Acetoxyacetyl chloride (CAS 13831-31-7) is a highly reactive organic compound that serves as a crucial building block in modern organic synthesis. With the molecular formula C4H5ClO3 and a molecular weight of 136.53 g/mol, this chemical intermediate plays a vital role in pharmaceutical, agrochemical, and specialty chemical manufacturing. This comprehensive guide explores the properties, applications, safety considerations, and practical uses of acetoxyacetyl chloride in various industrial sectors.

What Is Acetoxyacetyl Chloride?

Acetoxyacetyl chloride, also known by its systematic name 2-acetoxyacetyl chloride, is an acyl chloride derivative of acetoxyacetic acid. This compound appears as a colorless to light yellow liquid with a pungent, irritating odor. It is commonly referred to by several synonyms including:

• 2-Acetoxyacetyl chloride
• 2-(Acetyloxy)acetyl chloride
• (Chlorocarbonyl)methyl acetate
• Acetic acid (2-chloro-2-oxoethyl) ester

The compound is classified under EINECS number 237-542-4 and is widely recognized as an essential intermediate in synthetic organic chemistry. Its unique molecular structure combines an acetyl ester group with an acid chloride functionality, providing distinctive reactivity patterns that make it valuable for various chemical transformations.

Acetoxyacetyl chloride is commercially available in different purity grades, with the common commercial specification being 97% purity. The compound is typically stored and handled under controlled conditions to maintain its stability and reactivity.

Chemical Properties and Specifications

Acetoxyacetyl chloride exhibits several important chemical properties that define its behavior in synthesis applications:

Caractéristiques physiques

• Apparence : Liquide incolore à jaune clair
• Formule moléculaire : C4H5ClO3 (CH3CO2CH2COCl)
• Molecular Weight: 136.53 g/mol
• CAS Number: 13831-31-7
• Point d'ébullition : Approximately 70-72°C at 15 mmHg
• Densité : Approximately 1.27 g/cm³ at 25°C
• Solubilité : Reacts with water and alcohols; soluble in common organic solvents such as dichloromethane, chloroform, and ether

Réactivité chimique

The acid chloride functional group (-COCl) in acetoxyacetyl chloride makes it highly reactive toward nucleophiles. This reactivity enables various acylation reactions, including:

• Amination reactions: Reacts with amines to form amides
• Esterification reactions: Converts alcohols to esters
• Amide bond formation: Essential for peptide and β-lactam synthesis

The acetoxy group (-OCOCH3) provides additional synthetic flexibility, allowing for subsequent transformations such as hydrolysis to yield the corresponding carboxylic acid.

What Are the Benefits?

Acetoxyacetyl chloride offers several significant benefits that make it indispensable in chemical manufacturing:

1. Versatile Pharmaceutical Applications

Acetoxyacetyl chloride serves as a key intermediate in the synthesis of numerous pharmaceutical agents. Its role in β-lactam antibiotic synthesis is particularly notable, as these antibiotics represent one of the most important classes of antimicrobial drugs worldwide. The compound enables efficient construction of the four-membered β-lactam ring system that characterizes penicillins, cephalosporins, and related antibiotics.

2. Efficient Acylation Agent

The compound provides highly efficient acylation capabilities due to the reactivity of the acid chloride group. This makes it superior to many alternative acylating agents in terms of reaction rates and conversion efficiencies. The resulting acylated products often require minimal purification, reducing overall manufacturing costs.

3. Agricultural Chemical Development

In agrochemical synthesis, acetoxyacetyl chloride contributes to the development of advanced herbicides and pesticides. Its use in creating novel crop protection agents helps address evolving agricultural challenges and resistance issues in pest management.

4. Research and Development Value

For research institutions and chemical laboratories, acetoxyacetyl chloride provides a reliable building block for exploring new synthetic methodologies and developing novel compounds with potential therapeutic or industrial applications.

5. Streamlined Manufacturing Processes

The use of acetoxyacetyl chloride as an intermediate often simplifies multi-step synthesis routes, reducing the number of reaction steps required to reach target molecules. This streamlining translates to improved process economics and reduced waste generation.

What Are the Uses?

Acetoxyacetyl chloride finds extensive applications across multiple industries:

Pharmaceutical Synthesis

The primary application of acetoxyacetyl chloride lies in pharmaceutical manufacturing:

• β-Lactam Antibiotics: Used in the synthesis of various β-lactam antibiotics including penicillins and cephalosporins. The compound reacts with imine derivatives to form the characteristic four-membered lactam ring through a [2+2] cycloaddition mechanism.
• Spiro-β-Lactams: Employed in the synthesis of spiro-fused β-lactam compounds, which represent a newer class of antibiotic candidates with potential activity against resistant bacterial strains.
• Glycolylhydroxamic Acids: Used as a precursor in synthesizing glycolylhydroxamic acid derivatives, which exhibit various biological activities.
• Carbonic Anhydrase Inhibitors: Intermediate in producing compounds that inhibit carbonic anhydrase enzymes, relevant for treating glaucoma and other conditions.
• Acetylcholinesterase Inhibitors: Used in synthesizing cholinesterase inhibitors for potential neurological applications.

Agrochemical Industry

• Herbicide Development: Acts as a building block for novel herbicidal compounds
• Pesticide Synthesis: Contributes to the development of effective pest control agents
• Plant Growth Regulators: Used in synthesizing compounds that modulate plant growth patterns

Specialty Chemicals

• Polymer Modifiers: Employed in modifying polymer properties
• Industrie des arômes et des parfums : Serves as a precursor for certain flavor compounds
• Analytical Standards: Used as reference standards in chromatographic analysis

Academic Research

• Synthetic Methodology Development: Widely used in developing new synthetic reactions and strategies
• Medicinal Chemistry Studies: Essential for structure-activity relationship (SAR) studies
• Chemical Biology Applications: Used in labeling and modification of biomolecules

Safety and Handling Considerations

Acetoxyacetyl chloride requires careful handling due to its reactive nature and potential hazards:

Health Hazards

• Corrosive: Causes severe skin burns and eye damage
• Toxic Fumes: Releases irritating and potentially toxic vapors, including hydrogen chloride, upon contact with water or moisture
• Lachrymator: Causes eye irritation and tearing
• Sensitization: May cause allergic skin reactions upon repeated exposure

Précautions de sécurité

1. Personal Protective Equipment (PPE):

• Chemical-resistant gloves (nitrile or neoprene)
• Safety goggles or face shield
• Lab coat or chemical-resistant apron
• Respiratory protection in poorly ventilated areas

2. Storage Requirements:

• Store in a cool, dry, well-ventilated area
• Keep container tightly closed when not in use
• Store away from incompatible materials including water, alcohols, and bases
• Use appropriate corrosion-resistant containers (glass-lined or PTFE-lined)

3. Handling Guidelines:

• Work in a fume hood or well-ventilated area
• Avoid breathing vapors or mists
• Do not add water directly to the compound
• Handle with care to prevent spills and splashes
• Have emergency eyewash and safety shower readily accessible

4. Disposal Considerations:

• Dispose of in accordance with local environmental regulations
• Neutralize before disposal (consult SDS for specific procedures)
• Never pour down drains without proper treatment

Frequently Asked Questions

What is the molecular formula of acetoxyacetyl chloride?

Acetoxyacetyl chloride has the molecular formula C4H5ClO3, with a molecular weight of 136.53 g/mol. Its linear formula is CH3CO2CH2COCl.

What are the main industrial applications of acetoxyacetyl chloride?

The primary applications include pharmaceutical synthesis (especially β-lactam antibiotics), agrochemical development (herbicides and pesticides), and specialty chemical manufacturing.

Is acetoxyacetyl chloride dangerous to handle?

Yes, acetoxyacetyl chloride is classified as corrosive and can cause severe burns. It releases irritating and toxic fumes, particularly hydrogen chloride, when exposed to moisture. Proper PPE and handling procedures are essential.

How should acetoxyacetyl chloride be stored?

Store in a cool, dry, well-ventilated area in tightly sealed containers. Keep away from water, alcohols, and strong bases. Use appropriate corrosion-resistant storage containers.

Can acetoxyacetyl chloride be used in organic synthesis at scale?

Yes, it is used in industrial-scale synthesis, particularly in pharmaceutical manufacturing. However, due to its reactivity and hazards, processes must be carefully designed with appropriate safety measures.

What alternatives exist for acetoxyacetyl chloride in acylation reactions?

Alternatives include other acid chlorides (acetyl chloride, chloroacetyl chloride), anhydrides (acetic anhydride), and activated carboxylic acids. The choice depends on specific reaction requirements and cost considerations.

Is acetoxyacetyl chloride available for commercial purchase?

Yes, it is available from various chemical suppliers including Sigma-Aldrich, Santa Cruz Biotechnology, and other specialty chemical distributors. Typical commercial purity is 97%.

Why Choose Our Acetoxyacetyl Chloride?

When sourcing acetoxyacetyl chloride for your research or manufacturing needs, our company offers distinct advantages:

Quality Assurance

• High-purity products (97%+) with detailed certificate of analysis
• Rigorous quality control testing including HPLC and GC analysis
• Consistent batch-to-batch reproducibility

Technical Support

• Expert technical assistance for application questions
• Comprehensive safety data sheets (SDS) provided
• Formulation guidance for specific applications

Supply Chain Reliability

• Stable inventory for immediate shipment
• Flexible packaging options from grams to bulk quantities
• Reliable global logistics network

Competitive Pricing

• Market-competitive pricing for research and commercial quantities
• Volume discounts for large orders
• Custom synthesis options for specific requirements

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This article provides general information about acetoxyacetyl chloride (CAS 13831-31-7) for educational and informational purposes. For specific applications, consult with qualified chemical professionals and refer to official safety data sheets.