1-(5-Brom-2-thienyl)ethan-1-on

Bezeichnung:1-(5-Brom-2-thienyl)ethan-1-on

CAS-Nr5370-25-2

Englisch Name:2-Acetyl-5-bromothiophene

CBNumberCB0465458

SummenformelC6H5BrOS

Molgewicht205.07

MOL-Datei5370-25-2.mol

Synonyma

1-(5-Brom-2-thienyl)ethan-1-on

1-(5-Brom-2-thienyl)ethan-1-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	94-96 °C (lit.)
Siedepunkt	103 °C/4 mmHg (lit.)
Dichte	1.649 (estimate)
Flammpunkt	103°C/4mm
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	soluble in Methanol
Aggregatzustand	Crystalline Flakes or Powder
Farbe	Yellow
Sensitive	Light Sensitive
BRN	113949
InChI	InChI=1S/C6H5BrOS/c1-4(8)5-2-3-6(7)9-5/h2-3H,1H3
InChIKey	IGBZCOWXSCWSHO-UHFFFAOYSA-N
SMILES	C(=O)(C1SC(Br)=CC=1)C
CAS Datenbank	5370-25-2(CAS DataBase Reference)
NIST chemische Informationen	2-Acetyl-5-bromothiophene(5370-25-2)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	36/37/38-20/21/22
S-Sätze:	36/37/39-26-22
RIDADR	UN2811
WGK Germany	3
HazardClass	LIGHT SENSITIVE
HS Code	29339900
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

2-Acetyl-5-bromothiophene 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:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S22:Staub nicht einatmen.
Chemische Eigenschaften
white to light yellow crystal powder
Verwenden
2-Acetyl-5-bromothiophene was used as a starting reagent in the synthesis of bithiophene bis-imidazo[1,2-a]pyridine derivatives. It was also used in the preparation of phosphorus-containing fused bicyclic 5,6-membered compounds.
Synthesis Reference(s)
Journal of Heterocyclic Chemistry, 18, p. 1345, 1981 DOI: 10.1002/jhet.5570180714
Synthetic Communications, 11, p. 29, 1981 DOI: 10.1080/00397918108064279
Synthese

88-15-3

5370-25-2

The general procedure for the synthesis of 2-acetyl-5-bromothiophene from 2-acetylthiophene was as follows: 2-acetylthiophene (1.08 mL, 10 mmol), N-bromosuccinimide (NBS) (1.78 g, 30 mmol), and acetic anhydride (3.78 mL, 40 mmol) were added sequentially to a dry, 25 mL round-bottomed flask, which was equipped with a protective tube. Acetic acid (0.40 mL) was subsequently added to the mixture. The reaction mixture was stirred at 50 °C for 1 h protected from light and the color of the solution was observed to change from colorless to light yellow. Upon completion of the reaction, the mixture was cooled to room temperature and poured into 100 mL of water with continuous stirring until the acetic anhydride was completely hydrolyzed. At this point, 2-acetyl-5-bromothiophene precipitated as white crystals. The product was collected by filtration and washed in batches with 50 mL of water to give a final yield of 82%. The melting point of the product was 92-94 °C (acetone).1H NMR (300 MHz, CDCl3) data were as follows: δ 7.40 (d, J=3.9 Hz, 1H), 7.08 (d, J=3.9 Hz, 1H), 2.48 (s, 3H).
Einzelnachweise
[1] Tetrahedron Letters, 2010, vol. 51, # 1, p. 205 - 208
[2] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9180 - 9187
[3] Tetrahedron Letters, 2014, vol. 55, # 5, p. 996 - 1001
[4] Organic Letters, 2013, vol. 15, # 9, p. 2108 - 2111

2-Acetyl-5-bromothiophene Upstream-Materialien And Downstream Produkte

1-(5-Brom-2-thienyl)ethan-1-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

5370-25-2, 2-Acetyl-5-bromothiophene Verwandte Suche:

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