| Identification | More | [Name]
2-METHOXY-3-PYRIDINECARBOXALDEHYDE | [CAS]
71255-09-9 | [Synonyms]
2-METHOXY-3-PYRIDINECARBOXALDEHYDE
2-METHOXYNICOTINALDEHYDE
2-METHOXY-PYRIDINE-3-CARBALDEHYDE
3-Pyridinecarboxaldehyde, 2-methoxy-(9CI)
2-Methoxy-3-pyridinecarboxaldenhyde
2-Methoxy-3-pyridinecaarboxaldehyde
2-METHYOXYNICOTINALDEHYDE
2-Methoxypyridine-3-carboxaldehyde
2-Methoxy-3-pyridinecarboxaldehyde ,98% | [Molecular Formula]
C7H7NO2 | [MDL Number]
MFCD04115112 | [Molecular Weight]
137.14 | [MOL File]
71255-09-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
200-201 °C (lit.) | [density ]
1.161 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5500(lit.)
| [Fp ]
205 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Liquid or Low Melting Solid | [pka]
1.60±0.10(Predicted) | [color ]
Colorless to yellow | [Sensitive ]
Air Sensitive | [Detection Methods]
GC,NMR | [InChI]
InChI=1S/C7H7NO2/c1-10-7-6(5-9)3-2-4-8-7/h2-5H,1H3 | [InChIKey]
PIFFMIDNNWOQLK-UHFFFAOYSA-N | [SMILES]
C1(OC)=NC=CC=C1C=O | [CAS DataBase Reference]
71255-09-9(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact. | [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 . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to yellow liquid | [Uses]
2-Methoxy-3-pyridinecarboxaldehyde may be used to synthesize the following:
- ethyl 5-amino-4-(2-methoxy-3-pyridyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinoline-3-carboxylate, a potent AChE inhibitor
- N-hydroxy-2-pyridinone-based arylsulfone containing a Zn-binding group (ZBG) as MMP-2/-9 inhibitor
| [Synthesis Reference(s)]
Tetrahedron Letters, 29, p. 773, 1988 DOI: 10.1016/S0040-4039(00)80206-3 | [Synthesis]
Sodium metal (0.35 g, 15.0 mmol) was slowly added to dry methanol (6 mL) at 0 °C and stirred until completely dissolved. Subsequently, a solution of anhydrous methanol (2 mL) of 2-chloro-3-pyridinecarboxaldehyde (0.708 g, 5.0 mmol) was added to the reaction system via syringe. The reaction mixture was heated to reflux temperature and maintained for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently evaporated under reduced pressure. The residue was dissolved in water (10 mL), neutralized with dilute hydrochloric acid and extracted with ether (3 x 10 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: petroleum ether/ethyl acetate, 4:1) to afford the target compound 2-methoxy-3-pyridine aldehyde (0.473 g, 69% yield) as a colorless oil.1H NMR (300 MHz, CDCl3) δ 10.34 (d, J = 0.8 Hz, 1H), 8.36 (dd, J = 4.9, 2.1 Hz, 1H), 8.09 (dd, J = 7.4, 2.1 Hz, 1H), 7.00 (ddd, J = 7.4, 4.9, 0.8 Hz, 1H), 4.07 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 189.1, 164.4, 152.8, 137.6, 118.8, 117.3, 54.0. | [References]
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415 |
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