| Identification | More | [Name]
PYRIDINE-3,4-DICARBOXYLIC ANHYDRIDE | [CAS]
4664-08-8 | [Synonyms]
1,3-DIHYDROFURO[3,4-C]PYRIDINE-1,3-DIONE
3,4-PYRIDINEDICARBOXYLIC ACID ANHYDRIDE
3,4-PYRIDINEDICARBOXYLIC ANHYDRIDE
CINCHOMERONIC ANHYDRIDE
FURO[3,4-C]PYRIDINE-1,3-DIONE
PYRIDINE-3,4-DICARBOXYLIC ANHYDRIDE
3,4-Pyridinecarboxylic acid anhydride
Pyridine-3,4-dicarboxylic anhydride ,97% | [EINECS(EC#)]
628-335-3 | [Molecular Formula]
C7H3NO3 | [MDL Number]
MFCD00010680 | [Molecular Weight]
149.1 | [MOL File]
4664-08-8.mol |
| Chemical Properties | Back Directory | [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 | [form ]
solid | [pka]
-0.38±0.20(Predicted) | [color ]
White to off-white | [Water Solubility ]
Decomposes in water. | [Sensitive ]
Moisture Sensitive | [Detection Methods]
HPLC | [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) | [Storage Precautions]
Store under nitrogen;Moisture sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
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