Myristoyl chloride
Chemical Additives 2025-03-18
Myristoyl Chloride
Chemical Formula: C₁₄H₂₇ClO
Classification: Acyl chloride derived from myristic acid, with a 14-carbon myristoyl group (CH₃(CH₂)₁₂CO-) and a carbonyl chloride (-COCl).
Physical Properties
- Appearance: Clear, colorless to pale yellow liquid.
- Odor: Pungent.
- Reactivity:
- Moisture-sensitive: Reacts violently with water, releasing HCl gas.
- Highly reactive in acylation reactions (e.g., esterification, amidation).
Applications
- Organic Synthesis:
- Introduces myristoyl groups to synthesize esters, amides, and derivatives for pharmaceuticals and agrochemicals.
- Surfactant Production:
- Key intermediate in cosmetics, detergents, and personal care products.
Safety Considerations ⚠️
- Health Hazards:
- Corrosive: Causes severe burns to skin, eyes, and respiratory tract.
- Releases HCl gas upon hydrolysis.
- Handling:
- Use PPE (gloves, goggles, respirator) and work in a fume hood.
- Storage:
- Store in a cool, dry, airtight container away from moisture and incompatible substances (e.g., bases, oxidizers).
Summary:
Myristoyl chloride’s high reactivity and long-chain acyl group make it critical in synthesizing surfactants, pharmaceuticals, and specialty chemicals. Strict safety protocols are essential due to its corrosive nature and moisture sensitivity.
Myristoyl Chloride: Technical Overview
Myristoyl chloride (C₁₄H₂₇ClO) is a fatty acid chloride derived from myristic acid, widely used in organic synthesis, pharmaceuticals, and specialty chemicals. Below is a structured summary of its properties, applications, and safety data.
Basic Chemical Properties
| Category | Specifications |
|---|---|
| Chemical Name | Tetradecanoyl chloride |
| CAS No. | 112-64-1 |
| Molecular Formula | C₁₄H₂₇ClO |
| Molecular Weight | 246.82 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | Pungent, acrid |
| Density (20°C) | 0.91–0.93 g/cm³ |
| Boiling Point | 160–165°C (15 mmHg) |
| Flash Point | >110°C (closed cup) |
| Solubility | Reacts with water; soluble in organic solvents (e.g., ether, THF, chloroform) |
Key Chemical Characteristics
| Property | Description |
|---|---|
| Reactivity | Highly reactive with nucleophiles (e.g., alcohols, amines). |
| Hydrolysis | Rapidly hydrolyzes in water to myristic acid and HCl. |
| Acylation Efficiency | Excellent for introducing myristoyl groups in organic synthesis. |
| Thermal Stability | Stable at room temperature; decomposes at high temperatures (>200°C). |
Primary Applications
| Industry | Use Case |
|---|---|
| Pharmaceuticals | – Prodrug synthesis – Lipophilic modification of APIs |
| Cosmetics | – Surfactant precursor – Emollient ester production |
| Organic Synthesis | – Acylation agent for alcohols/amines – Fatty acid derivatives |
| Agrochemicals | – Intermediate for pesticide formulations |
| Polymers & Coatings | – Monomer for specialty polyesters |
Handling & Safety Data
| Parameter | Guidelines |
|---|---|
| Storage Conditions | – Dry, cool (<25°C), inert atmosphere – Moisture-sensitive |
| Corrosivity | Causes severe skin/eye burns; corrodes metals. |
| Toxicity | – Harmful if inhaled/swallowed – Causes respiratory irritation |
| First Aid Measures | – Skin contact: Rinse with water – Inhalation: Move to fresh air |
| Fire Hazards | Combustible at high temperatures; emits toxic HCl fumes when heated. |
| Environmental Impact | Toxic to aquatic life; avoid release into water systems. |
Regulatory Compliance
| Regulation | Status |
|---|---|
| REACH | Registered |
| OSHA Hazards | Corrosive, irritant |
| Transport Class | 8 (Corrosive) |
Note: Due to its reactivity, myristoyl chloride should be handled under controlled conditions (gloves, goggles, fume hood).
