2,4-Dichloro-5-iodopyrimidine
[CAS# 13544-44-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Iodopyrimidine
• Name: 2,4-Dichloro-5-iodopyrimidine
• Molecular Formula: C₄HCl₂IN₂
• Molecular Weight: 274.87
• CAS Registry Number: 13544-44-0
• EC Number: 621-974-9
• SMILES: C1=C(C(=NC(=N1)Cl)Cl)I

Properties

• Density: 2.3±0.1 g/cm³, Calc.^*
• Melting point: 65-69 °C (Expl.)
• Index of Refraction: 1.663, Calc.^*
• Boiling Point: 310.2±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 141.4±22.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2,4-Dichloro-5-iodopyrimidine is a halogenated pyrimidine derivative notable for its utility in chemical synthesis and pharmaceutical research. Its structure, featuring chlorine atoms at the 2 and 4 positions and an iodine atom at the 5 position of the pyrimidine ring, grants it unique reactivity and versatility. This compound was first reported in studies exploring the halogenation of pyrimidines to develop intermediates for more complex chemical entities.

The discovery of 2,4-dichloro-5-iodopyrimidine arose during the mid-20th century as part of efforts to create functionalized pyrimidine derivatives for use in medicinal chemistry. Its synthesis typically involves selective iodination of 2,4-dichloropyrimidine, a reaction facilitated by the electron-withdrawing nature of the chlorine atoms. This strategic halogenation provided chemists with a valuable building block for constructing biologically active compounds.

In modern applications, 2,4-dichloro-5-iodopyrimidine serves as a crucial intermediate in organic synthesis, particularly in the development of pharmaceuticals. The iodine atom in its structure allows for easy coupling reactions, such as Suzuki-Miyaura and Sonogashira couplings, enabling the formation of carbon-carbon and carbon-heteroatom bonds. These reactions are pivotal in synthesizing heterocyclic frameworks and bioactive molecules.

This compound is also employed in agrochemical research, where it contributes to the design of pesticides and herbicides. Its halogenated nature enhances interactions with biological targets, improving efficacy. Additionally, 2,4-dichloro-5-iodopyrimidine has been utilized in materials science for creating advanced materials with specific electronic or optical properties, demonstrating its broad applicability.

The discovery and ongoing utilization of 2,4-dichloro-5-iodopyrimidine reflect its importance as a versatile chemical intermediate. Its role in facilitating the synthesis of complex molecules underscores its value in advancing pharmaceutical, agricultural, and material science innovations.

References

2011. Coupling with Alkenes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-116-00356

1971. Synthesis of n-(2-chloro-5-bromo-4-pyrimidyl)- and N-(2-chloro-5-iodo-4-pyrimidyl)amino acids. Chemistry of Heterocyclic Compounds, 7(4).
DOI: 10.1007/bf00471492