21478-66-0 | Trimethylchloromethylammonium,chloride

CAS:21478-66-0 | Trimethylchloromethylammonium,chloride,Description

The chloromethyl group is a functional group in organic chemistry that has the chemical formula -CH2-Cl. This group is derived from the methyl group (which has the formula -CH3) by replacing one hydrogen atom with a chlorine atom. Compounds with this group are a subclass of the organochlorines.

Synthesis Analysis

The synthesis of compounds with a chloromethyl group, such as “(Chloromethyl)-trimethylammonium chloride”, often involves the chloromethylation of aromatic compounds. This process is typically catalyzed by Lewis acids such as zinc chloride. The reaction is carried out under acidic conditions, which protonate the formaldehyde carbonyl, making the carbon much more electrophilic. The aldehyde is then attacked by the aromatic pi-electrons, followed by rearomatization of the aromatic ring.

Molecular Structure Analysis

The molecular structure of compounds with a chloromethyl group, such as “(Chloromethyl)-trimethylammonium chloride”, can be represented by the formula CH3Cl. This indicates that the compound contains one carbon atom, three hydrogen atoms, and one chlorine atom.

Chemical Reactions Analysis

In chemical reactions, compounds with a chloromethyl group, such as “(Chloromethyl)-trimethylammonium chloride”, often act as alkylating agents. They are used in organic synthesis for introducing the methoxymethyl ether (MOM) protecting group.

Physical And Chemical Properties Analysis

Chloromethyl compounds, such as “(Chloromethyl)-trimethylammonium chloride”, are typically colorless and sweet-smelling. They are part of the haloalkanes group, which are known for being flammable gases.

Scientific Research Applications

Plant Growth Regulation

(Chloromethyl)-trimethylammonium chloride has been studied extensively for its influence on plant growth. Research conducted by N. Tolbert in 1960 found that this compound, particularly its derivative (2-chloroethyl) trimethylammonium chloride, significantly impacts wheat growth. It was observed to cause a reduction in plant height while increasing stem diameter, suggesting its potential as a plant growth regulator. This effect was found to be antagonistic to the action of gibberellin, a hormone that promotes growth, indicating a complex interaction between these substances in plant development (Tolbert, 1960).

Effects on Plant Inflorescence

In another study by A. Nourai and G. Harris in 1983, the application of (2-chloroethyl)trimethylammonium chloride as a growth retardant in tomatoes showed effectiveness in reducing the abortion of flower buds under unfavorable growing conditions. This suggests its utility in enhancing reproductive success in certain plant species (Nourai & Harris, 1983).

Interaction with Gibberellic Acid in Strawberries

G. Guttridge in 1966 discovered that the application of this compound in strawberries shortened petioles and decreased growth, but when applied with gibberellic acid, it led to an increase in stem elongation. This synergistic effect indicates a complex relationship between (chloromethyl)-trimethylammonium chloride and other plant hormones, impacting strawberry cultivation (Guttridge, 1966) .

Influence on Gibberellin Levels in Potatoes

In the context of potato cultivation, research by G. A. D. Bottini et al. in 1981 showed that (chloromethyl)-trimethylammonium chloride affected gibberellin levels, a class of growth hormones, in potato plants. This altered the process of tuberization, demonstrating the compound's potential role in managing potato growth and development (Bottini, Goleniowski, & Tizio, 1981).

Role in Flower Bud Development in Tomatoes

A. Nourai and G. Harris's research in 1983 also indicated that (2-chloroethyl)trimethylammonium chloride helped in reducing the abortion of flower buds in tomatoes, which is significant for agricultural practices, especially in challenging environmental conditions (Nourai & Harris, 1983).

Impact on Cytokinin Levels in Grapes

K. Skene in 1968 found that grapevines treated with (2-chloroethyl)trimethylammonium chloride exhibited higher levels of cytokinins, another class of plant growth hormones, in their sap. This discovery offers insight into the compound's potential role in influencing grapevine physiology and growth (Skene, 1968).

Safety And Hazards

Chloromethyl compounds, such as “(Chloromethyl)-trimethylammonium chloride”, can be hazardous. They are typically classified as flammable liquids and can be harmful if swallowed. They can cause serious eye irritation and may be fatal if inhaled. Some chloromethyl compounds may also cause cancer.

Future Directions

The future directions for research on chloromethyl compounds, such as “(Chloromethyl)-trimethylammonium chloride”, could involve finding more environmentally friendly methods for their synthesis. For example, using less toxic reactants in the chloromethylation process instead of hypertoxic chloromethyl ether (BCME) could make the process more sustainable.

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