89-01-0

Basic information

• Product Name: 2,3-Pyrazinedicarboxylic acid
• Synonyms: PYRAZINE-2,3-DICARBOXYLIC ACID;RARECHEM AL BO 1311;IFLAB-BB F2124-0042;AKOS BBS-00001996;2,3-PYRAZINEDICARBOXYLIC ACID;2,3-dicarboxypyrazine;2,3-Pyrazinedcarboxylicacid;2,3-Pyrazinedicarboxylic
• CAS NO: 89-01-0
• Molecular Formula: C₆H₄N₂O₄
• Molecular Weight: 168.11
• EINECS: 201-875-3
• Product Categories: Carboxylic Acids;Pyrazines, Pyrimidines & Pyridazines;Pyrazine;Organic acids;Pyrazines;Pyrazinecarboxylic Acid & Derivatives;Carboxylic Acids;Pyrazines, Pyrimidines & Pyridazines;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Pesticide intermediates
• Mol File: 89-01-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 188 °C (dec.)(lit.)
• Boiling Point: 297.01°C (rough estimate)
• Flash Point: 225.4 °C
• Appearance: white to pale brown crystalline powder
• Density: 1.6328 (rough estimate)
• Vapor Pressure: 7.51E-09mmHg at 25°C
• Refractive Index: 1.4738 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: soluble
• PKA: 1.66±0.10(Predicted)
• Water Solubility: soluble
• Merck: 14,7958
• BRN: 147982
• CAS DataBase Reference: 2,3-Pyrazinedicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Pyrazinedicarboxylic acid(89-01-0)
• EPA Substance Registry System: 2,3-Pyrazinedicarboxylic acid(89-01-0)

Safety Data

• Hazard Codes: F,C
• Statements: 36/37/38-34-11
• Safety Statements: 22-24/25-45-36/37/39-26-16
• WGK Germany: 3
• RTECS: UQ2500000
• TSCA: N
• Hazardous Substances Data: 89-01-0(Hazardous Substances Data)

Usage

Uses

2,3-Pyrazinedicarboxylic Acid has been found to exhibit antifungal and antibacterial acitivity. It has also been used as a reagent in the preparation of transition metal pyrazinedicarboxylate complexes.

Purification Methods

Crystallise the dicarboxylic acid from water and dry it at 100o. The dimethyl ester has m 62-63o (from Et2O or Et2O/pet ether). [Beilstein 25 H 168, 25 II 164, 25 III/IV 1064.]

InChI:InChI=1/C6H4N2O4/c9-5(10)3-4(6(11)12)8-2-1-7-3/h1-2H,(H,9,10)(H,11,12)/p-2

Synthetic route

pyrazine-2,3-dicarboxylatocopper(II) (46150-15-6) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With water; sodium hydroxide at 90℃; for 2h;	73%

2,3-diethynylquinoxaline (91-19-0) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With potassium permanganate In water at 95℃;	71%
With potassium hydroxide; potassium permanganate
With water; permanganate(VII) ion

2,3-Diaminosuccinic acid (921-52-8) + Glyoxal (131543-46-9) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With sodium hydroxide In methanol 1) 50 deg C, 30 min, 2) relux, 3h;	70%

polymer-bound 2,3-pyrazinedicarboxylic acid (19) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water for 48h; Heating;	56.3%

pyrazine-2,3-dicarbonitrile (13481-25-9) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide	40.3%
beim Verseifen;
With sodium peroxide
Multi-step reaction with 2 steps 1: methanol / 20 °C 2: water / Reflux View Scheme
Multi-step reaction with 5 steps 1: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 2: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 3: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 4: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 5: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 View Scheme

2,3-pyrazinedicarboxylic anhydride (4744-50-7) + water (7732-18-5) → 2,3-dicarboxypyrazine (89-01-0)

2,3-diethynylquinoxaline (91-19-0) + potassium permanganate + alkali → 2,3-dicarboxypyrazine (89-01-0)

3-cyanopyrazine-2-carboxamide (66505-29-1) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 2: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 3: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 4: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 View Scheme

3-cyanopyrazine-2-carboxylic acid (70546-26-8) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 2: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 3: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 View Scheme

3-amidecarbonylpyrazine-2-carboxylic acid (67367-37-7) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With K3Na[Mo(CN)4O2]·6H2O In ethanol; water at 39.84℃; pH=8.5;

5,5-dimethoxy-5H-pyrrolo[3,4-b]pyrazin-7-ylamine → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
With water Reflux;

pyrazine-2,3-dicarboxamide (6164-78-9) → 2,3-dicarboxypyrazine (89-01-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 2: K3Na[Mo(CN)4O2]·6H2O / ethanol; water / 39.84 °C / pH 8.5 View Scheme

methanol (67-56-1) + 2,3-dicarboxypyrazine (89-01-0) → pyrazine-2,3-dicarboxylic acid dimethyl ester (6164-77-8)

Conditions	Yield
With hydrogenchloride In isopropyl alcohol for 24h; Heating;	100%
hydrogenchloride In water for 16h; pH=2; Heating / reflux;	100%
With thionyl chloride for 5h; Heating;	91%

2,3-dicarboxypyrazine (89-01-0) → 2,3-Pyrazindicarbonsaeure-dichlorid (52304-61-7)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 5h; Reflux;	100%
With thionyl chloride; N,N-dimethyl-formamide for 5h; Reflux;	100%
With phosphorus pentachloride at 180℃; for 2h;	29%
With thionyl chloride for 18h; Reflux;
With thionyl chloride In N,N-dimethyl-formamide for 5h; Reflux;

hydrogenchloride (7647-01-0) + 2,3-dicarboxypyrazine (89-01-0) + water (7732-18-5) + lead(II) oxide → Pb2Cl2(Hpzdc)2(H2O)2

Conditions	Yield
With piperazine at 60℃;	100%

4-(aminomethyl)pyridine (3731-53-1) + 2,3-dicarboxypyrazine (89-01-0) → C12H8N4O2 (1146213-60-6)

Conditions	Yield
for 0.0333333h; Microwave irradiation;	98%

cobalt(II) nitrate hexahydrate + 2,3-dicarboxypyrazine (89-01-0) + water (7732-18-5) + hydrazine hydrate (7803-57-8) → cobalt(II) 2,3-pyrazinedicarboxylate hydrazinate trihydrate

Conditions	Yield
In water hot soln. of metal nitrate added to hot soln. of carboxylic acid and hydrazine hydrate with stirring; pptd. after 1 h, digested for 1 h, isolated, washed with water-alcohol, diethyl ether, dried under vac., elem. anal., powder XRD;	97%

2,3-dicarboxypyrazine (89-01-0) + bismuth(III) oxide (1304-76-3) → {Bi(pz-2-(COO)-3-(COO))2}(OH)

Conditions	Yield
In water soln. of the acid in H2O added to a suspn. of Bi2O3 in H2O, reflux, 48 h, until total consumption of the acid, mixt. cooled to room temp.; filtered, ppt. washed with H2O and EtOH, dried (vac.); elem. anal.;	96%

2-Aminomethylthiophene (27757-85-3) + 2,3-dicarboxypyrazine (89-01-0) → C11H7N3O2S (1146213-61-7)

Conditions	Yield
for 0.05h; Microwave irradiation;	96%

(2-aminomethylpyridine) (3731-51-9) + 2,3-dicarboxypyrazine (89-01-0) → C12H8N4O2 (1146213-59-3)

Conditions	Yield
for 0.0333333h; Microwave irradiation;	96%

1,4-pyrazine (290-37-9) + copper(I) nitrate trihydrate + 2,3-dicarboxypyrazine (89-01-0) → [Cu2(2,3-pyrazinedicarboxylate)2(pyrazine)]n

Conditions	Yield
With sodium hydroxide for 2h;	96%

1,4-pyrazine (290-37-9) + copper(II) nitrate trihydrate + 2,3-dicarboxypyrazine (89-01-0) → [Cu2(2,3-pyrazinedicarboxylate)2(pyrazine)]n

Conditions	Yield
With sodium hydroxide In water for 2h;	96%
With sodium hydroxide In water at 25℃; for 2h;	1.32 g

2,3-dicarboxypyrazine (89-01-0) + nickel(II) nitrate hydrate + water (7732-18-5) + hydrazine hydrate (7803-57-8) → nickel(II) 2,3-pyrazinedicarboxylate hydrazinate trihydrate

Conditions	Yield
In water hot soln. of metal nitrate added to hot soln. of carboxylic acid and hydrazine hydrate with stirring; pptd. after 1 h, digested for 1 h, isolated, washed with water-alcohol, diethyl ether, dried under vac., elem. anal., powder XRD;	95%

2,3-dicarboxypyrazine (89-01-0) + 1,2-diaminocyclohexane (694-83-7) → C12H12N4O (1225211-01-7)

Conditions	Yield
for 0.0666667h; Neat (no solvent); Microwave irradiation;	95%

1,4-pyrazine (290-37-9) + copper(II) perchlorate hexahydrate + 2,3-dicarboxypyrazine (89-01-0) → [Cu2(2,3-pyrazinedicarboxylate)2(pyrazine)]n

Conditions	Yield
With sodium hydroxide In water at 20℃; for 1h; Time;	95%

1,4-pyrazine (290-37-9) + 2,3-dicarboxypyrazine (89-01-0) + copper hydroxide (20427-59-2) → [Cu2(2,3-pyrazinedicarboxylate)2(pyrazine)]n

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.5h; pH=6.4; Time;	95%

1,4-pyrazine (290-37-9) + 2,3-dicarboxypyrazine (89-01-0) + copper nitrate hemi(pentahydrate) → [Cu2(2,3-pyrazinedicarboxylate)2(pyrazine)]n

Conditions	Yield
With sodium hydroxide In water at 20℃; for 1h; Time;	95%

2,3-dicarboxypyrazine (89-01-0) → 2,3-pyrazinedicarboxylic anhydride (4744-50-7)

Conditions	Yield
With acetic anhydride for 0.0833333h;	94%
With acetic anhydride Heating;	93%
With acetic anhydride for 0.166667h; Heating;	83%

2,3-dicarboxypyrazine (89-01-0) + cadmium(II) nitrate tetrhydrate + hydrazine hydrate (7803-57-8) → cadmium 2,3-pyrazinedicarboxylate hydrazinate (861888-11-1)

Conditions	Yield
In water hot soln. of metal nitrate added to hot soln. of carboxylic acid and hydrazine hydrate with stirring; pptd. after few min, digested for 1 h, isolated, washed with water-alcohol, diethyl ether, dried under vac., elem. anal., powder XRD;	93%

2,3-dicarboxypyrazine (89-01-0) + water (7732-18-5) + copper(ll) bromide (7789-45-9) → ([Cu(pyrazine-2,3-dicarboxylate)(H2O)]4*HBr)n

Conditions	Yield
With 2-(1-aminoethylamino)ethanol or triethanolamine In methanol; water CuBr2 (0.02 mol), a ligand (0.02 mol), 2-(2-aminoethylamino)ethanol or triethanolamine (ca. 0.02 mol) were dissolved in MeOH/water (1/1); the soln. was heated at 70-80°C for 2 h with stirring under a reflux condenser; the ppt. was filtered, washed with chloroform and dried in air; elem. anal.;	93%

2,3-dicarboxypyrazine (89-01-0) + zinc(II) nitrate hydrate + hydrazine hydrate (7803-57-8) → zinc 2,3-pyrazinedicarboxylate hydrazinate (861888-10-0)

Conditions	Yield
In water hot soln. of metal nitrate added to hot soln. of carboxylic acid and hydrazine hydrate with stirring; pptd. after few min, digested for 1 h, isolated, washed with water-alcohol, diethyl ether, dried under vac., elem. anal., powder XRD;	92%

TETRAHYDROFURFURYLAMINE (4795-29-3) + 2,3-dicarboxypyrazine (89-01-0) → 6-((tetrahydrofuran-2-yl)methyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione (1204831-09-3)

Conditions	Yield
for 0.05h; Microwave irradiation;	92%

2,3-dicarboxypyrazine (89-01-0) + Cyclopropylamine (765-30-0) → 6-cyclopropyl-6H-pyrrolo[3,4-b]pyrazine-5,7-dione (1204831-10-6)

Conditions	Yield
for 0.0333333h; Microwave irradiation;	90%

2,3-dicarboxypyrazine (89-01-0) + 1,2-diamino-benzene (95-54-5) → C12H6N4O (1225211-04-0)

Conditions	Yield
for 0.0833333h; Neat (no solvent); Microwave irradiation;	90%

2,3-dicarboxypyrazine (89-01-0) + Trimethylenediamine (109-76-2) → 6-(3-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)propyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione

Conditions	Yield
at 135℃; for 0.0666667h; Microwave irradiation;	89%

1-(2-aminoethyl)piperidine (27578-60-5) + 2,3-dicarboxypyrazine (89-01-0) → C13H16N4O2 (1089731-62-3)

Conditions	Yield
for 0.0833333h; Microwave irradiation;	88%

2,3-dicarboxypyrazine (89-01-0) + furan-2-ylmethanamine (617-89-0) → 6-(furan-2-ylmethyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione (950259-92-4)

Conditions	Yield
for 0.0833333h; Microwave irradiation;	88%

2,3-dicarboxypyrazine (89-01-0) + water (7732-18-5) + copper(ll) bromide (7789-45-9) → ([Cu3(pyrazine-2,3-dicarboxylic acid)2(pyrazine-2,3-dicarboxylate)2(H2O)3]*2H2O)n

Conditions	Yield
In methanol; water CuBr2 (2.3 mmol) and a ligand (3 mmol) were dissolved in MeOH/water (1/1); the soln. was heated at 70-80°C for 2 h with stirring under a reflux condenser; the ppt. was filtered, washed with chloroform and dried in air; elem. anal.;	88%

2,3-dimethylpyrazine (5910-89-4) + 2,3-dicarboxypyrazine (89-01-0) + silver nitrate → [Ag2(Hpyzdc)2(μ-dmpyz)]

Conditions	Yield
With sodium hydroxide In water pH=7;	88%

2,3-dicarboxypyrazine (89-01-0) + ethylenediamine (107-15-3) → 6-(2-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)ethyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione (134150-46-2)

Conditions	Yield
at 135℃; for 0.0666667h; Microwave irradiation;	88%

2,3-dicarboxypyrazine (89-01-0) + silver nitrate → NH4(1+)*Ag(1+)*C4H2N2(CO2)2(2-)=(NH4)[Ag(C4H2N2(CO2)2)] (172043-91-3)

Conditions	Yield
With NH3 In ammonia aq. ammonia=NH3; molar ratio Ag:carboxylic acid=2:1, in 10% NH3; crystn. on evapn. (room temp., in dark, 3 d); elem. anal.;	87%

[2,2]bipyridinyl (366-18-7) + 2,3-dicarboxypyrazine (89-01-0) + cadmium(II) acetate dihydrate (5743-04-4) → [Cd(pyrazine-2,3-dicarboxylate)(2,2'-bipyridine)]n*nH2O (1100056-86-7)

Conditions	Yield
With NaOH In water High Pressure; stirring mixt. of cadmium compd., pyrazine deriv., bipyridine, NaOH and water in air for 1 h, heating at 160°C for 3 d; isolation of crystals, washing with water, elem. anal.;	86%

Upstream product

• 91-19-0 2,3-diethynylquinoxaline 
• 13481-25-9 pyrazine-2,3-dicarbonitrile 
• 4744-50-7 2,3-pyrazinedicarboxylic anhydride 
• 7732-18-5 water 
• 66505-29-1 3-cyanopyrazine-2-carboxamide 
• 70546-26-8 3-cyanopyrazine-2-carboxylic acid 
• 67367-37-7 3-amidecarbonylpyrazine-2-carboxylic acid 
• 6164-78-9 pyrazine-2,3-dicarboxamide 
• 46150-15-6 pyrazine-2,3-dicarboxylatocopper(II) 
• 921-52-8 2,3-Diaminosuccinic acid 
• 131543-46-9 Glyoxal 

Downstream Products

• 6164-77-8 pyrazine-2,3-dicarboxylic acid dimethyl ester 
• 4744-50-7 2,3-pyrazinedicarboxylic anhydride 
• 102468-20-2 pyrazine-2,3-dicarboxylic acid diphenacyl ester 
• 98-96-4 pyrazinamide 
• 290-37-9 1,4-pyrazine 
• 98-97-5 2-pyrazylcarboxylic acid 
• 84619-47-6 (2R,3S)-piperazine-2,3-dicarboxylic acid 
• 404824-11-9 Ru[P(C₆H₅)3]2(C₄H₂N₂(COO)(COOH))2 
• 1352126-23-8 RuHCl(CO)(pyz-2-COO-3-COOCH₃)(PPh₃)2*H₂O 
• 754196-97-9 2-amino-3-nitropyrazine 
• 2427-90-9 diethyl pyrazine-2,3-dicarboxylate 

Relevant articles and documents

Method for preparing nitrogen-containing six-membered ring dicarboxylic acid

The invention relates to compound preparation, particularly to a method for preparing nitrogen-containing six-membered ring dicarboxylic acid from a benzo nitrogen-containing six-membered ring compound. According to the method, a raw material compound and a sodium chlorate aqueous solution are catalyzed under an acidic condition to obtain nitrogen-containing six-membered ring dicarboxylic acid, wherein the raw material is a nitrogen-containing six-membered heterocyclic benzocyclic compound. According to the invention, the catalyst of the reaction system is low in toxicity and low in cost, no new impurity is generated in the post-treatment step, and large-scale production is facilitated.

Nucleophically transformed N-heterocyclic nitriles trapped by cyanooxomolybdates(IV): Crystallographic and spectroscopic study

The reaction of K3Na[Mo(CN)4O2] ·6H2O with 2,3-dicyanopyrazine or 2-pyridinecarbonitrile in aqueous media results in isolation of two new compounds of formulae (PPh 4)2[Mo(CN)3O(pzac)]·2H2O (Hpzac = 3-carbamoyl-2-pyrazinecarboxylic acid) and (PPh4) 2[Mo(CN)3O(pynccn)]·3H2O·EtOH (Hpynccn = 2-pyridineiminocarbonitrile) respectively. X-ray single crystal structure measurements as well as physicochemical measurements confirm transformations of 2,3-dicyanopyrazine to 3-carbamoyl-2-pyrazinecarboxylic acid and 2-pyridinecarbonitrile to 2-pyridineiminocarbonitrile. All complexes are characterized by elemental analysis, IR and UV-Vis spectroscopy. Metal-assisted ligand transformations are studied spectrophotometrically in the pH range 8.5-11.5. Two different pathways of nitrile reactivity are shown and discussed.

Permanganate Oxidation of Quinoxaline and Its Derivatives

The oxidation reaction of a series of quinoxaline derivatives, using KMnO4 in the presence or absence of NaOH, are described.Neutral oxidation of 2-chloro- and 2,3-dichlorodioxalines 2-4 afforded the corresponding chloro- and dichloropyrazinedicarboxilic acids 13 and 14 in good yield.On the other hand, oxidation of quinoxalin-2(1H)-one and 1,4-dihydroquinoxaline-2,3-dione derivatives in alkaline medium gave different products, with the quinoxalin-2(1H)-one (5) forming 1,4-dihydroquinoxaline-2,3-dione (9), while various substituted quinoxalin-2,3-dione derivatives (see 9-11) gave a new type of dimeric products.The structural assignments for the new compounds were based on spectroscopic data.