2-Amino-1,3-propanediol CAS NO.534-03-2

1. Basic Parameter Table

2. Properties

Chemical Properties

Serinol (2-Amino-1,3-propanediol) is a prochiral amino alcohol compound, named for its structural similarity to natural amino acid serine. Its molecule contains two hydroxyl groups (-OH) and one amino group (-NH₂), endowing it excellent reactivity and multifunctionality. It is chemically stable and resistant to decomposition under normal storage conditions.

Physical Properties

It appears as white to off-white crystalline powder at room temperature with a melting point of 52–55°C and strong hygroscopicity, readily absorbing moisture when exposed to air. It is extremely soluble in polar solvents such as water, methanol and ethanol, and slightly soluble in non-polar organic solvents. It has a density of approximately 1.20 g/cm³, an atmospheric boiling point of 266.7°C and a flash point of 115°C.

Structural Characteristics

As a prochiral molecule, serinol features two symmetric hydroxymethyl groups (-CH₂OH), which can be converted into chiral derivatives (L-Serinol, D-Serinol) via asymmetric synthesis, making it highly valuable in pharmaceutical synthesis. Its bifunctional structure (amino group + dihydroxyl groups) enables wide applications in polymer modification, surfactant synthesis and pharmaceutical intermediate production.

3. Applications

Core Application: Pharmaceutical Intermediates

Serinol is the key raw material for synthesizing Iopamidol, a non-ionic X-ray contrast medium sold under brand name Iopamiro®. Widely used in cardiovascular angiography, CT enhanced scanning and urinary system diagnostic imaging, Iopamidol delivers high imaging quality with low vascular and neurotoxicity and excellent patient tolerance, sustaining steady global market demand. Besides, serinol is adopted for synthesizing chloramphenicol antibiotics, Type 2 diabetes drugs, multiple sclerosis therapeutics and analgesics.

Chemical & Material Industry

1. Manufacture high-efficiency anionic emulsifiers and nonionic polyethylene emulsions for personal care products and industrial emulsion systems;

2. Serve as polymer monomer or modifier in water-based and solvent-based coatings & adhesives to improve solubility and solution stability;

3. Act as pigment dispersing additive to enhance wettability and viscosity stability;

4. Synthesize water-soluble cationic flocculants, ion exchange resins and CO₂ absorbents;

5. Function as corrosion inhibitor and pH buffer in metal treatment and water treatment sectors.

Biological & Scientific Research

Serinol is a critical building block for synthesizing artificial nucleic acids, sphingolipids (sphingosine, dihydrosphingosine) and various bioactive molecules, occupying an irreplaceable position in molecular biology and medicinal chemistry research.

4. Production Methods

1. Main Industrial Process: Nitromethane Catalytic Hydrogenation

This mature process delivers high yield and controllable cost, dominating large-scale global serinol production.

1. Condensation Reaction Nitromethane (CH₃NO₂) undergoes Henry condensation reaction with formaldehyde (or paraformaldehyde) under alkaline catalysts (NaOH/KOH) in methanol or aqueous solvent to generate 2-nitro-1,3-propanediol or its sodium salt, with over 90% single-step yield.

2. Catalytic Hydrogenation The 20–25% methanolic solution of 2-nitro-1,3-propanediol is transferred into a high-pressure reactor. Using 5% Pd/C or Raney Ni as catalyst, the reaction proceeds under hydrogen pressure of 0.5–3.0 MPa at 70–80°C for 3–5 hours, reducing nitro group (-NO₂) to amino group (-NH₂) to form serinol solution with over 95% yield.

3. Separation & Purification The reaction liquid is filtered to remove catalysts. Methanol solvent is recovered and recycled via high-vacuum distillation (vacuum ≤40 Pa), followed by crystallization, recrystallization or ion exchange resin purification to obtain high-purity serinol finished product (purity ≥99.5%).

2. Alternative Route: 5-Nitro-1,3-dioxane Process

Trimethylolnitromethane reacts with acetone or cyclohexanone to form 5-nitro-1,3-dioxane derivatives. After catalytic hydrogenation to reduce nitro group to amino group, dioxane ring is hydrolyzed under acidic condition to obtain serinol. This route avoids explosive sodium 2-nitro-1,3-propanediol, featuring higher operational safety and suitable for industrial sites with strict safety requirements.

3. Biosynthesis (Cutting-edge Research Direction)

In recent years, researchers conduct metabolic engineering transformation on Escherichia coli to construct artificial biosynthetic pathways. Using glucose or glycerol as carbon sources, heterologous aminotransferase (RtxA) catalyzes dihydroxyacetone phosphate (DHAP) to produce serinol. This green method boasts renewable raw materials and mild reaction conditions, yet it remains at lab and pilot scale with productivity to be further optimized.

5. Safety Information

Hazard Overview

Serinol is classified as irritant (Xi), which irritates eyes, skin and respiratory tract. Long-term or repeated exposure may cause dry skin, redness or allergic reactions. Inhalation of dust may trigger respiratory discomfort.

First-aid Measures

· Skin Contact: Immediately take off contaminated clothing and rinse thoroughly with plenty of running water for at least 15 minutes; seek medical advice if necessary.

· Eye Contact: Immediately lift eyelids and flush thoroughly with running water or normal saline for minimum 15 minutes, then seek prompt medical treatment.

· Inhalation: Remove victim to fresh air and keep unobstructed breathing; administer oxygen if breathing difficulty occurs; perform artificial respiration and send to hospital if breathing stops.

· Ingestion: Let conscious patient drink plenty of warm water to induce vomiting and seek medical treatment right away.

Fire-fighting Measures

This product is combustible and risks ignition under open flame or high temperature. Fog water, foam, dry powder, carbon dioxide or sand can be used as extinguishing agents. Firefighters must wear gas masks and full-body fire suits and operate from upwind direction.

Leakage Emergency Handling

Isolate the leakage area and restrict access. Emergency responders shall wear dust masks and acid-base resistant work clothes. Collect spilled solid with clean shovels into dry, clean covered containers and transfer to safe zones. For massive leakage, recover the product or deliver to qualified waste disposal facilities for treatment.

Operation & Storage Requirements

Operators must receive professional training and strictly comply with operating procedures. Recommended protective equipment includes self-priming dust respirator, chemical safety goggles, chemical-resistant gloves and protective clothing. Avoid dust generation and contact with oxidants and acids. Store in cool, dry and well-ventilated warehouse at 2–8°C with tightly sealed containers, far away from fire and heat sources. Separate storage from oxidants and acids is mandatory; leakage containment materials shall be prepared in storage areas.

Waste Disposal

Incineration is recommended for waste treatment, or deliver waste to qualified hazardous waste disposal institutions for harmless treatment. Random dumping is prohibited.

6. Our Production Advantages & Capacity

1. Advanced Technology We adopt self-developed improved nitromethane catalytic hydrogenation process with mild reaction conditions, high catalyst activity and long service life. The single-pass conversion and selectivity reach top-tier industrial standards, effectively reducing by-product generation.

2. Green Manufacturing Methanol solvent recycling rate exceeds 95% with mature catalyst recovery and regeneration technology. Waste discharge is far below national environmental standards, balancing economic benefits and environmental protection.

3. Stable Supply Chain We possess complete raw material supply chain and finished product warehousing & logistics system, supporting flexible delivery from small R&D sample batches to large industrial orders to meet diversified demands of domestic and overseas clients.

4. Complete Qualifications Our factory has passed ISO 9001 quality management system certification. Products comply with USP/EP/CP standards. We can provide full set of COA, MSDS and registration supporting documents to assist customers with audit procedures.

5. Customized Service We supply serinol with customized purity grades (≥99.0%, ≥99.5%, ≥99.9%) and packaging specifications (25kg fiber drums, 500kg bulk bags, etc.) as per client’s special requirements.

Disclaimer: All data above is for reference only. Actual technical parameters shall be subject to Certificate of Analysis (COA). For samples or technical communication, please contact our sales and technical teams.