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N′′,N′′-Pentamethyl-dipropylenetriamine (a pentamethylated triamine with a dipropylene backbone) belongs to the class of tertiary/secondary polyamines used widely as catalysts, curing agents, and intermediates in polymer, surfactant and pharmaceutical chemistry.
Closely related is pentamethyldiethylenetriamine (PMDETA), a well-known tridentate ligand in organometallic chemistry.
This article compiles nomenclature, structural and physical properties, common syntheses, spectroscopic identifiers, acid–base and coordination behaviour, reactivity patterns, detailed applications (epoxy curing, polyurethane catalysis, complexation/ligand chemistry, corrosion inhibitors, flotation agents), toxicology and safety highlights from MSDS sources, environmental fate, and alternatives/analogues. CAS numbers, synonyms and vendor references are provided for both the dipropylene and diethylene pentamethylated triamines to avoid ambiguity.
Nomenclature, synonyms and identity
Names & synonyms — principal compounds discussed
N′′,N′′-Pentamethyl-dipropylenetriamine — name queried by the user; may be presented in commerce with variants of systematic naming.
A frequently encountered related compound is N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA) (note: diethylene backbone).
PMDETA (pentamethyldiethylenetriamine) — IUPAC / common name frequently appears in the literature; CAS 3030-47-5.
N,N-Dimethyldipropylenetriamine / N′-[3-(dimethylamino)propyl]propane-1,3-diamine — a dipropylene triamine (propyl linkers) sometimes quoted under CAS 10563-29-8 (often abbreviated DMAPAPA, DMDPTA).
This compound is structurally closer to a dimethylated dipropylenetriamine but appears in vendor records where naming variants (e.g., “pentamethyl” vs “dimethyl + additional alkylation”) can cause confusion; users asking about pentamethyl-dipropylenetriamine may be referring to or need to consider this CAS/structure.
Because literature and commercial catalogs sometimes mix diethylene vs dipropylene backbones or list different methylation patterns under similar trivial names, I list both main references and CAS numbers so you can cross-check with specific supplier documents or spectral data below.
For the rest of this article I treat the general chemical family (pentamethylated triamines and the closely related dimethyl-dipropyl triamines) and highlight differences where relevant.
Structures and basic molecular data
Structural formulae (representative)
PMDETA (pentamethyldiethylenetriamine) — empirical formula C₉H₂₃N₃, structural motif [(CH₃)₂NCH₂CH₂]₂NCH₃ (two N,N-dimethylaminoethyl units bound to a central tertiary nitrogen bearing one methyl). Molar mass ≈ 173.30 g·mol⁻¹. CAS 3030-47-5.
(Dimethyldipropylenetriamine) — empirical formula C₈H₂₁N₃, molar mass ≈ 159.27 g·mol⁻¹, typical SMILES CN(C)CCCNCCCN (representing N-[3-(dimethylamino)propyl]propane-1,3-diamine). CAS 10563-29-8 (DMDPTA / DMAPAPA).
Physical properties (typical, vendor / literature values)
PMDETA (3030-47-5):
Appearance: colorless to pale yellow liquid.
Density: ≈ 0.83 g·mL⁻¹ (at 20–25 °C).
Melting point: reported around −20 °C.
Boiling point: ~198 °C (literature value).
Refractive index (nD²⁰): ≈ 1.442.
N,N-Dimethyldipropylenetriamine (10563-29-8):
Appearance: liquid.
Molar mass ≈ 159.27 g·mol⁻¹.
Vendor pages report miscibility and typical properties consistent with low viscosity, amine odor, and typical tertiary/primary/secondary amine behaviour.
Note on reported numerical variance: measured melting/boiling points and flash points vary slightly between supplier MSDS sheets and handbooks; always use the lot-specific certificate of analysis (CoA) and the supplier MSDS for regulatory and safety decisions.
Synthesis and industrial production routes
General strategies for pentamethylated triamines
There are two broad approaches:
Alkylation of polyamines — start from diethylenetriamine (or dipropylenetriamine) and perform controlled methylation (e.g., Eschweiler–Clarke or reductive methylation) to reach tertiary methylation on the terminal nitrogens and the central nitrogen as required to produce the pentamethylated product.
Careful control avoids over-methylation or quaternization.
Typical reagents: formaldehyde + formic acid (Eschweiler–Clarke) or formaldehyde + hydrogen + catalyst (reductive methylation), or methyl halide + base for stepwise alkylation (less common at scale due to stoichiometric salt waste).
Building block approach — assemble the triamine backbone by reacting appropriately substituted amines (for example reacting dimethylamine derivatives with 1,2- or 1,3-dihalopropanes/diethanes) in nucleophilic substitution sequences, then finalize methylation if needed.
Manufacturing notes
Scale production must control water and salt formation, and avoid formation of quaternary ammonium salts which could complicate purification.
Industrial processes aim for high-purity product (≥99% for reagent grade) with azeotropic removal of water where needed and vacuum distillation/crystallization for final purification.
Vendor product pages and patents contain specific optimized routes for each backbone (diethylene vs dipropylene).
SAFETY INFORMATION ABOUT N'',N''-PENTAMETHYL-DIPROPYLENETRIAMINE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
