Ethyl 5,6-diaminonicotinate - ≥98% , CAS No.219762-81-9

CAS: 219762-81-9 Cat. No.: E1027346 PubChem CID: 9877541

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: CCOC(=O)C1=CC(=C(N=C1)N)N
• IUPAC Name: ethyl 5,6-diaminopyridine-3-carboxylate
• InChIKey: ZKTFWAVPUQOQSI-UHFFFAOYSA-N
• INCHI: 1S/C8H11N3O2/c1-2-13-8(12)5-3-6(9)7(10)11-4-5/h3-4H,2,9H2,1H3,(H2,10,11)
• Isomeri SMILES: CCOC(=O)C1=CC(=C(N=C1)N)N
• CAS alternativo: 219762-81-9
• PubChem CID: 9877541

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Pyridines and derivatives
      • Subclass Pyridinecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Pyridines and derivatives
• Subclass: Pyridinecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyridinecarboxylic acids
• Alternative Parents: Aminopyridines and derivatives Imidolactams Heteroaromatic compounds Carboxylic acid esters Amino acids and derivatives Azacyclic compounds Primary amines Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyridine carboxylic acid - Aminopyridine - Imidolactam - Heteroaromatic compound - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Azacycle - Primary amine - Organooxygen compound - Organonitrogen compound - Organic oxide - Amine - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 181.190 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 181.085 Da
• Monoisotopic Mass: 181.085 Da
• Topological Polar Surface Area: 91.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 186.000
• 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 assay or bioanalytical protocols are specified for this catalog item. As a synthetic intermediate:

• For stock solutions in screening or synthesis, dissolve in a suitable solvent (e.g., DMSO or DMF) and dilute into the reaction medium as needed.
• For parallel synthesis, standard solid-phase-compatible coupling and acylation protocols can be adapted after conversion to the corresponding acid or amide.

Refer to lab-specific SOPs and validate conditions on small scale.

Biological Roles

This product is a synthetic heteroaromatic building block and is not a biochemical reagent per se.

• General context (literature/knowledge; not item-specific and not medical):
  • Nicotinate derivatives are widely used motifs in chemical biology probes, coordination ligands, and materials. Diamino substitution on a pyridine ring can enhance hydrogen-bonding and metal-binding profiles in designed ligands.
  • The presence of two primary amines offers multiple derivatization points to append labels, linkers, or reporter groups for research tools.

No endogenous biological role is attributed to Ethyl 5,6-diaminonicotinate itself. Any biological testing must be designed and interpreted within laboratory research contexts only.

Buffer Applications

Not typically used as a buffer component. As a polyfunctional aromatic amine/ester, it does not form a defined buffering system over a useful pH range for biochemical assays.

• Practical note: If dissolution in aqueous media is required for research, forming a salt (e.g., with HCl) may increase water solubility, but this is for solubilization rather than buffering. Prefer dedicated buffer systems (e.g., phosphate, HEPES, Tris) for pH control.

Green Alternatives

While the molecule itself is a building block, greener choices can be made for solvents and reagents used with it.

• Greener solvent substitutions (general guidance):

  • Replace DMF/DMAc with Cyrene, Propylene carbonate, or N-butyl pyrrolidone (NBP) where feasible (e.g., amidations, SNAr-like steps).
  • Swap DCM with ethyl acetate or 2-MeTHF for acylations/couplings when reactivity allows.
  • Use MeOH/EtOH in place of isopropanol or higher alcohols for transesterifications when compatible.

• Coupling/activation strategies:

  • Favor EDC/HOBt substitutes (OxymaPure) in aqueous-organic media to reduce hazardous byproducts; explore enzymatic ester hydrolysis for mild deprotection to the acid.

• Comparison (general; not item-specific):

  | Conventional choice | Greener alternative | Trade-offs | |---|---|---| | DMF | Cyrene, PC, NBP | Viscosity, temperature requirements | | DCM | EtOAc, 2-MeTHF | Polarity/window differences, azeotrope behavior | | THF | 2-MeTHF, CPME | Peroxide management still needed for ethers |

• Waste minimization:

  • Employ microscale parallel chemistry to reduce solvent usage during library synthesis.
  • Use solid-supported scavengers to streamline workups and cut aqueous waste.

Always validate greener swaps with small-scale trials for solubility/reactivity on this substrate.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet if such information becomes available. This product is supplied strictly for research use only.

• General context (literature/knowledge, not medical claims):
  • Nicotinate-derived scaffolds are common in medicinal chemistry campaigns. Ethyl 5,6-diaminonicotinate can serve as a synthetic intermediate to generate amide/ester variants, ureas, and fused heteroaromatics during lead exploration.
  • Any use toward drug substance/intermediate development requires in-house qualification of identity, purity, and residual profiles in accordance with applicable guidelines; such qualifications are outside the scope of this catalog listing.

Physical Properties

• Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

• Expected characteristics (literature/general for this class of compounds; not item specifications):

  • Physical state/appearance: Typically a crystalline solid for aminated nicotinate esters.
  • Acid–base behavior: Aromatic diamines are basic; the pyridine nitrogen is also basic but less so when ring is substituted. Formation of salts with strong acids is common.
  • Solubility profile: Frequently soluble in polar aprotic solvents (e.g., DMF, DMSO, NMP) and alcohols; limited solubility in nonpolar hydrocarbons. Free-base amines often show modest water solubility; protonated salts markedly increase aqueous solubility.
  • Hydrogen bonding: Two –NH2 groups and the ring N support extensive H-bonding, which can influence crystal packing and melting behavior.
  • Reactivity considerations: Primary amines can undergo acylation/alkylation; the ethyl ester can be hydrolyzed to the acid (or converted to amide) under standard conditions.

• Numerical values (BP, MP, density, logP, pKa, refractive index): Not specified for this item; consult the SDS and CoA/Spec Sheet or primary literature for values determined under defined conditions.

Quality and Grades

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

• What the grade typically implies (general guidance):

  • Research grade materials are suitable for most synthetic and exploratory applications. Where HPLC or assay purity is specified, it reflects the predominant component by a defined analytical method.
  • If an inhibitor/stabilizer were present, it would be listed explicitly; none is specified here for this item.

• Recommended verifications for this heteroaromatic building block:

  • Identity: 1H/13C NMR (diagnostic –NH2 resonances; ethyl ester quartet/triplet; pyridine pattern), HRMS, and, if needed, IR (NH stretches, C=O ~1700–1750 cm−1) and melting point.
  • Purity: HPLC/UPLC with diode array detection can reveal aromatic impurities; LC–MS helpful for detecting poly-aminated byproducts or partial hydrolysis (acid or amide).

• Batch documentation:

  • Always consult the lot-specific CoA for assay %, water content, and residual solvent data when available. Absent explicit catalog specifications, these parameters are not guaranteed and should be confirmed as needed for your application.

Reaction and Applications

Ethyl 5,6-diaminonicotinate is a versatile, orthogonally functionalized building block combining an activated pyridine ring, two primary amines, and a masked carboxylate.

• Representative application spaces (literature/general):

  • Bifunctional linker in heterocycle synthesis: The 5,6-ortho-diamine motif enables annulations to furnish fused systems (e.g., imidazo[4,5-b]pyridines, quinazolinone-like frameworks) via condensation with carbonyl equivalents (e.g., 1,2-dicarbonyls, aldehydes, isocyanates).
  • Urea/carbamate formation: Each –NH2 can be individually protected or elaborated to ureas, thioureas, and carbamates for SAR arrays.
  • Ester as a handle: Hydrolysis to the nicotinic acid followed by amide coupling provides access to 3-carboxamide libraries on the pyridyl core.
  • Diazotization/derivatization of anilino nitrogens: Controlled conversion to diazonium surrogates (through nitrosation of anilines) can enable further functionalization; care required due to the pyridine N.
  • Ligand precursor: Multidentate coordination motifs arise after acylation or amidation, useful in catalysis/materials screening.

• Practical tips:

  • Chemoselectivity: Protect one amine (e.g., Boc, Cbz) to enable stepwise diversification. Carbamates often form cleanly under mild base in DCM or MeCN.
  • Pyridine N basicity: Transient protonation can suppress ring N coordination to catalysts if problematic.
  • Ester stability: Avoid strong base/alcohol at elevated heat when ester retention is required; otherwise leverage it for saponification.
  • Workup/chromatography: Include 0.1–1% base in silica eluents to prevent streaking of polyamines.

Reaction Conditions

Typical conditions reported in the literature for analogous substrates; adjust based on pilot experiments. Values here are general guidance, not specifications for this item.

• Saponification of the ethyl ester:

  • Base-mediated (NaOH or K2CO3) in MeOH/THF/H2O at 0–50 °C to give the acid; acidification then isolation. Avoid strong base if amine integrity/protection is a concern.

• Amide coupling (from acid):

  • EDC·HCl/Oxyma or HATU/DIPEA in DMF or MeCN at 0–25 °C to room temperature for 2–16 h. Monitor for overacylation of ring amines—protect if needed.

• Urea/carbamate formation:

  • Reaction with isocyanates or chloroformates in DCM/MeCN with a base (Et3N, DIPEA) at 0–25 °C. Stepwise protection enables mono- vs di-functionalization.

• Cyclocondensation to fused heterocycles:

  • With 1,2-dicarbonyls (e.g., glyoxal/diacetyl) under reflux in EtOH or in HOAc; or in high-boiling polar solvents (NMP/DMAc) at 80–140 °C with catalytic acid/base as appropriate.

• Quaternization of pyridine N:

  • Alkyl halides (e.g., MeI) in MeCN/acetone at room temperature to reflux; provides pyridinium salts that may alter subsequent reactivity/solubility.

• Protection strategies:

  • Boc protection using Boc2O, base (Na2CO3 or Et3N) in THF/MeCN at 0–25 °C; Cbz using Cbz–Cl in DCM with mild base. Deprotections under standard acidic (Boc) or hydrogenolysis (Cbz) conditions.

Always evaluate the stability of both amino groups and the ester under the chosen conditions; sequence-sensitive routes (protect → transform → deprotect) are often optimal.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the product SDS for authoritative safety information.

• General laboratory safety (applicable to aromatic diamines and nicotinate esters; not item-specific):

  • PPE: Lab coat, appropriate chemical-resistant gloves (e.g., nitrile), safety glasses or face shield. Use in a chemical fume hood to avoid inhalation of dust or vapors during reactions.
  • Avoid: Contact with strong oxidizers (amines can be reactive), acylating/alkylating agents unless intentionally used in synthesis, and strong acids/bases when not controlled (may lead to salt formation or hydrolysis of the ester).
  • Dust control: Minimize dust generation; handle solids gently and keep containers closed.
  • First aid (general): In case of skin contact, wash with soap and water; eye contact, rinse cautiously with water for several minutes and seek medical attention; inhalation, move to fresh air; ingestion, rinse mouth—seek medical advice. Always follow SDS guidance.

• Fire safety:

  • Many aromatic amines and esters are combustible. Use CO2, dry chemical, or foam for small fires. Avoid water jets that may spread material.

• Spill/leak response:

  • Contain and collect with inert absorbent; avoid creating dust. Dispose according to local regulations.

• SDS: Consult the Aladdin Scientific SDS for this specific catalog item prior to use.

• Storage compatibility:

  • Store away from strong oxidizing agents and moisture when possible (to limit ester hydrolysis).

Solvent Selection

As a polar, multifunctional heteroaromatic (pyridine N, two –NH2 groups, and an ethyl ester), this compound favors polar media for dissolution and reactions.

• Miscibility/solubility tendencies (general):

  • Highly suitable: Polar aprotics (DMSO, DMF, NMP) for stock solutions and coupling reactions.
  • Often suitable: Alcohols (MeOH, EtOH, i-PrOH) for salt formation, acylations, and transesterifications.
  • Limited solubility: Nonpolar hydrocarbons (hexanes, heptane); moderate in ethyl acetate, acetone, acetonitrile depending on salt/base state.

• Selection tips by transformation:

  • Amide couplings (after hydrolysis to acid): DMF, NMP, or MeCN with standard coupling reagents.
  • Acylation/alkylation of –NH2 groups: Use non-protic polar solvents (DCM, MeCN, THF) with base; alcohols when forming carbamates/urethanes.
  • Cyclizations/heteroannulations: High-boiling polar solvents (DMAc, NMP) can support elevated temperature.

• Comparison snapshot (general):

  • DMSO vs DMF: DMSO maximizes solubility; DMF often simplifies workup. MeCN offers volatility but may limit solubility.

Note: For chromatography, start with EtOAc/hexanes or EtOAc/MeOH gradients; amine modifiers (e.g., 0.1–1% Et3N) can reduce tailing of polyaminated aromatics.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature. Keep container tightly closed in a dry, well-ventilated place.

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

• General best practices for this class of compounds:

  • Moisture control: Store desiccated when practical to limit ester hydrolysis; avoid prolonged exposure to humid air.
  • Light/air: Protect from excessive light and air if long-term storage is expected; consider inert-atmosphere storage for sensitive derivatives.
  • Packaging: Use amber glass with PTFE-lined cap when possible; wipe cap threads to prevent crusting of amine salts.

• Reconstitution guidance (research use):

  • Prepare concentrated stock solutions in DMSO or DMF; filter if particulates are present (0.2 µm PTFE).
  • For aqueous work, consider forming a soluble salt (e.g., HCl) or co-solvent systems (DMSO/H2O, EtOH/H2O). Verify pH compatibility to avoid ester hydrolysis if the ester must be retained.
  • Avoid repeated freeze–thaw of solutions; aliquot and store at low temperature (e.g., −20 °C) if solutions are kept for extended periods.

• Research Use Note: For research use only.

Structure and Identity

Ethyl 5,6-diaminonicotinate is a functionalized nicotinate ester bearing two adjacent anilino-type substituents on a pyridine core.

• Item-specific identifiers (from Product Data):

  • Product Name: Ethyl 5,6-diaminonicotinate (SKU: E1027346)
  • CAS: 219762-81-9
  • PubChem CID: 9877541
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general description):

  • Core ring system: Pyridine (nicotinic acid scaffold = pyridine-3-carboxylate).
  • Substitution pattern: Carboxylate at the 3-position as an ethyl ester (–CO2Et), and adjacent amino groups (–NH2) at the 5- and 6-positions of the pyridine ring (peri to each other and meta/para relative to the ring nitrogen depending on numbering convention).
  • Functional groups: Aromatic heterocycle (pyridine N), two primary aromatic amines, and an ethyl ester.
  • 2D structure (verbal): A six-membered aromatic ring containing one ring nitrogen (pyridine). At ring position 3 is a carboxylate group esterified with ethyl (–CO2CH2CH3). Two neighboring ring carbons (positions 5 and 6) each bear a primary amino group (–NH2), forming an ortho-diamino motif on the heteroaromatic ring.

• Composition (literature/general):

  • Molecular formula (literature): Commonly reported for this scaffold as C8-based nicotinate ester with two amino groups; verify on CoA/Spec Sheet for this item.
  • Molecular weight (literature): Not specified here; verify on CoA/Spec Sheet.

Note: Exact line notations (SMILES/InChI) and formula/MW for this item should be confirmed against the certificate of analysis (CoA) for the supplied lot.

Synthetic Utility

Key reactive elements and how to exploit them (literature/general guidance):

• Two ortho anilines (5,6-diamino):

  • Stepwise protection (Boc/Cbz/Alloc) allows regioselective functionalization. Unprotected diamines enable rapid formation of cyclic ureas/imidazoles via diacylation or condensation with 1,2-dicarbonyls.
  • Electrophilic acylation/alkylation provides diverse N-substituted libraries; isocyanates afford ureas under mild conditions.

• Ethyl ester at C-3:

  • Saponification to 5,6-diaminonicotinic acid, then amide coupling (EDC/HOAt/Oxyma, HATU) for amide libraries.
  • Direct aminolysis (alcohol-free) to amides under heating in neat amines or in high-boiling polar solvents.
  • Transesterification to alter the alcohol component (Fischer or catalytic methods).

• Pyridine nitrogen:

  • Can coordinate metals or be quaternized (e.g., MeI) to tune electronics/solubility; temporary quaternization sometimes used to modulate reactivity of other sites.

• Ring annulations:

  • Condensation with carboxylic acids/aldehydes/1,2-dicarbonyls can yield fused bicyclic systems (e.g., imidazo[4,5-b]pyridines) relevant for materials and screening.

• Orthogonality:

  • Ester, two amines, and ring N present multiple handles, enabling convergent routes and rapid analog generation from a single core.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or targeted biological reagent. No target, clone, isotype, or species reactivity information applies.