Cas no 35709-99-0 (2,4-dimethylphenyl chloroformate)

2,4-Dimethylphenyl chloroformate is a reactive chloroformate ester widely used as an intermediate in organic synthesis, particularly for the introduction of the 2,4-dimethylphenoxycarbonyl (DMPOC) protecting group. Its key advantages include high reactivity with nucleophiles, enabling efficient derivatization of amines, alcohols, and thiols. The steric hindrance from the dimethyl groups enhances selectivity in protection reactions, reducing side reactions. The compound is typically employed in peptide synthesis and pharmaceutical applications where temporary protection of functional groups is required. It is moisture-sensitive and should be handled under inert conditions to prevent hydrolysis. Proper storage in a cool, dry environment ensures stability and prolonged shelf life.
2,4-dimethylphenyl chloroformate structure
35709-99-0 structure
Product Name:2,4-dimethylphenyl chloroformate
CAS No:35709-99-0
MF:C9H9ClO2
MW:184.619561910629
MDL:MFCD24141138
CID:2823633
PubChem ID:15917593
Update Time:2025-06-08

2,4-dimethylphenyl chloroformate Chemical and Physical Properties

Names and Identifiers

    • 2,4-dimethylphenyl chloroformate
    • 35709-99-0
    • 2,4-Dimethylphenyl carbonochloridate
    • JRVKFYMWXSDYEF-UHFFFAOYSA-N
    • Carbonochloridic acid, 2,4-dimethylphenyl ester
    • DTXSID90579533
    • EN300-281236
    • AKOS020225691
    • SCHEMBL8466385
    • MDL: MFCD24141138
    • Inchi: 1S/C9H9ClO2/c1-6-3-4-8(7(2)5-6)12-9(10)11/h3-5H,1-2H3
    • InChI Key: JRVKFYMWXSDYEF-UHFFFAOYSA-N
    • SMILES: ClC(=O)OC1=CC=C(C)C=C1C

Computed Properties

  • Exact Mass: 184.0291072g/mol
  • Monoisotopic Mass: 184.0291072g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 170
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.5
  • Topological Polar Surface Area: 26.3?2

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Additional information on 2,4-dimethylphenyl chloroformate

2,4-Dimethylphenyl Chloroformate (CAS No. 35709-99-0): An Overview of Its Properties, Applications, and Recent Research

2,4-Dimethylphenyl chloroformate (CAS No. 35709-99-0) is a versatile organic compound that has gained significant attention in various fields, including pharmaceuticals, chemical synthesis, and materials science. This compound is characterized by its unique structure, which consists of a 2,4-dimethylphenyl group attached to a chloroformate moiety. The combination of these functional groups imparts distinct chemical properties that make it a valuable reagent in numerous applications.

The chemical formula of 2,4-dimethylphenyl chloroformate is C10H11ClO3. It is a colorless to pale yellow liquid with a molecular weight of approximately 218.64 g/mol. The compound is soluble in common organic solvents such as dichloromethane, ethyl acetate, and toluene, but it is insoluble in water. These solubility characteristics make it suitable for use in various organic reactions and processes.

One of the key applications of 2,4-dimethylphenyl chloroformate is in the synthesis of carbamates and urethanes. These derivatives are widely used in the pharmaceutical industry for the production of drugs with diverse therapeutic effects. For example, carbamates are often employed as intermediates in the synthesis of analgesics, anticonvulsants, and other medicinal compounds. The reactivity of the chloroformate group allows for efficient coupling with primary and secondary amines to form the desired carbamate products.

In addition to its role in pharmaceutical synthesis, 2,4-dimethylphenyl chloroformate has found applications in the development of polyurethane materials. Polyurethanes are versatile polymers used in a wide range of products, including coatings, adhesives, and foams. The compound's ability to react with polyols to form urethane linkages makes it an important component in the formulation of these materials. Recent research has focused on optimizing the reaction conditions and catalysts to enhance the efficiency and sustainability of polyurethane production processes.

The physical properties of 2,4-dimethylphenyl chloroformate have also been extensively studied. Its boiling point is around 180°C at 760 mmHg, and its melting point is -15°C. These properties are crucial for determining its handling and storage conditions. The compound should be stored in a cool, dry place away from sources of heat and moisture to maintain its stability and purity.

In terms of safety and environmental considerations, 2,4-dimethylphenyl chloroformate should be handled with care due to its potential reactivity with water and other reactive substances. Appropriate personal protective equipment (PPE) should be used when handling this compound to minimize exposure risks. It is important to follow all relevant safety guidelines and regulations to ensure safe handling and disposal practices.

Recent advancements in computational chemistry have provided valuable insights into the molecular structure and reactivity of 2,4-dimethylphenyl chloroformate. Quantum mechanical calculations have been used to predict its electronic properties and reaction pathways, which can guide experimental design and optimization efforts. These computational studies have also helped identify potential side reactions and byproducts that may occur during synthesis processes.

In the field of materials science, 2,4-dimethylphenyl chloroformate has been explored as a functional monomer for the preparation of advanced polymers with tailored properties. For example, researchers have synthesized copolymers containing this monomer unit to achieve improved mechanical strength, thermal stability, and chemical resistance. These materials have potential applications in areas such as aerospace engineering, electronics, and biomedical devices.

The versatility of 2,4-dimethylphenyl chloroformate extends beyond its use as a synthetic intermediate or monomer. It has also been investigated for its potential as a catalyst or catalyst precursor in various chemical reactions. Studies have shown that this compound can promote certain types of catalytic processes under specific conditions, offering new opportunities for developing more efficient and sustainable chemical transformations.

In conclusion, 2,4-dimethylphenyl chloroformate (CAS No. 35709-99-0) is a multifaceted compound with a wide range of applications in pharmaceuticals, materials science, and chemical synthesis. Its unique chemical structure and properties make it an essential reagent for researchers and industry professionals alike. Ongoing research continues to uncover new possibilities for its use in various fields, further highlighting its importance in modern chemistry.

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