2,5-Dichlorpyridin

Bezeichnung:2,5-Dichlorpyridin

CAS-Nr16110-09-1

Englisch Name:2,5-Dichloropyridine

CBNumberCB9487592

SummenformelC5H3Cl2N

Molgewicht147.99

MOL-Datei16110-09-1.mol

Synonyma

2,5-Dichlorpyridin

2,5-Dichlorpyridin physikalisch-chemischer Eigenschaften

Schmelzpunkt	59-62 °C (lit.)
Siedepunkt	190-191 °C
Dichte	1.5159 (rough estimate)
Brechungsindex	1.5500 (estimate)
Flammpunkt	112 °C
storage temp.	Inert atmosphere,Room Temperature
pka	-2.25±0.10(Predicted)
Aggregatzustand	Crystalline Solid
Farbe	White to slightly yellow
Wasserlöslichkeit	insoluble
BRN	108886
InChI	InChI=1S/C5H3Cl2N/c6-4-1-2-5(7)8-3-4/h1-3H
InChIKey	GCTFDMFLLBCLPF-UHFFFAOYSA-N
SMILES	C1(Cl)=NC=C(Cl)C=C1
CAS Datenbank	16110-09-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-22
S-Sätze:	26-37/39-36
RIDADR	UN2811
WGK Germany	3
RTECS-Nr.	US8225000
Hazard Note	Harmful
HazardClass	IRRITANT
HazardClass	6.1
HS Code	29333990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2,5-Dichloropyridine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, 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.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white to slightly yellow crystalline solid
Verwenden
2,5-Dichloropyridine was used in the synthesis of 6-halo-pyridin-3-yl boronic acids and esters. It undergoes cross-coupling reaction with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride as catalyst.
Synthesis Reference(s)
Synthetic Communications, 20, p. 2971, 1990 DOI: 10.1080/00397919008051514
Allgemeine Beschreibung
2,5-Dichloropyridine undergoes cross-coupling reaction with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride as catalyst.
Synthese

624-28-2

16110-09-1

General procedure for the synthesis of 2,5-dichloropyridine from 2,5-dibromopyridine: Catalyst 1 (10 mol%), 2,5-dibromopyridine (1.0 mmol), tetramethylammonium chloride (Me4NCl, 2.0 mmol), and ethanol (EtOH, 2.0 mL) were added to a Schlenk tube under nitrogen protection. Schlenk tubes were sealed using polytetrafluoroethylene (Teflon) valves and the reaction mixture was stirred at 100 °C. The reaction process was monitored by gas chromatography (GC) analysis. After completion of the reaction, the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent ratio petroleum ether/ethyl acetate = 10:1) to give 2,5-dichloropyridine. The yield of the product was determined by high-resolution gas chromatography-mass spectrometry (GC-MS) analysis and the structure was confirmed by comparing its physical properties and spectral data with known compounds.
Einzelnachweise
[1] Applied Catalysis A: General, 2014, vol. 472, p. 178 - 183
[2] Chemical Communications, 2012, vol. 48, # 76, p. 9468 - 9470

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