Exploring the Potential of Ethyl 4-Iodobenzoate

Ethyl 4-iodobenzoate is a compound with significant chemical properties. This article aims to explore its unique characteristics and structural features to further understand its importance and potential applications in the field of chemistry. Through in-depth analysis of its properties and structure, we can gain a more comprehensive understanding of the characteristics and chemical behavior of ethyl 4-iodobenzoate.

What is Ethyl 4-Iodobenzoate?

Ethyl 4-iodobenzoate is an ester that can react with various substances, including retinoic acid and pemphigus. It is a reactive substance used in the synthesis of other substances such as iron oxide and transfer mechanisms. Ethyl 4-iodobenzoate is also used in the preparation of pyridine carboxylic acid and crystal structures. It can be cross-linked with ArMg(tmp)·2LiCl (tmp = trimethylpropane) intermediates to synthesize biphenyl derivatives. Additionally, it serves as the starting material for the synthesis of carboxymethoxyphenylmagnesium bromide, a multifunctional organic metal reagent used as a basic component for synthesizing complex target molecules.

Properties and Composition:

Ethyl 4-iodobenzoate is an organic compound with the molecular formula C9H9IO2 and CAS number 51934-41-9. The properties of Ethyl 4-iodobenzoate are as follows:

(1) Physical Properties:

Ethyl 4-iodobenzoate Molecular Weight: 276.07

Ethyl 4-iodobenzoate Molar Mass: 276.07 grams per mole

Ethyl 4-iodobenzoate Appearance: Colorless to pale yellow liquid

Ethyl 4-iodobenzoateMelting Point: 267°C

Ethyl 4-iodobenzoate Boiling Point: 281-283°C

Ethyl 4-iodobenzoate Density: 1.641 g/mL at 25°C (lit.)

Ethyl 4-iodobenzoate Solubility: Soluble in dichloromethane, chloroform, and acetone, and other organic solvents

Ethyl 4-iodobenzoate Stability: Stable under normal storage conditions

(2) Chemical Properties:

Ethyl 4-iodobenzoate is a halogenated aromatic hydrocarbon with typical properties of halogenated aromatic hydrocarbons.

It reacts with bases to form the corresponding carboxylate salts.

It undergoes halogenation reactions with halogens.

It undergoes nitration reactions with nitric acid.

It undergoes reduction reactions with reducing agents.

Ethyl 4-Iodobenzoate NMR:

Nuclear Magnetic Resonance (NMR) is an analytical method based on the resonance phenomenon of specific atomic nuclei absorbing radiofrequency field energy corresponding to the energy difference between their split energy levels in an external magnetic field. NMR spectrometer mainly consists of a magnet, probe, preamplifier, console, and workstation.

Liu Yaqin et al. analyzed the one-dimensional and two-dimensional NMR spectral signals of ethyl 4-iodobenzoate, especially in two-dimensional spectra, confirming the connection between various carbon and hydrogen groups and providing information on coupling of adjacent hydrogen atoms, long-range correlations, and spatial correlations. The experimental procedure is as follows:

Experimental Part:

(1) Instruments and Reagents:

Instruments: 1H NMR, 13C NMR, DEPT135, 1H-1H COSY, 1H-13C HSQC, and HMBC as well as ROESY spectra were determined using an Agilent DD2 600 NMR spectrometer (Agilent Technologies, USA) with deuterated dimethyl sulfoxide as the solvent. The observation frequency was 599.77 MHz for 1H NMR and 150.83 MHz for 13C NMR. The spectral width of 1H-1H COSY experiment was 6,648.9 Hz with a sampling data matrix of t2×t1=1,024×256. The spectral width of 1H-13C HSQC experiment was 30,165.9 Hz for 13C with a sampling data matrix of t2×t1=1,024×256. The spectral width of 1H-13C HMBC experiment was 36,199.1 Hz for 13C and 9,615.4 Hz for 1H, with a sampling data matrix of t2×t1=1,024×256.

Reagents: Deuterated dimethyl sulfoxide with purity greater than 98%. All reagents were analytical grade.

(2) Sample Preparation:

Approximately 30 mg of ethyl 4-iodobenzoate sample was weighed and dissolved in 0.6 mL of deuterated dimethyl sulfoxide, transferred to a nuclear magnetic tube, and then measured.

(3) Experimental Procedure:

The experimental operation process of NMR is shown in the figure.

Results:

(1) Structural Analysis of Ethyl 4-Iodobenzoate:

Ethyl 4-iodobenzoate contains four different types of carbon atoms: primary, secondary, tertiary, and quaternary, making it a compound with a representative structure. As shown in the figure, one-dimensional proton spectrum (1H spectrum), carbon spectrum (13C spectrum and DEPT135 spectrum), two-dimensional correlation spectrum (1H-1H COSY spectrum, 1H-13C HSQC spectrum, and HMBC spectrum) of ethyl 4-iodobenzoate were collected, and the spectra were analyzed in detail.

(2) Summary of Spectral Attribution of Ethyl 4-Iodobenzoate:

Based on the analysis of the nuclear magnetic resonance 1H-1H COSY spectrum, 1H-13C HSQC and HMBC spectra, ROESY spectrum, and 1H and 13C spectra of ethyl 4-iodobenzoate, the key signals of ethyl 4-iodobenzoate HMBC correlation spectrum were identified and marked, as shown in the figure. The results of carbon-hydrogen attribution of ethyl 4-iodobenzoate are listed in the table.

Conclusion:

Ethyl 4-iodobenzoate is a compound with specific properties and structural features. Its molecular structure contains iodine atoms, giving it certain chemical activity and reactivity. Understanding and mastering the properties and structural features of ethyl 4-iodobenzoate are of great significance for synthesizing organic compounds and developing new materials in laboratory research and industrial production. Further research can reveal its potential application value in the fields of chemistry and materials science.

References:

[1] Liu Yaqin, Yu Mingxin, He Ling. Experimental teaching design of structure of ethyl 4-iodobenzoate based on two-dimensional NMR spectrum analysis[J]. Laboratory Research and Exploration, 2023, 42(06):198-201+271. DOI:10.19927/j.cnki.syyt.2023.06.040.

[2] https://www.biosynth.com/p/FE23014/51934-41-9-ethyl-4-iodobenzoate

[3] https://pubchem.ncbi.nlm.nih.gov/compound/142891