, protect/modify N as needed, then address Ar–Cl.
• Catalyst/ligand choices: XPhos/SPhos or BrettPhos for C–N couplings; Pd–NHC or dialkylbiaryl phosphines for challenging Ar–Cl activation.
• Purification: use basic modifiers on silica to minimize tailing; consider salt switches (free base ⇄ HCl) to remove nonbasic byproducts.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity probe with defined biological target specificity.

• Antigen/epitope/clone/isotype: Not applicable.
• Any selectivity or potency toward biological targets would be context-dependent on derivatives made from this scaffold and is outside the scope of this listing.

Frequently Asked Questions

How is this product shipped?

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

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1255574-55-0, the molecular formula is C12H15NO2ClBr, and the molecular weight is 320.61 g/mol. InChIKey QPTYRKYUGKVPKH-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.

How should this product be stored?

Store at room temperature.

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.