PYRIDINE-3,4-DICARBOXYLIC ANHYDRIDE Chemical Properties

Melting point:

75-77 °C (lit.)

Boiling point:

139-142 °C(Press: 12 Torr)

Density 

1.556±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-0.38±0.20(Predicted)

form 

solid

color 

White to off-white

Water Solubility 

Decomposes in water.

Sensitive 

Moisture Sensitive

InChI

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

InChIKey

KFKMGUPDWTWQFM-UHFFFAOYSA-N

SMILES

C1=NC=CC2C(=O)OC(=O)C1=2

CAS DataBase Reference

4664-08-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

PYRIDINE-3,4-DICARBOXYLIC ANHYDRIDE Usage And Synthesis

Chemical Properties

White to light yellow solid

Uses

Pyridine-3,4-dicarboxylic anhydride is an important organic intermediate. It is used in agrochemical, pharmaceutical and dyestuff field.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 37, p. 828, 1994 DOI: 10.1021/jm00032a018
The Journal of Organic Chemistry, 14, p. 97, 1949 DOI: 10.1021/jo01153a015

Synthesis

The general procedure for the synthesis of pyridine-3,4-dicarboxylic anhydride from 3,4-pyridinedicarboxylic acid is as follows: in a 1 L round-bottomed flask fitted with a drying tube, 3,4-pyridinedicarboxylic acid (160 g, 1 mol) and acetic anhydride (500 mL) were added. The reaction mixture was refluxed in an oil bath at 165°C for 2 hours. Upon completion of the reaction, decompression concentration was carried out to remove excess acetic anhydride. After cooling, a residual oily substance was obtained. Methyl tert-butyl ether (500 mL) was added to the residue and stirred overnight at room temperature. Subsequently, a dark brown solid precipitate precipitated and was separated by filtration. The filter cake was washed with 100 mL of methyl tert-butyl ether (MTBE) and dried under vacuum at 45°C to give 99 g of solid product in 76% yield.

References

[1] Journal of Organic Chemistry, 1992, vol. 57, # 22, p. 5891 - 5899
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 6, p. 828 - 837
[3] Patent: EP503537, 1992, A1
[4] Patent: CN104557704, 2017, B. Location in patent: Paragraph 0042; 0043; 0044
[5] Monatshefte fuer Chemie, 1890, vol. 11, p. 144

PYRIDINE-3,4-DICARBOXYLIC ANHYDRIDE(4664-08-8)Related Product Information

• Dimethyl 2,6-Pyridinedicarboxylate
• 3,5-DIHYDROXYPYRIDINE
• Dimethyl 2,4-pyridinedicarboxylate
• 2,4-Pyridinedicarboxylic acid, 2-Methyl ester
• 2-Pyridinemethanethiol
• 2,4-PYRIDINECARBOXYLIC ACID, 4-METHYL ESTER
• 2,4-Pyridinedicarboxylic acid
• Pyridine hydrochloride
• 2,6-Pyridinedicarbonitrile
• 4-Pyridinesulfonamide(6CI,9CI)
• 2,3,5,6-Tetraaminopyridine trihydrochloride
• Pyridine trifluoroacetate
• PYRIDINE-2-THIOAMIDE
• 2-Pyridinesulfonamide(6CI,7CI,9CI)
• dimethyl pyridine-3,5-dicarboxylate
• METHYL ISONICOTINATE
• Pyridine-N-oxide
• 2-Pyridinecarbaldehyde oxime