Decylamine
[CAS 2016-57-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: Decylamine
• Synonyms: NDA; n-Decylamine; 1-Aminodecane
• Molecular Formula: C₁₀H₂₃N
• Molecular Weight: 157.30
• CAS Registry Number: 2016-57-1
• EC Number: 217-957-7
• SMILES: CCCCCCCCCCN

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*, 0.787 g/mL (Expl.)
• Melting point: 12 - 14 °C (Expl.)
• Boiling point: 221.4±3.0 °C 760 mmHg (Calc.)^*, 216 - 218 °C (Expl.)
• Flash point: 85.6 °C (Calc.)^*, 89 °C (Expl.)
• Index of refraction: 1.439 (Calc.)^*, 1.436 (Expl.)

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

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS09 Danger
• Risk Statements: H301-H311-H314-H400
• Safety Statements: P260-P262-P264-P270-P273-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P361+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 2922

Discovery and Applications

Decylamine is a primary aliphatic amine consisting of a linear decyl hydrocarbon chain attached to a primary amino group. It belongs to the class of long-chain fatty amines and is characterized by a combination of a basic nitrogen-containing functional group and a hydrophobic C10 alkyl chain. The compound is an important intermediate used in the preparation of surfactants, corrosion inhibitors, flotation agents, and other specialty chemicals.

Structurally, decylamine consists of a ten-carbon saturated hydrocarbon chain bonded to an amino group. The molecular framework can be described as a primary amine because the nitrogen atom is attached to only one carbon substituent and carries two hydrogen atoms. The decyl chain is composed entirely of carbon–carbon single bonds, with all carbon atoms being predominantly sp³-hybridized.

The nitrogen atom in the amino group is also sp³-hybridized and adopts a trigonal pyramidal geometry. It possesses a lone pair of electrons that is not involved in aromatic or conjugative systems, allowing it to function as a Lewis base. The lone pair enables protonation reactions with acids, forming decylammonium salts.

Because decylamine contains an N–H bond, it can participate in hydrogen bonding. The amino nitrogen can act as a hydrogen bond acceptor through its lone pair and as a hydrogen bond donor through its N–H hydrogens. These interactions contribute to the physical behavior of the compound and influence its association with polar molecules and surfaces.

The decyl group is a long, linear alkyl chain that provides strong hydrophobic character. The chain contains flexible C–C single bonds that allow numerous conformations through rotation. The extended hydrocarbon segment contributes significant van der Waals interactions between molecules and dominates many of the compound’s physical properties.

From an electronic perspective, the alkyl group attached to nitrogen donates electron density through inductive effects. This increases the electron density at the nitrogen atom and contributes to the basicity of decylamine compared with aromatic amines, where the nitrogen lone pair is partially delocalized into an aromatic ring.

Physicochemically, decylamine exhibits amphiphilic behavior. The amino group provides a polar and ionizable region, while the long hydrocarbon chain provides a nonpolar region. In its free-base form, the molecule has limited water solubility because the hydrophobic decyl chain dominates the overall structure. When protonated to form decylammonium salts, the ionic nitrogen center greatly increases compatibility with aqueous environments.

The molecule’s long alkyl chain also influences its aggregation behavior. Long-chain primary amines can associate through hydrophobic interactions and may form organized structures in suitable environments. Their amphiphilic nature allows interactions at interfaces between polar and nonpolar phases.

Chemically, the primary amine group is the main reactive site. Decylamine readily undergoes acid–base reactions to form salts with inorganic and organic acids. It can also participate in alkylation reactions to produce secondary and tertiary amines, and further alkylation can generate quaternary ammonium compounds. The presence of the N–H bonds allows acylation reactions, producing amides when reacted with suitable acylating agents.

The saturated hydrocarbon chain is relatively chemically inert under normal conditions. It generally undergoes reactions typical of alkanes, such as combustion and free-radical halogenation under appropriate conditions, but it does not readily participate in addition or aromatic substitution reactions.

The flexible structure of decylamine results from unrestricted rotation along the carbon chain and around the carbon–nitrogen bond. This flexibility allows the molecule to adapt its conformation depending on solvent environment, intermolecular interactions, and association with other molecules.

Overall, decylamine is a primary long-chain aliphatic amine composed of a single C10 alkyl chain attached to an amino group. Its combination of a basic, hydrogen-bonding nitrogen center and a hydrophobic hydrocarbon chain gives it characteristic amphiphilic properties and determines its chemical behavior, which is dominated by acid–base reactions and transformations of the primary amine functionality.

References

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