Cas no 145908-29-8 (Methyl 2-(bromomethyl)-4-chlorobenzoate)

Methyl 2-(bromomethyl)-4-chlorobenzoate is a versatile brominated aromatic ester with applications in organic synthesis and pharmaceutical intermediates. Its key structural features—a reactive bromomethyl group and an electron-withdrawing chloro substituent—make it a valuable building block for nucleophilic substitution reactions, particularly in the construction of complex heterocycles and functionalized benzoate derivatives. The ester group enhances solubility in organic solvents, facilitating further transformations. This compound is particularly useful in medicinal chemistry for the development of bioactive molecules due to its ability to introduce both halogen and ester functionalities in a single step. High purity and stability under controlled conditions ensure reliable performance in synthetic applications.
Methyl 2-(bromomethyl)-4-chlorobenzoate structure
145908-29-8 structure
Product Name:Methyl 2-(bromomethyl)-4-chlorobenzoate
CAS No:145908-29-8
MF:C9H8BrClO2
MW:263.515621185303
MDL:MFCD11505950
CID:859777
PubChem ID:20814722
Update Time:2025-11-06

Methyl 2-(bromomethyl)-4-chlorobenzoate Chemical and Physical Properties

Names and Identifiers

    • Methyl 2-(bromomethyl)-4-chlorobenzoate
    • 2-Bromomethyl-4-chloro-benzoic acid methyl ester
    • Methyl 2-bromomethyl-4-chlorobenzoate
    • benzoic acid, 2-(bromomethyl)-4-chloro-, methyl ester
    • LogP
    • Methyl-2-(brommethyl)-4-chlorbenzoat
    • 2-(Bromomethyl)-4-chloro-benzoic acid methyl ester
    • LGLIPOQXOPCFRN-UHFFFAOYSA-N
    • CL8531
    • methyl 4-chloro-2-bromomethylbenzoate
    • FCH1404214
    • AX8212838
    • AB0022
    • MDL: MFCD11505950
    • Inchi: 1S/C9H8BrClO2/c1-13-9(12)8-3-2-7(11)4-6(8)5-10/h2-4H,5H2,1H3
    • InChI Key: LGLIPOQXOPCFRN-UHFFFAOYSA-N
    • SMILES: BrCC1C=C(C=CC=1C(=O)OC)Cl

Computed Properties

  • Exact Mass: 261.93964
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 187
  • Topological Polar Surface Area: 26.3

Experimental Properties

  • Melting Point: 72-75°C
  • PSA: 26.3

Methyl 2-(bromomethyl)-4-chlorobenzoate Security Information

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Methyl 2-(bromomethyl)-4-chlorobenzoate Related Literature

Additional information on Methyl 2-(bromomethyl)-4-chlorobenzoate

Methyl 2-(bromomethyl)-4-chlorobenzoate: A Comprehensive Overview

Methyl 2-(bromomethyl)-4-chlorobenzoate (CAS No. 145908-29-8) is a versatile organic compound with a wide range of applications in the fields of chemical synthesis, pharmaceutical research, and materials science. This compound is characterized by its unique structural features, which include a bromomethyl group and a chlorobenzoate moiety, making it an attractive starting material for various synthetic pathways.

The molecular formula of Methyl 2-(bromomethyl)-4-chlorobenzoate is C10H9BrClO2, and its molecular weight is approximately 263.53 g/mol. The compound is a white to off-white solid at room temperature and has a melting point of around 75-78°C. Its solubility in common organic solvents such as dichloromethane, acetone, and ethanol makes it easy to handle and process in laboratory settings.

In the realm of chemical synthesis, Methyl 2-(bromomethyl)-4-chlorobenzoate serves as an important intermediate for the preparation of more complex molecules. The bromomethyl group can undergo various reactions, including nucleophilic substitution (SN2) and elimination (E2) reactions, which are crucial for the synthesis of functionalized aromatic compounds. Additionally, the chlorobenzoate moiety can be selectively modified through various chemical transformations, such as reduction to form an alcohol or substitution to introduce different functional groups.

Recent research has highlighted the potential of Methyl 2-(bromomethyl)-4-chlorobenzoate in the development of novel pharmaceuticals. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent anti-inflammatory properties. The bromomethyl group was found to enhance the bioavailability and metabolic stability of the resulting molecules, making them promising candidates for further clinical evaluation.

In another study, researchers at the University of California explored the use of Methyl 2-(bromomethyl)-4-chlorobenzoate in the synthesis of targeted drug delivery systems. By conjugating this compound with specific targeting ligands, they were able to achieve enhanced cellular uptake and selective delivery to cancer cells. This approach has significant implications for improving the efficacy and reducing the side effects of chemotherapy treatments.

The versatility of Methyl 2-(bromomethyl)-4-chlorobenzoate extends beyond pharmaceutical applications. In materials science, this compound has been used as a building block for the synthesis of advanced polymers and coatings. For example, a recent publication in Macromolecules reported the development of a new class of polymeric materials derived from this compound. These materials exhibit excellent thermal stability and mechanical properties, making them suitable for use in high-performance applications such as aerospace and electronics.

Safety considerations are an essential aspect when working with any chemical compound. While Methyl 2-(bromomethyl)-4-chlorobenzoate is generally considered safe when handled under appropriate conditions, it is important to follow standard laboratory safety protocols. This includes wearing personal protective equipment (PPE) such as gloves and goggles, working in well-ventilated areas, and properly disposing of waste materials.

In conclusion, Methyl 2-(bromomethyl)-4-chlorobenzoate (CAS No. 145908-29-8) is a valuable compound with diverse applications in chemical synthesis, pharmaceutical research, and materials science. Its unique structural features and reactivity make it an attractive starting material for various synthetic pathways. Ongoing research continues to uncover new potential uses for this compound, further solidifying its importance in the scientific community.

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