| Identification | More | [Name]
6-Methoxynicotinaldehyde | [CAS]
65873-72-5 | [Synonyms]
2-METHOXYPYRIDINE-5-CARBOXALDEHYDE
3-FORMYL-6-METHOXYPYRIDINE
5-FORMYL-2-METHOXYPYRIDINE
6-METHOXY-3-NICOTINALDEHYDE
6-METHOXY-3-PYRIDINECARBOXALDEHYDE
6-METHOXYNICOTINALDEHYDE
6-METHOXY-PYRIDINE-3-CARBALDEHYDE
3-Pyridinecarboxaldehyde, 6-methoxy-(9CI)
2-methoxy-5-pyridinecarboxaldehyde
2-Methoxypyridine-5-carboxaldehyde, 5-Formyl-2-methoxypyridine
6-methoxy-3-pyridinecorbaxaldehyde
6-Methoxypyridine-3-carboxaldehyde, 98%
6-Methoxy-3-pyridinecarboxaldehyde ,97% | [EINECS(EC#)]
627-354-4 | [Molecular Formula]
C7H7NO2 | [MDL Number]
MFCD02683446 | [Molecular Weight]
137.14 | [MOL File]
65873-72-5.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow crystalline powder | [Melting point ]
51-54 °C (lit.) | [Boiling point ]
65-70 °C(Press: 12 Torr) | [density ]
1.159±0.06 g/cm3(Predicted) | [Fp ]
225 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [form ]
Crystalline Powder | [pka]
1.60±0.10(Predicted) | [color ]
Off-white to light yellow | [Water Solubility ]
insoluble | [Detection Methods]
HPLC | [InChI]
InChI=1S/C7H7NO2/c1-10-7-3-2-6(5-9)4-8-7/h2-5H,1H3 | [InChIKey]
CTAIEPPAOULMFY-UHFFFAOYSA-N | [SMILES]
C1=NC(OC)=CC=C1C=O | [CAS DataBase Reference]
65873-72-5(CAS DataBase Reference) |
| 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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light yellow crystalline powder | [Uses]
An intermediate for the synthesis of the somatostatic sst3 receptor. | [General Description]
6-Methoxy-3-pyridinecarboxaldehyde, also known as 6-methoxy-3-nicotinaldehyde, can be prepared from 5-bromo-2-methoxypyridine. | [Synthesis]
At -78 °C, N-butyllithium (50 mL, 2.5 M hexane solution) was slowly added dropwise to a solution of 5-bromo-2-methoxypyridine (22.4 g, 119.1 mmol) in anhydrous tetrahydrofuran (240 mL). After the dropwise addition, the reaction mixture was continued to be stirred at -78 °C for 90 min. Subsequently, N,N-dimethylformamide (18.5 mL, 238.3 mmol) was added slowly dropwise and stirring was continued for 90 min at -78 °C. Upon completion of the reaction, the mixture was slowly warmed to room temperature. The reaction mixture was poured into saturated sodium bicarbonate solution (1000 mL) and extracted with ether (3 x 250 mL). The organic phases were combined, dried with magnesium sulfate, filtered and concentrated to dryness to give 15.4 g (94% yield) of 6-methoxy-3-pyridinecarboxaldehyde as a light yellow solid. The product was characterized by 1H NMR (DMSO-d6): δ= 9.97 (s, 1H), 8.77 (m, 1H), 8.12 (dd, 1H, J = 8.6, 2.3 Hz), 6.99 (d, 1H, J = 8.7 Hz), 3.97 (s, 3H).LC/MS analysis (Method A): retention time = 0.25 min, purity = 92.8%, calculated mass = 137, [M + H]+ = 138. HPLC analysis (Method C): retention time = 4.9 min, purity = 95.9% (210-370 nm) and 98.7% (256 nm). | [References]
[1] Synthesis, 2012, vol. 44, # 5, p. 735 - 746
[2] Journal of medicinal chemistry, 2004, vol. 47, # 20, p. 4829 - 4837
[3] Patent: US2006/19965, 2006, A1. Location in patent: Page/Page column 27
[4] Synthesis, 1994, # 1, p. 87 - 92
[5] Synlett, 2009, # 15, p. 2508 - 2512 |
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