3,5-Dibromopyridine-4-carboxaldehyde

Bezeichnung:3,5-Dibromopyridine-4-carboxaldehyde

CAS-Nr70201-42-2

Englisch Name:3,5-Dibromopyridine-4-carboxaldehyde

CBNumberCB9500149

SummenformelC6H3Br2NO

Molgewicht264.9

MOL-Datei70201-42-2.mol

3,5-Dibromopyridine-4-carboxaldehyde physikalisch-chemischer Eigenschaften

Schmelzpunkt	118-122 °C (lit.)
Siedepunkt	278.1±35.0 °C(Predicted)
Dichte	2.090±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	Choroform (Slightly), Methanol (Slightly, Sonicated)
pka	-1.47±0.28(Predicted)
Aggregatzustand	Solid
Farbe	Pale Yellow to Light Yellow
InChI	InChI=1S/C6H3Br2NO/c7-5-1-9-2-6(8)4(5)3-10/h1-3H
InChIKey	WPBYVMDYYFWYAY-UHFFFAOYSA-N
SMILES	C1=NC=C(Br)C(C=O)=C1Br

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38-43
S-Sätze:	26-36/37
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
HazardClass	6.1
PackingGroup	Ⅲ
HS Code	2933399990
Speicherklasse	6.1D - Non-combustible acute toxic Cat.3 toxic hazardous materials or hazardous materials causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3

Gefahreninformationscode (GHS)

3,5-Dibromopyridine-4-carboxaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R43:Sensibilisierung durch Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Verwenden
3,5-Dibromo-4-pyridinecarboxaldehyde is easily soluble in water and miscible with organic solvents. It is used as an intermediate for synthesising the insecticide pyrazinone and in textiles to improve the stiffness of cotton fabrics.
Synthese

625-92-3

107-31-3

70201-42-2

Step 1: Diisopropylamine (2.4 g, 24.0 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) under nitrogen protection and cooled to 0 °C. A n-butyllithium solution (9.6 mL, 24.0 mmol) in hexane was slowly added dropwise and stirred continuously for 30 min at this temperature. Subsequently, additional anhydrous tetrahydrofuran (30 mL) was added and the reaction mixture was further cooled to -78 °C. To this low-temperature solution, dry 3,5-dibromopyridine (4.7 g, 20 mmol) was added, diluted dropwise with tetrahydrofuran (50 mL), and stirring was continued for 30 minutes. Next, methyl formate (2.4 g, 40 mmol) was added and the reaction mixture was continued stirring at -78 °C for 30 min. After slowly warming to room temperature, the reaction was quenched with saturated sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (50 mL × 3). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to afford the target product 3,5-dibromopyridine-4-carbaldehyde (26-b) as a light yellow solid (4.0 g, 75% yield).1H NMR (300 MHz, DMSO-d6) δ: 10.06 (s, 1H), 8.87 (s, 2H).
Einzelnachweise
[1] Patent: US2017/158680, 2017, A1. Location in patent: Paragraph 0418; 0419; 0420
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2789 - 2794
[3] Journal of Fluorine Chemistry, 2006, vol. 127, # 6, p. 755 - 759
[4] Patent: US6232320, 2001, B1

3,5-Dibromopyridine-4-carboxaldehyde Upstream-Materialien And Downstream Produkte

3,5-Dibromopyridine-4-carboxaldehyde Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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