3,4-Dichloro-1,2-phenylenediamine
[CAS# 1668-01-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 3,4-Dichloro-1,2-phenylenediamine
• Molecular Formula: C₆H₆Cl₂N₂
• Molecular Weight: 177.03
• CAS Registry Number: 1668-01-5
• EC Number: 858-128-5
• SMILES: C1=CC(=C(C(=C1N)N)Cl)Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

3,4-Dichloro-1,2-phenylenediamine is an aromatic amine with the molecular formula C6H6Cl2N2, known for its importance in organic synthesis, especially in the production of dyes, pigments, and pharmaceuticals. The compound has two chlorine atoms and two amino groups attached to a benzene ring, making it a versatile intermediate for a variety of chemical reactions.

The discovery of 3,4-dichloro-1,2-phenylenediamine can be linked to the broader exploration of substituted phenylenediamines in organic chemistry. Researchers are particularly interested in understanding how different substituents, such as chlorine atoms, affect the reactivity and properties of the phenylenediamine core. The synthesis of such compounds typically involves the chlorination of 1,2-phenylenediamine, where the chlorine atoms are introduced into the aromatic ring in the presence of a suitable chlorinating agent.

One of the main applications of 3,4-dichloro-1,2-phenylenediamine is in the synthesis of dyes and pigments. Its unique structure allows it to serve as a precursor for the production of a variety of azo dyes, which are widely used in the textile, plastic, and ink industries. Azo dyes are characterized by the presence of an azo bond (N=N) connecting an aromatic group and are valued for their bright colors and strong bonding properties. Dichloro substitution in 3,4-dichloro-1,2-phenylenediamine helps produce dyes with specific hues and increased stability.

In the pharmaceutical industry, 3,4-dichloro-1,2-phenylenediamine is used as a building block for the synthesis of active pharmaceutical ingredients (APIs). The reactivity of this compound makes it an ideal intermediate for creating complex molecules with desired biological activities. It is particularly useful in the development of drugs that target specific enzymes or receptors, as the dichloro substitution pattern can enhance the binding affinity and selectivity of the compound.

In addition, research laboratories use 3,4-dichloro-1,2-phenylenediamine to study the effects of chlorine substitution on the chemical and physical properties of phenylenediamines. This research helps to deepen the understanding of how different substituents affect the reactivity, stability, and overall behavior of aromatic amines, which is crucial for designing new compounds with customized properties.

While 3,4-dichloro-1,2-phenylenediamine is valuable in a variety of industrial applications, it is important to recognize the potential health and environmental risks associated with its use. Due to its toxicity and potential environmental impacts, this compound is classified as a hazardous compound. Long-term exposure can lead to adverse health effects, including skin and respiratory irritation. Therefore, it is important to take appropriate safety precautions when handling this chemical, such as using protective equipment and following proper disposal methods.

In summary, 3,4-dichloro-1,2-phenylenediamine is a key intermediate in the synthesis of dyes, pigments, and pharmaceuticals. Its discovery and utilization highlight the importance of substituted phenylenediamines in organic chemistry and their wide range of applications. Despite its usefulness, the hazardous nature of this compound requires careful handling and adherence to safety procedures to minimize the risk.