207671-42-9

Basic information

• Product Name: PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE
• Synonyms: PYRIDINE-2,4-DICARBOXYLIC ACID HYDRATE;PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE;LUTIDINIC ACID MONOHYDRATE;2,4-PYRIDINEDICARBOXYLIC ACID MONOHYDRATE;2,4-PYRIDINECARBOXYLIC ACID MONOHYDRATE;2,4-Pyridinedicarboxylicacid, hydrate (1:1);2,4-Pyridinedicarboxylic acid Monohydrate 98%
• CAS NO: 207671-42-9
• Molecular Formula: C7H7NO5
• Molecular Weight: 185.13
• EINECS: 207-892-2
• Product Categories: C7 and C8;Heterocyclic Building Blocks;Pyridines;Building Blocks;C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 207671-42-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 246-248 °C (dec.)(lit.)
• Boiling Point: 668.9 °C at 760 mmHg
• Flash Point: 358.4 °C
• Appearance: /
• Vapor Pressure: 8.31E-19mmHg at 25°C
• BRN: 131631
• CAS DataBase Reference: PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE(207671-42-9)
• EPA Substance Registry System: PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE(207671-42-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 207671-42-9(Hazardous Substances Data)

Usage

Description

PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE, also known as 2,4-Pyridinedicarboxylic Acid (2,4-PDCA), is a compound that structurally resembles 2-oxoglutarate (2-OG) and chelates zinc, thereby influencing a variety of enzymes. As a 2-OG mimic, it inhibits the activity of 2-OG oxygenases, which include certain lysine demethylases and a range of hydroxylases (e.g., prolyl, collagen, lysyl). 2,4-PDCA is effective at low micromolar concentrations in inhibiting several Jumonji domain-containing lysine demethylases. Additionally, it modulates the turnover of hypoxia-inducible factors, collagen synthesis, and plant cell wall formation through its effects on hydroxylases, including prolyl hydroxylase 1 (IC50 = 1.5 μM). Furthermore, it can inhibit zinc-dependent enzymes, such as metallo-β-lactamase, and is translocated by organic anion transporters.

Uses

Used in Pharmaceutical Industry:
PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE is used as an inhibitor for targeting specific enzymes, such as Jumonji domain-containing lysine demethylases, due to its ability to inhibit these enzymes at low micromolar concentrations.
Used in Research Applications:
PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE is used as a research tool for studying the effects of 2-oxoglutarate oxygenases and their role in various biological processes, including hypoxia-inducible factor turnover, collagen synthesis, and plant cell wall formation.
Used in Enzyme Inhibition Studies:
PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE is used as an inhibitor of zinc-dependent enzymes, like metallo-β-lactamase, to investigate the role of these enzymes in different biological systems.
Used in Drug Development:
PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE is used as a lead compound in the development of new drugs targeting various enzymes and pathways, potentially leading to therapeutic applications in treating diseases associated with the dysregulation of these targets.

InChI:InChI=1/C7H5NO4.H2O/c9-6(10)4-1-2-8-5(3-4)7(11)12;/h1-3H,(H,9,10)(H,11,12);1H2

Synthetic route

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + potassium hydroxide + copper dichloride → K2[Cu(pyridine-2,4-dicarboxylate)2]*2H2O

Conditions	Yield
With KF In water High Pressure; aq. solns. 2 equiv. of N-compd., CuCl2 and 1.0 M KOH were stirred for 2 min, KF was added to adjust the Cu:OH:K ratio to 1:6:34.6, heating in a teflon-lined autoclave for 24 h at 200 °C; cooling to room temp. with 0.1 °C/min rate, crystals were filtered off, elem. anal.;	72%

copper(II) nitrate trihydrate + 2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + water (7732-18-5) + 1,10-phenanthroline hydrate (5144-89-8) → [Cu(2,4-pyridinedicarboxylate)(1,10-phenanthroline)(H2O)][Cu(2,4-pyridinedicarboxylate)2H2O]

Conditions	Yield
With NaOH In water High Pressure; mixt. of Cu(NO3)2*3H2O, 2,4-pyridinedicarboxylic acid monohydrate, 1,10-phenanthroline monohydrate, NaOH, H2O placed in bomb, heated at 100°C for 4 d, cooled to room temp. slowly; filtered; elem. anal.;	71.4%

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + vanadia → K3[VO(O2)2(2,4-pyridinedicarboxylato)] * 3.25H2O

Conditions

Yield

With KOH; H2O2 In water addn. of V2O5 to KOH soln., stirring with heating (15 min), then cooling (0°C), addn. of 30% H2O2, stirring (5 min), filtration, dissolving ppt. with H2O2, stirring combined filtrates (5 min, pptn.), addn. ofKOH and ligand, stirring (30 min); filtration, EtOH addn. (5°C, 12 h), filtration, dissolving the ppt. in 30% H2O2, fractional crystn. on EtOH addn. and cooling to 5°C, drying (vac.); elem. anal.;

57%

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + copper dichloride + manganese(ll) chloride → [CuMn(pyridine-2,4-dicarboxylate)2]

Conditions	Yield
With KOH; KCl In water High Pressure; 1.8 equiv. of the N-compd. neutralized with KOH and 1 equiv. of CuCl2 inH2O were stirred for 5 min, 1 equiv. of MnCl2 and KCl was added (Cu:OH: K molar ratio was 1:4:27), teflon-liend steel autoclave, 200 °C for 17 h; rapid cooling to room temp. by quenching in a water bath, crystals were filtered off in vac., elem. anal.;	46%

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + cobalt(II) chloride (7646-79-9) + copper dichloride → [CuCo(pyridine-2,4-dicarboxylate)2(H2O)4]

Conditions	Yield
With benzene-1,2-dicarboxylic acid; KOH In water the N-compd. and 1 equiv. of phthalic acid were deprotonated with 1.0 M KOH, 0.5 equiv. of CuCl2 soln. was added dropwise, stirring for 5 min, 1.5 equiv. of CoCl2 was added (Cu:OH ratio was 1:4.5), teflon-lined autoclave, 190 °C for 24 h; slow cooling (6 h) to room temp., crystals were filtered off, elem. anal.;	32%
With KOH In water the N-compd. was deprotonated with 1.0 M KOH, 0.5 equiv. of CuCl2 soln. was added dropwise, stirring for 5 min, 1.5 equiv. of CoCl2 was added (Cu:OH ratio was 1:4.5), teflon-lined autoclave, 190 °C for 24 h;	0%

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + cobalt(II) chloride (7646-79-9) + copper dichloride → [Cu2Co3(pyridine-2,4-dicarboxylate)4(μ3-OH)2(H2O)]

Conditions	Yield
With KOH In water High Pressure; 2 equiv. of N-compd. and 1.0 M KOH in H2O were added to CuCl2 soln., then 3 equiv. of CoCl2 soln. was added (Cu:OH ratio was 1:7), teflon-lined stainles steel autoclave, 200 °C over 14 h; cooling to 80 °C with 0.1 °C/min rate, crystals were manually sepd. from other two products under microscope, elem. anal.;	30%

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + water (7732-18-5) + zinc(II) sulfate (7733-02-0) → [Zn(2,4-pyridinedicarboxylate)(H2O)4]*H2O (518012-92-5)

Conditions	Yield
With NaOH In water NaOH (4 mmol) soln. was added to an aq. suspn. of a ligand (2.0 mmol); stirring for 30 min; then ZnSO4 (2 mmol) soln. was added (final pH 4.04); slow evapn. of the soln. at 298 K; elem. anal.;

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + water (7732-18-5) + zinc(II) sulfate (7733-02-0) + sodium hydroxide (1310-73-2) → Na2[Zn(2,4-pyridinedicarboxylate)2(H2O)2]*8H2O

Conditions	Yield
In water NaOH (2 mmol) soln. was added to an aq. suspn. of a ligand (2.0 mmol); stirring for 30 min; then ZnSO4 (1 mmol) soln. was added (final pH 4.5); slow evapn. of the soln. at 298 K; elem. anal.;

nickel(II) sulfate hexahydrate + 2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + water (7732-18-5) → [Ni(H2O)6][Ni(2,4-pyridinedicarboxylate)2(H2O)2] (1025760-77-3, 518013-06-4)

Conditions	Yield
With NaOH In water Ni-contg. compd. (2 mmol) was added to an aq. suspn. of a ligand (2.0 mmol); NaOH soln. (0.1 N) was added with stirring at 80°C; (final pH 4.21 at 298 K); slow evapn. of the soln. at 298 K; elem. anal.;

copper(II) nitrate trihydrate + manganese(II) perchlorate hexahydrate + 2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) + water (7732-18-5) → [Cu(2,4-pyridinedicarboxylic acid(-2H)(2-))2Mn(H2O)4]x

Conditions	Yield
With NaOH In sodium hydroxide; water aq. NaOH; organic ligand dissolved in H2O and NaOH; metal salts combined; added toligand soln.; react. mixt. left for several weeks at room temp.; filtered; elem. anal.;

2,4-pyridinedicarboxylic acid monohydrate (207671-42-9) → [Cu(2,4-pyridinedicarboxylic acid(-2H)(2-))2Mn]*H2O

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / water; sodium hydroxide 2: neat (no solvent) View Scheme