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Thiophene

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Identification
Molecular formula
C4H4S
CAS number
110-02-1
IUPAC name
thiophene
State
State

At room temperature, thiophene is a liquid. It has a relatively low boiling and melting point compared to larger aromatic compounds, making it volatile and easily vaporized.

Melting point (Celsius)
-38.30
Melting point (Kelvin)
234.85
Boiling point (Celsius)
84.20
Boiling point (Kelvin)
357.35
General information
Molecular weight
84.14g/mol
Molar mass
84.1400g/mol
Density
1.0510g/cm3
Appearence

Thiophene is a colorless liquid with a faint benzene-like odor. It is often used as a building block for more complex chemical compounds. This compound is insoluble in water but is soluble in organic solvents such as ethanol and ether.

Comment on solubility

Solubility of Thiophene

Thiophene, with the chemical formula C4H4S, exhibits unique solubility characteristics that are important in various chemical processes. This aromatic compound is a member of the heterocyclic compounds, which brings a distinct twist to its behavior in different solvents.

Key Solubility Insights

  • Water Solubility: Thiophene is insoluble in water due to its nonpolar nature and the presence of a sulfur atom, which does not favor hydrogen bonding.
  • Solvent Range: It readily dissolves in organic solvents, such as:
    • Ether
    • Benzene
    • Toluene
  • Polar vs. Nonpolar Solvents: The solubility behavior of thiophene is more prominently observed in nonpolar solvents compared to polar solvents.

In summary, thiophene demonstrates a clear preference for nonpolar solvents, making it an intriguing compound for studies in organic chemistry. Its ability to dissolve in specific environments while being insoluble in water underscores the importance of understanding solubility trends in chemical reactions and applications.

Interesting facts

Interesting Facts about Thiophene

Thiophene is a fascinating heterocyclic compound known for its unique properties and diverse applications. Here are some notable aspects:

  • Structure and Bonding: Thiophene features a five-membered ring structure that includes four carbon atoms and one sulfur atom. This ring is analogous to benzene, but the presence of sulfur imparts distinct electronic characteristics and reactivity.
  • Versatile Chemical Reactivity: Thiophene can undergo various chemical reactions. It is known to participate in electrophilic substitution, making it an important precursor in organic synthesis. Its ability to react with a range of electrophiles opens up pathways to synthesize more complex molecules.
  • Conductive Properties: Thiophene derivatives, such as polythiophene, are utilized in organic electronics. They exhibit semiconductive properties which make them suitable for applications in organic light-emitting diodes (OLEDs) and organic photovoltaic cells.
  • Natural Occurrence: Thiophene is not only synthetically accessible but can also be found in nature. It is present in some essential oils and contributes to the aroma of certain plants.
  • Biological Activity: Some thiophene derivatives display interesting biological activities, including antibacterial and antifungal properties. This has led to research investigating their potential use in pharmaceutical applications.

With its rich chemistry and wide-ranging applications, thiophene continues to be a subject of interest for chemists looking to innovate within various fields such as materials science, pharmacology, and organic synthesis.

Synonyms
THIOPHENE
110-02-1
Thiofuran
Thiole
Thiophen
Thiacyclopentadiene
Thiotetrole
Thiofurfuran
Divinylene sulfide
Thiaphene
Thiofuram
Furan, thio-
Huile HSO
Thiofen
Huile H50
CP 34
USAF EK-1860
CCRIS 2935
HSDB 130
NSC 405073
25233-34-5
UNII-SMB37IQ40B
EINECS 203-729-4
SMB37IQ40B
BRN 0103222
DTXSID8026145
CHEBI:30856
AI3-15417
MFCD00005413
NSC-405073
Hopkin's lactic acid reagent
DTXCID006145
EC 203-729-4
51325-05-4
Thiofen [Czech]
Thiophenes
UN2414
monothiophene
C4H4S
thio-furan
thiophene-
2-Thiophene
Divinylene sulphide
Thiophene, Reagent
MFCD26958734
Thiophene [UN2414] [Flammable liquid]
Thiophene, >=99%
THIOPHENE [MI]
HUILE HS0
THIOPHENE [HSDB]
WLN: T5SJ
THIOPHENE [WHO-DD]
Thiophene, analytical standard
CHEMBL278958
CP34
Tox21_200002
NSC405073
AKOS000120157
UN 2414
NCGC00091806-01
NCGC00091806-02
NCGC00257556-01
CAS-110-02-1
Thiophene [UN2414] [Flammable liquid]
DB-038045
NS00009124
T0223
EN300-19105
A802127
A802128
InChI=1/C4H4S/c1-2-4-5-3-1/h1-4
Q305364
F0001-0214
107760-19-0
203-729-4