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4-Nitrochlorobenzene

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Identification
Molecular formula
C6H4ClNO2
CAS number
100-00-5
IUPAC name
1-chloro-4-nitro-benzene
State
State

At room temperature, 4-Nitrochlorobenzene is in the solid state. It typically appears as crystalline and does not exhibit volatility typical of many liquid aromatic compounds. Its solid, stable structure and low reactivity at ambient conditions make it a commonly stored and used aromatic compound in industrial chemical processes.

Melting point (Celsius)
83.00
Melting point (Kelvin)
356.15
Boiling point (Celsius)
242.00
Boiling point (Kelvin)
515.15
General information
Molecular weight
157.56g/mol
Molar mass
157.5580g/mol
Density
1.2970g/cm3
Appearence

4-Nitrochlorobenzene appears as a light, pale yellow crystalline solid. It may form needle-like or plate-like structures when crystallized from solution. The compound is typically uniform in color and can be distinguished from other aromatic compounds by its yellow hue due to the presence of nitro groups.

Comment on solubility

Solubility of 1-chloro-4-nitro-benzene

1-chloro-4-nitro-benzene, with the chemical formula C6H4ClN2O2, exhibits unique solubility characteristics that are influenced by its molecular structure. The compound is known to be:

  • Slightly soluble in water due to the presence of polar nitro and chloro groups.
  • Readily soluble in organic solvents such as ethanol, acetone, and ether, which accommodate its hydrophobic benzene ring.
  • Notably non-polar characteristics arise from the balanced arrangement of functional groups, leading to lower solubility in polar solvents.

In terms of solubility parameters:

  • The presence of -Cl and -NO2 groups enhances interactions with organic solvents.
  • These groups lead to a higher solvation energy in non-polar environments, making the compound more stable in such solvents.
  • The mild solubility in water can be attributed to the hydrogen bonding potential of the nitro group, although it is not sufficiently strong to make the compound highly soluble.

Consequently, when working with 1-chloro-4-nitro-benzene, it is essential to consider the choice of solvent—as highlighted:

"The solubility of a compound is not merely a reflection of its chemical constituents, but rather a dance between polar and non-polar forces."

Understanding these solubility traits is crucial for various chemical applications and reactions involving 1-chloro-4-nitro-benzene.

Interesting facts

Interesting Facts about 1-Chloro-4-nitro-benzene

1-Chloro-4-nitro-benzene, a member of the aromatic nitro compounds family, carries both a chloro group and a nitro group attached to its benzene ring, making it a fascinating compound in the world of organic chemistry. Here are some interesting points about this compound:

  • Applications: This compound plays a vital role in the synthesis of various dyes, pharmaceuticals, and pesticides. Its unique structure allows it to act as an intermediate in many important chemical reactions.
  • Nitro Group Properties: The nitro group (-NO2) is known for its electron-withdrawing properties. This characteristic influences the reactivity of the compound, making it highly useful in electrophilic substitution reactions.
  • Safety Considerations: While 1-chloro-4-nitro-benzene is useful, it also poses safety risks. It is classified as a hazardous material, with potential carcinogenic effects. Proper handling and disposal are critical in laboratory settings.
  • Synthesis: This compound can be synthesized via the chlorination of nitrobenzene or the nitration of chlorobenzene. Such reactions are essential for chemists aiming to create more complex organic molecules.
  • Reactivity: The positions of substituents on the aromatic ring play a crucial role in reactivity. The combination of the chloro and nitro groups can lead to interesting electronic effects, making it a suitable candidate for further functionalization.

As noted by renowned chemist "The interaction between electron-donating and electron-withdrawing groups can lead to unexpected reactivity in organic compounds," highlighting the importance of structures like that of 1-chloro-4-nitro-benzene in advancing chemical research.

This compound serves as a prime example of how slight modifications in molecular structure can lead to profound changes in chemical behavior and applications.

Synonyms
4-Chloronitrobenzene
1-CHLORO-4-NITROBENZENE
100-00-5
p-Chloronitrobenzene
Benzene, 1-chloro-4-nitro-
p-Nitrochlorobenzene
4-Nitrochlorobenzene
PNCB
4-Chloro-1-nitrobenzene
p-Nitrophenyl chloride
p-Nitrochlorobenzol
p-Nitroclorobenzene
1-Nitro-4-chlorobenzene
4-Nitro-1-chlorobenzene
p-Nitrochloorbenzeen
1-Chlor-4-nitrobenzol
1-Cloro-4-nitrobenzene
1-Chloor-4-nitrobenzeen
CCRIS 142
HSDB 1666
1-Chloro-4-nitro-benzene
NSC 9792
EINECS 202-809-6
UNII-CVL66U249D
MFCD00007285
p-Nitrochloro benzene
DTXSID5020281
AI3-15387
Nitrochlorobenzene, p-
Nitrochlorobenzene, para
NSC-9792
1 Chloro-4-nitrobenzene
UN 1578 (Salt/Mix)
DTXCID10281
CVL66U249D
CHEBI:34399
P-CHLORONITROBENZENE [MI]
BENZENE,1-CHLORO,4-NITRO
EC 202-809-6
CHLORO-4-NITROBENZENE, 1-
1-CHLORO-4-NITROBENZENE [HSDB]
Nitrobenzene, 4-chloro-
p-Nitrochloorbenzeen [Dutch]
p-Nitrochlorobenzol [German]
CAS-100-00-5
p-Nitroclorobenzene [Italian]
NITROCHLOROBENZENE (M-OR P-, SOLID)
NITROCHLOROBENZENE [M-OR P-, SOLID]
1-Chlor-4-nitrobenzol [German]
1-Chloor-4-nitrobenzeen [Dutch]
1-Cloro-4-nitrobenzene [Italian]
pNitrochlorobenzol
pNitroclorobenzene
pChloronitrobenzene
pNitrochloorbenzeen
pNitrochlorobenzene
4chloronitrobenzene
1Chlor4nitrobenzol
4Nitrochlorobenzene
1Cloro4nitrobenzene
CNB
1Chloor4nitrobenzeen
1Chloro4nitrobenzene
1Nitro4chlorobenzene
4Chloro1nitrobenzene
4Nitro1chlorobenzene
parachloronitrobenzene
paranitrochlorobenzene
pNitrophenyl chloride
4-nitrochlorobenezene
p-chloro nitrobenzene
p-chloro-nitrobenzene
p-nitro-chlorobenzene
4-chloro-nitrobenzene
4-chloronitro benzene
4-nitro chlorobenzene
para-chloronitrobenzene
para-nitrochlorobenzene
1chloro-4-nitrobenzene
Benzene, 1chloro4nitro
1-chloro-4-nitrobenzen
CHLORONITROBENZENES
WLN: WNR DG
1-Chloro-4-nitro benzene
benzene, 1-chloro-4-nitro
SCHEMBL29242
ghl.PD_Mitscher_leg0.919
MLS001055334
BIDD:ER0244
CHEMBL56970
Chloronitrobenzene, para, solid
SCHEMBL13815839
1-Chloro-4-nitrobenzene, 99%
CHLORONITROBENZENES, SOLID
NITROCHLOROBENZENES, SOLID
DTXSID40881178
NSC9792
CHLORONITROBENZENES, LIQUID
NITROCHLOROBENZENES, LIQUID
HMS3039H08
UN 1578 (DOT)
p-Nitrochlorobenzene (ACGIH:OSHA)
Tox21_202291
Tox21_300033
BBL013182
STL163961
AKOS000119953
NCGC00090707-01
NCGC00090707-02
NCGC00090707-03
NCGC00090707-04
NCGC00253995-01
NCGC00259840-01
BP-13397
FC167947
PS-10611
SMR000674577
DB-038035
1-Chloro-4-nitrobenzene, analytical standard
NS00009240
EN300-19641
NITROCHLOROBENZENE, PARA-, SOLID (DOT)
AR-360/40217802
1-Chloro-4-nitrobenzene 100 microg/mL in Methanol
Q4637187
Chloronitrobenzene, para, solid [UN1578] [Poison]
F0001-0006
Z104474568