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Aniline

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Identification
Molecular formula
C6H7N
CAS number
62-53-3
IUPAC name
aniline
State
State

At room temperature, aniline is a liquid. It has a slightly oily consistency and is heavier than water.

Melting point (Celsius)
-6.30
Melting point (Kelvin)
266.85
Boiling point (Celsius)
184.13
Boiling point (Kelvin)
457.28
General information
Molecular weight
93.13g/mol
Molar mass
93.1290g/mol
Density
1.0220g/cm3
Appearence

Aniline is a colorless to slightly yellow liquid. It tends to darken on exposure to air and light. It has a characteristic amine odor that resembles that of rotten fish.

Comment on solubility

Solubility of Aniline (C6H7N)

Aniline, a simple aromatic amine, exhibits interesting solubility characteristics primarily due to its chemical structure. Here are some key points regarding the solubility of aniline:

  • Polar and Nonpolar Interactions: Aniline is somewhat polar because of the amino (-NH2) group, which is capable of forming hydrogen bonds with water molecules.
  • Solubility in Water: Aniline is only slightly soluble in water. The solubility is reported to be around 3.6 g/L at 25°C. This relatively low solubility is attributed to the hydrophobic nature of the benzene ring.
  • Solubility in Organic Solvents: Aniline shows good solubility in a variety of organic solvents including ethanol, acetone, and chloroform. This is due to its ability to engage in van der Waals interactions and dipole-dipole interactions with other organic molecules.
  • Effect of pH: The solubility of aniline can significantly increase in acidic conditions. In such environments, aniline can be protonated to form anilinium ions (C6H7N+), which are much more soluble in water.

In conclusion, while aniline possesses some polar characteristics, its overall solubility profile is largely dictated by its hydrophobic aromatic structure, leading to limited water solubility and greater compatibility with organic solvents. Understanding these solubility traits is essential for applications in various fields, including chemical synthesis and industrial processes.

Interesting facts

Fascinating Insights into Aniline

Aniline, often referred to by its IUPAC name aminobenzene, is a simple aromatic amine that has made a significant mark in both industrial applications and scientific research. Here are some intriguing facts about this compound:

  • Historical Importance: Aniline was first isolated from indigo dye in 1826, marking a pivotal moment in organic chemistry.
  • Industrial Use: It plays a crucial role in the manufacture of dyes, especially azo dyes, and pigments, which are essential in coloring textiles, inks, and plastics.
  • Biological Role: Aniline and its derivatives are often researched for their potential applications in pharmaceuticals, including analgesics and antiseptics.
  • Toxicity Awareness: Despite its utility, aniline is toxic and may lead to health risks such as methemoglobinemia if inhaled or ingested; hence, proper safety precautions are vital during handling.
  • Chemical Reactions: Aniline can undergo a variety of chemical reactions, including acetylation and oxidation, which make it a versatile substrate in organic synthesis.

As noted by chemists, "Aniline embodies the duality of chemistry—its potential for innovation and the responsibility it entails in its safe use."

This compound's ability to act as both a nucleophile and electrophile in chemical reactions showcases its fascinating chemical behavior, making it a compound of interest for those delving into the complexities of organic chemistry.

Synonyms
ANILINE
Benzenamine
Phenylamine
62-53-3
Aminobenzene
Aminophen
Arylamine
Kyanol
Anilin
Cyanol
Benzeneamine
Krystallin
Benzidam
Anyvim
Anilina
Huile D'aniline
C.I. Oxidation Base 1
Rcra waste number U012
CI Oxidation Base 1
Caswell No. 051C
Anilinum
C.I. 76000
HSDB 43
ANILINE-N,N-D2
CCRIS 44
NCI-C03736
Aniline and homologues
Aniline reagent
UN 1547
CHEBI:17296
UNII-SIR7XX2F1K
SIR7XX2F1K
EINECS 200-539-3
MFCD00007629
EPA Pesticide Chemical Code 251400
Aniline-1-13C
CI 76000
DTXSID8020090
AI3-03053
DTXCID9090
EC 200-539-3
Benzene, amino
Anilin [Czech]
ANILINE (IARC)
ANILINE [IARC]
ANILINE (MART.)
ANILINE [MART.]
ANILINE (USP-RS)
ANILINE [USP-RS]
Huile d'aniline [French]
ANILINE (USP IMPURITY)
ANILINE [USP IMPURITY]
Phenyleneamine
D'aniline
RCRA waste no. U012
Anilina [Italian, Polish]
FENTANYL IMPURITY F (EP IMPURITY)
FENTANYL IMPURITY F [EP IMPURITY]
Aniline and homologs
MESALAZINE IMPURITY K (EP IMPURITY)
MESALAZINE IMPURITY K [EP IMPURITY]
TRIMETHOPRIM IMPURITY K (EP IMPURITY)
TRIMETHOPRIM IMPURITY K [EP IMPURITY]
UN1547
benzenaminium
cyanole
BIDD:ER0581
phenyl amine
phenyl-amine
8-aniline
Benzene, amino-
Fentanyl impurity F
Aniline;Aminobenzene
PhNH2
Aniline, ACS Grade
ANILINUM [HPUS]
ANILINE [HSDB]
ANILINE [MI]
ANILINE [WHO-DD]
CHEMBL538
Epitope ID:117704
Aniline, analytical standard
Aniline, AR, >=99%
Aniline, LR, >=99%
C6H5NH2
Discontinued, see H924510
Aniline, 99.5%, ACS grade
BDBM92572
Trimethoprim specified impurity K
Aniline, ReagentPlus(R), 99%
BENZENE,AMINO (ANILINE)
DTXSID50207744
DTXSID70178043
Aniline [UN1547] [Poison]
BAA12259
STR00216
Aniline, ACS reagent, >=99.5%
Tox21_200345
Aniline 10 microg/mL in Cyclohexane
STK301792
AKOS000268796
Aniline 100 microg/mL in Cyclohexane
DB06728
FA07686
NCI 176889
Aniline, ASTM, ACS reagent, 99.5%
Aniline, SAJ first grade, >=99.0%
CAS-62-53-3
Aniline, JIS special grade, >=99.0%
Aniline, p.a., ACS reagent, 99.0%
NCGC00091297-01
NCGC00091297-02
NCGC00091297-03
NCGC00257899-01
BP-12047
Aniline, PESTANAL(R), analytical standard
DB-013441
A0463
NS00010656
EN300-33390
C00292
SBI-0653858.0001
A833829
AMINOBENZOIC ACID IMPURITY C [EP IMPURITY]
Q186414
SR-01000944923
SR-01000944923-1
Q27121173
F2190-0417
InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H
Aniline, United States Pharmacopeia (USP) Reference Standard
136260-71-4
200-539-3