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HomeProduct name list2-Bromo-3-methylthiophene

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: 2024-12-13 13:23:53
2-Bromo-3-methylthiophene Structural

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  n20/D 1.572(lit.)
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)
ghs
Corrosion
Corrosives
GHS05
ghs
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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