2-Bromo-3-methylthiophene
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2-Bromo-3-methylthiophene
structure -
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CAS No:
14282-76-9
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Formula:
C5H5BrS
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Chemical Name:
2-Bromo-3-methylthiophene
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Synonyms:
Thiophene,2-bromo-3-methyl-;2-Bromo-3-methylthiophene;5-Bromo-4-methylthiophene
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CAS No:
Safety Information
III
6.1
UN 2810
3
25-41-43-36/37/38-20/21/22
26-36/37/39-45
T,Xi,Xn
Harmful
P280-P305 + P351 + P338
H302-H318
|Danger|H302 (97.78%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Bromo-3-methylthiophene Use and Manufacturing
NBS (8.90 g, 50.0 mmol) was added portion wise to a stirred solution of 3-mehylthiophene (4.90 g, 50.0 mmol) in acetic acid (20 mL) at rt. After complete addition, the reaction was stirred at rt until it was complete. The reaction mixture was poured into ice- water, and then extracted with a 3:1 mixture solvent of hexane and ether. The organic layer was washed with IN aq. NaOH and brine. After dried over anhydrous sodium sulphate, the organic phase was concentrated on vacuum to afford 2-bromo-3-methylthiphene (8.20 g, 92.7 percent), which was used directly in the next step without further purification.Compound 4 (5.00g, 51.01mmol) was dissolved in 30mL of anhydrous DMF. The mixture of N-bromosuccinimide (NBS) (9.08g, 51.01mmol) and anhydrous DMF (40mL) was added dropwise to the solution and stirred for 24h in the dark. The mixture was then poured into water and extracted with petroleum ether. The organic phase was dried over anhydrous MgSOIn a 1 L two-necked flask, 24.5 g of 3-methylthiophene (98 g mol-1, 24.5 g, 250 mmol) was added and 400 mL of chloroform / glacial acetic acid (V: V = 1: / L, Favoring the inhibition of the bis-brominated product), 44.5 g of NBS (178 g mol-1, 44.5 g, 250 mmol) were added in portions in an ice-water bath.After the addition of NBS to continue stirring for 2-3 hours, TLC monitoring.After treatment: deionized water to quench the reaction, liquid separation, the organic phase was NaOH solution, washed with water, dried, concentrated vacuum pump with fractional distillation.
New pharmaceutical intermediates.
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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