| Identification | More | [Name]
5-Methylpyridine-2,3-dicarboxylic acid | [CAS]
53636-65-0 | [Synonyms]
5-Methylpyridine-2,3-dicarboxylic acid
(5-Methyl-2,3-pyridinedicarboxylic acid) | [Molecular Formula]
C8H7NO4 | [MDL Number]
MFCD05662425 | [MOL File]
53636-65-0.mol | [Molecular Weight]
181.15 |
| Chemical Properties | Back Directory | [Boiling point ]
436.2±45.0 °C(Predicted) | [density ]
1.460 | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
5.41±0.20(Predicted) | [Appearance]
Light yellow to brown Solid | [InChI]
InChI=1S/C8H7NO4/c1-4-2-5(7(10)11)6(8(12)13)9-3-4/h2-3H,1H3,(H,10,11)(H,12,13) | [InChIKey]
JPIJMXOJEHMTPU-UHFFFAOYSA-N | [SMILES]
C1(C(O)=O)=NC=C(C)C=C1C(O)=O | [CAS DataBase Reference]
53636-65-0 | [EPA Substance Registry System]
2,3-Pyridinedicarboxylic acid, 5-methyl- (53636-65-0) |
| Hazard Information | Back Directory | [Chemical Properties]
White or light yellow crystalline powder | [Uses]
5-Methoxymethylpyridine-2,3-dicarboxylic acid is used in the preparation of herbicides of the class imidazolinones. | [Synthesis]
A) 3-methyl-8-hydroxyquinoline (15.9 g, 0.10 mol) is dissolved in dichloromethane and slowly added dropwise to 70% nitric acid (126 g, 1.8 mol) at 80°C to 100°C over a period of 1 hour while stirring is maintained. The gases generated during the reaction are scrubbed and vented. The reaction mixture is then heated at 100°C to 105°C for 4 h. After cooling to 85°C, the reaction mixture is treated with 88% formic acid (85%-95% concentration) for 20 min and continued heating at 85°C to 95°C for 0.5 h. The reaction solution is cooled to 0.5°C. The reaction solution was cooled to 0°C, stirred for 1 hour and filtered. The resulting solid was washed with acetone and dried to give 10.6 g of 5-methyl-2,3-pyridinedicarboxylic acid (58.6% yield), which was analyzed by HPLC for 97.4% purity. | [References]
[1] Patent: US5371229, 1994, A
[2] Patent: US5371229, 1994, A
[3] Journal of the Chemical Society, 1956, p. 4433,4437
[4] Synthesis, 1989, # 11, p. 880 - 882 |
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