2-Bromo-3-nitrotoluene

Bezeichnung:2-Bromo-3-nitrotoluene

CAS-Nr41085-43-2

Englisch Name:2-Bromo-3-nitrotoluene

CBNumberCB0111100

SummenformelC7H6BrNO2

Molgewicht216.03

MOL-Datei41085-43-2.mol

2-Bromo-3-nitrotoluene physikalisch-chemischer Eigenschaften

Schmelzpunkt	38-41 °C (lit.)
Siedepunkt	135-136 °C/8 mmHg (lit.)
Dichte	0.803 g/mL at 25 °C (lit.)
Brechungsindex	1.6120 (estimate)
Flammpunkt	>230 °F
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	soluble in Methanol
Aggregatzustand	Low Melting Solid
Farbe	Pale yellow
InChI	1S/C7H6BrNO2/c1-5-3-2-4-6(7(5)8)9(10)11/h2-4H,1H3
InChIKey	GCAAVRIWNMTOKB-UHFFFAOYSA-N
SMILES	Cc1cccc(c1Br)[N+]([O-])=O
CAS Datenbank	41085-43-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-36/37/38
S-Sätze:	26-36
WGK Germany	3
HS Code	29049090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2-Bromo-3-nitrotoluene Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
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.
Chemische Eigenschaften
Pale yellow low melting solid
Verwenden
2-Bromo-3-nitrotoluene may be used in the preparation of unsymmetrical dimethyl dinitro biphenyl, via Ullmann reaction. It may be used as starting material in the synthesis of 10-methylfluoranthene.
Allgemeine Beschreibung
Crystal structure of 2-bromo-3-nitrotoluene has been studied and the dihedral angle between the nitro group and the phenyl ring is reported to be 54.1(4)°.
Synthese

570-24-1

41085-43-2

The general procedure for the preparation of 2-bromo-3-nitrotoluene by diazotization reaction using 2-methyl-6-nitroaniline as starting material was as follows: first, 2-methyl-6-nitroaniline (30.4 g, 0.2 mol) was suspended in water (250 mL) and 40% aqueous hydrobromic acid (100 mL), refluxed for 10 min and then cooled to 0 °C. A solution of sodium nitrite (13.8 g, 0.2 mol) in water (80 mL) was added slowly and dropwise at a temperature below 5 °C. The resulting diazonium salt solution was continued to be stirred at 0-5 °C for 30 min, followed by the slow addition of a stirring mixed solution of cuprous bromide (28.7 g, 0.2 mol) in hydrobromic acid (80 mL) and water (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 30 minutes and then heated and stirred on a steam bath for 1 hour. Upon completion of the reaction, it was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography using petroleum ether as eluent to give 2-bromo-3-nitrotoluene as a light yellow solid (25.9 g, 60% yield).
Einzelnachweise
[1] European Journal of Organic Chemistry, 2005, # 16, p. 3536 - 3541
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 12, p. 2925 - 2929
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 40, p. 7257 - 7260
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651
[5] Patent: WO2011/22337, 2011, A1. Location in patent: Page/Page column 97

2-Bromo-3-nitrotoluene Upstream-Materialien And Downstream Produkte

2-Bromo-3-nitrotoluene Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

41085-43-2, 2-Bromo-3-nitrotoluene Verwandte Suche:

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