Understanding Furan and Thiophene: Structures, Properties, and Uses

 
Furan
 
By
Dr.S.V. Lamture
Asso. Prof. &Head
Dept  of chemistry
 
Furan 
Furan 
(C
(C
4
4
H
H
4
4
O)
O)
 
Furan is a heterocyclic organic compound,
consisting of a five-membered aromatic ring
with four carbon atoms and one oxygen.
The class of compounds containing such rings
are also referred to as furans.
 
Structurer  Fig. Of Furan
Structurer  Fig. Of Furan
 
Preparation of Furan
Preparation of Furan
 
Industrially, furan is manufactured by the palladium-
catalyzed decarboxylation of furfural, or by the copper-
catalyzed oxidation of 1,3-butadiene.
 
 
 
 
In the laboratory, furan can be obtained from furfural
by oxidation to furan-2-carboxylic acid, followed by
decarboxylation.
 It can also be prepared directly by thermal
decomposition of pentose-containing materials,
cellulosic solids especially pine-wood.
 
Properties of Furan
Properties of Furan
 
1.
Furan is a colourless volatile liquid.
Furan is a colourless volatile liquid.
2.
It’s boiling point is 31.4°C and melting point
It’s boiling point is 31.4°C and melting point
−85.6 °C.
−85.6 °C.
3.
Furan having odor of chloroform.
Furan having odor of chloroform.
4.
It is insoluble in ether but soluble in most
It is insoluble in ether but soluble in most
organic solvents.
organic solvents.
 
U
U
SES
SES
 
 
OF
OF
 F
 F
URAN
URAN
 
Furan is used as a starting point to other
Furan is used as a starting point to other
specialty chemicals
specialty chemicals
.
.
 
3.
Thiophene 
Thiophene 
(C
(C
4
4
H
H
4
4
S)
S)
 
Thiophene, also commonly called thiofuran, is a
Thiophene, also commonly called thiofuran, is a
heterocyclic compound with the formula C4H4S.
heterocyclic compound with the formula C4H4S.
Consisting of a flat five-membered ring, it is
Consisting of a flat five-membered ring, it is
aromatic as indicated by its extensive substitution
aromatic as indicated by its extensive substitution
reactions.
reactions.
 
 
Thiophene
Thiophene
 
Structurer fig. of Thiophene
Structurer fig. of Thiophene
 
Properties Of Thiophene
Properties Of Thiophene
 
At room temperature, thiophene is a colorless liquid
At room temperature, thiophene is a colorless liquid
with a mildly pleasant odor reminiscent of benzene.
with a mildly pleasant odor reminiscent of benzene.
It’s boiling point is 84°C and melting point -38°C.
It’s boiling point is 84°C and melting point -38°C.
It is insoluble in water but freely soluble in ethanol,
It is insoluble in water but freely soluble in ethanol,
ether and acetone.
ether and acetone.
The high reactivity of thiophene toward sulfonation
The high reactivity of thiophene toward sulfonation
is the basis for the separation of thiophene from
is the basis for the separation of thiophene from
benzene.
benzene.
Thiophene is much more reactive than benzene ,
Thiophene is much more reactive than benzene ,
thus thiophene undergoes the electrophilic
thus thiophene undergoes the electrophilic
substitution reactions like benzene , under moderate
substitution reactions like benzene , under moderate
condition.
condition.
 
Uses of Thiophene
Uses of Thiophene
 
Thiophenes are important heterocyclic compounds
Thiophenes are important heterocyclic compounds
that are widely used as building blocks in many
that are widely used as building blocks in many
agrochemicals and pharmaceuticals.
agrochemicals and pharmaceuticals.
The benzene ring of a biologically active compound
The benzene ring of a biologically active compound
may often be replaced by a thiophene without loss
may often be replaced by a thiophene without loss
of activity.
of activity.
This is seen in examples such as the NSAID
This is seen in examples such as the NSAID
lornoxicam, the thiophene analog of piroxicam.
lornoxicam, the thiophene analog of piroxicam.
 
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Furan and Thiophene are important heterocyclic organic compounds with distinct structures and properties. Furan, a five-membered aromatic ring, is used in specialty chemical production and has unique physical properties. Thiophene, a sulfur-containing compound, finds applications in agrochemicals and pharmaceuticals due to its reactivity and versatility. Both compounds have specific preparation methods and exhibit different behaviors in various solvents. Understanding their structures, properties, and uses is essential in the field of chemistry.


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  1. Furan By Dr.S.V. Lamture Asso. Prof. &Head Dept of chemistry

  2. Furan (C4H4O) Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans. Structurer Fig. Of Furan

  3. Preparation of Furan Industrially, furan is manufactured by the palladium- catalyzed decarboxylation of furfural, or by the copper- catalyzed oxidation of 1,3-butadiene. In the laboratory, furan can be obtained from furfural by oxidation to furan-2-carboxylic acid, followed by decarboxylation. It can also be prepared directly by thermal decomposition of pentose-containing materials, cellulosic solids especially pine-wood.

  4. Properties of Furan 1. Furan is a colourless volatile liquid. 2. It s boiling point is 31.4 C and melting point 85.6 C. 3. Furan having odor of chloroform. 4. It is insoluble in ether but soluble in most organic solvents. USESOF FURAN Furan is used as a starting point to other specialty chemicals.

  5. 3. Thiophene (C4H4S) Thiophene, also commonly called thiofuran, is a heterocyclic compound with the formula C4H4S. Consisting of a flat five-membered ring, it is aromatic as indicated by its extensive substitution reactions. Structurer fig. of Thiophene Thiophene

  6. Properties Of Thiophene At room temperature, thiophene is a colorless liquid with a mildly pleasant odor reminiscent of benzene. It s boiling point is 84 C and melting point -38 C. It is insoluble in water but freely soluble in ethanol, ether and acetone. The high reactivity of thiophene toward sulfonation is the basis for the separation of thiophene from benzene. Thiophene is much more reactive than benzene , thus thiophene undergoes the electrophilic substitution reactions like benzene , under moderate condition.

  7. Uses of Thiophene Thiophenes are important heterocyclic compounds that are widely used as building blocks in many agrochemicals and pharmaceuticals. The benzene ring of a biologically active compound may often be replaced by a thiophene without loss of activity. This is seen in examples such as the NSAID lornoxicam, the thiophene analog of piroxicam.

  8. Thanks

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