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2-Aminopyridine
2-Aminopyridine
2-Aminopyridine
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2-Aminopyridine
Names
Preferred IUPAC name
Pyridin-2-amine
Other names
2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine; α-Pyridylamine[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.263 Edit this at Wikidata
EC Number
  • 207-988-4
RTECS number
  • US1575000
UNII
UN number 2671
  • InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7) checkY
    Key: ICSNLGPSRYBMBD-UHFFFAOYSA-N checkY
  • InChI=1/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
    Key: ICSNLGPSRYBMBD-UHFFFAOYAM
  • n1ccccc1N
  • c1ccnc(c1)N
Properties
C5H6N2
Molar mass 94.117 g·mol−1
Appearance colourless solid
Melting point 59 to 60 °C (138 to 140 °F; 332 to 333 K)
Boiling point 210 °C (410 °F; 483 K)
>100%[1]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H301, H311, H312, H315, H319, H335, H411
P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, P501
Flash point 68 °C; 154 °F; 341 K
Lethal dose or concentration (LD, LC):
200 mg/kg (rat, oral)
50 mg/kg (mouse, oral)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.5 ppm (2 mg/m3)[1]
REL (Recommended)
 TWA 0.5 ppm (2 mg/m3)[1]
IDLH (Immediate danger)
 5 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2-Aminopyridine is an organic compound with the formula H2NC5H4N. It is one of three isomeric aminopyridines. It is a colourless solid that is used in the production of the drugs piroxicam, sulfapyridine, tenoxicam, and tripelennamine.[3] It is produced by the reaction of sodium amide with pyridine, the Chichibabin reaction.[4]

Reactions

[edit]
The bifunctionality of 2-aminopyridine is illustrated by this 1:2 adduct with maleic anhydride.[5]

Although 2-hydroxypyridine converts significantly to the pyridone tautomer, the related imine tautomer (HNC5H4NH) is less important for 2-aminopyridine.

2-Aminopyridine catalyzes the conversion of maleic anhydride to 2,3-dimethylmaleic anhydride.[6]

Toxicity

[edit]

The acute toxicity is indicated by the LD50 = 200 mg/kg (rat, oral).

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

2-Aminopyridine

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from Grokipedia
2-Aminopyridine, also known as pyridin-2-amine, is a with the molecular formula C₅H₆N₂ and a molecular weight of 94.11 g/mol. It consists of a six-membered ring with an (-NH₂) attached at the 2-position adjacent to the atom, making it a primary . This compound appears as a white to light yellow crystalline solid, with a of 59 °C and a of 204–210 °C at standard pressure. It is highly soluble in (greater than 100 g/L), , and , but less so in non-polar solvents. Commercially, 2-aminopyridine is produced via the , involving the amination of with under high temperature conditions. As a versatile synthetic intermediate, 2-aminopyridine plays a key role in the for manufacturing analgesics, antihistamines, and other drugs, as well as in the production of dyes and agrochemicals. Its derivatives exhibit diverse pharmacological activities, including inhibition and modulation, contributing to applications in . However, it is toxic by and of dust, classified as a skin and respiratory irritant, necessitating proper measures in handling.

Structure and properties

Molecular structure

2-Aminopyridine is a heterocyclic consisting of a six-membered ring with the atom at position 1 and an amino group (-NH₂) attached to the carbon at position 2. The molecule's core is derived from , where the exocyclic amino group is bonded to the ortho position relative to the ring , enabling significant electronic interactions between the two atoms. X-ray crystallographic studies of neutral 2-aminopyridine and its derivatives reveal typical bond lengths for the ring C-N (between C2 and N1) of approximately 1.34 Å and the exocyclic C-N (between C2 and the amino ) of about 1.37 Å, with bond angles around the ring maintaining near 120° planarity consistent with sp² hybridization. The molecule exhibits tautomerism between the amino form (2-aminopyridine) and the imino form (2(1H)-pyridinimine), with the amino tautomer strongly favored in both gas phase and solution. In the gas phase, the energy difference favors the amino form by approximately 12-15 kcal/mol, corresponding to an equilibrium constant K_tautomer (imino/amino) of around 0.001 at room temperature. In polar solvents like water, the equilibrium shifts even further toward the amino form due to solvation effects, with K_tautomer ≈ 0.0001 or less, as determined by computational and spectroscopic studies. The electronic structure of 2-aminopyridine features delocalization of the on the exocyclic amino into the π-system of the aromatic ring, conferring partial double-bond character to the C-NH₂ linkage and reducing its single-bond length compared to aliphatic amines. This delocalization is described by structures in which the amino group acts as a donor, contributing to quinoid-like forms that enhance at the ring and ortho/para positions. These contributions promote overall molecular planarity, with the amino group adopting a configuration that maximizes π-overlap, as confirmed by DFT optimizations showing dihedral angles near 0° for the NH₂ plane relative to the ring. Due to extensive conjugation across the planar framework, 2-aminopyridine lacks chiral centers and exhibits no beyond potential conformational variations in the NH₂ group, which are minimized by the energetic preference for .

Physical properties

2-Aminopyridine appears as a colorless to light yellow crystalline solid exhibiting a characteristic . Its molecular weight is 94.11 g/mol. The compound has a of 57–58 °C and a of 204–205 °C at 760 mmHg. Its density is 1.11 g/cm³ at 20 °C. 2-Aminopyridine is highly soluble in (>100 g/100 mL at 20 °C), , and , while showing sparing in non-polar solvents such as . The (log P) is approximately 0.5, reflecting moderate hydrophilicity. The is 0.8 mmHg at 25 °C, and the is 1.57.

Chemical properties

2-Aminopyridine exhibits weak basicity, with the pKa of its conjugate acid measured at 6.86 in , rendering it a stronger base than unsubstituted (pKa 5.23 of conjugate acid) owing to stabilization of the protonated ring by the adjacent amino substituent. This enhanced basicity arises from the ability of the amino group to delocalize positive charge in the protonated form via electron donation. The compound's amino group, in turn, displays weak acidity, with the pKa of the N-H proton approximately 28 in , permitting only under strongly basic conditions. Tautomerism between the amino and imino forms further influences this acidity, though the amino overwhelmingly predominates in solution and solid state. The molecule demonstrates moderate thermal stability, with decomposition initiating around 112 °C and completing by 158 °C as determined by , though it remains intact up to its near 205 °C under inert conditions. Exposure to air promotes gradual oxidation, resulting in the formation of colored impurities and a shift from colorless to cream or light yellow appearance over time; this sensitivity necessitates storage away from strong oxidizing agents to prevent degradation. In concentrated strong acids or bases, 2-aminopyridine undergoes slow , yielding and derivatives, though the process requires elevated temperatures for appreciable rates. The ortho positioning of the amino group relative to the ring nitrogen enables both intramolecular and intermolecular hydrogen bonding, which contributes to dimeric or chain-like arrangements in the crystal lattice and modestly enhances in polar solvents through such interactions. This hydrogen-bonding capability also underlies the compound's tendency toward nucleophilic activation at the ring, though without leading to spontaneous solvolysis under ambient conditions.

Synthesis

Industrial methods

The primary industrial route for producing 2-aminopyridine is the , which involves the direct of with (NaNH₂) at elevated temperatures (typically 100–130 °C in boiling or ), followed by of the intermediate 2-sodamido-1,2-dihydropyridine to yield the product in high yields (often >70%). This method, discovered in 1914, has been commercialized since the mid-20th century by companies such as Reilly Industries and remains a key process due to its directness and scalability using readily available as the starting material. As of the early , global production of 2-aminopyridine was estimated at approximately 1,000 tons per year, primarily driven by demand in pharmaceutical intermediates. The process involves careful control of reaction conditions to manage the exothermic addition step and byproduct , with the product purified by under reduced pressure (boiling point ~125–130 °C at 10–20 mmHg) to avoid . Byproduct management includes neutralization of sodium salts, and modern implementations emphasize recycling of amide reagents and to minimize environmental impact. An alternative route utilizes the of 2-pyridinecarboxamide with and , proceeding via an N-bromoamide intermediate, migration, and to yield the in 70–80% overall yield. The balanced reaction equation is: C5H4N-CONH2+Br2+4NaOH→C5H4N-NH2+Na2CO3+2NaBr+2H2O\text{C}_5\text{H}_4\text{N-CONH}_2 + \text{Br}_2 + 4 \text{NaOH} \rightarrow \text{C}_5\text{H}_4\text{N-NH}_2 + \text{Na}_2\text{CO}_3 + 2 \text{NaBr} + 2 \text{H}_2\text{O} This method starts from (derived from via oxidation of or ), converted to the , and then rearranged; it is less common industrially but suitable for facilities with amide handling capabilities. Byproduct management focuses on recovery of and carbonate salts, with staged addition to control hypobromite formation and reduce halogen release in effluents.

Laboratory preparations

One common laboratory method for preparing 2-aminopyridine involves the reduction of 2-nitropyridine. This can be achieved using stannous chloride in , where the nitro group is selectively reduced to the under mild acidic conditions. Alternatively, catalytic with (Pd/C) and gas in provides a clean reduction, typically achieving yields of 85–95% while minimizing side products. The reaction proceeds according to : C5H4N−NO2+6H→C5H4N−NH2+2H2O\mathrm{C_5H_4N-NO_2 + 6 H \rightarrow C_5H_4N-NH_2 + 2 H_2O} A variant of the Chichibabin amination starting from 2-pyridone utilizes sodium amide (NaNH₂) in liquid ammonia, followed by acidification to yield 2-aminopyridine with approximately 60% efficiency; this approach is particularly advantageous for preparing isotopically labeled variants due to the controlled environment. Yields in this method can vary based on reaction time and temperature, often requiring several hours at reflux to optimize conversion. A copper-catalyzed of 2-halopyridines, such as 2-chloropyridine with over a catalyst at 200–300 °C, achieves selectivity greater than 90% via at the activated 2-position. This method offers potential economic advantages in settings co-producing halopyridines, with catalyst recycling possible. For a modern, selective synthesis, the Buchwald-Hartwig coupling of 2-bromopyridine with employs a catalyst such as Pd₂(dba)₃, a ligand like , and a base like sodium tert-butoxide (NaOtBu) in at 100 °C, delivering 2-aminopyridine in yields exceeding 90%. This palladium-catalyzed cross-coupling is versatile for small-scale preparations and avoids harsh reducing agents, making it suitable for research applications where purity is paramount. Purification of 2-aminopyridine is typically accomplished by recrystallization from hot , leveraging its profile to isolate high-purity crystals upon cooling. Sublimation under reduced pressure serves as an effective alternative for further refinement, especially to remove volatile impurities. Analytical confirmation often involves ¹H NMR spectroscopy, revealing characteristic aromatic signals between 6.5 and 8.0 ppm, such as the proton at 8.05 ppm (H-6) and 6.47 ppm (H-3). Common challenges in these syntheses include preventing over-reduction during , which can form intermediates if pressure or catalyst loading is excessive, and avoiding side at the 4-position or formation of bipyridyl byproducts in the Chichibabin variant, often mitigated by precise control of and reaction monitoring.

Reactions and applications

Reactivity overview

The amino group of 2-aminopyridine exhibits significant nucleophilicity, enabling it to participate in electrophilic substitutions such as reactions. For instance, treatment with in acetone leads to at the amino , forming 2-acetamidopyridine as the primary product, with this step being rate-determining due to the nucleophilic attack. The ortho positioning of the amino group relative to the ring enhances the compared to meta or para isomers, attributed to favorable electronic interactions facilitating nucleophilic behavior. In , the ring in 2-aminopyridine is deactivated at the 2-position due to electrostatic repulsion between the positively charged atoms, which hinders approach of the . However, the amino group activates the ring at the 4- and 6-positions through resonance donation, directing substitution preferentially to these sites; with typically yields 2-amino-5-nitropyridine as the major product (approximately 90% ), with minor formation of the 3-nitro . 2-Aminopyridine functions as a bidentate , coordinating to metal ions via the nitrogen and the amino nitrogen lone pairs, as evidenced by shifts in IR and NMR spectra of the complexes. With Cu(II), it forms 1:1 and 1:2 metal-to-ligand complexes with stability constants of log K1=6.10K_1 = 6.10 and log K2=5.17K_2 = 5.17 at 298 K, indicating exothermic and spontaneous formation with predominant covalent character. The amino group undergoes diazotization upon treatment with NaNO2_2 in HCl to generate the 2-pyridinediazonium salt: 2-aminopyridine+NaNO2+HCl→2-pyridinediazonium chloride+NaCl+H2O\text{2-aminopyridine} + \text{NaNO}_2 + \text{HCl} \rightarrow \text{2-pyridinediazonium chloride} + \text{NaCl} + \text{H}_2\text{O} This diazonium salt is highly unstable in dilute acid, rapidly hydrolyzing to 2-hydroxypyridine rather than persisting for further substitution.

Industrial applications

2-Aminopyridine is widely utilized as an intermediate in the production of azo dyes and pigments, where it undergoes coupling reactions with diazonium salts to yield acid dyes suitable for textile applications. These dyes provide vibrant coloration and good fastness properties on fabrics such as wool and nylon, contributing to its role in the global textile industry. In the sector, 2-aminopyridine acts as a key precursor for synthesizing herbicides, fungicides, and insecticides, particularly pyridine-based compounds that enhance crop protection. For instance, it is incorporated into formulations of pyridine-derived fungicides that target fungal pathogens in , supporting efficient and control without excessive environmental impact. Its versatility stems from the nucleophilic nature of the amino group, enabling targeted derivatization in these processes. As a polymer additive, 2-aminopyridine functions as a curing agent in resins, promoting cross-linking that improves thermal stability and mechanical strength in composite materials. This application is valuable in industries producing adhesives, coatings, and structural composites, where enhanced durability under heat is required. It also serves as a cross-linking agent in unsaturated resins, further broadening its utility in polymer formulations. The global market for 2-aminopyridine reflects its industrial significance. Overall demand is projected to grow modestly, supported by expansions in dyes, agrochemicals, and polymers sectors.

Pharmaceutical and biological uses

2-Aminopyridine serves as a versatile intermediate in pharmaceutical synthesis, particularly for non-steroidal anti-inflammatory drugs such as piroxicam, tenoxicam, and lornoxicam, where it contributes to the core heterocyclic structure essential for their analgesic and anti-inflammatory efficacy. It also forms the basis for sulfasalazine, a prodrug used in treating inflammatory bowel diseases like ulcerative colitis by releasing the antibacterial sulfapyridine moiety. In antimalarial development, 3,5-diaryl-2-aminopyridine derivatives have emerged as a promising class, exhibiting nanomolar potency against Plasmodium falciparum strains (IC50 = 25–28 nM) and achieving single-dose cures in P. berghei-infected mouse models at 30 mg/kg orally. Derivatives of 2-aminopyridine are frequently modified via at the amino group to yield 2-(alkylamino)pyridine scaffolds, which are incorporated into inhibitors targeting enzymes like c-Met, with optimized compounds displaying sub-micromolar inhibitory activity and potential for cancer therapy. These structural conversions enhance binding affinity to active sites through hydrogen bonding and hydrophobic interactions. Biologically, 2-aminopyridine derivatives demonstrate enzyme inhibitory properties, notably against (AChE) at micromolar concentrations; for example, an aryl-substituted analog inhibits human AChE with an IC50 of 34.81 ± 3.71 µM via mixed-type inhibition, positioning them as candidates for research. Such compounds are also utilized in studies of modulation, where they inhibit neuronal (nNOS), altering levels to influence synaptic transmission. In medicinal applications, 2-aminopyridine-based derivatives feature in treatments for autoimmune conditions, including , by functioning as NO-synthase inhibitors that reduce and ; patented compounds exhibit IC50 values below 30 µM in relevant assays. While (fampridine) is clinically approved for improving walking in patients, 2-aminopyridine derivatives have been explored as NO-synthase inhibitors for . Biochemically, the H-bonding pattern of 2-aminopyridine closely resembles , enabling it to substitute as a nucleobase in DNA-like structures by pairing with isosteres, which supports its use in design and artificial for biosensing and therapeutic targeting. Emerging highlights 2-aminopyridine scaffolds in anticancer , with 2024 studies describing dual CDK9/HDAC1 inhibitors (e.g., IC50 = 88.4 nM for CDK9) that induce and S-phase arrest in cells, achieving a tumor growth inhibition of 70% in MV-4-11 xenografts. These trends underscore ongoing patent activity for PI3K-related analogs, building on earlier substituted 2-aminopyridine inhibitors of PI3Kδ isoforms for hematological malignancies.

Safety and toxicology

Acute toxicity

2-Aminopyridine exhibits moderate acute toxicity via oral and dermal routes, with an oral LD50 of 200 mg/kg in rats and a dermal LD50 of 500 mg/kg () or greater than 1,000 mg/kg (). Inhalation toxicity data indicate a threshold limit concentration (TCLo) of 5 ppm over 5 hours in humans, leading to severe symptoms without at this level. Its volatility contributes to risk in occupational settings, where vapor or dust exposure can occur. Symptoms of acute exposure vary by route. Ingestion causes nausea, vomiting, headache, dizziness, excitement, and central nervous system (CNS) effects such as convulsions and respiratory depression at higher doses. Dermal contact results in skin irritation, including redness and pain, while eye exposure leads to severe irritation and potential damage. Inhalation irritates the eyes, nose, and throat, accompanied by , , elevated , respiratory distress, and lassitude. The compound acts as an irritant primarily due to its basic group, causing local tissue damage upon contact. It is rapidly absorbed through the following , with involving conjugation to form derivatives that contribute to systemic effects. Occupational exposure limits include an OSHA (PEL) of 0.5 ppm as an 8-hour time-weighted average to prevent acute effects. Industrial case studies demonstrate reversible acute effects at low doses; for instance, a worker exposed to approximately 5.2 ppm experienced severe , , flushing, and elevated , with symptoms resolving after removal from exposure. First aid measures emphasize immediate action: for , dilute with or without inducing ; for , move to and provide ventilation; for contact, wash with and ; and for eye exposure, rinse thoroughly with for at least 15 minutes.

Chronic exposure effects

Limited data exist on the chronic exposure effects of 2-aminopyridine, as comprehensive subchronic and long-term studies are lacking in the . No dedicated investigations into repeated or prolonged exposure have been identified, limiting the understanding of cumulative impacts in humans or animals. In terms of relevant to potential long-term risks, 2-aminopyridine was negative in the Ames bacterial mutagenicity test across Salmonella typhimurium strains TA98, TA100, TA1535, and TA1537 at concentrations up to 10,000 µg/plate, both with and without metabolic activation; it was also non-mutagenic in WP2 uvrA. The International Agency for Research on Cancer (IARC) has not classified 2-aminopyridine as mutagenic or carcinogenic, reflecting the absence of sufficient evidence for such effects. No data from chromosomal aberration assays specific to 2-aminopyridine were located. Reproductive toxicity, including potential teratogenic effects on fetal development, remains unstudied in animal models or humans as of 2025, with no reports of impacts at any dose level. Similarly, no human epidemiological data exist on cancer risks associated with chronic exposure, including from chemical plant workers, though ongoing monitoring is advised due to the compound's use in industrial settings. Neurological effects from chronic low-level exposure are undocumented, though the compound's mechanism of blocking channels and enhancing release suggests possible risks for akin to pyridoxine-related antagonism, warranting further investigation.

Handling and regulatory aspects

2-Aminopyridine should be stored in a cool, dry place in tightly closed containers to prevent moisture absorption and degradation, and it must be kept away from incompatible materials such as strong oxidizers to avoid hazardous reactions. Suitable containers include glass or (HDPE) to prevent , as the compound can react with certain metals. Handling of 2-aminopyridine requires appropriate (PPE), including chemical-resistant gloves, safety goggles, and protective clothing to minimize skin and eye contact; respiratory protection such as a or is recommended when handling powders to avoid . Due to its flammability, with a of 92 °C, ignition sources like open flames, sparks, and hot surfaces should be avoided, and handling should occur in well-ventilated areas to prevent vapor accumulation. In the event of a spill, the area should be evacuated and ventilated, then the material absorbed using an inert absorbent like or sand, swept up, and placed in suitable containers for disposal; larger spills may require professional cleanup to prevent environmental contamination. Environmental releases are reportable under U.S. Environmental Protection Agency (EPA) regulations, such as those under the Comprehensive Environmental Response, Compensation, and Liability Act (CERCLA), if quantities exceed reportable thresholds. 2-Aminopyridine is registered under the European Union's REACH regulation with EC number 207-988-4 and is listed on the U.S. Toxic Substances Control Act (TSCA) inventory as an active substance. It is classified under the Globally Harmonized System (GHS) as 3 (oral and dermal), Skin Corrosion 1A, Serious Eye Damage 1, and Aquatic Acute 3, indicating hazards from ingestion, skin contact, severe irritation, and environmental toxicity. Disposal of 2-aminopyridine must follow protocols, typically involving in a licensed facility equipped with afterburners and operating above 1,000 °C to ensure complete combustion and control of emissions, or treatment as in accordance with local regulations.

References

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