N,N-Dimethylpropylamine (926-63-6) Physical and Chemical Properties
N,N-Dimethylpropylamine
A tertiary aliphatic amine used as an intermediate and reagent in industrial and research organic synthesis and process chemistry.
| CAS Number | 926-63-6 |
| Family | Aliphatic tertiary amines |
| Typical Form | Colorless liquid |
| Common Grades | EP |
N,N-Dimethylpropylamine is a tertiary aliphatic amine belonging to the N,N-dialkylamine structural class. The molecule comprises a propyl chain bound to a tertiary nitrogen bearing two methyl substituents (IUPAC: N,N-dimethylpropan-1-amine; SMILES: CCCN(C)C). The nitrogen lone pair confers basicity typical of trialkylamines; the compound is a small, volatile, tertiary amine with limited polar surface area and a single hydrogen-bond acceptor site.
Electronically and chemically, the tertiary amine functionality dominates behavior: it is readily protonated in aqueous media (\(\mathrm{p}K_a = 10.2\)), forming a soluble ammonium salt, and it acts as a nucleophilic base in organic reactions. Physicochemically the molecule is of low-to-moderate lipophilicity (XLogP = 1.2) with a low topological polar surface area (TPSA = 3.2), consistent with good miscibility in both polar and many aprotic organic solvents and with appreciable vapor pressure and flammability at ambient conditions. As a tertiary amine it is susceptible to oxidation and to exothermic neutralization with acids; it can be incompatible with strong electrophiles and oxidants.
Industrial relevance is primarily as an intermediate and process regulator in chemical manufacture and as a building block for specialty chemical synthesis. It is reported in commerce and is available in defined commercial grades. Common commercial grades reported for this substance include: EP.
Basic Physical Properties
Density
No experimentally established value for this property is available in the current data context.
Melting Point
No experimentally established value for this property is available in the current data context.
Boiling Point
No experimentally established value for this property is available in the current data context.
Vapor Pressure
No experimentally established value for this property is available in the current data context.
Flash Point
No experimentally established value for this property is available in the current data context.
Chemical Properties
Solubility and Phase Behavior
N,N-Dimethylpropylamine is reported as a colorless liquid and is water soluble. It is described as less dense than water and produces vapors that can be heavier than air and therefore prone to accumulate in low-lying or confined areas. Vapors may form explosive mixtures with air; appropriate ventilation and vapor-control measures are required during handling and processing. In solution the tertiary amine will be present as the free base (neutral) at high pH and predominantly as the protonated ammonium ion below its \(\mathrm{p}K_a\), increasing water solubility and reducing volatility.
Reactivity and Stability
The tertiary amine functionality undergoes typical amine chemistry: exothermic neutralization with acids to give ammonium salts and potential alkylation or acylation with strong electrophiles. Documented incompatibilities include isocyanates, certain halogenated organics, peroxides, acidic phenols, epoxides, acid anhydrides, and acid halides. Reaction with strong reducing agents (e.g., metal hydrides) can evolve flammable hydrogen gas. The compound is classified as highly flammable; it is chemically stable under normal handling when kept away from ignition sources, oxidizers, and strong acids, but precautions are required to avoid conditions that can lead to oxidation, polymerization, or violent reactions with incompatible reagents.
Thermodynamic Data
Standard Enthalpies and Heat Capacity
No experimentally established value for this property is available in the current data context.
Molecular Parameters
Molecular Weight and Formula
- Molecular formula: C5H13N
- Molecular weight: 87.16
- Exact / Monoisotopic mass: 87.104799419
LogP and Polarity
- XLogP: 1.2
- Topological Polar Surface Area (TPSA): 3.2
- Hydrogen-bond donor count: 0
- Hydrogen-bond acceptor count: 1
- Rotatable bond count: 2
These values indicate modest lipophilicity and low overall polarity for a small tertiary amine; protonation at acidic pH markedly increases aqueous solubility and reduces partitioning into nonpolar phases.
Structural Features
- IUPAC name: N,N-dimethylpropan-1-amine
- SMILES: CCCN(C)C
- InChI: InChI=1S/C5H13N/c1-4-5-6(2)3/h4-5H2,1-3H3
- InChIKey: ZUHZZVMEUAUWHY-UHFFFAOYSA-N
Structurally the molecule is an aliphatic tertiary amine (no hydrogen-bond donors), with the nitrogen lone pair localized on a tertiary nitrogen center; two methyl groups on nitrogen reduce steric hindrance compared with bulkier dialkyl substituents and maintain good nucleophilicity/basicity. The small size and two rotatable bonds confer conformational flexibility and volatility consistent with the observed physical descriptions.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS number: 926-63-6
- EC number: 213-139-9
- UN/NA number: UN2266 (Dimethyl-N-propylamine)
- UNII: 4Y5WCW87J9
- CHEMBL ID: CHEMBL2448976
- DSSTox Substance ID: DTXSID8074813
- Nikkaji Number: J71.079B
- InChI: InChI=1S/C5H13N/c1-4-5-6(2)3/h4-5H2,1-3H3
- InChIKey: ZUHZZVMEUAUWHY-UHFFFAOYSA-N
- SMILES: CCCN(C)C
Synonyms and Structural Names
Common synonyms reported include (selection): N,N-Dimethylpropylamine; Dimethyl-N-propylamine; N,N-dimethylpropan-1-amine; Dimethyl(propyl)amine; Propyldimethylamine; 1-Propanamine, N,N-dimethyl-; dimethylaminopropane; propylamine, N,N-dimethyl-; and several registry annotations including “DIMETHYLPROPYLAMINE” and “Dimethyl-N-propylamine [UN2266]”. (A broader list of depositor-supplied synonyms and historical variant names is available in supplier and regulatory documentation.)
Industrial and Commercial Applications
Representative Uses and Industry Sectors
N,N-Dimethylpropylamine is used as an intermediate and process regulator in chemical manufacturing. Reported commercial activity includes use as an intermediate in basic organic chemical production and as a processing agent in other manufacturing sectors. Aggregated U.S. product volumes for several recent years are reported in the range “<1,000,000 lb” per year for 2016–2019, indicating commercial-scale but not high-volume commodity production.
Role in Synthesis or Formulations
As a tertiary amine, it is employed as a basic reagent or nucleophilic component in alkylation, condensations, and other transformations where a non-nucleophilic or sterically small tertiary amine is advantageous. It is also used to prepare ammonium salts and as an intermediate in synthesis pathways for specialty chemicals. Selection for use in formulations is typically driven by its basicity (\(\mathrm{p}K_a = 10.2\)), volatility, solubility behavior, and compatibility with other process reagents.
Safety and Handling Overview
Acute and Occupational Toxicity
Hazard classification elements reported include flammability and acute toxic/irritant endpoints. Representative hazard statements and classifications associated with the material include:
- H225 (100%): Highly Flammable liquid and vapor
- H302 (100%): Harmful if swallowed
- H315 (99.5%): Causes skin irritation
- H318 (99.5%): Causes serious eye damage
- H331 (86.2%): Toxic if inhaled
- H332 (12.2%): Harmful if inhaled
- H335 (85.6%): May cause respiratory irritation
- H412 (13.3%): Harmful to aquatic life with long lasting effects
Acute exposure can produce severe irritation or burns to skin and eyes, respiratory tract irritation, central nervous system effects (dizziness, asphyxiation at high concentrations), and systemic toxicity if inhaled or ingested. Fire will produce irritating, corrosive and/or toxic combustion products. Vapors can travel to ignition sources and flash back; many amine vapors are heavier than air and may accumulate in low-lying areas.
For emergency response and medical treatment, immediate decontamination (removal of contaminated clothing, prolonged flushing of skin and eyes with water) and rapid medical evaluation are required for significant exposures. Emergency responders should use appropriate respiratory protection (positive-pressure SCBA) and chemical-protective clothing.
Storage and Handling Considerations
- Store in a cool, well-ventilated area away from heat, sparks, open flames and oxidizing agents.
- Ground and bond containers and equipment during transfer to prevent static discharge.
- Eliminate ignition sources in handling areas; use non-sparking tools and intrinsically safe equipment where applicable.
- Segregate from acids, oxidizers and incompatible organics (e.g., isocyanates, acid anhydrides) to avoid exothermic or hazardous reactions.
- For spills and leaks: isolate area, eliminate ignition sources, ventilate, prevent entry into waterways and drains, and collect with inert absorbent using non-sparking tools; dike large spills for later disposal.
- Firefighting: use dry chemical, CO2 or alcohol-resistant foam for small fires; water spray/fog or alcohol-resistant foam for larger fires, while cooling nearby containers to prevent rupture. Containers exposed to fire should be cooled with flooding quantities of water from maximum distance.
For worker protection, implement engineering controls (local exhaust ventilation), exposure monitoring, and PPE (chemical-resistant gloves, eye/face protection, and respiratory protection when required). Consult the product-specific Safety Data Sheet (SDS) and applicable local regulations for detailed handling, storage, exposure limits and emergency procedures.
