Methyl 2,5-dibromobenzoate

Bezeichnung:Methyl 2,5-dibromobenzoate

CAS-Nr57381-43-8

Englisch Name:Methyl 2,5-dibromobenzoate

CBNumberCB5689697

SummenformelC8H6Br2O2

Molgewicht293.94

MOL-Datei57381-43-8.mol

Methyl 2,5-dibromobenzoate physikalisch-chemischer Eigenschaften

Schmelzpunkt	48-51 °C (lit.)
Siedepunkt	291.3±20.0 °C(Predicted)
Dichte	1.840±0.06 g/cm3(Predicted)
Flammpunkt	>230 °F
storage temp.	Sealed in dry,Room Temperature
Aggregatzustand	powder to crystal
Farbe	White to Orange to Green
Wasserlöslichkeit	Slightly soluble in water.
InChI	1S/C8H6Br2O2/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4H,1H3
InChIKey	RBCUIRIGTNHLPS-UHFFFAOYSA-N
SMILES	COC(=O)c1cc(Br)ccc1Br
CAS Datenbank	57381-43-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
TSCA	N
HS Code	2916399090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

Methyl 2,5-dibromobenzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die 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.
Verwenden
Methyl 2,5-dibromobenzoate, an aromatic ester, can be prepared from 2,5-dibromobenzoic acid via esterification with methanol. It undergoes Ni(0)-catalyzed polymerization to form soluble polyphenylenes.
Allgemeine Beschreibung
Methyl 2,5-dibromobenzoate, an aromatic ester, can be prepared from 2,5-dibromobenzoic acid via esterification with methanol. It undergoes Ni(0)-catalyzed polymerization to form soluble polyphenylenes.
Synthese

67-56-1

610-71-9

57381-43-8

Step 1: A methanol (2L) solution of 2,5-dibromobenzoic acid (250 g, 0.90 mol) and concentrated sulfuric acid (18.4 g, 0.19 mol) were added to a 2L round bottom flask. The reaction mixture was heated to reflux overnight and subsequently cooled to room temperature. The resulting precipitate was collected by filtration, washed with cold methanol and dried under vacuum to give 203.6 g of methyl 2,5-dibromobenzoate as a yellow solid. Step 2: To another 2L round-bottomed flask was added a solution of methyl 2,5-dibromobenzoate (198.2 g, 0.68 mol) in anhydrous DMF (1L). Copper cyanide (122 g, 1.36 mol) and sodium iodide (22.8 g, 0.15 mol) were subsequently added. The mixture was stirred at 130 °C overnight under nitrogen protection. Upon completion of the reaction, extraction was carried out with ethyl acetate (500 mL x 3), the organic layer was washed with water (500 mL), and finally purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to afford 95.2 g of methyl 2,5-dicyanobenzoate as a brown solid in 75.1% yield.
Einzelnachweise
[1] Tetrahedron, 2016, vol. 72, # 24, p. 3454 - 3467
[2] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6655 - 6657

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