This compound belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.
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
135.170 g/mol
XLogP3
0.600
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
135.08 Da
Monoisotopic Mass
135.08 Da
Topological Polar Surface Area
62.800 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
133.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Not applicable — no validated immunoassay or imaging protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic or coordination uses, refer to the Reaction Conditions and Synthetic Utility sections for general procedural guidance.
Biological Roles
This product is offered strictly for research use. No medical or clinical claims are made.
General biochemical context (literature; not product-specific)
Picolinate-derived ligands are well-known for metal binding; amidine substitution increases basicity and can enhance coordination to transition metals via bidentate N,N-chelation (pyridine N and imine N). Such motifs are used in bioinorganic model complexes and as tools for probing metalloenzyme mimicry in vitro.
Protonation state: Amidines are strongly basic (conjugate acid pKa typically ~11–13). At physiological pH, amidines are predominantly protonated (amidinium), affecting membrane permeability and binding interactions in biochemical assays.
Hydrogen bonding: The –C(=NH)–NH2 group can donate two H-bonds and accept one, enabling specific interactions with polyanions (e.g., nucleic acids) in binding studies; however, binding strength and selectivity are context-dependent.
Practical notes for researchers
Solubility in aqueous buffers can be improved by forming the hydrochloride or by dissolving in a small amount of DMSO before dilution.
For metal-binding assays, adjust pH to limit over-protonation that quenches ligand donor ability.
No endogenous biological role is assigned to this specific synthetic heteroaromatic amidine.
Buffer Applications
This compound is not a buffering reagent and does not form a recognized buffer system with defined pKa spacing. Amidines are basic and can influence solution pH upon dissolution, but they are not used to prepare standard laboratory buffers.
Practical guidance
If aqueous handling is required, dissolve first in a minimal volume of DMSO or ethanol, or prepare an acidified aqueous solution (e.g., 0.01–0.1 M HCl) to form the water-soluble amidinium salt. Adjust final buffer composition after dissolution.
Avoid using this compound to control pH; instead select established buffers (e.g., phosphate, HEPES, acetate) appropriate to the desired pH range.
Green Alternatives
Context
This product is a nitrogen-rich heteroaromatic building block/ligand rather than a process solvent. Green considerations focus on solvent/catalyst choices and step economy when using it.
Solvent selection: Prefer water/ethanol blends for crystallizations and salt formations when feasible; avoid high-toxicity dipolar aprotics (DMF/NMP) unless necessary. DMSO and propylene carbonate can be greener alternatives to DMF/NMP for dissolving amidines.
Catalysis: For condensations or cyclizations, employ catalytic rather than stoichiometric acids/bases; explore heterogeneous acid catalysts (e.g., zeolites, sulfonated resins) to simplify workup.
Energy minimization: Microwave or flow conditions can reduce reaction times and energy consumption during heterocycle construction.
Avoid hazardous dehydrants where possible: Replace SOCl2/POCl3 with greener dehydrative couplings or carbodiimide-based protocols when substrate-compatible.
Illustrative comparison (general guidance; not item-specific)
DMF vs Ethanol/Water
Health/environment: DMF is reproductive toxin; EtOH/H2O is low-tox, renewable.
Performance: DMF dissolves more; EtOH/H2O may require slight heating or acidification for complete dissolution of amidines.
NMP vs DMSO
Health/environment: NMP is SVHC in EU; DMSO has a better safety profile.
Performance: Both dissolve amidines well; DMSO higher bp may complicate removal.
Waste and lifecycle
Where coordination chemistry is involved, choose less toxic metals (e.g., Fe, Cu) and recover catalysts. Neutralize and segregate amine-containing aqueous wastes to facilitate treatment.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is provided for this item; it is supplied for research use only.
General formulation context (literature-based; not product-specific)
Amidine-containing heteroaromatics are commonly encountered as intermediates or ligands in medicinal chemistry campaigns due to their high basicity and potential for bidentate binding. However, amidines often display poor oral permeability when protonated; therefore, they are typically explored in discovery settings rather than as excipients.
Salt forms: If needed for formulation studies, hydrochloride salts of amidines are frequently prepared to enhance aqueous solubility.
Process/CMC considerations
For any preclinical enabling work, define counterion, polymorph, and residual solvent profile via CoA and solid-state characterization. No claims are made here regarding compliance with USP/EP monographs or GMP manufacture.
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.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for context; not product specifications)
Physical state: typically a solid aromatic amidine; amidines are often crystalline and may be hygroscopic depending on counterion state (free base vs salt).
Acid–base behavior: basic (amidines have conjugate acid pKa typically ~11–13; pyridine N pKaH ~5–6) leading to high water solubility upon protonation (literature, general ranges).
Solubility (qualitative):
Free base: generally soluble in polar organic solvents (MeOH, EtOH, DMSO, DMF); limited solubility in nonpolar solvents; moderate in water; markedly increased in dilute mineral acid (literature, general).
Partitioning: logP expected to be low to moderate due to multiple nitrogens; logD strongly pH-dependent (literature, general trend).
Melting/boiling points, density, refractive index: Not readily available in common references for this specific substitution pattern.
Notes
Use the Certificate of Analysis (CoA) for any lot-specific values (mp, water content, residual solvents, metal limits, UV cutoff). Absent explicit specification, do not assume these values.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general; for context)
Research/biochemical grade: Typically indicates suitability for research use, with impurities controlled for common lab applications. Low levels of inorganic residues and residual solvents are desirable for synthesis and assay work.
Screening/HTS grade (if applicable): Focus on identity and sufficient purity for biological screening; UV transparency may be less critical than for HPLC grade reagents.
HPLC/spectrophotometric grade (not claimed here): Ensures low baseline absorbance; chosen when the compound is used as a standard or in detection-sensitive workflows.
Identity and documentation
Identity confirmation normally relies on NMR, HRMS/ESI-MS, and HPLC purity. Where applicable, chloride content (for amidinium salts), water (KF), and residual solvent data are provided on the CoA.
Stabilizers: None stated. If supplied as a free base vs. a hydrochloride salt, spectral and assay parameters will differ; consult the CoA for the exact supplied form.
Recommendations
For trace-sensitive catalysis or materials synthesis, request metal analysis if critical. For bioassays, confirm residual solvent profile and counterion state, as amidines/protonated amidiniums can affect assay pH/ionic strength.
Reaction and Applications
Overview (chemistry focus)
6-Methylpicolinimidamide provides a bidentate N,N-donor motif (pyridine N + imine N) and a nucleophilic exocyclic –NH2, making it useful as a ligand, directing group precursor, and as a versatile building block in heterocycle synthesis (literature, general).
Representative application families (literature; not exhaustive)
Chelating ligand/auxiliary: The picolinamidine scaffold can chelate late transition metals (e.g., Pd, Cu, Ni) to stabilize catalytic intermediates. The 6-methyl substituent modulates sterics/electronics around the coordination pocket.
Heterocycle construction:
Imidazole formation from amidines + α-haloketones/α-dicarbonyls (e.g., Debus–Radziszewski-type variants) yielding 1,2,4- or 1,3,4-substituted imidazoles.
1,2,4-triazines/1,2,4-triazoles via condensation of amidines with nitriles or hydrazides (under dehydrative/oxidative conditions).
Amidrazone intermediates from reaction with hydrazines, enabling further cyclizations.
Functional group interconversions:
Acylation/sulfonylation at the exocyclic –NH2 to give N-acyl/sulfonyl amidines.
Conversion to nitriles via dehydrating conditions in specific systems (literature precedents for amidines → nitriles using POCl3/SOCl2 variants), though substrate dependence applies.
Directing-group chemistry: Picolinamide-type auxiliaries are widely used in C–H activation; amidines can serve analogously as removable/transformable directing groups, with deprotection paths to amides, nitriles, or acids depending on conditions.
Practical tips
Drying: While the free base is less hygroscopic than the salt, dry under vacuum at ambient to 40 °C before moisture-sensitive couplings.
Protonation state control: For metal-binding applications, adjust pH to manage donor availability (avoid full protonation which suppresses binding).
Counterion effects: If using as salt (e.g., HCl), neutralize carefully to the free base for nucleophilic condensations.
Reaction Conditions
General conditions drawn from literature precedents for aromatic amidines (adapt as needed to your substrate/scope). These are not item-specific specifications.
Imidazole formation (amidines + α-haloketones)
Solvent: EtOH, iPrOH, MeOH, or DMF/DMSO when needed.
Base: K2CO3, Et3N, or NaOEt; catalytic acid variants also exist.
Temperature/time: 50–100 °C, 2–16 h; microwave 120–160 °C, 10–60 min.
Typical outcomes: 40–85% isolated yields depending on substrates.
Reagents: SOCl2 or POCl3 (caution), or milder systems like T3P; catalytic DABCO variants reported for select cases.
Solvent: DCM/MeCN; temperatures from 0 °C to reflux depending on reagent.
Always run small-scale trials; confirm identity/purity by NMR/HRMS. Optimize equivalents and temperature for your exact substrate combination.
Safety and Handling
Item-specific hazard information
Signal word: Not specified for this item; refer to SDS.
H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
General safety guidance for aromatic amidines (literature-based; not product-specific)
Hazards: Amidines are basic and can be irritating/corrosive to eyes, skin, and respiratory tract, especially in salt forms or as fine powders. Dust may cause respiratory irritation. Avoid inhalation and contact.
Peroxide formation: Not applicable (no ether functionality).
Incompatibilities: Strong oxidizers; strong acids/bases may cause decomposition or exothermic neutralization; acylating agents/isocyanates may react vigorously with the –NH2 group.
PPE: Lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use a fume hood to avoid dust/aerosol exposure.
Handling: Minimize dust generation. For weighing, use antistatic tools. If hygroscopic, keep containers tightly closed and limit air exposure.
First aid (consult SDS for definitive instructions):
Skin/eye: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention for persistent symptoms.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire: Treat as an organic combustible solid; use CO2, dry chemical, or foam. Thermal decomposition may produce nitrogen oxides.
Waste: Dispose of in accordance with institutional and local regulations; segregate from oxidizers.
Always consult the official Safety Data Sheet (SDS) for authoritative hazard, exposure limits, and emergency procedures for this product.
Polar aprotic: DMSO, DMF, NMP — typically excellent solubility for amidines; good for stock solutions and coupling chemistry.
Polar protic: Methanol, ethanol, isopropanol — generally good; useful for recrystallization and routine handling.
Water: Free base shows moderate solubility; solubility increases markedly in dilute acid (e.g., 0.1 M HCl) due to amidinium formation.
Nonpolar: Poor solubility in ethers, alkanes, and chlorinated solvents.
Polarity class and acid–base considerations
Basic heteroaromatic with an amidine; pH strongly determines solubility and partitioning. For aqueous work, acidify to pH 2–5 to favor complete dissolution; for extractions, basify to pH >10 to partition into organic phase (literature, general practice).
When to choose specific solvents
Analytical stocks for screening/biology: DMSO (prepare concentrated stocks, then dilute into aqueous buffers with co-solvent ≤1–2%).
Synthetic transformations: Alcohols (EtOH, iPrOH) for salt formation/recrystallization; DMF/DMSO for nucleophilic additions and condensations.
Purification: Protonation (HCl in EtOH/Et2O) can convert to a crystalline salt to aid isolation.
Comparison notes (general)
DMSO vs DMF: DMSO offers broader solvency and lower volatility; DMF is easier to remove but may require higher vacuum. For greener choices, consider ethanol/water mixtures when feasible.
Always verify actual solubility of your lot; absent item-specific data, run a small-scale solubility screen before committing to process-scale operations.
Storage and Reconstitution
Storage (item-specific): Store at room temperature (per Product Data). Protect from moisture and strong light. Keep container tightly closed.
Form supplied: Not specified for this item; refer to CoA/Spec Sheet (free base vs salt form will affect solubility and handling).
Stability: In general, amidines are stable solids under ambient conditions. If hygroscopic (especially as salts), limit air exposure and reseal promptly. For long-term storage, consider desiccation.
Reconstitution and solution handling (general guidance)
Stock solutions: Prepare 10–100 mM in DMSO or methanol. For aqueous use, dissolve in minimal DMSO or acidified water (e.g., 0.01–0.1 M HCl) to form the soluble amidinium salt, then adjust pH as needed.
Filtration: If particulates are present, sterile-filter through 0.22 µm PTFE or PES (compatibility depends on solvent).
Freeze–thaw: For DMSO stocks, aliquot and store at −20 °C to avoid repeated freeze–thaw. Inspect for precipitation/crystallization upon warming and redissolve with gentle heating if required.
Research Use Notice: For research use only. Not for human or veterinary use.
Structure and Identity
Brief description: 6-Methylpicolinimidamide is the 6-methyl-substituted pyridine-2-carboximidamide (picolinamidine) scaffold, featuring a pyridine ring bearing an amidine functionality ortho to the ring nitrogen.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general chemistry description)
Core ring: pyridine (one ring nitrogen at position 1).
Functional group: carboximidamide [–C(=NH)–NH2] at the 2-position relative to the ring N (picolinamidine framework).
Substituent: methyl group at the 6-position of the pyridine ring (para to the ring N across the ring, ortho to C(2)).
Donor/acceptor pattern: bidentate chelation motif possible via pyridine N (acceptor) and imine N of the amidine (donor), with an additional exocyclic –NH2 (donor).
Charge/tautomerism: neutral amidine (can exist in imidamide tautomers); readily protonated to an amidinium cation under acidic conditions (literature, general).
Literature/computed identifiers (informational; not item-specific specs)
Preferred IUPAC-like name (literature): 6-methylpyridine-2-carboximidamide (aka 6-methylpicolinamidine).
Empirical formula (literature inference): C7H9N3.
Formula weight (literature calculation): ~135.17 g/mol.
2D structure in words: a six-membered aromatic ring with N at position 1; at C2 a C(=NH)–NH2 group is attached; at C6 a –CH3 group is attached.
Synthetic Utility
Functional group portfolio
Aromatic heterocycle (pyridine) with a 6-methyl substituent: provides electronic modulation and a handle for further substitution via directed lithiation or SEAr where applicable.
Amidine (carboximidamide) at C2: nucleophilic –NH2 and imine nitrogen enable condensations, acylations, and metal coordination; tautomerizable.
Key transformations (literature examples; not exhaustive)
Heterocycle synthesis
Imidazoles from amidines + α-haloketones or 1,2-dicarbonyls (base or acid catalysis; typically 60–90 °C, polar solvents).
Triazoles/triazines via condensation of amidines with hydrazides or nitriles under dehydrative or oxidative conditions (e.g., POCl3, CDI, or catalytic dehydrations).
Functional group interconversions
N-Acylation/sulfonylation to tune electronics and reduce basicity for downstream steps.
Conversion of amidines to nitriles under strong dehydrating conditions (substrate dependent) or to amides via controlled hydrolysis/oxidation pathways.
Coordination/ligand chemistry
Formation of chelate complexes with Cu(II), Ni(II), Pd(II), etc., leveraging the pyridine N and imine N; 6-Me can influence bite angle and sterics for catalysis.
Retrosynthetic value
Serves as a masked nitrile/carboxamide equivalent at the 2-position of a 6-methylpyridine. Access via Pinner-type conversion of 6-methylpicolinonitrile or via amidation of the corresponding imidate.
Practical notes
Control protonation (base present) to maximize nucleophilicity at –NH2 during acylations. For ligand formation, avoid strong acid which suppresses coordination.
Target Specificity
Not applicable — this product is a small-molecule heteroaromatic amidine, not an antibody or affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
Domande frequenti
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.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 190004-35-4, the molecular formula is C7H10ClN3, and the molecular weight is 171.63 g/mol. InChIKey PIZYALZCFPRXAD-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.
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