| 2-Bromo-3-methylthiophene Basic information |
| Product Name: | 2-Bromo-3-methylthiophene |
| Synonyms: | Thiophene,2-bromo-3-methyl-;2B3MT;2-BROMO-3-METHYLTHIOPHENE;2-Bromo-3-Methylthiophene99.5%;2-bromo-3-methyltiophene;2-Bromo-3-methylthiophene 97%;178.04;2-BROMO-3-METHYLTHIOPHENE 98+% |
| CAS: | 14282-76-9 |
| MF: | C5H5BrS |
| MW: | 177.06 |
| EINECS: | 238-175-2 |
| Product Categories: | Building Blocks;C4 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-oher series;Halogenated;Organohalides;Thiophene;Thiophens;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiophenesBuilding Blocks;Thiophene Series;Thiophenes;blocks;Bromides;Heterocycles;Thiophene&Benzothiophene |
| Mol File: | 14282-76-9.mol |
| 2-Bromo-3-methylthiophene Chemical Properties |
| Melting point | <25 °C |
| Boiling point | 173-176 °C (lit.) |
| density | 1.572 g/mL at 25 °C (lit.) |
| refractive index | n |
| Fp | 155 °F |
| storage temp. | 2-8°C |
| Water Solubility | Insoluble in water |
| Specific Gravity | 1.580 |
| BRN | 105719 |
| CAS DataBase Reference | 14282-76-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Thiophene, 2-bromo-3-methyl-(14282-76-9) |
| Safety Information |
| Hazard Codes | T,Xi,Xn |
| Risk Statements | 25-41-43-36/37/38-20/21/22 |
| Safety Statements | 26-36/37/39-45 |
| RIDADR | UN 2810 |
| WGK Germany | 3 |
| Hazard Note | Harmful |
| HazardClass | IRRITANT-HARMFUL, KEEP COLD |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29349990 |
| MSDS Information |
| Provider | Language |
|---|---|
| 2-Bromo-3-methylthiophene | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| 2-Bromo-3-methylthiophene Usage And Synthesis |
| Chemical Properties | clear colorless to light yellow liquid |
| Uses | 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. |
| 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. |
| 2-Bromo-3-methylthiophene Preparation Products And Raw materials |
| Raw materials | Acetic acid-->Acetic anhydride-->3-Methylthiophene-->N-Bromosuccinimide |
| Preparation Products | 2,3,5-Trimethylthiophene-->3-METHYLTHIOPHENE-2-BORONIC ACID-->3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER-->2-BROMOTHIOPHENE-3-CARBALDEHYDE |
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