2-Bromo-3-methylthiophene

Base Information

• Chemical Name: 2-Bromo-3-methylthiophene
• CAS No.: 14282-76-9
• Molecular Formula: C5H5BrS
• Molecular Weight: 177.065
• Hs Code.: 29349990
• European Community (EC) Number: 238-175-2
• DSSTox Substance ID: DTXSID20162194
• Nikkaji Number: J149.674C
• Wikidata: Q72448154
• Mol file: 14282-76-9.mol

Synonyms:2-Bromo-3-methylthiophene;14282-76-9;Thiophene, 2-bromo-3-methyl-;2-bromo-3-methyl-thiophene;EINECS 238-175-2;MFCD00059741;2-bromo-3-methythiophene;2-bromo-3-methyl thiophene;SCHEMBL43816;2-Bromo-3-methylthiophene #;BIDD:GT0358;DTXSID20162194;2-Bromo-3-methylthiophene, 95%;BBL021712;STK894429;AKOS005144510;CS-W002276;PB25943;PS-6020;AC-18074;AM20080325;B1025;FT-0611420;EN300-49995;Q-101194

Chemical Property of 2-Bromo-3-methylthiophene

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 1.41mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: n20/D 1.572(lit.)
• Boiling Point: 177.3 °C at 760 mmHg
• Flash Point: 68.3 °C
• PSA: 28.24000
• Density: 1.589 g/cm³
• LogP: 2.81900
• Storage Temp.: Keep Cold
• Water Solubility.: Insoluble in water
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 175.92953
• Heavy Atom Count: 7
• Complexity: 65.1

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-methylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi,Xn
• Hazard Codes: T,Xi,Xn
• Statements: 25-41-43-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(SC=C1)Br
• 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.

Technology Process of 2-Bromo-3-methylthiophene

There total 8 articles about 2-Bromo-3-methylthiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-Methylthiophene (616-44-4,84928-92-7) → 2-bromo-3-methylthiophene (14282-76-9)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; Inert atmosphere;

DOI:10.1246/cl.131222

Reference yield: 81.0%

→ 2-bromo-3-methylthiophene (14282-76-9) + 3-thiophene carboxaldehyde (498-62-4)

Guidance literature:

Reference yield:

3-Methylthiophene (616-44-4,84928-92-7) → 2-bromo-3-methylthiophene (14282-76-9) + 2,5-dibromo-3-methylthiophene (13191-36-1)

Guidance literature:

With dihydrogen peroxide; ammonium bromide; acetic acid; In water; for 20h; Time; Solvent; Reagent/catalyst; regioselective reaction; Green chemistry;

DOI:10.1139/cjc-2013-0058

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

3-Methylthiophene

2,5-dibromo-3-methylthiophene

Downstream raw materials:

1-(5-bromo-4-methylthiophen-2-yl)ethan-1-one

2-bromo-3-(bromomethyl)thiophene

3,3”-dimethyl-2,2’:5’,2”-terthiophene

4-Bromo-1,1-bis-(3-methyl-thiophen-2-yl)-butan-1-ol

Refernces

Design, synthesis, and structure-activity relationships of pyrazolo[3,4-d]pyrimidines: A novel class of potent enterovirus inhibitors

10.1016/j.bmcl.2004.02.092

The study focuses on the design, synthesis, and evaluation of a novel class of pyrazolo[3,4-d]pyrimidines as potent inhibitors of enteroviruses, specifically coxsackieviruses. The researchers synthesized a series of these compounds and tested their antiviral activity using a plaque reduction assay. They discovered that these compounds showed remarkable specificity for human enteroviruses, with some derivatives highly effective at nanomolar concentrations. Structure-activity relationship (SAR) studies indicated that the phenyl group at the N-1 position and the hydrophobic diarylmethyl group at the piperazine significantly influenced the in vitro antienteroviral activity. Notably, compounds with a thiophene substituent, such as 20–24, exhibited high activity against coxsackievirus B3 and moderate activity against enterovirus 71, without apparent cytotoxic effects on RD cell lines. The findings highlight the potential of these compounds as new antiviral agents against enteroviral infections, for which effective treatments are currently lacking.