2-Bromo-3-methylthiophene
- CAS NO.:14282-76-9
- Empirical Formula: C5H5BrS
- Molecular Weight: 177.06
- MDL number: MFCD00059741
- EINECS: 238-175-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-31 13:32:20
What is 2-Bromo-3-methylthiophene?
Chemical properties
clear colorless to light yellow liquid
The Uses of 2-Bromo-3-methylthiophene
2-Bromo-3-methylthiophene was used in the preparation of poly(3,3′′′-dimethyl-(2,2′:5′,2′:5′,2′′′)tetrathiophene)). It was also used in the preparation of 2-bromo-3-(bromomethyl)thiophene, lachrymatory compound.
What are the applications of Application
2-Bromo-3-methylthiophene is used as a pharmaceutical intermediate. It is used to prepare pyrazolo[3,4-d]pyrimidine derivatives as inhibitors of human enterovirus, coxsackievirus, echovirus, influenza virus, herpes simplex virus and rhinovirus. It is also used in the synthesis of oral α7 nicotinic receptor agonists.
Preparation
2-Bromo-3-methylthiophene synthesis: To a solution of glacial AcOH (100 mL), acetic anhydride (4.0 g, 0.039 mol), and 3-methylthiophene (9.82 g, 0.100 mol) as a stirred mixture was added NBS (19.6 g, 0.11 mol) in one portion with a slight exotherm to 44 oC. After 20 min the reaction mixture was poured onto ice, neutralized with sodium bisulfite and extracted with ether. The ether layer was washed with water and concentrated to give 11.3 g (64%) of 2-bromo-3-methylthiophene as a tan colored liquid in 88% purity by GC area % analysis: 1H NMR (CDCl3) d 7.1 (d, 1H, J=5.7 Hz), 6.7 (d, 1H, J=5.9 Hz), 2.2 (s, 3H).
General Description
2-Bromo-3-methylthiophene is formed (approx. 90%) by bromination of 3-methyl thiophene with N-bromosuccinimide in the absence of benzoyl peroxide.
Properties of 2-Bromo-3-methylthiophene
Melting point: | <25 °C |
Boiling point: | 173-176 °C (lit.) |
Density | 1.572 g/mL at 25 °C (lit.) |
refractive index | n |
Flash point: | 155 °F |
storage temp. | 2-8°C |
Water Solubility | Insoluble in water |
solubility | soluble in Chloroform, Ethyl Acetate |
Specific Gravity | 1.580 |
color | Pale yellow |
BRN | 105719 |
CAS DataBase Reference | 14282-76-9(CAS DataBase Reference) |
NIST Chemistry Reference | Thiophene, 2-bromo-3-methyl-(14282-76-9) |
Safety information for 2-Bromo-3-methylthiophene
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H318:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-Bromo-3-methylthiophene
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