Skip to main content

o-Phenylenediamine

ADVERTISEMENT
Identification
Molecular formula
C6H8N2
CAS number
95-54-5
IUPAC name
benzene-1,2-diamine
State
State

o-Phenylenediamine is typically found as a solid at room temperature.

Melting point (Celsius)
102.00
Melting point (Kelvin)
375.00
Boiling point (Celsius)
256.00
Boiling point (Kelvin)
529.00
General information
Molecular weight
108.14g/mol
Molar mass
108.1420g/mol
Density
1.2430g/cm3
Appearence

o-Phenylenediamine appears as white to light yellow crystals that darken when exposed to air and light due to oxidation. It has a distinct aromatic odor.

Comment on solubility

Solubility of Benzene-1,2-diamine

Benzene-1,2-diamine, also known as o-phenylenediamine, presents intriguing characteristics when it comes to its solubility. This aromatic amine is primarily soluble in a variety of solvents, with its solubility profile influenced by both temperature and the specific solvent in question.

Key Solubility Features:

  • Water Solubility: Benzene-1,2-diamine has limited solubility in water. At room temperature, it exhibits a solubility of approximately 0.1 g/100 mL.
  • Solvent Compatibility: It is more soluble in organic solvents such as ethanol, ether, and chloroform.
  • Effect of Temperature: Increasing the temperature can enhance the solubility, particularly in organic solvents.
  • Hydrophobic Character: The presence of the aromatic benzene rings contributes to its hydrophobic nature, limiting its interaction with polar solvents like water.

In summary, the solubility of benzene-1,2-diamine is a complex interplay of its molecular structure, environmental conditions, and the types of solvents used. It showcases moderate solubility in non-polar solvents while remaining relatively insoluble in water, making it an interesting compound for various chemical applications.

Interesting facts

Interesting Facts about Benzene-1,2-Diamine

Benzene-1,2-diamine, commonly known as ortho-phenylenediamine (o-PDA), is an aromatic amine with unique properties and applications that make it quite interesting in the world of chemistry. Here are some noteworthy aspects of this compound:

  • Structure & Conformation: The structure of benzene-1,2-diamine consists of a benzene ring substituted with two amine groups at the 1 and 2 positions. This arrangement results in an intriguing planar geometry that contributes to its reactivity.
  • Applications: Benzene-1,2-diamine is widely used in various industries, including:
    • As an intermediate in the synthesis of dyes and pigments, helping to produce vibrant colors.
    • In the manufacture of rubber chemicals, specifically as a curing agent.
    • In the production of hair dyes, where its ability to react with other components results in color development.
    • As a building block in pharmaceuticals research, creating compounds with potential therapeutic properties.
  • Biological Significance: While benzene-1,2-diamine has various applications, it’s important to note that some studies suggest it may have potential toxicity and carcinogenicity. It’s crucial to handle it with care and understand its impact on human health.
  • Reactivity: The presence of two amine groups makes benzene-1,2-diamine a versatile reactant. It can engage in various chemical reactions, such as:
    • Nucleophilic substitution reactions, where it can replace halogens in aromatic compounds.
    • Redox reactions, especially in the formation of azo dyes.
    • Self-condensation, leading to the formation of polymers and other complex structures.
  • Safety Precautions: It's vital for laboratory personnel and students working with benzene-1,2-diamine to follow appropriate safety protocols due to its potential hazards. Always use personal protective equipment (PPE) and conduct experiments in well-ventilated areas.

In conclusion, benzene-1,2-diamine is more than just a chemical compound; it is a fascinating substance with a broad range of applications and implications in various fields. Understanding its properties and potential impacts not only enhances our knowledge of organic chemistry but also informs safer working practices.

Synonyms
O-PHENYLENEDIAMINE
benzene-1,2-diamine
95-54-5
1,2-Phenylenediamine
1,2-Diaminobenzene
2-Aminoaniline
1,2-Benzenediamine
o-Diaminobenzene
Orthamine
o-Benzenediamine
OPDA
ortho-Phenylenediamine
PODA
C.I. Oxidation Base 16
o-Phenylene diamine
o-Fenylendiamin
1,2-Fenylendiamin
2-Phenylene diamine
IK 3
o-Aminoaniline
EK 1700
SQ 15500
CI Oxidation Base 16
C.I. 76010
orthophenylenediamine
NSC 5354
PHENYLENDIAMINE
CCRIS 508
phenylene-1,2-dimaine
HSDB 2893
CI 76010
EINECS 202-430-6
MFCD00007721
UNII-8B713N8Q0F
BRN 0606074
DTXSID3025881
CHEBI:34043
AI3-24343
8B713N8Q0F
NSC-5354
O-AMINOPHENYLAMINE
DTXCID905881
OPD
NSC5354
EC 202-430-6
4-13-00-00038 (Beilstein Handbook Reference)
aniline, 2-amino-
NCGC00090885-03
o-Fenylendiamin [Czech]
1,2-Fenylendiamin [Czech]
TIABENDAZOLE IMPURITY A (EP IMPURITY)
TIABENDAZOLE IMPURITY A [EP IMPURITY]
o-PDA
Phenylenediamine, ortho-
o-phenylendiamin
o-phenylendiamine
Phenylene diamine
2-Amino-aniline
ortho-aminoaniline
0-phenylendiamine
0-phenylenediamine
2-aminophenylamine
o-phenyl-enediamine
o-phenyle-nediamine
o-phenylene-diamine
ortho-diaminobenzene
Phenylenediamine, o-, and its salt
1.2-diaminobenzene
1,2-phenylendiamine
1,2 phenylenediamine
1,2-benzenedi-amine
1.2-phenylenediamine
ortho phenylene diamine
(2-aminophenyl)-amine
1,2-phenylene diamine
1,2-phenylene-diamine
Lansoprazole Impurity 22
WLN: ZR BZ
NCIMech_000739
SCHEMBL6187
IK 3 (AMINE)
1,2-DIAMINO-BENZENE
BIDD:ER0680
CHEMBL70582
O-PHENYLENEDIAMINE [MI]
SCHEMBL11062175
O-PHENYLENEDIAMINE [HSDB]
BCP25295
STR03001
Tox21_400014
CCG-35856
MSK000851
o-Phenylenediamine, flaked, 99.5%
STK301816
AKOS000119133
o-Phenylenediamine, sublimed, >=99%
AT28018
FP26951
CAS-95-54-5
NCGC00090885-01
NCGC00090885-02
NCGC00090885-04
NCGC00090885-05
NCGC00090885-06
BP-11855
NCI60_004318
PD011925
2-Phenylene diamine (1,2Phenylenediamine)
NS00006526
P0168
P0968
P1805
EN300-19093
o-Phenylenediamine, for fluorescence, free base
AC-907/25014349
Q3596763
o-Phenylenediamine [UN1673] [Keep away from food]
o-Phenylenediamine, tablet, 20 mg substrate per tablet
Z104472742
1,2-Benzenediamine;o-Phenylenediamine;1,2-Diaminobenzene
o-Phenylenediamine, Peroxidase substrate, >=98.0%, powder
o-Phenylenediamine, suitable for fluorescence, >=99.0% (NT)
InChI=1/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H
202-430-6