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2-(2-aminophenyl)aniline

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Identification
Molecular formula
C12H12N2
CAS number
553-00-4
IUPAC name
2-(2-aminophenyl)aniline
State
State

At room temperature, 2-(2-aminophenyl)aniline resides in a solid state. It can be handled safely under standard laboratory conditions without immediate transition to a liquid or gas state.

Melting point (Celsius)
67.00
Melting point (Kelvin)
340.15
Boiling point (Celsius)
392.50
Boiling point (Kelvin)
665.65
General information
Molecular weight
184.24g/mol
Molar mass
184.2440g/mol
Density
1.2200g/cm3
Appearence

2-(2-aminophenyl)aniline appears as a solid compound in its raw form. It may present as off-white or light yellowish powder, but can also crystallize into forms depending on purity and other conditions.

Comment on solubility

Solubility of 2-(2-aminophenyl)aniline

The solubility of 2-(2-aminophenyl)aniline presents some interesting characteristics that are particularly noteworthy for its applications in various fields. This compound is generally considered to be soluble in organic solvents but demonstrates limited solubility in water. Here, we break down its solubility attributes:

  • Organic Solvents: 2-(2-aminophenyl)aniline is often soluble in non-polar and mildly polar organic solvents such as:
    • Alcohols (e.g., methanol, ethanol)
    • Aromatic hydrocarbons (e.g., toluene, xylene)
    • Dimethyl sulfoxide (DMSO)
  • Water Solubility: This compound exhibits low solubility in water due to:
    • The presence of hydrophobic aromatic rings which hinder interaction with water
    • The amine groups which, while polar, are not enough to overcome the hydrophobic effects
  • pH Dependency: The solubility may be influenced by pH as the amine groups can accept protons:
    • At lower pH (acidic conditions), increased solubility may occur due to protonation.
    • At higher pH (basic conditions), it tends to remain less soluble.

In summary, the solubility profile of 2-(2-aminophenyl)aniline is governed by its molecular structure, showcasing a preference for organic solvents while maintaining a generally low solubility in water. Understanding these properties is crucial for its use in chemical synthesis and industrial applications.

Interesting facts

Interesting Facts about 2-(2-Aminophenyl)aniline

2-(2-Aminophenyl)aniline, also known as an anthranilic derivative, is a fascinating compound in the realm of organic chemistry. It exhibits several intriguing characteristics and applications that make it a topic of interest for both researchers and students. Here are some key points to consider:

Unique Structure

  • This compound features a biphenyl structure where two phenyl rings are linked by an amine group, creating a rich site for chemical reactivity.
  • The presence of the amino group (-NH2) allows it to participate in a variety of chemical reactions, such as nucleophilic substitution and redox reactions.

Applications in Dyes and Pigments

  • 2-(2-Aminophenyl)aniline is recognized for its potential use in the synthesis of various dyes, notably azo dyes, which are used to impart vibrant colors in textiles.
  • Its ability to form chelates with metal ions can also make it valuable in developing pigments with enhanced stability and colorfastness.

Pharmaceutical Significance

  • This compound may provide a scaffold for designing novel pharmaceuticals, particularly in the field of anti-cancer agents, due to its ability to engage in multiple types of binding interactions with biological targets.
  • Research has indicated that analogs of this compound exhibit significant biological activity, opening pathways for medicinal chemistry explorations.

Noteworthy Reactions

The compound's amino and phenyl groups facilitate a wide range of reactions, making it a versatile intermediate. Common reaction pathways include:

  • Amination reactions: Allowing the introduction of additional functional groups.
  • Electrophilic aromatic substitutions: Enabling further functionalization of the aromatic rings.

In summary, 2-(2-Aminophenyl)aniline is more than just a compound; it represents a significant intersection of aromatic chemistry, industrial application, and pharmaceutical development. The continued study of this compound holds promise for innovations in various fields.

Synonyms
2,2'-BIPHENYLDIAMINE
2,2'-Diaminobiphenyl
[1,1'-Biphenyl]-2,2'-diamine
o-Benzidine
o,o'-Diaminobiphenyl
2,2'-Diaminodiphenyl
(1,1'-Biphenyl)-2,2'-diamine
0DJ0J26MNW
NSC 99367
BRN 1949579
NSC-99367
UNII-0DJ0J26MNW
2,2'-diamino-1,1'-biphenyl
DTXSID00163003
4-13-00-00356 (Beilstein Handbook Reference)
DTXCID6085494
(1,1'-Biphenyl)-2,2'-diamine (9CI)
685-728-2
holgxwdgcvtmtb-uhfffaoysa-n
1454-80-4
Biphenyl-2,2'-diamine
2-(2-aminophenyl)aniline
1,1'-Biphenyl-2,2'-diamine
2,2/'-Biphenyldiamine
MFCD00034060
2,2 inverted exclamation marka-Biphenyldiamine
NSC99367
Enamine_000878
2,2''-Biphenyldiamine
NCIOpen2_002089
MLS000765308
SCHEMBL169281
CHEMBL1384563
HMS1396H20
HMS2620M18
ALBB-010500
AKOS000269002
NCGC00245148-01
2'-Amino[1,1'-biphenyl]-2-ylamine #
FB120363
LS-03557
SMR000289413
SY234655
2,2'-Biphenyldiamine, >=96.5% (GC)
DB-080996
CS-0196799
D5255
2,2 inverted exclamation mark -Diaminobiphenyl
T70293
AE-641/02339059
[1,1'-biphenyl]-2,2'-diamine;2,2'-Biphenyldiamine
Z56786620