Quick Search
Hydroxyalkylamine esters are multifunctional organic compounds containing both an amine and an ester group, giving them amphiphilic properties and making them versatile intermediates in organic, medicinal, and industrial chemistry.
Hydroxyalkylamine esters are widely used as intermediates in pharmaceuticals (often as prodrugs to improve solubility and absorption), and in the production of surfactants, corrosion inhibitors, agrochemicals, and specialty polymers.
Because of their dual functional groups, Hydroxyalkylamine esters are also valuable in polymer chemistry, coatings, and drug delivery systems, where they enhance curing, flexibility, stability, and bioavailability.
CAS Number: 59-46-1
EC Number: 200-426-9
Molecular Formula: C15H21N3O2
Molecular Weight: 275.35
Synonyms: 1313020-26-6 isopropyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 1H-Benzimidazole-2-butanoic acid, 5-amino-1-methyl-, 1-methylethyl ester, 4-(5-Amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester, SCHEMBL2016350, WNNXAWPAXNZYEF-UHFFFAOYSA-N, AKOS032961211isopropyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate;4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester;1H-Benzimidazole-2-butanoic acid, 5-amino-1-methyl-, 1-methylethyl ester;4-(5-amino-1-methyl-1H-benzimidazol-2-yl)-butyricacid isopropyl ester;4-(5-Amino- 1 -methyl-1H-benzoimidazol-2-y1)-butyric acid isopropylester;Benzimidazole Impurity 1;1-Methylethyl 5-amino-1-methyl-1H-benzimidazole-2-butanoate
Hydroxyalkylamine esters are a class of organic compounds containing both an amino group (–NH₂ or substituted amine) and a hydroxyl group (–OH) within an alkanol chain, which is further esterified with a carboxylic acid.
This dual functionality makes them highly versatile intermediates in organic and medicinal chemistry.
They typically appear as clear to pale yellow liquids or crystalline solids, depending on chain length and substituents, and are generally soluble in polar solvents such as alcohols and water.
Due to the presence of both basic (amine) and polar (hydroxyl/ester) groups, Hydroxyalkylamine esters participate in a wide range of condensation, substitution, and complexation reactions.
Industrially, they are important in the synthesis of pharmaceuticals, surfactants, corrosion inhibitors, and agrochemicals, as well as in the preparation of chiral auxiliaries and specialty polymers.
Some derivatives also exhibit bioactive properties, making them useful as drug precursors, local anesthetics, or intermediates in the production of active pharmaceutical ingredients (APIs).
Hydroxyalkylamine ester is an Hydroxyalkylamine ester (ester amine).
Hydroxyalkylamine ester also shortens the pot-life of the formulation.
To facilitate metering, Hydroxyalkylamine ester should be used as a 10% solution in butyl acetate, ethyl acetate, methylisobutyl ketone or methylethyl ketone.
Suitable for use in polyurethane coatings recommended dosage level of Hydroxyalkylamine ester is 0.1-0.5%.
Hydroxyalkylamine ester has a shelf life of 6 months.
Hydroxyalkylamine esters are a class of organic compounds that contain both an amino group (-NH₂ or substituted amine) and an alkanol ester functional group, typically derived from the esterification of an aminoalkanol with a carboxylic acid.
Hydroxyalkylamine esters are characterized by having a molecular structure in which a hydroxyalkyl group (from the alkanol) and an amine group are present, often on adjacent or nearby carbon atoms, and the hydroxyl group has been converted into an ester.
In simpler terms, Hydroxyalkylamine esters are formed when a molecule that has both an alcohol (-OH) and an amine (-NH₂) reacts with a carboxylic acid or its derivatives (such as acid chlorides or anhydrides), resulting in the formation of an ester bond at the alcohol site while retaining the amine functionality elsewhere in the molecule.
The presence of both functional groups makes these compounds highly versatile and reactive.
These compounds are of significant importance in pharmaceutical and chemical industries, as they serve as intermediates in the synthesis of active pharmaceutical ingredients (APIs), surfactants, plasticizers, and bioactive molecules.
Due to their amphiphilic nature—having both polar and nonpolar regions—they are also used in emulsifying agents and cosmetic formulations.
In medicinal chemistry, certain Hydroxyalkylamine esters are designed to act as prodrugs, where the ester form enhances Hydroxyalkylamine ester’s absorption or stability in the body and is later hydrolyzed into the active drug.
Hydroxyalkylamine esters are a group of organic compounds that contain both an amino group (–NH₂, –NHR, or –NR₂) and an esterified alkanol group in the same molecular framework.
These compounds typically originate from aminoalkanols, which are molecules that contain both an alcohol (–OH) and an amine (–NH2 or substituted variants) functional group.
Through esterification, the hydroxyl (–OH) part of the aminoalkanol is chemically converted into an ester by reacting it with a carboxylic acid or its derivatives.
In terms of chemical structure, these esters are defined by the presence of an ester linkage (–COOR) adjacent to or within proximity to an amine functionality, which gives them a unique balance of hydrophilic (water-attracting) and lipophilic (fat-attracting) properties.
This dual nature makes them especially useful in various applications where such balance is necessary—such as in pharmaceuticals, surfactants, or emulsifiers.
Hydroxyalkylamine ester is an Hydroxyalkylamine ester (ester amine).
Hydroxyalkylamine ester acts as a catalyst.
Hydroxyalkylamine ester also shortens the pot-life of the formulation.
To facilitate metering, Hydroxyalkylamine ester should be used as a 10% solution in butyl acetate, ethyl acetate, methylisobutyl ketone or methylethyl ketone.
Hydroxyalkylamine ester is suitable for use in polyurethane coatings.
Hydroxyalkylamine ester can vary widely depending on the chain length of the alkanol part, the type of amine (primary, secondary, or tertiary), and the nature of the acid used for esterification.
This structural flexibility allows chemists to fine-tune the physical, chemical, and biological properties of the molecules for specific applications.
In conclusion, Hydroxyalkylamine esters are multifunctional compounds with broad chemical utility and industrial relevance, combining the reactivity of amines with the solubility and ester properties of alcohol-derived esters, enabling their use in a wide range of scientific and commercial fields.
From a pharmaceutical perspective, Hydroxyalkylamine esters are highly valuable.
Many drugs or drug candidates are developed in ester form because the ester group improves lipophilicity, helping the drug cross biological membranes like the intestinal wall or the blood-brain barrier.
Once inside the body, enzymatic hydrolysis often converts the ester back into Hydroxyalkylamine ester's active form (e.g., a free acid or alcohol).
This strategy is commonly used in the design of prodrugs, where the ester form is pharmacologically inactive or less active and becomes effective only after metabolic conversion.
In cosmetic and personal care products, Hydroxyalkylamine esters are used for their conditioning properties, ability to form stable emulsions, and mild surfactant characteristics.
Because they can interact with both water and oil phases, they are particularly useful in formulating creams, lotions, and shampoos where stability and texture are key.
In industrial and chemical processes, Hydroxyalkylamine esters may function as solvents, intermediates in organic synthesis, plasticizers, and additives in lubricants or coatings.
Their ability to undergo further chemical modifications allows them to be tailored for specific performance characteristics, including thermal stability, volatility, or compatibility with other materials.
Hydroxyalkylamine esters are a diverse group of organic compounds characterized by the presence of both an amino functional group and a hydroxyl group within an aliphatic chain, which is further esterified with a carboxylic acid.
This unique structural arrangement imparts amphiphilic and multifunctional properties, as the amino group provides basicity and nucleophilicity, the hydroxyl group enables hydrogen bonding and enhanced solubility, and the ester moiety contributes to reactivity and chemical stability.
Typically, Hydroxyalkylamine esters occur as clear to pale yellow liquids or crystalline solids, with solubility in water and polar organic solvents depending on chain length and substitution pattern.
These compounds are highly versatile in both laboratory and industrial chemistry: they serve as key intermediates in pharmaceutical synthesis, particularly in the development of local anesthetics, anticholinergic agents, and central nervous system drugs, where their amphiphilic nature supports membrane permeability and drug–receptor interactions.
Beyond pharmaceuticals, Hydroxyalkylamine esters are also used in the manufacture of surfactants, corrosion inhibitors, agrochemicals, and polymer modifiers, as well as in analytical chemistry where they may act as derivatizing agents.
Certain derivatives function as complexing or chelating agents, improving the solubility and stability of metal ions in solution.
From a biochemical perspective, Hydroxyalkylamine esters demonstrate relevance as bioactive molecules due to their structural similarity to naturally occurring amino alcohols and neurotransmitter analogues, while their synthetic flexibility allows the design of tailored compounds with specific physicochemical or pharmacological properties.
Industrially, they are often prepared through esterification reactions of amino alcohols with carboxylic acids or their derivatives, and their applications continue to expand in specialty polymers, coatings, and advanced materials, where multifunctionality is advantageous.
Market Overview of Hydroxyalkylamine Ester:
The global market for Hydroxyalkylamine esters, considered within the broader amino alcohols sector, is experiencing steady growth due to their expanding role in pharmaceuticals, agrochemicals, and specialty chemicals.
The amino alcohols market was valued at about USD 2.3 billion in 2024 and is projected to reach USD 3.5 billion by 2033, with a CAGR of around 5%, reflecting rising demand for derivatives such as Hydroxyalkylamine esters.
These compounds are increasingly utilized as intermediates in drug synthesis, surfactants, corrosion inhibitors, and polymer modifiers, while also contributing to specialty esters and formulations in industrial applications.
In the broader context, the global esters market—valued at nearly USD 94 billion in 2023—is forecasted to grow to USD 137 billion by 2030, highlighting the significant opportunities for Hydroxyalkylamine esters as a high-value niche within the rapidly expanding ester industry.
Uses of Hydroxyalkylamine Ester:
Hydroxyalkylamine ester is a mild catalyst for PUR paints which are cured with aromatic isocyanates like Desmodur L.
Hydroxyalkylamine ester accelerates the drying and curing of PUR paints.
Hydroxyalkylamine ester also shortens the potlife of the formulation.
In the pharmaceutical field, Hydroxyalkylamine esters are often used as intermediates or prodrugs.
A prodrug is a chemically modified version of an active pharmaceutical ingredient (API) that becomes biologically active after being metabolized in the body.
Esterifying an aminoalkanol can improve Hydroxyalkylamine ester’s lipid solubility, thereby enhancing its absorption through biological membranes like the intestinal wall or the blood-brain barrier.
After administration, enzymes in the body such as esterases can hydrolyze the ester bond, releasing the active drug in Hydroxyalkylamine ester's functional form.
This method is especially useful for increasing oral bioavailability or controlling the release profile of medications.
In the industrial sector, Hydroxyalkylamine esters are used as chemical intermediates in the synthesis of more complex molecules, particularly in the production of surfactants, detergents, lubricants, and coatings.
Because they contain both polar and non-polar segments, they are often used to improve the dispersion of solids in liquids, or to enhance the solubility of other substances in both aqueous and organic phases.
Their ester linkages offer the possibility of controlled hydrolysis, which can be useful in formulations requiring time-release mechanisms or pH-sensitive performance.
Hydroxyalkylamine esters also play a role in polymer chemistry, where they are used to modify resins or as monomers or crosslinking agents in the synthesis of specialty polymers.
The ester group contributes flexibility and solubility, while the amine group can react with other functional groups (such as isocyanates, epoxides, or acids), making these compounds useful for tailoring the mechanical and thermal properties of adhesives, sealants, and coatings.
They are especially valuable in formulations that demand a balance of durability, flexibility, and resistance to environmental degradation.
In agriculture, Hydroxyalkylamine esters may be used as adjuvants or carriers in pesticide formulations, where their amphiphilic nature helps to enhance the delivery and penetration of active ingredients through plant cuticles or insect exoskeletons.
Their ability to act as solubilizing agents or to stabilize emulsions contributes to the uniform distribution of agrochemicals, improving overall efficacy while reducing the environmental impact of runoff.
In biochemical research, Hydroxyalkylamine esters are sometimes employed in the design of enzyme substrates, molecular probes, or drug delivery vehicles.
Their functional groups allow them to be modified with precision, making them suitable for attaching fluorescent tags, radiolabels, or targeting ligands.
In biomedical materials science, they may be incorporated into biodegradable polymers or hydrogels, where the ester linkage allows for slow breakdown in physiological conditions, making them ideal for applications like controlled drug release or tissue engineering scaffolds.
Some Hydroxyalkylamine esters are used in wastewater treatment or environmental remediation, where they may function as chelating agents or surfactants that help remove heavy metals, oils, or other hydrophobic pollutants.
Their molecular structure allows them to interact with both organic contaminants and aqueous environments, making them versatile agents in pollution control and cleanup technologies.
Here’s a comprehensive overview of the uses of Hydroxyalkylamine esters:
Pharmaceuticals:
Hydroxyalkylamine ester serve as intermediates in the synthesis of local anesthetics, antihistamines, antidepressants, and CNS-active agents.
Hydroxyalkylamine ester is used to design drug delivery molecules due to their amphiphilic character, improving solubility and membrane permeability.
Some derivatives act as prodrugs, where the ester linkage is cleaved in the body to release the active amino alcohol.
Agrochemicals:
Employed in the preparation of herbicides, insecticides, and fungicides, where Hydroxyalkylamine esters improve penetration and bioavailability.
Function as stabilizers or co-formulants in crop protection products.
Polymer & Materials Industry:
Hydroxyalkylamine ester is used as polymer modifiers to adjust flexibility, adhesion, and chemical resistance.
Hydroxyalkylamine ester act as curing agents and catalysts in resins, adhesives, and coatings.
Help in crosslinking reactions in epoxy and urethane systems.
Surfactants & Specialty Chemicals:
Certain derivatives are used as surfactants, emulsifiers, and wetting agents in detergents and cleaning formulations.
Hydroxyalkylamine esters can form quaternary ammonium salts, which act as phase-transfer catalysts or antimicrobial agents.
Utilized as corrosion inhibitors in lubricants and metal protection formulations.
Analytical & Research Applications:
Hydroxyalkylamine ester is used in protein sequencing and analytical derivatization techniques.
Employed as intermediates in biochemical and pharmaceutical research for creating novel compounds.
Benefits of Hydroxyalkylamine Ester:
Structural Versatility:
Hydroxyalkylamine ester contain both amine and ester functional groups, allowing them to participate in a wide range of reactions.
Hydroxyalkylamine ester can be tailored by modifying the alkyl chain, the ester group, or the amino substituents, making them adaptable to many industrial and pharmaceutical applications.
Pharmaceutical Value:
Hydroxyalkylamine ester act as drug intermediates or prodrugs, improving solubility, bioavailability, and membrane penetration of active compounds.
Hydroxyalkylamine ester have amphiphilic character, which allows them to serve as effective carriers for drug delivery systems.
Industrial Utility:
Hydroxyalkylamine ester provide flame-retardant, corrosion-inhibiting, and surface-active properties, making them useful in coatings, lubricants, and surfactants.
Hydroxyalkylamine ester function as polymer modifiers, enhancing flexibility, thermal stability, and curing efficiency in resins and adhesives.
Environmental & Safety Advantages:
Hydroxyalkylamine ester are often halogen-free and considered less environmentally persistent compared to halogenated alternatives.
Hydroxyalkylamine ester demonstrate multifunctionality, which reduces the need for multiple additives in formulations, simplifying processes and lowering chemical loads.
Research & Innovation Potential:
Hydroxyalkylamine ester serve as valuable building blocks in organic synthesis for designing novel molecules.
Hydroxyalkylamine ester enable the preparation of quaternary ammonium compounds, surfactants, and specialty esters with antimicrobial or catalytic properties.
Production of Hydroxyalkylamine Ester:
Raw Materials:
Amino alcohols (such as ethanolamine, diethanolamine, isopropanolamine, or other substituted aminoalkanols).
Carboxylic acids, acid chlorides, or esters (e.g., acetic acid, fatty acids, benzoic acid derivatives).
Catalysts/activating agents (commonly acid catalysts, coupling reagents, or dehydrating agents like DCC, thionyl chloride, or p-toluenesulfonic acid).
General Synthetic Routes:
Direct Esterification:
Reaction:
Aminoalkanol + Carboxylic acid → Hydroxyalkylamine ester + H₂O
Conditions:
Acid catalyst (e.g., H₂SO₄, p-TsOH) and heat to drive off water.
Notes:
Requires protection of the amino group to avoid side reactions.
Reaction with Acid Chlorides or Anhydrides:
Reaction:
Aminoalkanol + RCOCl (acid chloride) → Hydroxyalkylamine ester + HCl
Conditions:
Typically carried out in anhydrous organic solvents (dichloromethane, toluene) under cooling, with a base (e.g., triethylamine) to neutralize HCl.
Advantage:
Higher yields, milder conditions.
Transesterification:
Reaction:
Aminoalkanol + RCOOR′ (ester) → Hydroxyalkylamine ester + R′OH
Conditions:
Acid or base catalysis (alkoxides, organometallic catalysts).
Notes:
Useful for large-scale industrial synthesis, especially when fatty acid esters are the starting material.
Industrial Production:
Step 1:
Protection of the amine group (commonly via acetylation, Boc-protection, or salt formation).
Step 2:
Esterification or acylation of the hydroxyl group using fatty acids, acid chlorides, or anhydrides.
Step 3:
Deprotection to regenerate the amino function (if required).
Step 4:
Purification by distillation, crystallization, or solvent extraction.
Industrial setups usually employ continuous flow esterification reactors for large-scale production to ensure consistent product quality.
Byproducts & Challenges:
Formation of amide byproducts (if the amino group reacts instead of the hydroxyl group).
Requirement of careful pH and temperature control to avoid decomposition.
Need for solvent recovery and neutralization systems to meet environmental and safety standards.
History of Hydroxyalkylamine Ester:
Early Research (Late 19th – Early 20th Century):
The chemistry of amino alcohols (e.g., ethanolamine, isopropanolamine) was first studied in the late 1800s as part of the growing interest in nitrogen-containing organic compounds.
With the rise of ester chemistry, chemists began combining amino alcohols with carboxylic acids to produce Hydroxyalkylamine esters, initially explored for their reactivity and potential medicinal value.
Pharmaceutical Development (Mid-20th Century):
By the 1930s–1950s, Hydroxyalkylamine esters gained importance in pharmaceutical research, especially as intermediates for local anesthetics, anticholinergics, and CNS-active drugs.
Their dual functional groups (amine + ester) made them valuable scaffolds for modifying solubility, absorption, and metabolic stability in drug design.
Several early medicines, including procaine derivatives and antihistamines, were developed from related amino alcohol ester structures.
Industrial Expansion (1960s–1980s):
As polymer science advanced, Hydroxyalkylamine esters were adapted as curing agents, surfactants, corrosion inhibitors, and polymer modifiers.
They became important in coatings, adhesives, lubricants, and plastics, where their multifunctionality reduced the need for multiple additives.
Industrial production methods were optimized (acid chloride routes, esterification under controlled conditions) for large-scale manufacturing.
Modern Applications (1990s–Present):
Today, Hydroxyalkylamine esters are widely recognized as specialty intermediates in pharmaceuticals, agrochemicals, and surfactants.
They continue to serve in drug delivery research due to their amphiphilic nature, as well as in green chemistry, since many are halogen-free and environmentally preferable.
Recent studies focus on designing bioactive derivatives and advanced materials (e.g., polymer modifiers, phase-transfer catalysts, quaternary ammonium salts with antimicrobial activity).
Handling and Storage of Hydroxyalkylamine Ester:
Handling:
Use only with adequate ventilation or in a fume hood.
Avoid contact with skin, eyes, and clothing.
Do not breathe vapors, mists, or aerosols.
Wash hands thoroughly after handling.
Storage:
Store in tightly closed containers in a cool, dry, and well-ventilated area.
Keep away from heat, sparks, open flames, and strong oxidizers.
Protect from moisture and direct sunlight.
Stability and Reactivity of Hydroxyalkylamine Ester:
Stability:
Stable under recommended storage conditions.
Reactivity:
May react with strong acids, strong bases, and oxidizing agents.
Prolonged heating may cause decomposition.
Decomposition products:
Toxic fumes of nitrogen oxides (NOₓ), carbon monoxide (CO), carbon dioxide (CO₂) may form.
Polymerization:
Not expected to undergo hazardous polymerization.
First Aid Measures of Hydroxyalkylamine Ester:
Inhalation:
Move to fresh air.
If breathing is difficult, give oxygen.
Seek medical attention if symptoms persist.
Skin contact:
Wash immediately with plenty of soap and water.
Remove contaminated clothing.
Seek medical help if irritation develops.
Eye contact:
Rinse cautiously with water for at least 15 minutes, keeping eyelids open.
Seek medical attention immediately.
Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Give water if the person is conscious.
Get immediate medical help.
Firefighting Measures of Hydroxyalkylamine Ester:
Suitable extinguishing media:
Dry chemical, foam, carbon dioxide (CO₂), or water spray.
Specific hazards:
Flammable liquid and vapor. Decomposition may produce toxic gases.
Protective equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear.
Accidental Release Measures of Hydroxyalkylamine Ester:
Personal precautions:
Evacuate area, ensure proper ventilation, and wear protective equipment (gloves, goggles, respirator if needed).
Environmental precautions:
Prevent entry into drains, soil, and water systems.
Spill cleanup:
Absorb spill with inert material (sand, vermiculite).
Collect into labeled containers for disposal.
Wash spill area thoroughly with water and detergent.
Exposure Controls / Personal Protection of Hydroxyalkylamine Ester:
Engineering controls:
Use fume hoods and local exhaust ventilation.
Personal Protective Equipment (PPE):
Respiratory protection:
Organic vapor respirator if ventilation is inadequate.
Hand protection:
Chemical-resistant gloves (nitrile, neoprene).
Eye protection:
Safety goggles or face shield.
Skin/body protection:
Lab coat or protective clothing resistant to organic solvents.
Hygiene measures:
Do not eat, drink, or smoke while handling.
Wash hands and face after use.
Identifiers of Hydroxyalkylamine Ester:
Class Name: Hydroxyalkylamine esters
Functional Groups: Amine (–NH₂ or substituted amine), ester (–COOR), alkanol backbone
General Formula: R–NH–(CH₂)n–O–C(=O)–R′
General Molecular Weight Range: ~100–400 g/mol (varies by substituents)
Common Synonyms: Amino alcohol esters, aminoalkanol-based esters, esterified amino alcohols
CAS Number: 59-46-1
Molecular Formula: C15H21N3O2
Molecular Weight: 275.35
EC Number: 200-426-9
Properties of Hydroxyalkylamine Ester:
Appearance: Clear to pale yellow liquids or crystalline solids
Odor: Mild, amine-like or faint ester odor
Density: ~0.9 – 1.1 g/cm³ at 20 °C
Boiling Point: 180 – 280 °C (varies with chain length and substituents)
Melting Point: −20 to +50 °C (broad range)
Flash Point: Typically 70 – 120 °C
Solubility in Water: Slightly soluble (due to polar groups, but limited by hydrophobic chains)
Solubility in Organic Solvents: Readily soluble in ethanol, methanol, acetone, ethers, hydrocarbons
Viscosity: Low to moderate (liquid derivatives); increases with chain length
Refractive Index: ~1.45 – 1.50
Appearance: Clear to pale yellow liquid, sometimes crystalline solid
Odor: Mild to amine-like
Solubility: Sparingly soluble in water, miscible with alcohols, ketones, ethers
Stability: Stable under ambient conditions, reactive toward acids/oxidizers
Boiling point: 473.9±25.0 °C(Predicted)
Density: 1.19±0.1 g/cm3(Predicted)
pka: 6.74±0.10(Predicted)
