5-(3-Anilinopropyl)-6-methylpyrimidine-2,4-diamine
[CAS# 2387-89-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 5-(3-Anilinopropyl)-6-methylpyrimidine-2,4-diamine
• Synonyms: 6-methyl-5-[3-(phenylamino)propyl]pyrimidine-2,4-diamine; NSC86195
• Molecular Formula: C₁₄H₁₉N₅
• Molecular Weight: 257.33
• CAS Registry Number: 2387-89-5
• SMILES: CC1=C(C(=NC(=N1)N)N)CCCNC2=CC=CC=C2

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 558.3±60.0 ºC 760 mmHg (Calc.)^*
• Flash point: 291.5±32.9 ºC (Calc.)^*
• Index of refraction: 1.678 (Calc.)^*

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

Discovory and Applicatios

5-(3-Anilinopropyl)-6-methylpyrimidine-2,4-diamine is an organic compound belonging to the class of substituted pyrimidines, a group of heterocyclic aromatic compounds containing nitrogen atoms in a six-membered ring. It has the molecular formula C₁₄H₁₉N₅ and a molecular weight of approximately 257.34 g/mol. The structure consists of a 6-methylpyrimidine core substituted at the 5-position with a 3-anilinopropyl chain and amino groups at the 2- and 4-positions. This arrangement of functional groups contributes to both its chemical stability and its potential for biological activity, particularly in interactions with enzymes or receptors involving hydrogen bonding and aromatic stacking.

Information from chemical databases such as ChemSpider and the EPA CompTox Dashboard confirms that this compound is a defined and registered substance, referenced under multiple identifiers. ChemSpider lists its chemical structure, connectivity descriptors (SMILES and InChI codes), and registry links to major chemical databases. The EPA CompTox record (DTXSID10292873) identifies it as an organic intermediate and includes data fields related to physicochemical properties and potential environmental behavior, although detailed toxicological studies are not reported in public sources. The available database information places this compound within a set of synthetic pyrimidine derivatives that are commonly explored in medicinal chemistry and industrial research due to the versatility of the pyrimidine nucleus.

Compounds with closely related structures—especially diamino-substituted pyrimidines—are widely known for their biological significance. Many analogs of this compound act as intermediates or core structures in the synthesis of antimetabolites, enzyme inhibitors, and receptor modulators. While specific pharmacological or industrial uses of 5-(3-anilinopropyl)-6-methylpyrimidine-2,4-diamine have not been detailed in publicly accessible literature, its structural similarity to other functionalized pyrimidines suggests it may serve as a synthetic intermediate for more complex heterocycles or pharmacologically active molecules. Substituted pyrimidines are fundamental in the design of drugs targeting folate metabolism, nucleic acid synthesis, and kinase activity, areas where aromatic and amino-functionalized systems like this compound can exhibit useful binding characteristics.

From a chemical synthesis standpoint, the compound can be categorized among substituted diamino-pyrimidines that are typically prepared through multi-step reactions involving alkylation or reductive amination of preformed pyrimidine intermediates. The presence of both amino groups at positions 2 and 4 makes the compound a potential nucleophilic building block for condensation reactions with carbonyl or acyl derivatives, while the anilinopropyl chain can undergo further functionalization to yield derivatives with tailored solubility or bioactivity profiles. The methyl substitution at the 6-position contributes to hydrophobic balance and may influence its interaction with hydrophobic sites in biochemical systems or with polymeric materials when used as a monomeric additive.

In regulatory and environmental contexts, registration of this compound in the EPA CompTox database indicates an interest in tracking its presence as an industrial or research chemical. The lack of detailed hazard or biodegradation data suggests it has not yet been extensively characterized toxicologically, and it may exist primarily as a research or intermediate compound rather than a substance of large-scale commercial use. Nonetheless, its combination of aromaticity, amino substituents, and aniline functionality make it of potential interest for future applications in chemical biology, material science, or synthetic organic chemistry.

In summary, 5-(3-anilinopropyl)-6-methylpyrimidine-2,4-diamine represents a structurally well-defined, heterocyclic organic compound that fits within the broader chemical space of functionalized pyrimidines. Its registration in chemical and environmental databases confirms its identity and existence within research and regulatory frameworks. Although specific discovery records and commercial applications are not documented in open literature, its chemical features align closely with compounds known to have relevance in the development of biologically active molecules and synthetic intermediates. As such, it remains a potentially valuable scaffold for future research exploring substituted pyrimidine derivatives and their roles in chemistry and biotechnology.