2-Brom-5-methylthiophen

Bezeichnung:2-Brom-5-methylthiophen

CAS-Nr765-58-2

Englisch Name:2-Bromo-5-methylthiophene

CBNumberCB4684448

SummenformelC5H5BrS

Molgewicht177.06

MOL-Datei765-58-2.mol

Synonyma

2-Brom-5-methylthiophen

2-Brom-5-methylthiophen physikalisch-chemischer Eigenschaften

Siedepunkt	65 °C/15 mmHg (lit.)
Dichte	1.552 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.569(lit.)
Flammpunkt	173 °F
storage temp.	2-8°C
Aggregatzustand	Liquid Which May Contain Some Precipitate
Farbe	Yellow
Wichte	1.552
InChI	InChI=1S/C5H5BrS/c1-4-2-3-5(6)7-4/h2-3H,1H3
InChIKey	ACDLOOGOFKSUPO-UHFFFAOYSA-N
SMILES	C1(Br)SC(C)=CC=1
CAS Datenbank	765-58-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	20/21/22-36/37/38-22
S-Sätze:	23-36/37/39-37/39-26
WGK Germany	3
HazardClass	IRRITANT
HS Code	29339900
Speicherklasse	10 - Combustible liquids

Gefahreninformationscode (GHS)

2-Bromo-5-methylthiophene 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:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Yellow liquid
Synthese

554-14-3

765-58-2

General procedure for the synthesis of 2-bromo-5-methylthiophene from 2-methylthiophene: A bromine solution was prepared by dissolving 48.0 g of bromine (0.3 mol) in 260 cm3 dioxane. This bromine solution was slowly added dropwise under stirring conditions to a solution of 29.4 g 2-methylthiophene (0.3 mmol) dissolved in 140 cm3 dioxane. The reaction mixture was stirred continuously for 3 hours at room temperature. Subsequently, the reaction system was cooled to 0 °C and saturated aqueous sodium bicarbonate solution was carefully added to neutralize the reaction. The mixture was extracted with ethyl acetate and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent. The residue was purified by distillation to give 37.2 g 2-bromo-5-methylthiophene (0.21 mol, 70% yield). Boiling point: 68-70 °C (20 mbar). 1H NMR (400 MHz, CDCl3): δ = 2.42 (s, 3H), 6.51 (d, 1H, J = 3.6 Hz), 6.83 (d, 1H, J = 3.6 Hz) ppm. LC-MS: retention time tR = 1.65 min; MS: m/z = 176, 178 ([M+ 1]+, [M+3]+).
Einzelnachweise
[1] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1836 - 1841
[2] Synthesis, 2002, # 9, p. 1133 - 1135
[3] Green Chemistry, 2018, vol. 20, # 19, p. 4448 - 4452
[4] Synthesis, 2011, # 2, p. 207 - 209
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 20, p. 2592 - 2602

2-Bromo-5-methylthiophene Upstream-Materialien And Downstream Produkte

2-Brom-5-methylthiophen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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