Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
No standardized biological assay or analytical protocols are validated for this specific catalog item. Typical laboratory uses include:
Synthetic protocol outlines (general):
Cross-coupling: Charge aryl bromide, base (2–3 equiv), boronate (1.2–1.5 equiv), Pd catalyst (0.1–3 mol%), and solvent mixture (e.g., dioxane/H2O). Heat 80–100 °C until complete by HPLC.
Nitrile hydrolysis: Stir in EtOH/H2O with NaOH at reflux to amide; acidify and isolate.
Stock solutions: Prepare 10–50 mM in dry DMSO for screening; dilute into assay buffer to ≤1% DMSO.
For any validated, method-specific parameters (WB, IHC, IF, FC, HPLC-grade details), refer to your internal method development or the CoA/Spec Sheet. This product is for research use only.
Biological Roles
This compound is a synthetic small-molecule building block. No intrinsic biological role has been established for the isolated reagent.
Morpholine-substituted pyridines are common motifs in kinase inhibitors and other target classes, but the roles pertain to final drug-like compounds rather than the intermediate itself.
The nitrile can act as a polar, directional group in ligands after further elaboration; here it primarily serves as a synthetic handle.
Biotransformation expectations (literature-based generalities, not item-specific):
Tertiary amines (morpholine) are often protonated under physiological conditions; heteroaromatic nitriles tend to be metabolically stable unless transformed during synthesis into other functionalities.
Note: For research use only (per Product Data). No clinical or diagnostic claims are implied.
Buffer Applications
Not typically applicable. This is a hydrophobic heteroaromatic building block, not a buffering agent. For experimental work requiring dissolution in aqueous buffers, prepare concentrated DMSO stocks and dilute into the buffer with gentle mixing; include surfactants or co-solvents if necessary and verify solubility/precipitation. Adjust pH only if forming salts intentionally (e.g., with HCl) for solubility; otherwise, see Solvent Selection.
Green Alternatives
Greener choices focus on solvent/catalyst selection rather than the scaffold itself.
Solvent alternatives (literature-based):
Replace DMF/DMAc/NMP with 2-MeTHF, CPME, propylene carbonate, or bio-derived esters where compatible with the reaction manifold.
Employ aqueous/ethanol mixtures for Suzuki couplings using water-tolerant catalysts.
Catalyst/base considerations:
Use ligand-efficient Pd systems at ppm levels (e.g., precatalysts enabling 0.01–0.1 mol% Pd) to reduce metal footprint.
Consider Ni-catalyzed couplings for certain partners to reduce reliance on Pd.
Opt for carbonate or phosphate bases over strong inorganic bases where feasible.
Comparison (general guidance):
Conventional vs greener setups:
DMF + Pd(PPh3)4 + K2CO3 (benchmark) → robust, but DMF has disposal concerns.
2-MeTHF/H2O or EtOH/H2O + modern Pd precatalyst + K2CO3 → reduced solvent hazard; comparable yields often achievable.
MeCN or green esters (EtOAc/izn) for nitrile hydrolysis vs concentrated mineral acids → milder, safer operations with catalysts or flow.
Trade-offs:
Greener solvents may alter solubility and rate; modest temperature or ligand adjustments often compensate.
Water-rich media can protonate basic sites (morpholine), affecting catalyst speciation—buffering or base loading may be needed.
Pharmaceutical Uses
No excipient or pharmacopeial use is indicated. This reagent is intended as a research intermediate for the synthesis of drug-like molecules.
Typical roles in pharma R&D (general):
Scaffold for SAR exploration via C-5 cross-coupling while retaining a transformable nitrile for vector extension.
The morpholine substituent can improve aqueous compatibility and enable salt formation of advanced intermediates.
Regulatory note: Not a GMP-grade material; not for human or veterinary use. For process development or preclinical supply, consult CoA/Spec Sheet for impurity profiles and consider additional quality controls (residual metals, halides, solvents) as required by your program.
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for this chemotype (for planning only):
Physical state: typically a solid crystalline heteroaromatic building block.
Solubility: poor in water; good in polar aprotic organic solvents (DMSO, DMF, NMP); moderate in dichloromethane/ethyl acetate; limited in hexanes. Actual solubility can vary with polymorph and purity.
Acid/base: contains a basic pyridine N (pKaH often ~2–6 for pyridines, literature) and a tertiary morpholine N (pKaH typically ~8–9, literature). Overall, the free base is neutral but becomes water-soluble upon protonation.
Lipophilicity: nitrile and morpholine reduce hydrophobicity compared to unsubstituted aryl bromides; anticipated moderate logP (literature expectation for related scaffolds ~1–2.5). Exact value not verified for this item.
UV characteristics: heteroaromatic ring and nitrile absorb in UV; typical analytical monitoring by 220–280 nm (literature).
Do not treat the above as specifications. For definitive values (mp, bp, density, refractive index, water/peroxide/trace metal/UV cutoff), consult the item’s CoA/Spec Sheet.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
Research-use reagent quality from Aladdin Scientific is intended for synthetic and analytical laboratory applications, not for human or veterinary use.
In the absence of an explicit grade, chemists typically verify identity and purity by 1H/13C NMR, LC/HPLC, HRMS, and, where relevant, elemental analysis. Trace residual palladium or halides (from cross-coupling precursors) may be assessed by ICP-MS if required for sensitive applications.
If planning catalytic cross-couplings, low water content can be advantageous; verify Karl Fischer moisture if your process is water-sensitive. When chromatographic baselines matter (e.g., in medicinal chemistry), request UV and LC purity characterization on the CoA.
If stabilizers are present (none specified here), be mindful of downstream reactivity and remove during workup if necessary.
For batch-to-batch consistency, reference the lot-specific CoA/Spec Sheet for exact purity assay, residual solvent profile, and any additional quality attributes.
Reaction and Applications
As a 5-bromonicotinonitrile bearing a 2-morpholinyl substituent, this reagent is a versatile fragment for heteroaryl diversification in medicinal chemistry and agrochemical discovery.
Key application families (literature/general):
Cross-coupling at C-5 (Ar–Br):
Suzuki–Miyaura with aryl/heteroaryl/alkenyl boronates to elaborate SAR around the nitrile-bearing pyridine core.
Buchwald–Hartwig amination or Ullmann-type N-arylation to install anilines or amides at C-5 (if desired over Suzuki).
Stille/Negishi/Kumada for specialized coupling partners.
Nitrile transformations at C-3:
Hydrolysis to amide or acid (stepwise or direct) under acidic, basic, or oxidative conditions.
Partial reduction (e.g., to imine/aldehyde) or full reduction to primary amine (e.g., catalytic hydrogenation or borane; protect morpholine if needed).
Pinner-type chemistry to imidates and subsequent heterocycle formation.
Heteroaromatic manipulations:
N-oxidation of the pyridine followed by rearrangements or as a handle to tune electronics.
Directed metalation strategies leveraging the nitrile as an ortho-directing group (with care due to bromide reactivity).
Role of the morpholine:
Solubilizing, electron-donating substituent that can modulate binding motifs; serves as a tertiary amine for salt formation.
Use cases: library synthesis, fragment-to-lead expansion, and installation of vectors at C-5 while retaining a transformable nitrile handle for rapid scaffold hopping.
Reaction Conditions
General, literature-style guidance for this scaffold (not item-specific specifications):
Suzuki–Miyaura at C-5:
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI-type/NHC systems (0.1–1 mol%).
Base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
Solvent: dioxane/H2O, EtOH/H2O, DMF, or 2-MeTHF/H2O.
Temperature: 60–100 °C; time: 2–16 h.
Tips: Add water to enhance boronate transmetalation; consider Buchwald ligands (SPhos/XPhos) for challenging partners.
Buchwald–Hartwig amination (if forming C–N at C-5):
Catalyst: Pd2(dba)3 with BINAP/XPhos/SPhos (1–2 mol% Pd); base: NaOtBu or K3PO4.
Solvent: toluene, dioxane, or CPME.
80–110 °C; 4–18 h. Protonate morpholine or use protecting strategy if competitive binding is observed.
Nitrile hydrolysis:
Acidic: H2SO4 or HCl (aq), 60–120 °C to amide/acid; or catalytic methods in MeOH/H2O.
Basic: NaOH/KOH in EtOH/H2O, reflux; work up carefully to avoid salt precipitation.
Nitrile reduction:
Catalytic hydrogenation (Raney Ni, Pd/C) or borane/DiBAl-H; solvents: THF/Et2O/MeOH; 0–25 °C to reflux depending on reagent.
Analytical monitoring: HPLC-UV at 254 nm is typically effective; LC–MS provides rapid confirmation due to bromine isotopic pattern (M and M+2).
Adjust ligands/bases to manage potential coordination of the pyridine nitrogen to the metal center.
Safety and Handling
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
Storage: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from strong acids, strong bases, and oxidizers. Protect from moisture and prolonged light exposure.
Handling guidance (general for halogenated heteroaromatics and nitriles):
Avoid inhalation of dust and contact with skin/eyes. Use appropriate PPE: lab coat, safety glasses, and chemical-resistant gloves (e.g., nitrile). Handle in a chemical fume hood.
Nitrile-containing aromatics are not inherently cyanide releasers but should still be handled to minimize exposure; do not heat to decomposition.
The aryl bromide can form irritant dust; morpholine functionality may cause irritation upon contact.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: rinse cautiously with water for several minutes; remove contaminated clothing; seek medical advice if irritation occurs.
Ingestion: rinse mouth; do not induce vomiting; get medical attention.
Spill response: Avoid dust; collect with inert absorbent; place in suitable container for disposal. Prevent entry to drains.
Fire safety: Combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may release nitrogen oxides, HBr, and other irritants.
Always consult the product-specific SDS for authoritative safety information.
Solvent Selection
This heteroaromatic bromide with a morpholine and nitrile substituent exhibits mixed polarity: polar functionalities with an overall neutral backbone.
Likely solubility profile (general):
High: DMSO, DMF, NMP, DMAc.
Moderate: CH2Cl2, CHCl3, MeCN, EtOAc.
Low to very low: alcohols (MeOH/EtOH; may improve with slight acid), water, and nonpolar hydrocarbons (toluene/hexanes).
Practical choices by task:
Stock solutions for screening/biology-adjacent assays: DMSO (e.g., 10–50 mM), then dilute into buffered media with surfactant; filter if needed.
Cross-coupling: DMF/DMAc/NMP or toluene with a polar co-solvent; alcohol/water mixtures can work for Suzuki couplings.
Nucleophilic or reductive nitrile transformations: polar aprotic media (THF, MeCN, DMF); add acid/base as required by mechanism.
Polarity context (literature): morpholine increases polarity and H-bond basicity; the nitrile is strongly polar but nonprotic; pyridine N adds Lewis basicity that can coordinate metals.
Comparison (when to choose alternatives):
If base-sensitive steps are involved, minimize amide solvents that can participate in side reactions; try MeCN or 2-MeTHF.
For greener processing, consider 2-MeTHF or CPME over THF/DMF where feasible (see Green Alternatives).
Packaging and shipping: Not specified for this item; refer to CoA/Spec Sheet. General practice: ship at ambient conditions in a sealed container with desiccant when appropriate.
Shelf-life guidance (general): Store in original, tightly closed container in a dry place. Avoid prolonged exposure to air and light. If long-term storage is planned, consider desiccation and inert atmosphere.
Prepare concentrated stock solutions in anhydrous DMSO, DMF, or MeCN. Typical screening stocks: 10–50 mM in DMSO.
For aqueous use, dilute DMSO stocks slowly into buffer under stirring to minimize precipitation; filter (0.22 µm) if required.
For synthetic operations, dry solvents and glassware as appropriate; degas for metal-catalyzed couplings.
Stability in solution (general): Neutral organic solutions are typically stable for days at 2–8 °C; for extended storage, aliquot and freeze (–20 °C) to minimize freeze–thaw and moisture ingress. Discard if discoloration or precipitation inconsistent with expected behavior is observed.
Always consult the lot-specific CoA/Spec Sheet and SDS for definitive storage and handling instructions.
Structure and Identity
A halogenated, nitrile-bearing morpholinylpyridine building block suited for cross-coupling and late-stage diversification.
Item-specific identifiers (from Product Data):
CAS: 1354223-80-5
CID: 68609793
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (provided value appears truncated in source)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general, non-spec):
Preferred name (descriptive): 5-Bromo-2-(morpholin-4-yl)nicotinonitrile
Putative molecular formula (literature inference): C10H10BrN3O
Core: a nicotinonitrile (3-cyanopyridine) ring system.
Substituents: bromo at the 5-position; a tertiary amino substituent (morpholin-4-yl) at the 2-position; nitrile at the 3-position.
Functional groups: aryl bromide (for cross-coupling), pyridine nitrogen (basic heteroaromatic), tertiary amine within morpholine (polar, H-bond accepting), and a nitrile (electrophilic handle, strong EW group).
2D structure in words: a six-membered pyridine ring bearing, clockwise from the ring nitrogen, a morpholin-4-yl substituent (C–N bond to morpholine N), then a cyano group, then (after one carbon) a bromine atom; morpholine is a six-membered O,N-heterocycle (–O–CH2–CH2–NH–CH2–CH2–) bound via its ring nitrogen.
Notes: Where exact identifiers (SMILES, InChIKey) are critical, consult the CoA/Spec Sheet for this specific lot.
Synthetic Utility
Strategic value arises from orthogonal handles embedded in a single scaffold:
Aryl bromide (C-5):
Engages in Pd/Ni-catalyzed cross-couplings (Suzuki, Stille, Negishi, Kumada). Electronics of the nicotinonitrile core (EW nitrile, pyridine N) typically facilitate oxidative addition.
Suitable for direct C–N formation (Buchwald–Hartwig) or C–O/S coupling under copper catalysis.
Nitrile (C-3):
Convertible into amides/acids (hydrolysis), amidines/imidates (Pinner), or primary amines (reductions), enabling rapid vector switching without altering the heteroaryl core.
Acts as a directing group for metalation/formylation in certain regimes.
Heteroaryl nitrogen(s):
Pyridine N can coordinate catalysts, occasionally necessitating ligand/base adjustments or additive acids (e.g., HBF4·OEt2) to temper binding.
Morpholine N provides basicity/solubility; may be transiently protected or protonated to steer chemoselectivity in multistep sequences.
Retrosynthetic utility:
Disconnection at C-5 to diverse boron partners → rapid diversification libraries.
Convergent routes: assemble nicotinonitrile core, install morpholine at C-2 (SNAr or Buchwald amination on a 2-halo precursor), retain bromide at C-5 for late-stage coupling.
Overall, the scaffold’s design supports stepwise, chemoselective modifications enabling efficient SAR campaigns.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological probe with defined target specificity. If you require target-binding data, it would pertain to derivatives synthesized from this scaffold rather than the reagent itself.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
