1. Product Overview
3,18-Diimino-2,4,17,19-tetraazaeicosanediimidamide (CAS 2773484-02-7), systematically named 2,4,17,19-tetraazaeicosanediimidamide, 3,18-diimino-, is a symmetric bis(amidino/guanidino) aliphatic compound with the molecular formula C₁₆H₃₆N₁₀ and a molecular weight of 368.52 g/mol. The structure consists of a C₁₆ dodecamethylene chain bearing two terminal 2,4-diamino-1,3-diazabutadiene (amidino-guanidino) moieties. This highly basic, polycationic molecule is used as a custom-synthesis building block for polyamine analogs, cationic surfactants, and antimicrobial/antiparasitic agent development, as well as a reference for polyguanidine-type biocides.
2. Key Features and Benefits
• Symmetric Bis-Amidino Architecture: Two terminal –N=C(NH₂)N– groups (tautomeric with guanidine form) provide strong cationic character at physiological pH (pKa ~11–12 per amidino group), enabling electrostatic interactions with negatively charged biomolecules (DNA, phospholipids).
• Long Alkylene Spacer: The C₁₂ (dodecamethylene) linker separates the two cationic heads by ~1.7 nm, suitable for bidentate binding or crosslinking applications.
• Highly Basic & Water-Soluble: Multiple basic N atoms facilitate salt formation (HCl, sulfate) for enhanced aqueous solubility.
• Custom Synthesis Intermediate: Valuable scaffold for synthesizing polyamine-mimicking drugs, cationic antimicrobial peptides (CAMPs) mimetics, and DNA-binding agents.
• High Purity: Supplied at ≥95% (HPLC), suitable for research-scale use.
3. Major Applications
• Polyamine & Guanidine Derivative R&D: Used in the synthesis of polyamine analog drugs targeting trypanosomes, Plasmodium, and cancer cells (polyamine transport inhibition).
• Antimicrobial / Antiparasitic Lead Development: The bis-amidino structure resembles pentamidine/furamidine pharmacophores; explored for antibacterial, antifungal, and antiprotozoal activity.
• Cationic Surfactant / Biocide Research: Polyguanidine-type structures are precursors to quaternary ammonium biocides; this compound informs structure-activity studies.
• DNA Intercalator / Minor Groove Binder Scaffold: The cationic amidino groups can interact with DNA minor groove (AT-rich sequences), serving as a simplified DAPI/berenil analog scaffold.
• Custom Organic Synthesis: Employed as a di-functional nucleophile or coupling partner in the construction of macrocycles, dendrimers, and polymeric cationic materials.
4. Technical Specifications
Item Description
Product Name 3,18-Diimino-2,4,17,19-tetraazaeicosanediimidamide
Synonyms 2,4,17,19-Tetraazaeicosanediimidamide, 3,18-diimino-; N,N'-[1,20-Dodecanediylbis(carbamimidoyl)]diamide (tautomeric form)
CAS Number 2773484-02-7
Molecular Formula C₁₆H₃₆N₁₀
Molecular Weight 368.52 g/mol
MDL Number —
Assay (Purity) ≥95% (HPLC)
Appearance White to off-white powder or crystalline solid
Melting Point Not reported (predicted >200 °C with decomposition)
Boiling Point ~490.7 °C (Predicted)
Density ~1.27 g/cm³ (Predicted)
pKa (Predicted) ~11–12 (amidino N); ~3–4 (conjugate acid)
Calculated LogP ~1.5–2.0 (log D at pH 7 would be lower due to protonation)
Polar Surface Area (PSA) ~164 Ų
Hydrogen Bond Donors 6–8 (depending on tautomer)
Hydrogen Bond Acceptors 4
Rotatable Bonds 15
Solubility Soluble: Water (as protonated polycation, especially as HCl salt), Dilute HCl, Methanol, Ethanol, DMSO, DMF.
Slightly Soluble:DCM, THF, Acetone.
Insoluble:Hexane, Ether.
Spectral Data (Predicted) ¹H NMR (DMSO‑d₆, 400 MHz): δ 1.20–1.45 (m, 20H, (CH₂)₁₀), 2.95 (t, J≈7.0 Hz, 4H, N-CH₂ terminal), 3.10 (t, J≈7.0 Hz, 4H, CH₂-N amidino), 6.80 (br s, 4H, NH₂), 8.50 (br s, 2H, N=C-NH₂), 9.20 (br s, 2H, C=NH).
¹³C NMR (DMSO‑d₆):δ 26–30 ((CH₂)₈ interior), 38.0 (N-CH₂ terminal), 42.0 (CH₂-N amidino), 156.0 (C=N).
SMILES N=C(N)NC(=N)NCCCCCCCCCCCCCCNC(=N)NC(=N)N
InChI Key ZVQEBWERKXWJOU-UHFFFAOYSA-N
Storage (Powder) 2–8 °C or RT, sealed, protected from moisture; stable ≥12–18 months
HS Code 2925.29.90 / 2933.99.90
5. Storage and Handling
• Storage: Store in a tightly sealed container at 2–8 °C (or room temperature for short-term), protected from moisture. The compound is hygroscopic as the free base; the hydrochloride salt form is less hygroscopic. Stable for ≥12–18 months.
• Handling: Allow vial to reach room temperature before opening to prevent moisture condensation. Dissolve in water, dilute HCl, MeOH, EtOH, DMSO, or DMF. For poorly soluble free base, convert to HCl salt by adding 2 eq. of 1 M HCl in MeOH.
• Solution Preparation: Highly soluble in acidic aqueous media. Prepare fresh for biological assays; DMSO stocks stable at -20 °C for 1–3 months.
• Freeze-Thaw: Aliquot to minimize freeze-thaw cycles.
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.
• Precautionary Statements:
• P261: Avoid breathing dust/mist/vapors. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid / Fire / Spill: Standard organic base protocol — water spray/CO₂ extinguisher; sweep up; rinse eyes/skin; do not induce vomiting if ingested. Decomposes to NOₓ, HCN (trace from N-containing organics), CO.
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use.
