Cas no 83277-23-0 (2,4-Dichloro-3-methylbenzoic acid)

2,4-Dichloro-3-methylbenzoic acid is a chlorinated aromatic carboxylic acid with the molecular formula C?H?Cl?O?. This compound features a benzoic acid core substituted with two chlorine atoms at the 2- and 4-positions and a methyl group at the 3-position, imparting distinct electronic and steric properties. It serves as a versatile intermediate in organic synthesis, particularly in the preparation of agrochemicals, pharmaceuticals, and specialty chemicals. The dichloro and methyl substitutions enhance its reactivity in electrophilic and nucleophilic transformations, making it valuable for derivatization. Its crystalline solid form and moderate solubility in organic solvents facilitate handling and purification. The compound’s stability under standard conditions ensures consistent performance in synthetic applications.
2,4-Dichloro-3-methylbenzoic acid structure
83277-23-0 structure
Product Name:2,4-Dichloro-3-methylbenzoic acid
CAS No:83277-23-0
MF:C8H6Cl2O2
MW:205.03804063797
MDL:MFCD16659660
CID:1028166
Update Time:2025-11-02

2,4-Dichloro-3-methylbenzoic acid Chemical and Physical Properties

Names and Identifiers

    • 2,4-Dichloro-3-methylbenzoic acid
    • 2,4-Dichloro-m-toluic acid
    • 2,4-Dichloro-3-methylbenzoic acid (ACI)
    • MDL: MFCD16659660
    • Inchi: 1S/C8H6Cl2O2/c1-4-6(9)3-2-5(7(4)10)8(11)12/h2-3H,1H3,(H,11,12)
    • InChI Key: KYAATGSGTLPBHN-UHFFFAOYSA-N
    • SMILES: O=C(C1C(Cl)=C(C)C(Cl)=CC=1)O

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1

Experimental Properties

  • Density: 1.442±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Very slightly soluble (0.11 g/l) (25 o C),

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2,4-Dichloro-3-methylbenzoic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: sec-Butyllithium Solvents: Tetrahydrofuran ,  Cyclohexane ;  45 min, -75 °C
1.2 cooled
1.3 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 25 °C
Reference
Proton mobility in 2-substituted 1,3-dichlorobenzenes: "ortho" or "meta" metalation?
Schlosser, Manfred; et al, European Journal of Organic Chemistry, 2006, (19), 4398-4404

2,4-Dichloro-3-methylbenzoic acid Raw materials

2,4-Dichloro-3-methylbenzoic acid Preparation Products

Additional information on 2,4-Dichloro-3-methylbenzoic acid

2,4-Dichloro-3-methylbenzoic Acid (CAS No. 83277-23-0): Properties, Applications, and Market Insights

2,4-Dichloro-3-methylbenzoic acid (CAS No. 83277-23-0) is a chlorinated aromatic carboxylic acid derivative with significant industrial and research applications. This compound, characterized by its methyl and chloro substituents on the benzene ring, is widely utilized in organic synthesis, agrochemicals, and pharmaceutical intermediates. Its molecular formula is C8H6Cl2O2, and it exhibits unique chemical properties due to the electron-withdrawing effects of the chlorine atoms.

The physical and chemical properties of 2,4-dichloro-3-methylbenzoic acid make it a versatile building block in synthetic chemistry. It typically appears as a white to off-white crystalline powder with a melting point ranging between 150-155°C. The presence of the carboxylic acid group allows for further functionalization, making it valuable in the synthesis of esters, amides, and other derivatives. Researchers often highlight its stability under standard conditions, though it should be stored in a cool, dry place to prevent degradation.

One of the most common applications of 2,4-dichloro-3-methylbenzoic acid is in the agrochemical industry, where it serves as a precursor for herbicides and plant growth regulators. With the growing demand for sustainable farming solutions, this compound has gained attention for its role in developing eco-friendly crop protection products. Additionally, its use in pharmaceutical intermediates is notable, particularly in the synthesis of active pharmaceutical ingredients (APIs) with antimicrobial or anti-inflammatory properties.

Recent trends in green chemistry have spurred interest in optimizing the synthesis of 2,4-dichloro-3-methylbenzoic acid to reduce environmental impact. Innovations such as catalytic chlorination and solvent-free reactions are being explored to enhance yield and purity while minimizing waste. These advancements align with global efforts to promote sustainable chemical manufacturing practices.

The market demand for 2,4-dichloro-3-methylbenzoic acid is influenced by its applications in diverse sectors. Regions with strong agrochemical and pharmaceutical industries, such as North America, Europe, and Asia-Pacific, are key consumers. Market analysts project steady growth, driven by increasing agricultural needs and the expansion of the pharmaceutical sector. Suppliers and manufacturers are focusing on high-purity grades to meet the stringent requirements of end-users.

For researchers and industry professionals, understanding the safety and handling of 2,4-dichloro-3-methylbenzoic acid is crucial. While it is not classified as a hazardous substance under standard regulations, proper laboratory practices, including the use of personal protective equipment (PPE), are recommended. Material Safety Data Sheets (MSDS) provide detailed guidelines for storage, handling, and disposal to ensure workplace safety.

In summary, 2,4-dichloro-3-methylbenzoic acid (CAS No. 83277-23-0) is a multifaceted compound with broad utility in agrochemicals, pharmaceuticals, and organic synthesis. Its unique structural features and reactivity make it indispensable in modern chemistry. As industries continue to innovate, the role of this compound is expected to expand, reinforcing its importance in scientific and industrial applications.

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