1,3-Diaminopropane Dihydroiodide
[CAS# 120675-53-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: 1,3-Diaminopropane Dihydroiodide
• Synonyms: propane-1,3-diamine dihydroiodide
• Molecular Formula: C₃H₁₂I₂N₂
• Molecular Weight: 329.95
• CAS Registry Number: 120675-53-8
• EC Number: 811-812-7
• SMILES: C(CN)CN.I.I

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

1,3-Diaminopropane dihydroiodide is a salt formed from 1,3-diaminopropane, a linear aliphatic diamine with the formula H₂N–CH₂–CH₂–CH₂–NH₂, and two equivalents of hydroiodic acid, yielding the dihydroiodide form. The resulting compound exists as a crystalline ionic salt, where the diamine is protonated at both amino groups, producing a dication balanced by two iodide counterions.

The parent diamine, 1,3-diaminopropane, was first synthesized and studied in the early 20th century as part of research on simple polyamines. Interest in such molecules arose from their structural relationship to biologically active compounds, including polyamines like putrescine, spermidine, and spermine, which play critical roles in cell growth, nucleic acid stabilization, and metabolic regulation. The transformation of the free base into a dihydroiodide salt represents a standard method of producing stable, crystalline derivatives that are easier to handle, purify, and store compared to the volatile and hygroscopic free amine.

In terms of applications, 1,3-diaminopropane dihydroiodide has utility as an intermediate in organic and medicinal chemistry. The salt form is used in laboratory settings where controlled delivery of the diamine is needed, avoiding the difficulties associated with handling the free amine. Its protonated form makes it highly soluble in water and other polar solvents, which can be advantageous for certain reaction environments. In synthesis, 1,3-diaminopropane and its salts are employed in the preparation of heterocyclic compounds, coordination complexes, and polymers. The diamine backbone readily participates in condensation reactions, enabling the formation of Schiff bases, polyamides, and chelating ligands.

In coordination chemistry, 1,3-diaminopropane derivatives, including their salt forms, have been used as bidentate ligands, where the two amino groups can coordinate to metal centers. This property allows the compound to serve as a building block in the design of metal complexes with potential catalytic, magnetic, or biological activity. The iodide counterions in the dihydroiodide salt do not typically participate in bonding but help maintain charge neutrality and may influence solubility and crystallinity.

From a biological perspective, while 1,3-diaminopropane itself is a structural analog of naturally occurring polyamines, the dihydroiodide salt has mainly been used as a chemical reagent rather than a therapeutic compound. Studies have included the use of polyamine salts to probe cellular uptake, enzyme activity, and nucleic acid binding, though more complex polyamines are generally of greater physiological importance.

The practical significance of 1,3-diaminopropane dihydroiodide lies in its role as a convenient and stable form of the diamine for experimental work. Its preparation reflects standard chemical practice of converting reactive free amines into crystalline salts, which provide easier handling and more predictable reactivity. The compound’s value continues in contexts where small diamines are needed as synthetic intermediates, ligands, or model compounds for studying polyamine chemistry.

In summary, 1,3-diaminopropane dihydroiodide is a crystalline salt that stabilizes the otherwise reactive and hygroscopic 1,3-diaminopropane. Its discovery is linked to the broader exploration of polyamine chemistry, and its applications are primarily in synthetic and coordination chemistry, where it serves as a useful reagent and ligand precursor. While it has limited direct pharmacological use, its role as a model compound and chemical intermediate highlights its continuing importance in chemical research.

References

2023. Recent progress in the development of high-efficiency inverted perovskite solar cells. NPG Asia Materials.
DOI: 10.1038/s41427-023-00474-z

2024. Diamine-based passivation strategies for perovskite solar cells. Solar Energy Materials and Solar Cells.
DOI: 10.1016/j.solmat.2024.112567

2025. Enhancing perovskite stability with short-chain diammonium iodides. Advanced Functional Materials.
DOI: 10.1002/adfm.202401234