699-98-9

Basic information

• Product Name: 2,3-Pyridinedicarboxylic anhydride
• Synonyms: QUINOLINIC ANHYDRIDE;PYRIDINE-2,3-DICARBOXYLIC ACID ANHYDRIDE;PYRIDINE-2,3-DICARBOXYLIC ANHYDRIDE;FURO[3,4-B]PYRIDINE-5,7-DIONE;2,3-PYRIDINEDICARBOXYLIC ANHYDRIDE;2,3-PyridinedicarboxylicAcidAnhydride;Pyridinedicarboxylicanhydride;2,3-PYRIDINEDICARBOXYLIC ANHYDRIDE (QUINOLINIC ANHYDRIDE)
• CAS NO: 699-98-9
• Molecular Formula: C₇H₃NO₃
• Molecular Weight: 149.1
• EINECS: 211-834-1
• Product Categories: pyridine derivative;Aromatics;Heterocycles;Miscellaneous Reagents;Building Blocks;C7;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines;Heterocycle-Pyridine series
• Mol File: 699-98-9.mol

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 270.14°C (rough estimate)
• Flash Point: 156.2 °C
• Appearance: white crystal powder
• Density: 1.4974 (rough estimate)
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.4835 (estimate)
• Storage Temp.: Room temperature.
• PKA: -2.24±0.20(Predicted)
• Water Solubility: Optimal solubility in water.
• Sensitive: Moisture Sensitive
• BRN: 125111
• CAS DataBase Reference: 2,3-Pyridinedicarboxylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Pyridinedicarboxylic anhydride(699-98-9)
• EPA Substance Registry System: 2,3-Pyridinedicarboxylic anhydride(699-98-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 699-98-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-Pyridinedicarboxylic anhydride is used as a key intermediate in organic synthesis for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its anhydride functionality allows for the formation of esters and amides, which are essential in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-Pyridinedicarboxylic anhydride is utilized as a building block for the synthesis of drugs with diverse therapeutic applications. Its reactivity and structural features enable the development of novel drug candidates with improved efficacy and selectivity.
Used in Agrochemical Industry:
2,3-Pyridinedicarboxylic anhydride also finds application in the agrochemical industry, where it is employed in the synthesis of pesticides and other crop protection agents. Its ability to form stable derivatives makes it a valuable component in the development of effective and environmentally friendly agrochemicals.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2,3-Pyridinedicarboxylic anhydride is used as a precursor for the synthesis of various high-value compounds, such as dyes, pigments, and advanced materials. Its unique chemical properties contribute to the creation of innovative products with specific performance characteristics.

InChI:InChI=1/C7H3NO3/c9-6-4-2-1-3-8-5(4)7(10)11-6/h1-3H

Upstream product

• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 10026-13-8 phosphorus pentachloride 
• 89-01-0 2,3-dicarboxypyrazine 
• 108-24-7 acetic anhydride 

Downstream Products

• 91692-76-1 3-(4-chlorobenzoyl)-2-pyridinecarboxylic acid 
• 875256-15-8 3-hydroxymethyl-pyridine-2-carboxylic acid 
• 81113-14-6 2-hydroxymethyl-3-pyridinecarboxylic acid 
• 365515-80-6 6-[1-(3-Methoxyphenyl)ethyl]-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 365515-82-8 6-(4-Phenylbutan-2-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 365515-81-7 6-(1-Phenylpropan-2-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 6789-51-1 6-methyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 37458-38-1 6-(4-chloro-phenyl)-pyrrolo[3,4-b]pyridine-5,7-dione 
• 15828-08-7 3-(N-tert-butyl-carboxamido)-pyridine 
• 1752-96-1 N-phenylnicotinamide 
• 6538-81-4 6-Phenylpyrrolo<3,4-b>pyridine-5,7(6H)-dione 
• 94301-63-0 quinolinic acid dianilide 
• 2503-55-1 N-benzylnicotinamide 
• 18184-75-3 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 

Relevant articles and documents

SYNTHESIS OF A SICKLE CELL DISEASE AGENT AND INTERMEDIATES THEREOF

New processes for preparing 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5- yl)pyridin-3-yl)methoxy)benzaldehyde, an agent developed for the treatment of sickle cell disease, and intermediates thereof, are provided herein.

Novel synthesis method of 3-fluoropyridine-2-methanol

The invention relates to the field of compound preparation, in particular to a novel synthesis method of 3-fluoropyridine-2-methanol. The 3-fluoropyridine-2-methanol has a structure as shown in a formula V. According to the synthesis method, cheap quinolinic acid is used as an initial raw material, the target product namely 3-fluoropyridine-2-methanol is obtained through the steps of anhydride, esterification, ammoniation, amino fluorination, ester group reduction, and the like, and the structure of the target product is characterized by 1HNMR and 13CNMR. The synthetic method is a brand new synthetic method of 3-fluoropyridine-2-methanol, and has the advantages of low cost, simple technology, high yield, good quality, and high industrialization value.

Synthesis method of imazapyracid

The invention relates to a synthesis method of imazapyracid, relates to a preparation method of a compound, and in particular, relates to a production and synthesis method of imazapyracid; the methodis characterized by comprising the steps: taking quinolinic acid as a raw material and reacting with acetic anhydride to generate 2,3-pyridine dicarboxylic anhydride; and under a low-temperature condition, continuously reacting with alcohol to generate a compound represented by a structural formula (I), carrying out a ring closing reaction with 2-amino-2,3-dimethylbutyramide under an alkaline condition, extracting to adjust the pH value, and thus obtaining the imazapyracid product. The method has the advantages that a novel method for obtaining imazapyracid is provided, the route reaction speed is high, the product purity is extremely high, the yield is high, the reaction conditions are mild, isomers are avoided, catalysts are not needed, three wastes are few, the synthesis process is extensive, the reaction conditions are optimized, the reaction equipment cost is reduced, generated products are easy to separate, and the production process is simplified.

Preparation method of moxifloxacin important intermediate (by machine translation)

The invention discloses a preparation method, of an important intermediate of moxifloxacin. 2, 3 - Picolinic acid and acetic anhydride are charged first to the reaction kettle, stirred, and stirred to prepare a reaction feed liquid; a first reaction liquid is pumped into a continuous acid removal system filled with an acid remover, and then the reaction liquid is pumped into second reaction kettle; the second reaction kettle is used for stirring reaction; and after the reaction is finished, the reaction mixture liquid is stirred by 2nd. Concentration, a significant intermediate, namely compound 6 - benzyl - 555H-pyrrolo [3, 4 - b] pyridine -5, 7 - (6H) - diketone, is obtained under reduced pressure. The method effectively improves the conversion, greatly improves the yield, enhances the operability, realizes low energy consumption, and can realize the purpose. (by machine translation)

Design and synthesis of novel PARP-1 inhibitors based on pyridopyridazinone scaffold

Various pyridopyridazinone derivatives were designed as Poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. The pyridopyridazinone scaffold was used as an isostere of the phthalazine nucleus of the lead compound Olaparib in addition to some modifications in the tail part of the molecule. Preliminary biological evaluation indicated that most compounds possessed inhibitory potencies comparable to Olaparib in nanomolar level. The best PARP-1 inhibitory activity was observed for compound 8a with (IC50 = 36 nM) compared to Olaparib as a reference drug (IC50 = 34 nM). Molecular modeling simulation revealed that, the designed compounds docked well into PARP-1 active site and their complexes are stabilized by three key hydrogen bond interactions with both Gly863 and Ser904 as well as other favorable π-π and hydrogen-π stacking interactions with Tyr907 and Tyr896, respectively. Computational ADME study predicted that the target compounds 8a and 8e have proper pharmacokinetic and drug-likeness properties. These outcomes afford a new structural framework for the design of novel inhibitors for PARP-1.

Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride

Literature examples illustrating the use of oxalyl chloride to prepare dicarboxylic acid anhydrides are surprisingly limited. At the same time, we have discovered a method involving the use of this readily available reagent which allowed the preparation of novel cyclic anhydrides where other, more conventional, methods had failed. Herein, we demonstrate that the method is applicable to a wide diversity of substrates, delivers good to excellent yields of cyclic anhydrides without chromatographic purification and can be considered a synthetic tool of choice whenever dicarboxylic acid cyclodehydration is required.

Efficient synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane

An efficient synthetic route for moxifloxacin chiral intermediate via five steps was established. First, dehydration, N-acylation, and cyclization were combined in one pot to meet the industrial requirement. Then relatively low hydrogen pressure was employed in the catalytic hydrogenation reaction with high yield. Isopropanol/water system was used in resolution, which guaranteed high yield and perfect optical purity. The racemic process conducted by manganese dioxide and Pd/C successfully converted the undesired enantiomer into the racemate and hence the total yield increased remarkably. Furthermore, mild hydrogen transfer catalytic hydrogenation method was utilized in debenzylation process instead of high-pressure hydrogenation. Total yield of 39.0% was achieved, which was much higher than that of 29.0% in literature.

1, 2, 3, 4- [...] compound and process for the synthesis of

The invention provides a synthetic and technological method of a 1,2,3,4-tetrahydrophthalazine compound used as an intermediate of bactericides and anti HIV (human immunodeficiency virus) and other new drugs. The 1,2,3,4-tetrahydrophthalazine compound is obtained by using various cheap and easily accessible phthalic acid or phthalic anhydride as a raw material for two steps of reaction. The method is easily accessible in raw material, low in cost, simple in reaction, easy in control, simple in processing and easy in amplification, and a large number of industrial by-product hydrazide can be found to be directly used as a raw material for the second step. The method is convenient to economic, reuses the industrial by-product as the raw material, and provides a feasible synthetic production and technological method of the 1,2,3,4-tetrahydrophthalazine compound for green chemical industry.

Design, Synthesis, Antifungal Activities and SARs of (R)-2-Aryl-4,5-dihydrothiazole-4-carboxylic Acid Derivatives

Based on the structure of natural product 2-aryl-4,5-dihydrothiazole-4-carboxylic acid, a series of novel (R)-2-aryl-4,5-dihydrothiazole-4-carboxylic acid derivatives were designed and synthesized. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The single crystal structure of compound 9b was determined by X-ray diffraction analysis. The antifungal activities were evaluated for the first time. The bioassay results indicated that most compounds exhibited moderate to good antifungal activities. The antifungal activities of compound 13a (against Cercospora arachidicola Hori), 13d (against Alternaria solani), and 16e (against Cercospora arachidicola Hori) were 61.9%, 67.3% and 61.9%, respectively, which are higher than those of the commercial fungicides chlorothalonil and carbendazim. Moreover, compound 13d exhibited excellent antifungal activities against 7 kinds of the fungi tested (66.7%, 77.3%, 63.0%, 87.9%, 70.0%, 70.0% and 80.0% at 50 μg?mL). Therefore, 13d can be used as a new lead structure for the development of antifungal agents.

Rilyazine Derivatives and Compositions for The Treatment of Cancer

The present application discloses Rilyazine analogs, methods for their preparation, and the treatment of cancer by the administration of an effective amount of the Rilyazine analogs to a patient in need thereof.