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Pyrrole

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Identification
Molecular formula
C4H5N
CAS number
109-97-7
IUPAC name
pyrrole
State
State

At room temperature, pyrrole is a liquid.

Melting point (Celsius)
-23.00
Melting point (Kelvin)
250.15
Boiling point (Celsius)
129.00
Boiling point (Kelvin)
402.15
General information
Molecular weight
67.09g/mol
Molar mass
67.0890g/mol
Density
0.9670g/cm3
Appearence

Pyrrole is a colorless or pale yellow, light-sensitive liquid with an unpleasant odor. Upon exposure to air, it can turn dark over time due to oxidation. It is less dense than water and is soluble in many organic solvents.

Comment on solubility

Solubility of Pyrrole

Pyrrole, with the chemical formula C4H5N, is an intriguing organic compound known for its distinctive properties and behavior in various solvents. When it comes to solubility, pyrrole demonstrates an interesting profile:

  • Polar Solvents: Pyrrole is highly soluble in polar solvents such as water and alcohols due to its ability to engage in hydrogen bonding.
  • Non-Polar Solvents: It is also soluble in non-polar solvents, including hydrocarbons like benzene and toluene, owing to its aromatic character.
  • Solubility Limitations: However, it is important to note that there are limitations to its solubility; factors such as temperature and concentration can impact the overall dissolution process.

In essence, pyrrole’s solubility is influenced by its structure, which allows it to interact favorably with both polar and non-polar environments. Understanding these solubility characteristics is crucial for its applications in organic synthesis and materials science.

Interesting facts

Discovering Pyrrole

Pyrrole is a fascinating organic compound that stands out due to its unique structure and reactivity. As a five-membered aromatic ring containing one nitrogen atom, it is a pivotal building block in various chemical compounds and plays a significant role in biological systems.

Key Characteristics of Pyrrole

  • Aromatic Nature: Pyrrole is known for its aromaticity, which imparts stability and distinct chemical properties.
  • Biological Significance: It serves as a precursor to several important biological molecules, including hemoglobin and chlorophyll.
  • Applications in Synthesis: Pyrrole is a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes.
  • Reactivity: It readily participates in electrophilic substitution reactions, making it versatile for further chemical modifications.

Interesting Historical Context

First identified in the early 19th century, pyrrole has since become a subject of extensive study among chemists due to its prevalence in nature and utility in synthetic chemistry. The name pyrrole is derived from its association with the chemical property of pyrolysis, referring to its formation from heating organic compounds.

Quotes from Scientists

James B. Conant once remarked, "Pyrrole and its derivatives are silent champions of the chemical world, underpinning life itself." These words capture the essence of pyrrole's significance in both nature and synthetic chemistry.

In summary, pyrrole is much more than a simple compound; it is a cornerstone of organic synthesis and an essential player in biological systems, making it a compound worthy of detailed study and appreciation.

Synonyms
PYRROLE
1H-Pyrrole
109-97-7
Divinylenimine
Imidole
Azole
Pyrrol
Monopyrrole
Divinyleneimine
1-Aza-2,4-cyclopentadiene
30604-81-0
FEMA No. 3386
Pyrrole-15N
NSC 62777
CCRIS 2933
HSDB 119
CHEBI:19203
EINECS 203-724-7
UNII-86S1ZD6L2C
NSC-62777
(1H-Pyrrole)x
PYROLLE
86S1ZD6L2C
DTXSID5021910
AI3-18817
MFCD00005216
DTXCID201910
26120-22-9
Pyrroles
C4H5N
Pyrrhol
Pyrole
beta-pyrrole
a pyrrole
pyrrole-
Pyrrole, Reagent
Polypyrrole (undoped, extent of labeling: ~20 wt. % loading, composite with carbon black)
1-H-pyrrole
Pyrrole1539
1-aza-cyclopentadiene
PYRROLE [FHFI]
PYRROLE [HSDB]
PYRROLE [FCC]
1H-PYRROLE [MI]
Epitope ID:136031
WLN: T5MJ
Pyrrole, analytical standard
CHEMBL16225
Pyrrole, reagent grade, 98%
QSPL 001
CHEBI:35556
FEMA 3386
Pyrrole, >=98%, FCC, FG
NSC62777
NSC72470
STR00296
Tox21_303910
BBL011520
NSC-72470
STL146636
AKOS000120094
FP14738
NCGC00357161-01
BP-21154
CAS-109-97-7
1H-Pyrrole; Azole; Divinylenimine; Imidole
DB-003771
NS00014390
P0574
EN300-20590
C19907
H27771
A802120
InChI=1/C4H5N/c1-2-4-5-3-1/h1-5
Q242627
F2190-0643
Z104479036
107760-17-8
203-724-7