5-Methyl 2,5-pyridinedicarboxylate
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5-Methyl 2,5-pyridinedicarboxylate
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CAS No:
17874-79-2
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Formula:
C8H7NO4
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Chemical Name:
5-Methyl 2,5-pyridinedicarboxylate
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Synonyms:
2,5-Pyridinedicarboxylic acid,5-methyl ester;5-Methyl 2,5-pyridinedicarboxylate;2-Carboxy-5-(methoxycarbonyl)pyridine;Methyl 2-carboxypyridine-5-carboxylate;5-Methoxycarbonylpyridine-2-carboxylic acid;NSC 236641;5-Carbomethoxypyridine-2-carboxylic acid;5-(Methoxycarbonyl)picolinic acid
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CAS No:
Characteristics
76.5
0.6
1.361±0.06 g/cm3(Predicted)
175.5-180 °C
347.9±27.0 °C(Predicted)
164.2±23.7 °C
1.560
21.5 [ug/mL]
Safety Information
IRRITANT
36/37/38-22
26-36/37/39-22
Xi,Xn
Irritant
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Methyl 2,5-pyridinedicarboxylate Use and Manufacturing
Pyridine 2, 5-dicarboxylic acid 5-methyl ester Pyridine 2, 5-dicarboxylic acid 5-methyl ester. The protocol of Faul et al. was followed (Faul, M.M., et al., 'Synthesis of Novel Retinoid X Receptor-Selective Retinoids' J Org. Chem. 2001, 66, 5772-5782). To a suspension of dimethyl pydrine-2, 5-dicarboxylate (10.09 g, 51.7 mmol) in methanol (130 mL) was added sodium hydroxide pellets (2.20 g, 55.0 mmol), and the heterogeneous reaction was stirred and refluxed for 4 h. After cooling to 65 °C, 2.0 N HCl (38 mL, 76 mmol) was slowly added, and over the course of addition, the solid dissolved and a precipitate formed. The reaction solution was allowed to cool to room temperature, and then it was cooled in an ice-bath and filtered. The filter-cake was washed with water to give an off-white product (7.71 g, 82percent). A sample of this crude, filtered product (1.09 g) was dissolved in boiling water (70 mL), and the solution was slowly cooled to room temperature, and then cooled in an ice-bath, before it was filtered to give a white, crystalline powder (0.98 g) at a 74percent overall yield:? NMR (400 MHz, d6-DMSO) ' 9.15 (dd, J= 2.0, 0.8, 1H), 8.44 (dd, J= 8.0, 2.0, 1H), 8.15 (dd, J= 8.0, 0.8, 1H), 3.91 (s, 3H), 3.34 (br s, 1H);
Compound has been shown to have insulin mimetic properties.
Computed Properties
Molecular Weight:181.15
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:181.03750770
Monoisotopic Mass:181.03750770
Topological Polar Surface Area:76.5
Heavy Atom Count:13
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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