6-Methoxynicotinaldehyde

Bezeichnung:6-Methoxynicotinaldehyde

CAS-Nr65873-72-5

Englisch Name:6-Methoxynicotinaldehyde

CBNumberCB3390560

SummenformelC7H7NO2

Molgewicht137.14

MOL-Datei65873-72-5.mol

6-Methoxynicotinaldehyde physikalisch-chemischer Eigenschaften

Schmelzpunkt	51-54 °C (lit.)
Siedepunkt	65-70 °C(Press: 12 Torr)
Dichte	1.159±0.06 g/cm3(Predicted)
Flammpunkt	225 °F
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
pka	1.60±0.10(Predicted)
Aggregatzustand	Crystalline Powder
Farbe	Off-white to light yellow
Wasserlöslichkeit	insoluble
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 Datenbank	65873-72-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
HazardClass	IRRITANT
HS Code	29339900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

6-Methoxynicotinaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
off-white to light yellow crystalline powder
Verwenden
Substrate used in a synthesis of flavanones via an L-proline-catalyzed condensation with o-hydroxyarylketones.
Verwenden
An intermediate for the synthesis of the somatostatic sst3 receptor.
Allgemeine Beschreibung
6-Methoxy-3-pyridinecarboxaldehyde, also known as 6-methoxy-3-nicotinaldehyde, can be prepared from 5-bromo-2-methoxypyridine.
Synthese

13472-85-0

68-12-2

65873-72-5

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).
Einzelnachweise
[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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