2-Bromo-2-nitro-1,3-propanediol
[CAS# 52-51-7]

Identification

• Classification: Chemical pesticide >> Fungicide >> Other fungicides
• Name: 2-Bromo-2-nitro-1,3-propanediol
• Synonyms: Bronopol
• Molecular Formula: C₃H₆BrNO₄
• Molecular Weight: 199.99
• CAS Registry Number: 52-51-7
• EC Number: 200-143-0
• SMILES: C(C(CO)([N+](=O)[O-])Br)O

Properties

• Solubility: 25 g/100 mL (water 22 °C), 30 mg/mL (DMSO) (Expl.)
• Density: 2.0±0.1 g/mL, Calc.^*
• Melting point: 130-133 °C (Expl.)
• Index of Refraction: 1.575, Calc.^*
• Boiling Point: 358.0±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 170.3±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS09 Danger
• Risk Statements: H301-H302+H312-H302-H312-H315-H318-H335-H400-H410-H411
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Flammable solids	Flam. Sol.	2	H228
Self-reactive substances or mixtures	Self-react.	C	H242
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	2	H310

• Transport Information: UN 3241

Discovery and Applications

2-Bromo-2-nitro-1,3-propanediol is an organic compound with both bromine and nitro groups attached to a three-carbon chain. It is widely recognized for its use as a biocide and preservative in various industrial and consumer products. The chemical is typically synthesized through the reaction of 1,3-propanediol with bromine and nitric acid, introducing the bromine and nitro functional groups into the molecule.

The discovery of 2-bromo-2-nitro-1,3-propanediol dates back to the early research into biocides and antimicrobial agents, where the compound was identified as having effective antimicrobial properties. The bromine and nitro groups in the structure contribute to its ability to disrupt microbial cells by interfering with their metabolic processes and by reacting with nucleophilic components, such as proteins and nucleic acids.

One of the primary applications of 2-bromo-2-nitro-1,3-propanediol is in the formulation of preservatives for personal care products, such as shampoos, conditioners, lotions, and creams. Its antimicrobial properties make it highly effective in preventing the growth of bacteria, fungi, and yeast, extending the shelf life and stability of these products. It is also used in cosmetic formulations where preventing microbial contamination is critical, especially in water-based products that are more prone to bacterial growth.

In addition to personal care products, 2-bromo-2-nitro-1,3-propanediol is employed in industrial applications. It is used as a preservative in paints, coatings, and adhesives, where its ability to inhibit microbial growth ensures the longevity and quality of these products. It also finds use in the treatment of wood products, where it helps protect against fungal and bacterial degradation.

Furthermore, 2-bromo-2-nitro-1,3-propanediol has been investigated for its role in water treatment. The compound’s ability to act as a biocide has made it suitable for controlling microbial populations in water systems, such as in cooling towers, swimming pools, and other water reservoirs where microbial growth is a concern.

While effective as a preservative and antimicrobial agent, 2-bromo-2-nitro-1,3-propanediol has raised concerns regarding its safety and environmental impact. As a halogenated compound, it has been subject to scrutiny due to potential toxicity and environmental persistence. Consequently, its use is regulated in various regions, and alternatives are being explored to reduce the reliance on halogenated biocides in consumer and industrial products.

In summary, 2-bromo-2-nitro-1,3-propanediol is a versatile biocide with applications in personal care, industrial products, and water treatment. Its antimicrobial properties have made it a valuable compound in preserving the integrity and longevity of various products, although its safety and environmental concerns continue to influence its use.

References

1964. The antibacterial activity of 2-bromo-2-nitropropane-1,3-diol (Bronopol). Journal of Pharmacy and Pharmacology, 16(11).
DOI: 10.1111/j.2042-7158.1964.tb07552.x

2023. Rapid determination of 2-bromo-2-nitropropane-1,3-diol in aquaculture products by liquid chromatography-tandem mass spectrometry. Analytical Methods, 15(35).
DOI: 10.1039/D3AY00857A

1976. The metabolism of 2-bromo-2-nitropropane-1,3-diol (bronopol) in the rat. Xenobiotica, 6(6).
DOI: 10.3109/00498257609151647