This compound belongs to the class of organic compounds known as pyridinecarboxamides. These are compounds containing a pyridine ring bearing a carboxamide.
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
215.050 g/mol
XLogP3
1.500
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
213.974 Da
Monoisotopic Mass
213.974 Da
Topological Polar Surface Area
42.000 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
151.000
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
Recensioni dei clienti
Application Protocols
No vendor-validated bioassay or analytical application protocols are specified for this item. Typical laboratory use is as a synthetic building block in organic synthesis and cross-coupling.
General lab usage tips (literature/general)
For cross-coupling, use oven-dried glassware, inert atmosphere, and degassed solvents. Record TLC/LC-MS at intervals to track conversion.
For solubility-limited reactions, pre-slurry in a minimal volume of polar aprotic solvent (e.g., DMF) before charging bulk solvent such as 2-MeTHF or dioxane.
Work-up: quench hot reactions cautiously; filter through celite/silica to remove metal residues; use EDTA washes during extraction if needed.
If you require a standardized protocol for a specific transformation with this substrate, contact Technical Support with your coupling partner and scale.
Biological Roles
Item-specific biological data are not provided. The following points reflect general, literature-level context for heteroaromatic amide scaffolds and should not be construed as biological activity claims for this material.
Structural motif: pyridine amides are common in bioactive small molecules due to their capacity for hydrogen bonding and metal coordination. The pyridine nitrogen serves as a hydrogen-bond acceptor and potential metal ligand; the amide carbonyl is a strong H-bond acceptor, and N–H (even when N-methylated) is a weak donor.
Polarity: the amide reduces basicity and modulates lipophilicity relative to simple bromopyridines, often aiding aqueous compatibility in screening libraries.
Synthetic intermediate role: this compound functions primarily as a building block to access diverse analogs that may later be screened for biochemical interactions (enzymes, receptors, metalloproteins). Any such roles depend on the appended substituents introduced via the 6-bromide handle.
No specific biochemical pathway involvement, receptor affinity, or enzymatic interactions are established for 6-bromo-N-methylpicolinamide itself in the available references. Use strictly for research and method development; do not use for diagnostic or therapeutic applications.
Buffer Applications
This product is a heteroaromatic amide building block and is not used as a buffering agent. It lacks appropriate acid/base pairs and solubility characteristics for preparing laboratory buffers.
If aqueous work is required (e.g., bioconjugation after derivatization), select conventional buffers (phosphate, HEPES, MOPS, acetate) compatible with your downstream chemistry.
For cross-coupling work-ups, buffered aqueous phases (e.g., saturated NH4Cl, NaHCO3) are sometimes used during quench/extraction, but the compound itself does not serve a buffering role.
Green Alternatives
Greener strategies focus on solvent and catalyst choices rather than changing the building block itself.
Solvent selection (literature/general)
Prefer 2-MeTHF, CPME, or aqueous dioxane mixtures over DMF/NMP when feasible for cross-couplings.
Employ ethanol/water or isopropanol/water media for Suzuki reactions with compatible substrates/bases to lower solvent toxicity.
Catalyst/ligand economy
Use highly active Pd systems (e.g., XPhos, SPhos, PAd2Bu-based ligands) at low loadings (≤0.5–1 mol%) to reduce precious metal usage.
Consider nickel catalysis for certain couplings (Suzuki, amination) to decrease reliance on palladium, recognizing potential tradeoffs in scope and robustness.
Process intensification
Continuous-flow cross-coupling in 2-MeTHF or water-tolerant media can improve safety and solvent economy.
Tradeoff: sometimes slower kinetics; ensure catalyst/ligand compatibility.
Option: Aqueous Suzuki (water/t-BuOH or water/EtOH)
Benefit: reduced organic solvent, easier work-up.
Tradeoff: lower solubility of some partners; may require phase-transfer or surfactants.
Note: While chloro analogs are sometimes proposed as greener (avoiding bromides), reactivity can be significantly lower on pyridines, increasing energy/time footprints. Holistic assessment (yield, steps, waste) should guide selection.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet.
General, non-clinical context (literature)
Role: heteroaromatic amide building block for discovery chemistry. The 6-bromide enables late-stage diversification to produce analog libraries while maintaining a polar amide and a pyridine nitrogen—features valued in medicinal chemistry for tuning solubility, permeability, and metabolic stability.
Process chemistry: the amide confers crystallinity and manageable handling; derivatives may purify well by crystallization or normal-phase chromatography.
Compliance and use restrictions
For research use only (per Product Data). Not for human or veterinary use. No clinical or therapeutic claims are made or implied.
If you require GMP-grade intermediates or documentation (ICH Q7, elemental impurities, residual solvents by ICH Q3C), contact Technical Support to discuss custom manufacturing; none of these attributes are specified for this catalog item.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Water, residual solvents, UV cutoff, metals: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed properties for context (not item specifications)
Physical state: typically a solid for analogous bromopyridine amides (literature).
Molecular formula (computed): C7H7BrN2O.
Formula weight (computed): ~215.05 g/mol.
Acid–base: weakly basic ring nitrogen (pyridine N); amide is non-basic and weakly acidic at N–H (here N-methylated, so less acidic). pKa values vary by substitution; specific pKa not established for this exact compound (literature not readily consolidated).
Solubility: polar aprotic organics (DMF, DMSO, NMP) and moderately in EtOAc/MeCN; low in water expected for aryl bromides with one amide (literature trends). Quantitative solubilities are not established here.
LogP/logD: not widely reported for this exact structure; expect moderate polarity due to amide and pyridine (literature trends).
Melting/boiling points, density, refractive index: Not found in standard references for this exact compound; treat as not specified for this item.
Notes
Provide experimental data from the CoA/SDS if property limits are critical to your application.
Amide and pyridine heteroatoms increase hydrogen-bonding capacity; hygroscopicity is generally low-to-moderate for such solids but should be verified experimentally.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret common grades (general guidance)
Research grade: suitable for general synthesis and exploratory medicinal chemistry; may not include low-UV or low-metal specifications.
Purified/98%+: typical for building blocks intended for cross-coupling; ensures lower levels of halide scrambling and fewer side-products in Pd-catalyzed reactions.
HPLC grade (for solvents) or LC/MS grade (for reagents used in analytical contexts): optimized for chromatographic cleanliness and low background—less relevant to solid building blocks unless stated.
Stabilizers/impurities
No stabilizers are typical or required for this class; none are specified for this item. If trace metal content, halide purity, or residual solvent profile is critical, request the CoA/Spec Sheet.
Batch-to-batch considerations
For cross-coupling, trace metal impurities and residual moisture can influence reaction rates. Verify assay purity by NMR/LC before scale-up. If you require specific limits (e.g., water, halogen content, metals), contact Technical Support for the current batch CoA.
Regulatory/analytical documentation
CoA will provide assay, identity confirmation (NMR/HRMS/IR), and where available, chromatographic purity. Spectral data and impurity profiles are batch-specific and not stated here.
Reaction and Applications
This building block is optimized for heteroaryl functionalization via the bromide at C6 and the polar amide/pyridine motif, making it valuable in medicinal and coordination chemistry programs.
Key reaction families (literature/general)
Cross-couplings at C6–Br
Suzuki–Miyaura C–C coupling with aryl/heteroaryl/alkenyl boron reagents to diversify the 6-position; pyridine substrates often couple smoothly with Pd(PPh3)4, Pd(dppf)Cl2, or XPhos-type systems.
Buchwald–Hartwig amination to introduce (hetero)arylamines or alkyl amines; ligands such as BrettPhos/XPhos effective for challenging pyridyl bromides.
Sonogashira and Heck reactions to append alkynes/alkenes, respectively (Cu co-catalyst optional for Sonogashira under modern conditions).
Miyaura borylation (B2pin2) to access the corresponding 6-boronate for subsequent iterative diversification.
Nucleophilic aromatic substitution (SNAr)
Activated by the ring nitrogen; certain hard nucleophiles may displace bromide under forcing conditions, though cross-coupling is generally preferred.
Metal–halogen exchange/electrophile capture
Halogen–lithium exchange (e.g., n-BuLi, s-BuLi) at low temperature to install electrophiles (formylation, silylation, stannylation). The amide and ring nitrogen can coordinate and may require careful temperature control and base choice.
Application contexts
Scaffold elaboration for ligand design (bidentate motifs combining pyridine N and amide O/N for metal binding in materials/coordination studies).
SAR libraries where the amide polarity is retained while probing 6-position vectors on the ring.
Practical tips
Pre-dry the solid before coupling if stored in humid environments; use molecular sieves when water-sensitive catalysts are employed.
For pyridyl bromides, base selection (K3PO4, Cs2CO3, NaOtBu) and ligand choice strongly influence turnover; screen 2–3 ligand/base sets on microscale.
Reaction Conditions
General, literature-derived guidance (adjust to your system; not item specifications)
Suzuki–Miyaura coupling (6-bromopyridine amide to biaryl)
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd(dppf)Cl2·DCM (1–2 mol%).
Ligand: XPhos/SPhos for challenging partners.
Base: K3PO4 (2–3 equiv), Cs2CO3 or K2CO3.
Solvent: 1,4-dioxane/H2O (3:1), 2-MeTHF/H2O, or toluene/H2O.
Temperature/time: 70–100 C, 2–16 h.
Notes: Aqueous base improves transmetalation; degas and maintain inert atmosphere.
Buchwald–Hartwig amination (C–N formation)
Catalyst: Pd2(dba)3 (0.5–1 mol% Pd) with BrettPhos or XPhos (1–2 mol% ligand) or precatalysts (e.g., XPhos Pd G3).
Base: NaOtBu, KOtBu, or Cs2CO3.
Solvent: toluene, dioxane, CPME.
Temperature/time: 80–110 C, 4–18 h.
Notes: Amines that chelate strongly may require increased ligand loading.
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol% optional), base: Et3N or DIPEA.
Solvent: THF/2-MeTHF or DMF; 50–80 C.
Halogen–lithium exchange
Base: n-BuLi or s-BuLi (1.1–1.3 equiv) at −78 to −40 C in 2-MeTHF or TBME.
Electrophile: DMF (formyl), CO2 (carboxyl), Me3SiCl, etc.
Notes: Heteroatom coordination can affect selectivity; stringent dryness and temperature control required.
Yields vary with partners; consult current literature and run small-scale screens to optimize.
Safety and Handling
Item-specific hazard information
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
H-statements/Pictograms: Not specified for this item; refer to SDS.
General safety guidance for halogenated heteroaromatic amides (literature/general)
Likely hazards: may cause irritation to skin, eyes, or respiratory tract upon contact or inhalation of dust. Avoid dust generation. No data on acute toxicity is provided here.
PPE: lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust or decomposition vapors.
Thermal stability: aryl bromides generally stable; avoid excessive heat. Combustion can produce HBr, NOx, CO/CO2.
Special risks: none specific to peroxides; not an ether. Dust management is recommended.
First aid overview: eye/skin contact—rinse with water for ≥15 min; inhalation—move to fresh air, seek medical attention if symptoms persist; ingestion—rinse mouth, do not induce vomiting, obtain medical attention. Always follow institutional protocols.
Storage and transport
Storage: Room temperature (per Product Data), dry, tightly closed container; segregate from strong oxidizers/bases.
Shipping: Shipped under normal conditions (per Product Data).
Always consult the product SDS for authoritative, up-to-date hazard and response information.
Solvent Selection
Compound class and polarity
6-Bromo-N-methylpicolinamide is a polar, heteroaromatic amide with an aryl bromide handle. It exhibits hydrogen-bond accepting ability (pyridine N, carbonyl O) and limited donating ability (N–H present despite N-methylation). Expect good solubility in polar aprotic solvents and DMSO/DMF, with moderate solubility in mid-polar organics.
Suzuki–Miyaura: dioxane/water, toluene/water, or 2-MeTHF/water mixtures; DMF/water for more polar partners.
Buchwald–Hartwig amination: toluene, dioxane, CPME, or 2-MeTHF; polar systems (t-AmOH or alcohol/cosolvent) sometimes beneficial.
Miyaura borylation: dioxane, 2-MeTHF, or THF alternatives (CPME) with KOAc.
Halogen–lithium exchange/electrophile trapping: anhydrous ethereal solvents (2-MeTHF or TBME) at low temperature.
Comparison notes
THF vs 2-MeTHF: 2-MeTHF offers improved safety/greenness and often higher solubility for heteroaryls, with similar performance in cross-couplings.
DMSO/DMF provide high solubility but can complicate workup and metal-catalyst turnover; prefer dioxane/2-MeTHF when feasible for scale-up.
Always verify actual solubility with a small-scale test before committing to conditions.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Store in a tightly closed container in a dry place. Protect from excessive heat and direct sunlight.
Shipping (item-specific): Shipped under normal conditions.
Stability (general)
Aryl bromides and amides are typically stable on the bench when dry and protected from moisture. No stabilizer is required.
Avoid prolonged exposure to strong light or base if not intended for reaction; pyridine substrates can slowly discolor with adventitious impurities.
Reconstitution/solution preparation
Not applicable to a solid building block; prepare solutions freshly in suitable dry solvents (DMSO, DMF, 2-MeTHF, dioxane, MeCN) as needed.
For stock solutions (e.g., screening), filter through 0.2 µm PTFE to remove particulates; store aliquots in amber vials at 2–8 C when using high-boiling polar aprotics (DMSO/DMF) and use within a few weeks to minimize hydrolysis/oxidation risk.
Freeze–thaw guidance
Not typically required. If storing solutions, minimize freeze–thaw cycles by aliquoting.
Always consult the product CoA/SDS for batch-specific recommendations.
Structure and Identity
Brief description: 6-Bromo-N-methylpicolinamide is a brominated, N-methylated amide derivative of picolinic acid (pyridine-2-carboxamide), placing a bromine at the 6-position of a pyridine ring and an N-methyl substituent on the amide nitrogen.
Item-specific identifiers (from Product Data)
CAS: 337535-94-1
CID: 22049738
InChIKey: 211136 (as provided; not a standard-length InChIKey)
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.
Literature/computed structural details (for context; not item specifications)
Expected core scaffold: pyridine ring (positions numbered with N at position 1), bearing a carboxamide at C2 and Br at C6; the amide nitrogen is methylated (–CONHCH3).
Computed/typical molecular formula for 6-bromo-N-methylpicolinamide: C7H7BrN2O (literature/computed).
Computed formula weight: ~215.05 g/mol (literature/computed).
2D structure (verbal): a six-membered pyridine ring with ring nitrogen at position 1; a carboxamide at C2 oriented ortho to the ring nitrogen; the amide nitrogen carries a methyl group (–NHCH3); a bromine substituent at C6 (para to the ring nitrogen, ortho to the amide).
Synthetic Utility
Reactivity map
C–Br at C6: versatile electrophile site for Pd/Ni-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Heck) and for borylation/silylation. Enables rapid SAR at the 6-position without perturbing the amide or pyridine nitrogen.
Amide (N-methyl): robust under many coupling conditions; can engage in intramolecular H-bonding and metal coordination, sometimes influencing regioselectivity/reactivity. Less nucleophilic than anilides; typically inert to bases used in cross-coupling.
Pyridine nitrogen: coordinates metals (Pd, Ni, Cu), occasionally retarding or accelerating catalysis depending on ligand/base; additive/ligand screening mitigates such effects.
Suzuki–Miyaura to install aryl/heteroaryl/alkenyl units.
Buchwald–Hartwig amination to replace Br with primary/secondary amines.
Miyaura borylation (B2pin2) followed by iterative couplings/oxidations (to phenols) or Suzuki.
Sonogashira coupling to introduce alkynes; subsequent cyclizations or click reactions expand diversity.
Halogen–lithium exchange to introduce formyl (DMF quench), carboxyl (CO2 quench), or other electrophiles at C6.
Retrosynthetic value
Serves as a convergent junction: maintain the core polarity (pyridine amide) while vectoring diverse substituents from the 6-position. Useful for late-stage diversification of lead-like scaffolds with minimal re-optimization of purification.
Practical notes
Protect catalysts from pyridine poisoning by using bulky electron-rich ligands (XPhos/BrettPhos). Aqueous base and water-tolerant solvents improve turnover for Suzuki couplings.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biomolecular reagent (e.g., antibody, enzyme, or probe) with defined biological targets. No antigen/epitope, clone, isotype, or species-reactivity information applies.
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