This compound belongs to the class of organic compounds known as n,n-dialkyl-m-toluamides. These are aromatic that contain a m-toluamide, where the carboxamide group is N- substituted with two alkyl chains.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
284.150 g/mol
XLogP3
2.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
283.021 Da
Monoisotopic Mass
283.021 Da
Topological Polar Surface Area
29.500 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
253.000
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
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Recensioni
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Application Protocols
No vendor-validated biological application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block.
Typical laboratory uses (chemistry-focused, general guidance):
For cross-coupling library prep, dissolve in dry solvent (e.g., 0.1–0.5 M in 1,4-dioxane or 2-MeTHF), add base and coupling partner under inert atmosphere, then charge catalyst/ligand solution. Heat as required and monitor by LC-MS/HPLC.
For analytical assays, prepare a DMSO stock (e.g., 10–50 mM) and dilute into organic mobile phase for HPLC-UV or LC–MS characterization.
Refer to internal SOPs and literature precedents when designing reaction-specific protocols.
Biological Roles
This compound is a synthetic organic building block and is not known as a natural metabolite or cofactor.
General context (literature):
Morpholine-containing amides are common in medicinal chemistry as polarity-modulating motifs and solubilizing handles, but the biological activity depends entirely on the broader scaffold and substituents.
An aryl bromide is typically a synthetic handle rather than a pharmacophore; it enables diversification by cross-coupling to explore structure–activity relationships (SAR).
No endogenous role: There are no established roles in metabolic pathways, signaling cascades, or structural biomacromolecules for 4-(2-bromo-3-methylbenzoyl)morpholine itself.
Research use only: Per Product Data, this material is supplied strictly for research use only. Any biological testing should be performed by qualified personnel under appropriate approvals. No medical, diagnostic, or therapeutic uses are implied.
Buffer Applications
This product is a neutral organic building block (aryl bromide amide) and is not a buffering agent. It does not form conventional laboratory buffer systems, and it is not typically used to control pH in biochemical assays.
For experimental work, select buffers matched to your biology/chemistry (e.g., phosphate, HEPES, Tris). Dissolution of this compound for screening assays commonly uses organic cosolvents (e.g., DMSO) rather than aqueous buffers.
Green Alternatives
Greenness considerations for using 4-(2-bromo-3-methylbenzoyl)morpholine focus on solvent and coupling strategy selection rather than the substrate itself.
Solvent substitution (literature/general):
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or green acetonitrile where feasible.
For cross-couplings, water/ethanol cosolvent systems or micellar catalysis (e.g., TPGS-750-M) can reduce organic solvent usage.
Catalysis and bases:
Choose highly active Pd catalysts/ligands that operate at lower loadings (≤0.5 mol%) and moderate temperatures to reduce energy and metal footprint.
Opt for inorganic carbonate or phosphate bases over strong hydroxides to reduce hazards; or use organic bases (e.g., BTMG, DBU) in flow.
Workup and waste:
Employ telescoped sequences and crystallization-based purifications to avoid chromatographic silica waste.
If halogenated waste is unavoidable, segregate and minimize volumes; consider solvent recovery where facilities allow.
Compact comparison (general guidance):
THF vs 2-MeTHF: similar performance in many couplings; 2-MeTHF is bio-derived and less miscible with water, aiding separation.
DCM vs EtOAc: EtOAc is biodegradable and less toxic; check solubility and stability.
DMF/DMAc vs CPME/MeCN: lower boiling alternatives ease solvent removal; assess catalyst solubility and reaction rate impacts.
Pharmaceutical Uses
Status: This reagent is offered for research use only and is not an active pharmaceutical ingredient (API) or excipient.
Context (general, formulation/manufacturing):
Compounds of this class (aryl-bromobenzamide morpholine derivatives) may serve as intermediates in drug discovery campaigns, enabling rapid analog generation via cross-coupling and subsequent functional group interconversions.
The morpholine amide can enhance solubility and modulate basicity when embedded in larger frameworks, which is valuable during lead optimization; however, no compendial (USP/Ph. Eur.) status is implied for this item.
Regulatory note: If material from this product is used to prepare development candidates, ensure appropriate specification setting, impurity profiling, and qualification according to internal SOPs and applicable guidelines (e.g., ICH Q3A/B for impurities), using lot-specific CoA data.
Physical Properties
Item-specific measured specifications are not provided in the Product Data. Values below are general/literature-style guidance for closely related aryl-bromobenzamide morpholine derivatives; do not treat as product specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight / Formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting/Boiling: Aromatic bromobenzamides are typically crystalline solids with melting points often in the 80–180 °C range (literature, compound-dependent). Thermal decomposition may precede boiling under ambient pressure (literature).
Density: Aryl bromides commonly exhibit densities around 1.3–1.6 g/cm³ (literature, qualitative trend due to Br), but amide functionality and solid-state packing strongly influence the actual value.
Limited: low-polarity hydrocarbons (hexanes, heptane). Practically insoluble in water.
logP/logD (qualitative): Moderate lipophilicity tempered by the tertiary amide and morpholine heteroatoms (literature expectation for acylmorpholines).
UV characteristics: Aromatic chromophore absorbs in the UV (200–300 nm region, literature), useful for HPLC-UV tracking.
Note: For exact numeric physicochemical data relevant to your lot (e.g., mp, solubility, refractive index, water content), consult the product’s CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
UV, water, metals, residual solvents, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Context for professional users:
For synthetic building blocks like 4-(2-bromo-3-methylbenzoyl)morpholine, typical quality determinants include assay purity (HPLC/GC), identity confirmation (1H/13C NMR, HRMS), and residual solvent/moisture content. Where applicable, elemental analysis or ICP for metals may be provided.
If intended for cross-coupling, low levels of halide scrambling impurities and biaryl byproducts are important. Trace transition metals from prior steps should be minimized when your downstream chemistry is metal-sensitive.
Chromatographic purity claims (e.g., 98% by HPLC) indicate area% at a given wavelength but do not assure residue limits; confirm by orthogonal methods if critical to your process.
If a stabilizer or salt form were used to enhance shelf life, it would be disclosed; none is specified here.
Recommendation: Request the latest CoA/Spec Sheet for your lot to verify purity, analytical methods (HPLC conditions, NMR solvent), and any specific acceptance criteria relevant to regulated workflows.
Reaction and Applications
As an aryl bromide-containing benzamide tethered to morpholine, this compound is well-suited as a platform for diversification in medicinal and materials chemistry.
Cross-coupling via Ar–Br (literature/general):
Suzuki–Miyaura: Coupling with boronic acids/esters to access biaryl libraries; bases such as K3PO4, K2CO3, or Cs2CO3; Pd(0/II) with phosphine or NHC ligands. Water-tolerant conditions are common.
Buchwald–Hartwig amination: Installation of aryl amines; Pd catalysts (e.g., Pd2(dba)3/XPhos/BrettPhos) or precatalysts; alkoxide or carbonate bases in toluene/dioxane/THF.
Kumada/Negishi/Stille: For C–C bond formation with Grignard, organozinc, or stannanes; useful for rapid SAR exploration.
Directed functionalization (literature): The amide can act as a weak directing group for ortho-functionalization on compatible scaffolds; however, here the aryl bromide is already ortho-substituted.
Carbonyl chemistry:
Amide stability: Resistant to many nucleophiles under neutral conditions; can undergo activation (e.g., via CDI, POCl3, or coupling reagents) for further derivatization if N–C(O) cleavage or transformation is desired.
Hydrolysis (forcing): Strong acid/base and heat can cleave to the corresponding acid/amine—useful for deprotection to the acid.
Heterocycle utility: The morpholine moiety enhances polarity and solubility, commonly retained in bioactive analogs; N-acyl morpholine can serve as a masked acid equivalent in acyl-transfer strategies.
Applications: library synthesis, late-stage diversification, and preparation of biaryl/multisubstituted benzamide analogs where bromine serves as a synthetic handle.
Reaction Conditions
Representative conditions from literature for aryl bromide benzamides (guidance only; optimize per substrate):
Suzuki–Miyaura biaryl formation:
Catalyst: 0.5–2 mol% Pd(PPh3)4 or Pd-PEPPSI/NHC; Ligands: SPhos/XPhos for hindered partners.
Base: K3PO4 (2–3 eq) or Cs2CO3; Solvent: 1,4-dioxane/H2O or 2-MeTHF/H2O; 60–100 °C; 2–16 h.
Notes: Degas solvents; add water to accelerate transmetallation; monitor by HPLC-UV.
Solvent: toluene, dioxane, or CPME; 80–110 °C; 4–20 h.
Notes: Tertiary amide is typically compatible; avoid excessively strong bases if amide integrity is critical.
Carbonyl transformations (amide activation):
Activators: CDI (DMF/THF, 0–25 °C), Ghosez reagent, or POCl3 (DCM) to form reactive intermediates for substitution.
Yields: Many literature examples of aryl bromide couplings achieve 60–95% isolated yields depending on partner sterics/electronics and catalyst system.
Workup: Quench base with water; extract with EtOAc; wash with brine; dry (Na2SO4); concentrate and purify by crystallization or silica gel (avoid strong base on silica to prevent amide rotamer issues).
Safety and Handling
Safety information specific to this item is not provided in the Product Data. The following are prudent, general laboratory precautions for aryl bromide benzamides and morpholine amides. Always consult the SDS for authoritative guidance.
GHS classification, pictograms, H-statements: Not specified for this item; refer to SDS.
Anticipated hazards (general): May cause skin/eye irritation; harmful if swallowed or inhaled. Dust or fine particulates should be minimized. Avoid contact and inhalation.
PPE: Laboratory coat, safety glasses or chemical splash goggles, and appropriate gloves (e.g., nitrile). Use a fume hood to control vapors/particulates during weighing or reaction charging.
Handling: Avoid strong bases and strong acids that can hydrolyze or degrade amides under forcing conditions. Keep away from strong oxidizers and reducing agents. Prevent prolonged exposure to elevated temperatures.
Incompatibilities (general): Strong nucleophiles under high temperature may lead to amide bond cleavage; reactive metals may undergo oxidative addition into Ar–Br under catalytic conditions—store away from metal catalysts to avoid contamination.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Combustion may release HBr and nitrogen/oxygenated organics.
Waste: Dispose of in accordance with institutional and local regulations; halogenated organic waste stream is typical.
Solvent Selection
This product is a moderately polar, non-ionic organic solid (aryl bromide tertiary amide) and is typically handled in organic media.
Polarity/miscibility (general):
Preferred solvents for dissolution: DMSO, DMF, NMP, CH2Cl2, CHCl3, EtOAc, and often THF or MeCN.
Limited solubility: Alkanes (hexane/heptane). Aqueous solubility is generally poor due to aromaticity and amide neutrality.
Application-driven solvent choices:
Cross-coupling (Suzuki, Buchwald–Hartwig): 1,4-dioxane, toluene, CPME, or THF mixed with aqueous base; for high polarity ligands/catalysts, DMF/DMAc can be advantageous.
Nucleophilic acyl substitution or derivatization at amide nitrogen: Dry polar aprotic solvents (THF, DCM, DMF) under base or activating agents.
Analytical prep (HPLC): Reverse-phase methods benefit from acetonitrile/water or MeOH/water with formic acid or TFA modifiers; the aryl chromophore enables UV detection.
Practical tips:
Warm the solution gently (30–50 °C) to accelerate dissolution in less polar solvents.
For moisture-sensitive couplings, dry solvents and degassing (argon/nitrogen sparge) improve reliability.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Container: Store in a tightly closed container with desiccant to limit moisture uptake. Protect from prolonged exposure to light and heat.
Stability (general): Tertiary amides and aryl bromides are typically stable at ambient conditions. Avoid strong bases/acids and reactive metals during storage. Minimize repeated opening to reduce atmospheric moisture/CO2 ingress.
Solution handling (general):
Prepare concentrated stocks in dry DMSO, DMF, or DCM as needed for reactions; store aliquots to avoid multiple freeze–thaw or evaporative concentration cycles.
For analytical standards, filter (0.2 µm PTFE) and store in amber vials at 2–8 °C if stability in solution is required beyond several days.
Reconstitution: No aqueous reconstitution is typical. Dissolve directly in an appropriate organic solvent with gentle warming and/or sonication.
Always consult the lot-specific CoA/SDS for any additional storage notes or observed sensitivities. Research use only, as stated in the Product Data.
Structure and Identity
Brief overview: 4-(2-Bromo-3-methylbenzoyl)morpholine is an aryl bromide-bearing benzamide featuring a morpholine ring linked through a benzoyl carbonyl to a substituted o-bromotoluoyl moiety. It is a versatile synthetic building block for cross-coupling and late-stage diversification.
SMILES: 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.
Structural features (general/interpretive description):
Core motif: A benzoyl group substituted on the ring at the 2-position by bromine and at the 3-position by methyl, forming an o-bromo-m-tolyl benzoyl fragment.
Linkage: The benzoyl carbonyl is bound to the morpholine nitrogen (a tertiary amide), yielding a 4-acylmorpholine framework.
Functional groups: Aryl bromide (Ar–Br), tertiary amide (–CON<), heterocycle (morpholine) containing one oxygen and one nitrogen in a six-member ring.
2D description: A disubstituted benzene ring (Br at ortho, Me at meta relative to carbonyl), with the carbonyl carbon attached to the morpholine N; the morpholine ring is saturated, with O and N opposite each other.
Stereochemistry: None (achiral, no stereocenters).
Synthetic Utility
Key functionalities and how they can be leveraged (literature/general):
Aryl bromide (Ar–Br):
Robust handle for C–C (Suzuki, Negishi, Kumada, Stille), C–N (Buchwald–Hartwig), C–O and C–S couplings.
Facilitates metal–halogen exchange (e.g., with iPrMgCl·LiCl or nBuLi at low temperature) to access arylmagnesium/aryllithium species for electrophile trapping, with due caution regarding amide compatibility.
Tertiary amide (acyl morpholine):
Stable directing group in some metal-catalyzed C–H functionalizations.
Platform for amide activation to form acylating agents (e.g., via CDI or Ghosez/POCl3 reagents) when cleavage or transamidation is desired.
Can act as a masked acid: hydrolysis under forcing conditions returns the corresponding acid for further coupling (amide/ester formation).
Morpholine ring:
Enhances polarity/solubility of intermediates; can be retained or removed depending on design.
Retrosynthetic value:
Disconnection at Ar–Br enables late-stage diversification of a fixed amide core.
Alternatively, assemble the benzamide via acyl chloride or activated ester coupling to morpholine, then introduce or transform the aryl bromide substituents by electrophilic aromatic substitution or cross-coupling.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and not a biological reagent (e.g., antibody, enzyme, or ligand with defined biomolecular targets). No target, clone, isotype, or species reactivity information is associated with this item.
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