9-Bromanthracen

Bezeichnung:9-Bromanthracen

CAS-Nr1564-64-3

Englisch Name:9-Bromoanthracene

CBNumberCB5319891

SummenformelC14H9Br

Molgewicht257.13

MOL-Datei1564-64-3.mol

Synonyma

9-Bromanthracen

9-Bromanthracen physikalisch-chemischer Eigenschaften

Schmelzpunkt	97-100 °C (lit.)
Siedepunkt	303.85°C (rough estimate)
Dichte	1.4251 (rough estimate)
Brechungsindex	1.6404 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Powder
Farbe	Yellow
Wasserlöslichkeit	Insoluble in water.
BRN	1869747
InChIKey	ZIRVQSRSPDUEOJ-UHFFFAOYSA-N
CAS Datenbank	1564-64-3(CAS DataBase Reference)
NIST chemische Informationen	9-Bromoanthracene(1564-64-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
S-Sätze:	22-24/25
WGK Germany	3
Hazard Note	Irritant
HS Code	29049090

Gefahreninformationscode (GHS)

9-Bromoanthracene Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
9-bromoanthracene is a kind of bromine-derived anthracene. It is known to be able to reversibly photodimerize in a head-to tail fashion upon irradiation by long-wavelength ultraviolet light. The photodimers of 9-bromoanthracene are suitable to be used as alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions. It is also used as the intermediate for the preparation of the 9-substitued form of the polycyclic aromatic hydrocarbon (PAH) anthracene.
Chemische Eigenschaften
white to light yellow crystal powder. boiling point 190°C (0.16kPa, sublimation), relative density 1.409. soluble in acetic acid; carbon disulfide.
Verwenden
9-Bromoanthracene acts as an intermediate in the preparation of 9-substituted derivative of the polycyclic aromatic hydrocarbon (PAH) anthracene.
synthetische
Anthracene (5 g, 28.05 mmol) was dissolved in CHCl3. Then N-bromosuccinimide (NBS，4.99 g, 28.05 mmol) was added in batches away from light, and the reaction solution was continuously stirred for 12 h. The resulting mixture was stirred for another 30 min with appropriate water, and extracted with CH2Cl2. The CH2Cl2 solution was dried over anhydrous MgSO4. After removing CH2Cl2 solvent, the residue was recrystallized from anhydrous ethanol to give 4.78 g (66.3 %) of a green-yellow needle solid. 1H NMR (500 MHz, CDCl3) δ 8.55 (d, J = 8.9 Hz, 2H), 8.48 (s, 1H), 8.03 (d, J = 8.4 Hz, 2H), 7.67 – 7.60 (m, 2H), 7.56 – 7.51 (m, 2H). EI-MS (m/z): Calculated for C14H9Br: 257.13. Found [M+ ]: 255.96.

Synthesis of 9-bromoanthracene
Synthesis Reference(s)
The Journal of Organic Chemistry, 57, p. 2740, 1992 DOI: 10.1021/jo00035a038
läuterung methode
Crystallise 9-bromoanthracene from MeOH or EtOH followed by sublimation in vacuo. [Masnori et al. J Am Chem Soc 108 126 1986, Beilstein 5 IV 2295.]
Einzelnachweise
Cohen, Nicole A., et al. Macromolecular Chemistry and Physics 210.3 ‐4 (2009): 263-268.
Xu, Xiaoming, Wenzhe Lu, and Richard B. Cole. Analytical chemistry 68.23 (1996): 4244-4253.
Dang, Hung, and Miguel A. Garcia-Garibay. Journal of the American Chemical Society 123.2 (2001): 355-356.

9-Bromoanthracene Upstream-Materialien And Downstream Produkte

9-Bromanthracen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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