PENTYLAMINE

Pentylamine is a primary aliphatic amine with the molecular formula C₅H₁₃N, typically occurring as a colorless to pale yellow liquid with a strong ammonia-like odor.
As a highly reactive amine, Pentylamine undergoes alkylation, acylation, condensation, and neutralization reactions, making it a versatile building block in organic synthesis.
Pentylamine is widely used in the production of pharmaceuticals, agrochemicals, surfactants, corrosion inhibitors, rubber chemicals, and specialty coatings.

CAS Number: 110-58-7
EC Number: 203-782-3
Molecular Formula: C5H13N
Molecular Weight: 87.16 g/mol

Synonyms: Pentylamine, n-Amylamine,99%, n-Amylamine,97%, Amylamine, n-: (1-Pentylamine), Pentylamine, 98+%, n-Pentylamine, 98+%, 1-Aminopentane, n-Amylamine, 1-Aminopentane, n-Amylamine, Pentylamine, Monoamylamine, n-Amylamine, 1-Pentanamine, Pentan-1-amine, n-Pentylamine, Pentylamine, Primary amylamine, Amylamine, n-Pentyl amine, 1-Aminopentane, Pentane-1-amine, Normal amylamine, n-C5H11NH2, n-Amylamin, Pentylamin, Pentyl amine, Amylamine (normal), Primary pentylamine, 1-Pentylamine, n-Pentanamine, Pentaneamine, Normal pentylamine, Pentylamine, normal, n-Amyl-1-amine, n-Pentyl-1-amine, 1-Pentyl amine, n-Amylaminum (Latinized), Amylaminum, Monoamylamin, Pentanamine

Pentylamine is a primary aliphatic amine with the molecular formula C₅H₁₃N.
Pentylamine appears as a colorless to pale yellow liquid with a strong, ammonia-like odor and is miscible with alcohols and ethers, but only moderately soluble in water.

As a reactive amine, Pentylamine readily undergoes alkylation, acylation, and condensation reactions, making it a useful intermediate in organic synthesis.
Pentylamine is widely employed in the production of pharmaceuticals, agrochemicals, surfactants, corrosion inhibitors, and rubber processing chemicals.

In addition, Pentylamine can act as a solvent, flotation agent, and building block for specialty chemicals.
Due to Pentylamine's volatility and corrosive, irritant nature, safe handling requires the use of protective equipment and proper ventilation to avoid inhalation and skin or eye contact.

Pentylamine is a straight-chain aliphatic amine with the molecular formula C₅H₁₃N and a molecular weight of 87.16 g/mol.
Pentylamine typically occurs as a colorless to pale yellow liquid with a penetrating, ammonia-like odor and exhibits moderate volatility.

Pentylamine is slightly soluble in water but miscible with most organic solvents such as alcohols and ethers, which makes it useful in diverse chemical processes.
As a primary amine, Pentylamine is highly reactive and undergoes a wide range of organic transformations, including alkylation, acylation, condensation, and neutralization reactions, enabling it to serve as a versatile building block in industrial chemistry.

Pentylamine is used extensively in the synthesis of pharmaceuticals, agrochemicals, surfactants, and corrosion inhibitors, where it contributes to the development of herbicides, pesticides, and specialty drug intermediates.
The rubber and plastics industries employ Pentylamine in the manufacture of vulcanization accelerators, stabilizers, and antidegradants, enhancing the performance and durability of polymer materials.

Additionally, Pentylamine finds application as a solvent, flotation agent in ore processing, and intermediate for dyes, resins, and specialty coatings.
Due to its irritant and corrosive nature, Pentylamine poses risks to the skin, eyes, and respiratory system, requiring controlled handling conditions with protective gloves, goggles, and effective ventilation.
Although hazardous in concentrated form, Pentylamine's strong reactivity and functional versatility ensure its continued importance as a key chemical intermediate in both bulk and fine chemical production.

Uses of Pentylamine:
Pentylamine is a versatile industrial chemical used as a reactive intermediate and functional additive across multiple sectors.
In the pharmaceutical industry, Pentylamine serves as a building block for the synthesis of active pharmaceutical ingredients and intermediates, particularly in drugs requiring aliphatic amine groups.

The agrochemical sector employs Pentylamine in the manufacture of herbicides, pesticides, and fungicides, where it enhances biological activity and stability of formulations.
In the rubber and plastics industry, Pentylamine is used in the production of vulcanization accelerators, stabilizers, and antidegradants, improving the strength and durability of finished materials.

Pentylamine is also applied in the production of surfactants, emulsifiers, and corrosion inhibitors, contributing to the performance of cleaning agents, metal protection systems, and specialty coatings.
Additionally, Pentylamine functions as a flotation agent in ore processing, a solvent in chemical synthesis, and an intermediate for the preparation of dyes, resins, and specialty fine chemicals.
Pentylamine's wide reactivity and compatibility with organic systems make it a critical component in both bulk chemical processing and fine chemical manufacturing, despite the need for strict handling controls due to its irritant and corrosive properties.

Pentylamine is a useful reactant in organic synthesis.
Pentylamine is a general reagent used in functionalizing the target molecules with pentyl chain. 

Pentylamine has also been used as a cosurfactant to increase the phase stability of the bilayer systems.
Chemical intermediate, dyestuffs, rubber chemicals, insecticides, synthetic detergents, flotation agents, corrosion inhibitors, solvent, gasoline additive, pharmaceuticals.

Pentylamine, as a primary aliphatic amine, plays an important role in many industrial and specialty applications due to its strong nucleophilicity, reactivity, and compatibility with organic systems.
In the pharmaceutical industry, Pentylamine is widely utilized as a synthetic intermediate in the production of active pharmaceutical ingredients (APIs) and drug intermediates, particularly those requiring aliphatic amine functionalities for bioactivity.

The agrochemical sector relies on Pentylamine for the development of herbicides, pesticides, and fungicides, where its reactive amino group enhances the stability, solubility, and biological efficacy of formulations used in crop protection.
In the rubber and polymer industry, Pentylamine is incorporated into the synthesis of vulcanization accelerators, stabilizers, and antidegradants, improving mechanical strength, flexibility, and resistance to oxidative degradation in rubber products.

The plastics industry also employs Pentylamine as a precursor for additives that extend durability and performance under environmental stress.
Beyond these major fields, Pentylamine finds application in the formulation of surfactants, emulsifiers, corrosion inhibitors, and specialty coatings, where it contributes to wetting, dispersion, and protective properties.
In mineral processing, Pentylamine is used as a flotation agent to improve the separation of valuable ores, while in dyes and resins manufacturing it acts as a building block for producing high-performance colorants and polymers.

Pentylamine can also serve as a solvent and processing aid in certain chemical reactions, enhancing reaction efficiency and product yields.
Although Pentylamine is classified as corrosive and requires strict occupational safety measures—including proper ventilation, gloves, and protective eyewear—its versatility and efficiency ensure that Pentylamine remains a critical raw material in both bulk chemical production and fine chemical synthesis.

Industrial uses:
In 1976, 800 tons of Pentylamine was produced for a variety of commercial purposes. 
Pentylamine is used in textiles, lubrication and in the manufacture of dyestuffs, emulsifying agents, anti-oxidants and desizing agents for the textile and pharmaceutical industry. 
Pentylamine is also valuable as a corrosion inhibitor and as a base for emulsifiers which are soluble in vegetable and mineral oils.

Benefits of Pentylamine:
Pentylamine offers several benefits that make it valuable as both a chemical intermediate and a functional additive across industries.
Pentylamine's primary amine group provides high reactivity, allowing it to participate in a wide range of organic transformations such as alkylation, acylation, and condensation, which makes it an excellent building block for pharmaceuticals, agrochemicals, and specialty chemicals.

In the rubber and polymer industry, Pentylamine enhances product performance by enabling the synthesis of stabilizers, vulcanization accelerators, and antidegradants, which improve durability, elasticity, and resistance to oxidative damage.
Pentylamine's use in corrosion inhibitors and surfactants provides protective and surface-active properties that extend equipment life and improve cleaning or emulsifying efficiency.

In mineral processing, Pentylamine's benefit lies in improving the separation of ores as a flotation agent, contributing to more efficient resource extraction.
Economically, Pentylamine reduces dependency on more complex or expensive intermediates, offering cost-effectiveness, scalability, and consistent quality in large-scale production. 
From a functional standpoint, Pentylamine's combination of chemical versatility, process efficiency, and broad industrial applicability makes it a highly beneficial compound despite its irritant and corrosive nature, which can be controlled through proper handling and storage.

Production of Pentylamine:
Pentylamine is produced through several established industrial synthesis routes designed to yield high-purity primary amines.
The most common method involves the amination of pentanol (amyl alcohol), where the hydroxyl group is replaced by an amino group through catalytic processes, often in the presence of ammonia and hydrogen over metal catalysts such as nickel or cobalt.

Another route includes the reaction of 1-bromopentane or other pentyl halides with ammonia, producing Pentylamine along with possible secondary and tertiary amine byproducts, which are later separated by fractional distillation.
In large-scale production, manufacturers may also employ reductive amination of pentanal (valeraldehyde), where the aldehyde is reacted with ammonia and then reduced to the amine. 

Depending on the feedstock and intended application, these methods can be adjusted to maximize yields of the primary amine while minimizing higher amine formation.
After synthesis, the crude product undergoes purification by distillation to remove impurities, unreacted starting materials, and byproducts, ensuring consistency for downstream use in pharmaceuticals, agrochemicals, rubber chemicals, and surfactants.
Modern production emphasizes catalytic efficiency, selectivity, and safety measures due to Pentylamine’s volatility, flammability, and corrosive properties, while also incorporating environmental controls to reduce emissions and waste byproducts.

Synthesis of Pentylamine:
Pentylamine can be synthesized through several well-established organic chemistry methods, each tailored to maximize yields of the primary amine.
One common laboratory approach is the amination of 1-bromopentane (or pentyl chloride/iodide) with excess ammonia, producing Pentylamine via a nucleophilic substitution reaction (SN2). 

In this route, secondary and tertiary amines may also form, but careful control of reaction conditions and subsequent fractional distillation allows the isolation of the primary amine.
Another important method is the reductive amination of valeraldehyde (pentanal), in which the aldehyde reacts with ammonia to form an imine intermediate that is then reduced—typically using hydrogen in the presence of nickel, cobalt, or palladium catalysts—to yield Pentylamine.

On an industrial scale, catalytic amination of amyl alcohol (pentan-1-ol) is also employed, where ammonia and hydrogen react over metal catalysts to replace the hydroxyl group with an amino group.
These methods highlight the flexibility of synthesis, with halide substitution favored in laboratory settings and reductive or catalytic amination dominating commercial production.
Purification is generally achieved by distillation under reduced pressure, ensuring a high-purity, colorless to pale yellow liquid suitable for downstream use in pharmaceuticals, agrochemicals, rubber processing, and surfactant production.

History of Pentylamine:
The history of Pentylamine reflects the broader development of aliphatic amine chemistry during the late 19th and early 20th centuries.
Early chemists first obtained Pentylamine by treating amyl halides with ammonia, a classical substitution reaction that became a foundational method in amine synthesis.

As industrial chemistry advanced in the early 20th century, interest in Pentylamine grew because of its potential as a chemical intermediate for pharmaceuticals, rubber additives, and agrochemicals.
By the mid-20th century, improvements in catalytic hydrogenation and reductive amination technologies allowed manufacturers to produce Pentylamine more efficiently from valeraldehyde and amyl alcohols, enabling large-scale industrial availability.

Pentylamine's role expanded rapidly with the growth of the rubber industry, where it contributed to the production of vulcanization accelerators and stabilizers, and in the agrochemical sector, where it became a precursor for herbicides and pesticides.
Over time, regulatory frameworks were introduced to ensure safer handling of this volatile, irritant compound, while advances in purification and distillation improved product consistency.
Today, Pentylamine remains a specialty amine valued for its reactivity and versatility, with its historical trajectory illustrating the evolution of amine chemistry from small-scale laboratory discovery to critical industrial intermediate in pharmaceuticals, polymers, surfactants, and specialty chemical production.

Handling and Storage of Pentylamine:
Handle in a well-ventilated area; avoid inhalation of vapors and contact with skin and eyes.
Store in tightly sealed containers made of compatible materials (stainless steel, polyethylene).

Keep away from heat, sparks, open flame, and oxidizing agents.
Recommended storage temperature: cool, dry, well-ventilated place.
Protect from moisture and direct sunlight.

Stability and Reactivity of Pentylamine:

Stability:
Stable under normal ambient and recommended storage conditions.

Incompatible materials:
Strong oxidizing agents, acids, acid chlorides, acid anhydrides, and CO₂ (may form carbamates).

Hazardous reactions:
May react violently with oxidizers; exothermic reactions with acids.

Decomposition products:
Nitrogen oxides (NOx), carbon oxides, and ammonia vapors may form on heating or combustion.

First Aid Measures of Pentylamine:

Inhalation:
Move victim to fresh air.
If breathing is difficult, provide oxygen.
Seek medical attention if symptoms persist.

Skin contact:
Immediately wash with plenty of water and soap for at least 15 minutes.
Remove contaminated clothing.
Seek medical help if irritation continues.

Eye contact:
Rinse cautiously with water for at least 15 minutes, lifting eyelids occasionally.
Get medical attention immediately.

Ingestion:
Do not induce vomiting.
Rinse mouth with water.
Seek immediate medical advice.

Firefighting Measures of Pentylamine:

Suitable extinguishing media:
Water spray (fog), alcohol-resistant foam, dry chemical, or CO₂.

Specific hazards:
Vapors may form explosive mixtures with air; releases toxic nitrogen oxides on combustion.

Protective equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear.

Special advice:
Cool containers exposed to fire with water spray to prevent rupture.

Accidental Release Measures of Pentylamine:
Evacuate area; ensure proper ventilation.
Eliminate ignition sources.

Wear suitable personal protective equipment (PPE).
Absorb spill with inert material (sand, vermiculite), place in suitable closed container for disposal.
Prevent entry into waterways, drains, or confined spaces.

Exposure Controls / Personal Protective Equipment of Pentylamine:

Engineering controls:
Local exhaust ventilation or general dilution ventilation to keep airborne concentrations below occupational exposure limits.

Respiratory protection: 
Use NIOSH/EN-approved respirator if exposure limits are exceeded.

Skin protection:
Chemical-resistant gloves (e.g., nitrile, neoprene), protective clothing, boots.

Eye/face protection:
Safety goggles with side-shields or face shield.

Hygiene measures:
Wash hands and face thoroughly after handling.
Remove contaminated clothing before reuse.

Identifiers of Pentylamine:
CAS Number: 110-58-7
EC Number (EINECS): 203-782-3
UN Number (Transport): UN 1114 (Class 3 – flammable liquid; also corrosive)
Molecular Formula: C₅H₁₃N
Molecular Weight: 87.16 g/mol
InChI: InChI=1S/C5H13N/c1-2-3-4-5-6/h2-6H2,1H3
InChI Key: KZJWHVRUYTVRFL-UHFFFAOYSA-N
SMILES: CCCCCN

CAS Registry Number: 110-58-7
EC (EINECS) Number: 203-782-3
RTECS Number: RH5075000
UN Number (Transport): UN 1114
HS Code (Customs): 2921.19 (Acyclic primary amines, other)
Index Number (CLP): 612-061-00-9
Molecular Formula: C₅H₁₃N
Molecular Weight: 87.16 g/mol
Structural Formula: H₂N–(CH₂)₅H
SMILES: CCCCC[NH2]
InChI: InChI=1S/C5H13N/c1-2-3-4-5-6/h2-6H2,1H3
InChI Key: KZJWHVRUYTVRFL-UHFFFAOYSA-N

Properties of Pentylamine:
Melting point: −55 °C(lit.)
Boiling point: 104 °C(lit.)
Density: 0.752 g/mL at 25 °C(lit.)
Vapor density: 3.01 (vs air)
Vapor pressure: 120.9 hPa (47 °C)
FEMA: 4242 | PENTYLAMINE
Refractive index: n20/D 1.411(lit.)
Fp: 42 °F
Storage temp.: Flammables area
Solubility: Soluble in alcohol, ether.
pka: 10.63(at 25℃)
Form: Liquid
Color: Clear colorless to very slightly yellow
Odor: at 0.10 % in propylene glycol. ammoniacal fishy
Odor Type: fishy
Biological source: synthetic
Explosive limit: 2.2-22%(V)
Water Solubility: soluble
Sensitive: Air Sensitive
JECFA Number: 1585
Merck: 14,598
BRN: 505953
Dielectric constant: 4.6（22℃）
LogP: 1.49
CAS DataBase Reference: 110-58-7(CAS DataBase Reference)
NIST Chemistry Reference: Pentylamine (MAA)(110-58-7)
EPA Substance Registry System: Pentylamine (MAA) (110-58-7)

Chemical Formula: C₅H₁₃N
Molecular Weight: 87.16 g/mol
Appearance: Colorless to pale yellow liquid
Odor: Strong, ammonia-like, fishy odor
Physical State: Liquid (under ambient conditions)

Melting Point: ~ –60 °C
Boiling Point: 104–106 °C at 760 mmHg
Flash Point: 21–25 °C (closed cup) → highly flammable
Autoignition Temperature: ~ 267 °C

Lower (LEL): ~ 1.4 vol%
Upper (UEL): ~ 11 vol%
Vapor Pressure: ~ 31 mmHg at 25 °C
Vapor Density (air=1): ~ 3.0
Density: 0.76–0.77 g/cm³ at 20 °C
Viscosity: ~ 0.5 mPa·s (at 20 °C)
pKa (conjugate acid): ~ 10.7 (weak base)
Log P (octanol/water): ~ 1.3 (moderately hydrophobic)
Solubility in Water: Miscible, forms alkaline solutions
Solubility in Organic Solvents: Soluble in alcohol, ether, hydrocarbons