The reaction of geminal bromonitroalkanes with nucleophiles. Part 1. The decomposition of 2-bromo-2-nitropropane-1,3-diol (‘Bronopol’) in aqueous base

doi:10.1039/P29910000283

Paper

The reaction of geminal bromonitroalkanes with nucleophiles. Part 1. The decomposition of 2-bromo-2-nitropropane-1,3-diol (‘Bronopol’) in aqueous base

Published 1991 · B. C. Challis, T. Yousaf

Journal of The Chemical Society-perkin Transactions 1

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11

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Abstract

2-Bromo-2-nitropropane-1,3-diol decomposes in aqueous base to give tris(hydroxymethyl)-nitromethane, glycolic acid, formic acid, methanol and 2,2-dinitroethanol. It also releases NO2– and Br– ions but not BrO–. These products are shown to form via four concurrent decomposition pathways, three of which involve 2-bromo-2-nitroethanol as a reactive intermediate.

Study Snapshot

Bronopol decomposes in aqueous base to produce tris(hydroxymethyl)-nitromethane, glycolic acid, formic acid, methanol, and 2,2-dinitroethanol, with four concurrent pathways and three reactive intermediates.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

The reaction of geminal bromonitroalkanes with nucleophiles. Part 1. The decomposition of 2-bromo-2-nitropropane-1,3-diol (‘Bronopol’) in aqueous base

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References

Some aspects of the mode of action of the antibacterial compound bronopol (2-bromo-2-nitropropan-1,3-diol).

Bronopol effectively inhibits bacteria by oxidizing thiol groups to disulphides, causing membrane damage and affecting enzyme activity.

Organic Electronic Spectral Data

Organic Electronic Spectral Data is a comprehensive collection of ultraviolet-visible spectra of organic compounds from journal literature, providing a comprehensive overview of their properties.

An h-1, c-13 and n-15 nmr study of the paal-knorr condensation of acetonylacetone with primary amines

Acetonylacetone-primary amine reaction leads to N-substituted -2, 5-dimethylpyrroles through the intermediacy of N-substituted imines, with increased steric hindrance reducing imine formation and decay rates.

2-Bromo-2-nitropropane-1,3-diol as a nitrosating agent for diethanolamine: a model study.

BNPD is a nitrosating agent that is most effective in alkaline media, releasing nitrite ion for nitrosation of diethanolamine and triethanolamine.

Citations

A rapid method for detecting bronopol in fresh fish, shrimp, crab, and shellfish samples using liquid chromatography-tandem mass spectrometry.

This study presents a rapid, efficient, and reliable method for detecting bronopol in aquaculture tissues, improving product quality and public health protection.

Activated Sludge Respiration Activity Inhibition Caused by Mobile Toilet Chemicals

Mobile toilet chemicals, particularly formaldehyde and bronopol, negatively impact the aerobic wastewater treatment process, with Ralstonia sp. being a potential degrader.

Pharmacologic alternatives to riboflavin photochemical corneal cross-linking: a comparison study of cell toxicity thresholds.

Topical cross-linking compounds have significant differences in cell toxicity, highlighting the need to balance tissue cross-linking and cell toxicity in developing therapeutic tissue cross-linking strategies.

The impact of the various chemical and physical factors on the degradation rate of bronopol

Bronopol decomposes rapidly in cosmetic products when combined with sodium dodecylsulfate, and is accelerated by elevated temperatures and presence of citric acid and sodium dodecylsulfate.

Using the Griess colorimetric nitrite assay for measuring aliphatic β-nitroalcohols.

The Griess colorimetric nitrite assay is a simple and effective method for quantifying aliphatic -nitroalcohols, potentially useful for topical therapeutic corneoscleral cross-linking agents.

Aliphatic β‐Nitroalcohols for Therapeutic Corneoscleral Cross‐Linking: Chemical Stability Studies Using 1H‐NMR Spectroscopy

Higher order nitroalcohols (HONAs) exhibit excellent chemical stability under long-term storage conditions, while nitromonols are less stable.

Toxicity profile of labile preservative bronopol in water: the role of more persistent and toxic transformation products.

Bronopol's aquatic degradation produces more persistent and toxic transformation products, BNE and BNM, which may increase environmental risks.

Toxicology of Biocides

Biocides are widely used in industry, agriculture, and medical fields, but their use requires registration and approval due to potential toxic effects on human health and the environment.