2-Bromo-5-methylthiophene
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2-Bromo-5-methylthiophene
structure -
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CAS No:
765-58-2
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Formula:
C5H5BrS
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Chemical Name:
2-Bromo-5-methylthiophene
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Synonyms:
Thiophene,2-bromo-5-methyl-;2-Bromo-5-methylthiophene;5-Bromo-2-methylthiophene;5-Methyl-2-bromothiophene
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CAS No:
Characteristics
28.2
3
Yellow Liquid Which May Contain Some Precipitate
1.552 g/cm3 @ Temp: 20 °C
58ºC
178 °C
173 °F
n20/D 1.569(lit.)
Refrigerator
Safety Information
III
IRRITANT
NONH for all modes of transport
3
20/21/22-36/37/38-22
23-36/37/39-37/39-26
Xi
Irritant
Stable if stored as directed.
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H227 (33.33%): Combustible liquid [Warning Flammable liquids]|P210, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Bromo-5-methylthiophene Use and Manufacturing
A solution of 48.0 gbromine (0.3 mol) in 260 cm3 of dioxane was slowlyadded to a solution of 29.4 g 2-methylthiophene (23, 0.3 mmol) in 140 cm3 of dioxane. The reaction mixturewas stirred for 3 h at room temperature, then cooled to0 C. A saturated aqueous sodium bicarbonate solutionwas then carefully added and the mixture was extractedwith ethyl acetate. The organic layer was dried oversodium sulfate and evaporated under reduced pressure. The remainder was purified by distillation to deliver37.2 g 2-bromo-5-methylthiophene (24, 0.21 mol, 70percent).B.p.: 68–70 C (20 mbar); 1H NMR (400 MHz, CDCl3):d = 2.42 (s, 3H), 6.51 (d, 1H, J = 3.6 Hz), 6.83 (d, 1H, J = 3.6 Hz) ppm; LC–MS: tR = 1.65 min; MS: m/z = 176, 178 ([M'1]?, [M'3]?).NBS (1.1 eq, 4.0g, 22.7 mmol) was added to a solution of 2-methylthiophene (1.0 eq., 2 mL, 20.7 mmol) in a mixture of chloroform/AcOH (10:1, 20 mL) at 0 C in the absence of light. The mixture reaction was stirred at 0 C for 1h. Then the mixture was warmed to rt for 12 hours. The reaction was quenched with aqueous sat. NaHCO
Computed Properties
Molecular Weight:177.06
XLogP3:3
Hydrogen Bond Acceptor Count:1
Exact Mass:175.92953
Monoisotopic Mass:175.92953
Topological Polar Surface Area:28.2
Heavy Atom Count:7
Complexity:65.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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