2-tert-Butylthiophene
Overview
Description
2-tert-Butylthiophene is an organic compound with the molecular formula C8H12S. It is a derivative of thiophene, a five-membered aromatic ring containing a sulfur atom. The tert-butyl group at the second position of the thiophene ring significantly influences its chemical properties and reactivity. This compound is of interest due to its applications in various fields, including organic synthesis, material science, and medicinal chemistry .
Safety and Hazards
The safety information for 2-tert-Butylthiophene includes several hazard statements: H302 (Harmful if swallowed), H315 (Causes skin irritation), H320 (Causes eye irritation), and H335 (May cause respiratory irritation) . Precautionary measures include avoiding getting the substance in eyes, on skin, or on clothing, and avoiding ingestion and inhalation .
Mechanism of Action
Biochemical Pathways
The biochemical pathways affected by 2-tert-Butylthiophene are currently unknown
Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound . For instance, exposure to light may affect the stability of thiophene-containing compounds . .
Preparation Methods
Synthetic Routes and Reaction Conditions: 2-tert-Butylthiophene can be synthesized through several methods. One common approach involves the alkylation of thiophene with tert-butyl halides in the presence of a strong base. For example, the reaction of thiophene with tert-butyl bromide in the presence of a base such as potassium tert-butoxide can yield this compound .
Industrial Production Methods: Industrial production of this compound typically involves similar alkylation reactions but on a larger scale. The reaction conditions are optimized to maximize yield and purity, often involving the use of continuous flow reactors and advanced purification techniques .
Chemical Reactions Analysis
Types of Reactions: 2-tert-Butylthiophene undergoes various chemical reactions, including:
Oxidation: It can be oxidized to form thiophene oxides and dioxides.
Reduction: Reduction reactions can convert this compound to its corresponding dihydrothiophene derivatives.
Substitution: Electrophilic substitution reactions can introduce various functional groups into the thiophene ring.
Common Reagents and Conditions:
Oxidation: m-Chloroperbenzoic acid, hydrogen peroxide.
Reduction: Lithium aluminum hydride.
Substitution: Nitric acid, sulfuric acid.
Major Products Formed:
Oxidation: Thiophene oxides and dioxides.
Reduction: Dihydrothiophene derivatives.
Substitution: Nitrothiophene, sulfonated thiophene.
Scientific Research Applications
Comparison with Similar Compounds
Thiophene: The parent compound, lacking the tert-butyl group.
2-Methylthiophene: A similar compound with a methyl group instead of a tert-butyl group.
2-Butylthiophene: A compound with a butyl group at the second position.
Comparison: 2-tert-Butylthiophene is unique due to the presence of the bulky tert-butyl group, which can influence its steric and electronic properties. This can affect its reactivity and interactions with other molecules, making it distinct from other thiophene derivatives. For example, the tert-butyl group can provide steric hindrance, reducing the compound’s susceptibility to certain reactions compared to smaller substituents like methyl or butyl groups .
Properties
IUPAC Name |
2-tert-butylthiophene |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C8H12S/c1-8(2,3)7-5-4-6-9-7/h4-6H,1-3H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
SWCDOJGIOCVXFM-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)(C)C1=CC=CS1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C8H12S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID7073270 |
Source
|
| Record name | 2-tert-Butylthiophene | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID7073270 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
140.25 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
1689-78-7 |
Source
|
| Record name | 2-tert-Butylthiophene | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0001689787 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | 2-tert-Butylthiophene | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID7073270 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 2-TERT-BUTYLTHIOPHENE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/R5YF9YW3CR | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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