Chemical Structure and Synthesis of Glycine methyl ester hydrochloride

Glycine methyl ester hydrochloride is an amino acid derivative that appears as a white solid powder under normal temperature and pressure. It is soluble in water, highly hygroscopic, but poorly soluble in ether-based organic solvents. Primarily used as a household insecticide, a raw material for pyrethroids, and an industrial raw material in pharmaceutical manufacturing, Glycine methyl ester hydrochloride has also been reported in studies for the synthesis of chrysanthemic acid and dichlorochrysanthemic acid. Additionally, it serves as an intermediate in the production of the fungicide iprodione.

Chemical Structure

Glycine methyl ester hydrochloride, crystallizes as a salt, C3H8NO2+·Cl−, with the charged species inter­acting mutually via strong and highly directional N+—H⋯Cl− hydrogen bonds which lead to the formation of a supra­molecular tape running parallel to the c axis. Tapes close pack in the solid state mediated by multipoint recognition synthons based on weak C—H⋯O inter­actions and van der Waals contacts between adjacent methyl groups. On Glycine methyl ester hydrochloride, X-ray crystallographic (Lattice parameter), FT-IR, FT-Raman, DFT, HOMO-LUMO, MEP, ADMET, and molecular docking investigations are studied. The small Glycine methyl ester hydrochloride docking analysis with the target protein revealed that this is a good molecule that docks well with a target connected to the Human estrogen receptor macromolecule. The improvement of electrostatic interactions between the protein and the ligand is made possible by molecular electrostatic potential (MEP). DFT-B3LYP calculations using the 6–31++G (d,p) basis set are used to determine the optimized geometry of the Glycine methyl ester hydrochloride molecule, and the computed vibrational frequencies are assessed by comparing them to experimental results. Using a 2D fingerprint plot and Hirshfeld Surfaces, the molecular surface and hydrogen bonding interactions in the GMEHCl crystal structure were discovered and investigated. The parameters of absorption, distribution, metabolism, and excretion (ADME) were measured using the internet server preADMET. [1-2]

Single-Crystal Structure

Solvent evaporation was employed to grow an optical bulk single crystal of Glycine methyl ester hydrochloride, which was first reported in the literature. It crystallizes with the space group P21/c in a monoclinic system and was confirmed by single crystal X-ray diffraction. FT-IR analysis verified the various functional groups. Optical characteristics were evalu ated using UV-Vis-NIR analysis, it was observed with an optical bandgap of 5.10 eV, and the cut-off wavelength was 230 nm. Photoluminescence analysis of the material reveals great structural perfection, supporting the suitability of the produced crystal for the emission of blue fluorescence. Thermal assessment disclosed that the compound was steady until 176 °C. Third-order nonlinear optical properties of glycine methyl ester hydrochloride were determined using the Z-scan approach. Third-order nonlinear properties β, n2, and χ3 of Glycine methyl ester hydrochloride were determined to be 1.37 × 10−4 cm/W, 3.37 × 10−9 cm2/W, and 3.56 × 10−6 esu, respectively. This result indicates that the crystal may have uses in various NLO and photonic device configurations. [3]

Synthesis

Figure1: Synthesis of Glycine methyl ester hydrochloride

Glycine (5.00 g) was first dissolved in 100 mL of methanol, and the resulting solution was maintained at 0°C using an ice bath. Subsequently, thionyl chloride (SOCl₂, 8.40 g) was added dropwise to the chilled mixture, which was then allowed to react at 25°C for 12 hours. Finally, the product was recovered by rotary evaporation and subsequently dried to obtain the final material Glycine methyl ester hydrochloride. [4]

Application

Glycine methyl ester hydrochloride is commonly used as a raw material for household insecticides, pyrethroids, and the pharmaceutical industry, for instance, as an intermediate in the preparation of chrysanthemic acid and dichlorochrysanthemic acid, as well as the fungicide iprodione. Furthermore, Glycine methyl ester hydrochloride serves as a synthetic intermediate for various drugs containing glycine fragments, and acts as a precursor for antibiotics and protease inhibitors. Additionally, it can be employed in the synthesis of peptide analogs, heterocyclic compounds, and specialized surfactants.

Reference

[1] Vilela S M F, Almeida Paz F A, Tomé J P C, et al. Glycine methyl ester hydrochloride[J]. Structure Reports, 2009, 65: 1970-1970.

[2] Mahalakshmi N, Meeraa S R, Vinitha G, et al. Synthesis, Growth, Photoluminescence, Thermal, and Third-Order Nonlinear Optical Properties of Glycine Methyl Ester Hydrochloride Single Crystal for Opto-Electronic Applications[J]. Brazilian Journal of Physics, 2024, 54(2): 49.

[3] Mahalakshmi N, Parthasarathy M. Growth, structural, spectroscopic, DFT calculations, insilico biological analysis of glycine methyl ester hydrochloride (GMEHCl) against human estrogen receptor[J]. Chemical Physics Impact, 2023, 7: 100303.

[4] Yu, Dinghua; et al, Glass fiber treated with a glycine bridged silane coupling agent reinforcing polyamide 6(PA6): effect of hydrogen bonding, RSC Advances 2025, 15, 3331-3338.

You may like