Meldrum’s Acid (CAS 2033-24-1)

Physical Properties

  • Appearance: White to off-white or beige crystalline solid/powder.
  • Molecular Weight: 144.13 g/mol.
  • Melting Point: 92°C to 96°C; it typically decomposes upon reaching this temperature.
  • Boiling Point: Approximately 356.7°C (at 760 mmHg), though it often decomposes before reaching this state.
  • Density: Approximately 1.13 to 1.2 g/cm³.
  • Solubility:
    • Water: Soluble (approx. 2.5 g/100 mL at 20°C).
    • Organic Solvents: Soluble in methanol, ethanol, acetone, and dioxane.
  • Acidity (pKa): 4.83 to 4.97 (remarkably acidic for a cyclic ester).
  • Vapor Pressure: 0 mmHg at 25°C.
  • Flash Point: Approximately 195.1°C to >365°C depending on the source.

Storage and Safety

  • Storage: Should be stored in a cool (refrigerated at 2–8°C), dry place, often under an inert atmosphere (nitrogen), as it is heat-sensitive.
  • Stability: Stable under recommended storage conditions but decomposes upon heating.
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Key Uses:

  • Organic Synthesis: A fundamental building block for creating diverse organic structures with various functional groups.
  • Pharmaceutical Intermediates: Crucial in developing Active Pharmaceutical Ingredients (APIs) and specialty chemicals.
  • Heterocyclic Synthesis: Used to synthesize nitrogen-containing rings (like indoles, pyridines) and other complex ring systems.
  • Ester & Amide Synthesis: Serves as a scaffold to form esters and amides through reactions with alcohols and amines, often with high efficiency.
  • Knoevenagel Condensation: Accelerates reactions with aldehydes, making it valuable for forming carbon-carbon bonds.

Why it’s Used:

  • High Acidity: Its pKa (~4.83) makes it easily deprotonated, forming a stable carbanion.
  • Steric Rigidity: Its cyclic structure provides unique reactivity.
  • Versatile Reactivity: It’s an excellent starting material for many transformations, acting similarly to malonic esters but with enhanced reactivity, notes Wikipedia and Scimplify.

Applications

Key Uses:

  • Organic Synthesis: A fundamental building block for creating diverse organic structures with various functional groups.
  • Pharmaceutical Intermediates: Crucial in developing Active Pharmaceutical Ingredients (APIs) and specialty chemicals.
  • Heterocyclic Synthesis: Used to synthesize nitrogen-containing rings (like indoles, pyridines) and other complex ring systems.
  • Ester & Amide Synthesis: Serves as a scaffold to form esters and amides through reactions with alcohols and amines, often with high efficiency.
  • Knoevenagel Condensation: Accelerates reactions with aldehydes, making it valuable for forming carbon-carbon bonds.

Why it’s Used:

  • High Acidity: Its pKa (~4.83) makes it easily deprotonated, forming a stable carbanion.
  • Steric Rigidity: Its cyclic structure provides unique reactivity.
  • Versatile Reactivity: It’s an excellent starting material for many transformations, acting similarly to malonic esters but with enhanced reactivity, notes Wikipedia and Scimplify.

Applications

  • Pharmaceuticals: It serves as a key intermediate in the synthesis of Active Pharmaceutical Ingredients (APIs) and other specialty chemicals for drug development.
  • Agrochemicals: It is used as a reagent in the production of various agrochemical compounds.
  • Materials Science: The compound is used in the manufacturing of specialty chemicals and polymers.
  • Academic Research and Organic Synthesis:
    • It is a valuable starting material for synthesizing a wide range of organic compounds, including heterocyclic compounds, beta-keto esters, and carboxylic acids.
    • It is used in Knoevenagel condensation reactions, which are C-C bond formation reactions.
    • When heated, it produces highly reactive ketenes, which can then be used to form new amides, esters, and rings in a single “one-pot” reaction.

Specific Syntheses

Meldrum’s acid has been used in the synthesis of specific molecules, including:

  • Macrocyclic beta-keto lactones
  • 4-pyridyl-substituted heterocycles
  • 2-substituted indoles
  • Isofraxidin

 

  • Pharmaceuticals: It serves as a key intermediate in the synthesis of Active Pharmaceutical Ingredients (APIs) and other specialty chemicals for drug development.
  • Agrochemicals: It is used as a reagent in the production of various agrochemical compounds.
  • Materials Science: The compound is used in the manufacturing of specialty chemicals and polymers.
  • Academic Research and Organic Synthesis:
    • It is a valuable starting material for synthesizing a wide range of organic compounds, including heterocyclic compounds, beta-keto esters, and carboxylic acids.
    • It is used in Knoevenagel condensation reactions, which are C-C bond formation reactions.
    • When heated, it produces highly reactive ketenes, which can then be used to form new amides, esters, and rings in a single “one-pot” reaction.

Specific Syntheses

Meldrum’s acid has been used in the synthesis of specific molecules, including:

  • Macrocyclic beta-keto lactones
  • 4-pyridyl-substituted heterocycles
  • 2-substituted indoles
  • Isofraxidin

 

FAQs

What is Meldrum’s Acid (2033-24-1)?
Meldrum’s Acid (2033-24-1) is an organic compound widely used as a building block in organic and pharmaceutical synthesis.
What is the CAS number of Meldrum’s Acid?
The CAS number of Meldrum’s Acid is 2033-24-1.
What are the main uses of Meldrum’s Acid (2033-24-1)?
Meldrum’s Acid (2033-24-1) is commonly used in the synthesis of heterocycles, pharmaceuticals, agrochemicals, and fine chemicals.
Is Meldrum’s Acid hazardous?
Meldrum’s Acid (2033-24-1) may cause irritation to the skin, eyes, and respiratory system and should be handled with standard laboratory safety precautions.
What is the molecular formula of Meldrum’s Acid (2033-24-1)?
The molecular formula of Meldrum’s Acid (2033-24-1) is C₆H₈O₄.

FAQs

What is Meldrum’s Acid (2033-24-1)?
Meldrum’s Acid (2033-24-1) is an organic compound widely used as a building block in organic and pharmaceutical synthesis.
What is the CAS number of Meldrum’s Acid?
The CAS number of Meldrum’s Acid is 2033-24-1.
What are the main uses of Meldrum’s Acid (2033-24-1)?
Meldrum’s Acid (2033-24-1) is commonly used in the synthesis of heterocycles, pharmaceuticals, agrochemicals, and fine chemicals.
Is Meldrum’s Acid hazardous?
Meldrum’s Acid (2033-24-1) may cause irritation to the skin, eyes, and respiratory system and should be handled with standard laboratory safety precautions.
What is the molecular formula of Meldrum’s Acid (2033-24-1)?
The molecular formula of Meldrum’s Acid (2033-24-1) is C₆H₈O₄.