3-Bromo-2-hydroxypyridine

Bezeichnung:3-Bromo-2-hydroxypyridine

CAS-Nr13466-43-8

Englisch Name:3-Bromo-2-hydroxypyridine

CBNumberCB4747158

SummenformelC5H4BrNO

Molgewicht174

MOL-Datei13466-43-8.mol

3-Bromo-2-hydroxypyridine physikalisch-chemischer Eigenschaften

Schmelzpunkt	179-183 °C
Siedepunkt	336.6±42.0 °C(Predicted)
Dichte	1.776±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Aggregatzustand	Crystalline Powder
pka	10.53±0.10(Predicted)
Farbe	White to off-white
Wasserlöslichkeit	Slightly soluble in water.
BRN	109846
InChI	InChI=1S/C5H4BrNO/c6-4-2-1-3-7-5(4)8/h1-3H,(H,7,8)
InChIKey	YDUGVOUXNSWQSW-UHFFFAOYSA-N
SMILES	C1(=O)NC=CC=C1Br
CAS Datenbank	13466-43-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	36/37/38-41-37/38-22
S-Sätze:	26-36-39
WGK Germany	3
HS Code	29337900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

3-Bromo-2-hydroxypyridine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
R37/38:Reizt die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
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.
S39:Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Light yellow powder
Verwenden
3-Bromo-2-hydroxypyridine is sued as an active ingredient pharmaceuticals, in medicine.
Verwenden
3-Bromo-2-hydroxypyridine is used in the synthesis of pyrazolopyridines as γ-secratase modulators.
Synthese

13534-99-1

13466-43-8

The general procedure for the synthesis of 3-bromo-2-hydroxypyridine from 2-amino-3-bromopyridine was as follows: sodium nitrite (24.2 g, 0.35 mol, 4.84 eq.) was dissolved in water (175 mL) at 0 °C and slowly added dropwise to a solution containing 2-amino-3-bromopyridine (12.5 g, 72.4 mmol) and sulfuric acid (35 mL, 0.66 mol , 9.10 eq.) in a solution of water (175 mL). The reaction mixture was stirred at 0 °C for 1 hour. Subsequently, the reaction mixture was neutralized with sodium hydroxide solution to pH=7. The neutralized solution was extracted with chloroform (3 x 200 mL), the organic phases were combined and washed with brine (200 mL), dried over magnesium sulfate, filtered and concentrated in vacuum to afford the milky white solid product 3-bromo-2-hydroxypyridine (11.3 g, 90% yield). The product was characterized as follows: melting point 183 °C; IR (pure) νmax 3339, 3105, 2991, 2942, 1776, 1650, 1610, 1464 cm-1; 1H NMR (500 MHz, CDCl3) δ 7.87 (dd, J = 7.3, 1.9 Hz, 1H), 7.49 (dd, J = 6.4, 1.9 Hz, 1H), 6.24 (dd, J = 7.3, 6.4 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ 161.9, 143.9, 134.4, 115.7, 107.7 ppm; HRMS (ESI) m/z [M + Na]+ Calculated value: 195.9369, measured value: 195.9373 (deviation +2.07 ppm).
Einzelnachweise
[1] Organic Letters, 2016, vol. 18, # 13, p. 3106 - 3109
[2] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588

3-Bromo-2-hydroxypyridine Upstream-Materialien And Downstream Produkte

3-Bromo-2-hydroxypyridine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

13466-43-8, 3-Bromo-2-hydroxypyridine Verwandte Suche:

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