2,6-Diamino-4-chloropyrimidine 1-oxide
[CAS# 35139-67-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Chloropyrimidine
• Name: 2,6-Diamino-4-chloropyrimidine 1-oxide
• Synonyms: 6-chloro-3-hydroxy-2-iminopyrimidin-4-amine
• Molecular Formula: C₄H₅ClN₄O
• Molecular Weight: 160.56
• CAS Registry Number: 35139-67-4
• EC Number: 609-076-5
• SMILES: C1=C(N(C(=N)N=C1Cl)O)N

Properties

• Melting point: 185 ºC (dec.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Flammable solids	Flam. Sol.	1	H228
Unstable Explosives	Unst. Expl.		H200
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

2,6-Diamino-4-chloropyrimidine 1-oxide, commonly abbreviated as DACPO, is a heterocyclic compound. DACPO originated from the early 20th century research on pyrimidine derivatives. Pyrimidines are a class of nitrogen-containing heterocyclic compounds that are essential in various biological systems, including nucleic acids. Researchers have explored modifications to the pyrimidine core to discover new compounds with potential biological activity and unique chemical properties.

The structure of DACPO features a pyrimidine ring with amino groups at positions 2 and 6 and a chlorine atom at position 4. The presence of the 1-oxide group is noteworthy because it imparts oxidative properties and changes the electronic properties of the molecule, distinguishing DACPO from other pyrimidine derivatives.

In medicinal chemistry, DACPO is a valuable intermediate in the synthesis of various biologically active compounds. Its structure enables it to participate in a variety of chemical reactions, making it a versatile building block for the manufacture of drugs with specific therapeutic properties.

Derivatives of DACPO are explored for their antimicrobial properties. The amino and chlorine atoms in its structure facilitate interaction with microbial enzymes and receptors, which may lead to the development of new antibiotics. Research focuses on modifying DACPO to enhance its activity against a wider range of bacterial and fungal pathogens.

DACPO and its analogs are also being investigated for their potential in antiviral and anticancer therapy. The presence of the 1-oxide group introduces an oxidative stress mechanism that can disrupt viral replication or induce apoptosis in cancer cells. These properties make DACPO a promising scaffold for the design of novel drugs targeting viral infections and cancerous growth.

Besides pharmaceuticals, DACPO is also used in the development of agrochemicals, particularly herbicides and fungicides. Its ability to interfere with key biochemical pathways in plants and fungi makes it effective in controlling unwanted vegetation and fungal infections in crops.

As herbicides, DACPO derivatives can inhibit the growth of weeds by targeting specific enzymes essential for plant development. This mode of action allows for the selective elimination of weeds without affecting crop growth. The structure of the compound can be modified to enhance its specificity and reduce its environmental impact, becoming a valuable tool for sustainable agriculture.

In fungicides, DACPO derivatives can act by disrupting fungal cell membranes or interfering with their metabolic processes. These compounds are effective against a variety of fungal pathogens.

DACPO's unique structure makes it an important intermediate in organic synthesis. Its reactive amino and chloro groups are able to participate in coupling reactions, nucleophilic substitutions, and other transformations necessary to build complex molecules.

In organic synthesis, DACPO is used as a starting material for making more complex heterocyclic compounds. Its versatility allows the synthesis of a variety of derivatives, including those with potential pharmaceutical or agrochemical applications. Researchers have exploited its reactivity to develop new methods and expand the range of chemical entities that can be obtained.

DACPO's ability to form stable linkages with other monomers can also be used in polymer chemistry. It can be incorporated into polymers to introduce functionalities that improve material properties, such as thermal stability or resistance to degradation. These polymers can be used in a variety of industries, including electronics and materials science.

Ongoing research on DACPO focuses on optimizing its synthesis, exploring its derivatives, and evaluating its biological activity. Efforts are underway to improve its efficacy in pharmaceutical and agrochemical applications, as well as developing new uses for it in materials science and organic synthesis.