3,5-Dibrompyridin

Bezeichnung:3,5-Dibrompyridin

CAS-Nr625-92-3

Englisch Name:3,5-Dibromopyridine

CBNumberCB1333488

SummenformelC5H3Br2N

Molgewicht236.89

MOL-Datei625-92-3.mol

Synonyma

3,5-Dibrompyridin

3,5-Dibrompyridin physikalisch-chemischer Eigenschaften

Schmelzpunkt	110-115 °C (lit.)
Siedepunkt	222 °C
Dichte	2.0383 (rough estimate)
Brechungsindex	1.5800 (estimate)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly, Heated), Methanol (Slightly)
pka	0.52±0.20(Predicted)
Aggregatzustand	Needle-Like Crystals
Farbe	White to light beige
Wasserlöslichkeit	Soluble in Chloroform and Methanol. Insoluble in water.
BRN	108477
InChI	1S/C5H3Br2N/c6-4-1-5(7)3-8-2-4/h1-3H
InChIKey	SOSPMXMEOFGPIM-UHFFFAOYSA-N
SMILES	Brc1cncc(Br)c1
CAS Datenbank	625-92-3(CAS DataBase Reference)
NIST chemische Informationen	3,5-Dibromopyridine(625-92-3)
EPA chemische Informationen	3,5-Dibromopyridine (625-92-3)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-20/21/22
S-Sätze:	26-36-36/37/39
RIDADR	UN2811
WGK Germany	3
HazardClass	IRRITANT
HS Code	29333999
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2

Gefahreninformationscode (GHS)

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

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der 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.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Light-Yellow Solid
Verwenden
3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.
Application
3,5-Dibromopyridine (3,5-DBP) can be used for:
(1) Spectroscopic analysis: FTIR and FT Raman spectra in the solid phase of 3,5-DBP and 3,5- dichloro-2,4,6-trifluoropyridine (3,5-DCTFP) were recorded in the regions of 4000-400 cm-1 and 3500-100 cm-1, respectively^[1].
(2) Chemical reactions: 3,5-DBP can be reacted with phenyl isocyanate. chemoselective Staudinger-Phosphite reaction of 2,4,6-triazido-3,5-dibromopyridine azide moiety^[2-3].
(3) Organic synthesis: Using 3,5-dibromopyridine as raw material can be used to prepare 3-acetamido-5-ethoxypyridine^[4].
Definition
ChEBI: 3,5-dibromopyridine is a dibromopyridine.
Allgemeine Beschreibung
3,5-Dibromopyridine undergoes lithiation with lithium diisopropylamide and on subsequent reaction with electrophiles yields 4-alkyl-3,5-dibromopyridines.
Einzelnachweise
[1] V. KRISHNAKUMAR R. J X. Density functional theory calculations and vibrational spectra of 3,5-dibromopyridine and 3,5-dichloro-2,4,6-trifluoropyridine[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2005. DOI:10.1016/j.saa.2004.03.038.
[2] SERGEI V. CHAPYSHEV Igor K Y Alexander V Chernyak. Chemoselective Staudinger-Phosphite Reaction on the Azido Groups of 2,4,6-Triazido-3,5-dibromopyridine[J]. Journal of Heterocyclic Chemistry, 2015. DOI:10.1002/jhet.2339.
[3] T. HISANO M. I Toshikazu Matsuoka. THE REACTION OF 3,5-DIBROMOPYRIDINE N-OXIDE WITH PHENYL ISOCYANATE[J]. ChemInform, 1974. DOI:10.1002/CHIN.197448358.
[4] H. J. HERTOG A. V D L A W M Falter. The reactivity of bromine atoms in brominated pyridines. The preparation of 3-acetylamino-5-ethoxypyridine from 3,5-dibromopyridine[J]. Recueil des Travaux Chimiques des Pays-Bas, 1948. DOI:10.1002/RECL.19480670507.

3,5-Dibromopyridine Upstream-Materialien And Downstream Produkte

3,5-Dibrompyridin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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