| Identification | More | [Name]
5-(Methoxycarbonyl)pyridine-2-carboxylic acid | [CAS]
17874-79-2 | [Synonyms]
5-(METHOXYCARBONYL)-2-PYRIDINECARBOXYLIC ACID
5-(METHOXYCARBONYL)PYRIDINE-2-CARBOXYLIC ACID
BUTTPARK 43\57-32
5-(Methoxycarbonyl)picolinic acid
5-(Methoxycarbonyl)pyridine-2-carboxyic acid
5-(Methoxycarbonyl)-2-Pyridine
5-(Methoxycarbonyl)pyridine-2-carboxylic acid, 95+%
Pyridine-2,5-dicarboxylic acid 5-methyl ester | [Molecular Formula]
C8H7NO4 | [MDL Number]
MFCD00179343 | [Molecular Weight]
181.15 | [MOL File]
17874-79-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
187 °C | [Boiling point ]
347.9±27.0 °C(Predicted) | [density ]
1.361±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform (Sparingly, Heated), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.21±0.10(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C8H7NO4/c1-13-8(12)5-2-3-6(7(10)11)9-4-5/h2-4H,1H3,(H,10,11) | [InChIKey]
NTCKZTBRFXTYBD-UHFFFAOYSA-N | [SMILES]
C1(C(O)=O)=NC=C(C(OC)=O)C=C1 | [CAS DataBase Reference]
17874-79-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white powder | [Uses]
Compound has been shown to have insulin mimetic properties. | [Synthesis]
The general procedure for the synthesis of 5-(methoxycarbonyl)-2-pyridinecarboxylic acid from methyl 2,5-pyridinedicarboxylate was as follows: 5-methyl 2,5-pyridinedicarboxylate (28 g, 0.146 mol) was placed in a 500 mL three-necked, round-bottomed flask assembled with a condenser and a dropping funnel with methanol (260 mL). Sodium hydroxide (6.2 g, 0.155 mol) was added slowly with stirring and the addition process lasted for 3 hours and 30 minutes. Subsequently, the reaction mixture was heated to reflux condition to form a white suspension. Under reflux conditions, 2 M hydrochloric acid solution (121 mL) was added slowly and dropwise over a period of 1 h. The reaction solution gradually changed to yellow color. Upon completion of the reaction, the flask was transferred to an ice-water bath for cooling and the solid product precipitated at room temperature. The precipitate was collected by filtration and washed sequentially with a 2:1 methanol/water mixture (35 mL) and water (50 mL). The resulting solid product was dried overnight at room temperature to yield 19.68 g (75% yield) of the target compound. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, DMSO-d6) data: δ 9.12 (m, 1H), 8.40 (dd, J = 2.1 Hz and 8.1 Hz, 1H), 8.12 (dd, J = 0.9 Hz and 8.4 Hz, 1H), 3.89 (s, 3H). Nuclear magnetic resonance carbon (13C NMR, 75.45 MHz, DMSO-d6) data: δ 165.9, 165.0, 152.1, 150.2, 138.8, 128.3, 125.0, 53.2. | [References]
[1] Tetrahedron Letters, 2005, vol. 46, # 6, p. 967 - 969
[2] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5
[3] European Journal of Organic Chemistry, 2010, # 1, p. 174 - 182
[4] Patent: US2007/231300, 2007, A1. Location in patent: Page/Page column 14
[5] Patent: US2008/103192, 2008, A1. Location in patent: Page/Page column 14 |
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