2-bromo-2-nitro-1,3-propane diol

General Material Information

Preferred name	2-bromo-2-nitro-1,3-propane diol
Trivial Name	Bronopol
Short Description	2-nitro-2-bromo-1,3-propanediol
Formula	C3 H6 Br N O4
CAS Number	52-51-7
Deleted CAS Number	133248-96-1
ECHA Number	200-143-0
FDA UNII	6PU1E16C9W
Nikkaji Number	J1.911I
Beilstein Number	1705868
MDL	MFCD00007390
xLogP3-AA	-0.60 (est)
NMR Predictor	External link
Synonyms	1,3-propanediol, 2-bromo-2-nitro- 2-brom-2-nitro-1,3-propandiol 2-brom-2-nitropropan-1,3-diol 2-bromo-2-nitro-1,3-propanediol 2-bromo-2-nitropropane -1.3-diol 2-bromo-2-nitropropane-1,3-diol 2-nitro-2-bromo-1,3-propanediol bronocot bronopol bronosol onyxide 500 2-Bromo-2-nitropropan-1,3-diol Bronidiol Myacide AS Nalco 92RU093 Canguard 409 BNPK N 25 N 25 (antimicrobial) Myacide BT Bactrinol 100 Bioban Myacide Pharma BP Ultra-Fresh SAB NSC 141021 BNPD Pyceze BE 6 BE 6 (bactericide) Topcide 2520 Bronotak Acticide L 30 Myacide AS Plus Bioban BP Plus Protectol BN 98 Protectol BN 99 Preventol P 100 Bactronol Busan 1144 Bactrinashak Bioban BP 40 Bioban BP 10 Protectol BN Bactinash 200 Acticide L 10

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Literature & References

	2-bromo-2-nitropropane-1,3-diol
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	52-51-7
Pubchem (cid):	2450
Pubchem (sid):	134970525

Publications by PubMed
Molecular identification of a bronopol tolerant strain of Saprolegnia australis causing egg and fry mortality in farmed brown trout, Salmo trutta.
Occupational contact dermatitis in blue-collar workers: results from a multicentre study from the Danish Contact Dermatitis Group (2003-2012).
HaCaT Keratinocytes Response on Antimicrobial Atelocollagen Substrates: Extent of Cytotoxicity, Cell Viability and Proliferation.
Pharmacologic alternatives to riboflavin photochemical corneal cross-linking: a comparison study of cell toxicity thresholds.
Combination treatment against scuticociliatosis by reducing the inhibitor effect of mucus in olive flounder, Paralichthys olivaceus.
Contact sensitivity to preservatives in Singapore: frequency of sensitization to 11 common preservatives 2006-2011.
Trends in patch-test results and allergen changes in the standard series: a Mayo Clinic 5-year retrospective review (January 1, 2006, to December 31, 2010).
Cutaneous delayed-type hypersensitivity in patients with atopic dermatitis: reactivity to topical preservatives.
Detection and enumeration of Staphylococcus aureus from bovine milk samples by real-time polymerase chain reaction.
In vitro and in vivo efficacy of drugs against the protozoan parasite Azumiobodo hoyamushi that causes soft tunic syndrome in the edible ascidian Halocynthia roretzi (Drasche).
North American Contact Dermatitis Group patch test results: 2009 to 2010.
Frequency of positive patch test reactions to preservatives: The Australian experience.
Fungi, bacteria and soil pH: the oxalate-carbonate pathway as a model for metabolic interaction.
The impact of the various chemical and physical factors on the degradation rate of bronopol.
Effects of long duration, low dose bronopol exposure on the control of Ichthyophthirius multifiliis (Ciliophora), parasitising rainbow trout (Oncorhynchus mykiss Walbaum).
The anti-protozoal activity of bronopol on the key life-stages of Ichthyophthirius multifiliis Fouquet, 1876 (Ciliophora).
An assessment of the use of drug and non-drug interventions in the treatment of Ichthyophthirius multifiliis Fouquet, 1876, a protozoan parasite of freshwater fish.
Evidence for chemical and cellular reactivities of the formaldehyde releaser bronopol, independent of formaldehyde release.
Non-fragrance allergens in specific cosmetic products.
Preparation of active antibacterial LDPE surface through multistep physicochemical approach: I. Allylamine grafting, attachment of antibacterial agent and antibacterial activity assessment.
Effects of different storage conditions, the farm and the stage of lactation on renneting parameters of goat milk investigated using the Formagraph method.
Patch testing with formaldehyde and formaldehyde-releasers: multicentre study in Spain (2005-2009).
Risk of sensitization to preservatives estimated on the basis of patch test data and exposure, according to a sample of 3541 leave-on products.
Patch testing is a useful investigation in children with eczema.
Suitability of bronopol preservative treated milk for fatty acid determination.
Contact allergy to preservatives. Analysis of IVDK data 1996-2009.
Effect of preservatives on the accuracy of mid-infrared milk component testing.
Toxicity profile of labile preservative bronopol in water: the role of more persistent and toxic transformation products.
Preservatives in cosmetics: reactivity of allergenic formaldehyde-releasers towards amino acids through breakdown products other than formaldehyde.
Viability of Mycoplasma agalactiae and Mycoplasma mycoides subsp. capri in goat milk samples stored under different conditions.
Formaldehyde-releasers in cosmetics in the USA and in Europe.
Positivity ratio and reaction index: patch-test quality-control metrics applied to the north american contact dermatitis group database.
An in vitro bacterial adhesion assessment of surface-modified medical-grade PVC.
Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 2. Patch test relationship to formaldehyde contact allergy, experimental provocation tests, amount of formaldehyde released, and assessment of risk to consumers allergic to formaldehyde.
Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics.
Toxicity of fungicides to natural bacterial communities in wetland water and sediment measured using leucine incorporation and potential denitrification.
Short communication: effect of storage and preservation on total bacterial counts determined by automated flow cytometry in bulk tank goat milk.
Patch-test results of the North American Contact Dermatitis Group 2005-2006.
Reproducibility and repeatability of measures of milk coagulation properties and predictive ability of mid-infrared reflectance spectroscopy.
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
Contrasting short-term antibiotic effects on respiration and bacterial growth compromises the validity of the selective respiratory inhibition technique to distinguish fungi and bacteria.
Contact hypersensitivity to selected excipients of dermatological topical preparations and cosmetics in patients with chronic eczema.
A method for estimation of urea using ammonia electrode and its applicability to milk samples.
Examining the fungal and bacterial niche overlap using selective inhibitors in soil.
Antifungal activities of bronopol and 2-methyl-4-isothiazolin-3-one (MT) against saprolegnia.
The use of bronopol to control fungal infection in rainbow trout eggs.
Evaluation of the MilkoScan FT 6000 milk analyzer for determining the freezing point of goat's milk under different analytical conditions.
[Contact allergy to preservatives contained in cosmetics].
Evaluation of the overall accuracy of the DeLaval cell counter for somatic cell counts in ovine milk.
Synergistic inhibition of microbial sulfide production by combinations of the metabolic inhibitor nitrite and biocides.
Surface antibacterial characteristics of plasma-modified polyethylene.
Influence of storage and preservation on fossomatic cell count and composition of goat milk.
Plasma surface modification of poly vinyl chloride for improvement of antibacterial properties.
Preservatives in registered chemical products.
Evaluation of phototoxic properties of antimicrobials used in topical preparations by a photohaemolysis test.
Assessing the residual antibacterial activity of clinical materials disinfected with glutaraldehyde, o-phthalaldehyde, hydrogen peroxide or 2-bromo-2-nitro-1,3-propanediol by means of a bacterial toxicity assay.
[Allergy to cosmetics. II. Preservatives].
Evaluation of rapid somatic cell counters under different analytical conditions in ovine milk.
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
Efficacy of three surface disinfectants for dental radiographic films and gloves.
Reproducibility of patch tests: comparison of identical test allergens from different commercial sources.
Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives.
Biofilms, homoserine lactones and biocide susceptibility.
Development of a new method, based on a bioreactor coupled with an L-lactate biosensor, toward the determination of a nonspecific inhibition of L-lactic acid production during milk fermentation.
Effect of freezing on Fossomatic cell counting in ewe milk.
Fossomatic cell-counting on ewe milk: comparison with direct microscopy and study of variation factors.
[Determination of eleven preservatives including bronopol in cosmetic by reversed-phase ion-pair chromatography].
Efficacy of bronopol against infection of rainbow trout (Oncorhynchus mykiss) with the fungus Saprolegnia species.
Literature review--efficacy of various disinfectants against Legionella in water systems.
Evaluation of the repeatability of a crude adult indirect Ostertagia ostertagi ELISA and methods of expressing test results.
Evaluation of flow injection analysis for determination of urea in sheep's and cow's milk.
Direct toxicity assessment of wastewater: Baroxymeter, a portable rapid toxicity device and the industry perspective.
Determination of bronopol and its degradation products by HPLC.
Allergic contact dermatitis from 2-bromo-2-nitropropane-1,3-diol in Metrogel.
Reduction of mastitis caused by experimental challenge with Staphylococcus aureus and Streptococcus agalactiae by use of a quaternary ammonium and halogen-mixture teat dip.
[Cytotoxic and genotoxic activity of certain preservative agents in cosmetics].
Determination of bronopol in cosmetic products by HPLC with electrochemical detection.
Analytical control of preservative labelling on skin creams.
Refinement of the pressure assay for milk urea nitrogen.
Occupational allergic contact dermatitis from both 2-bromo-2-nitropropane-1,3-diol and methylchloroisothiazolinone plus methylisothiazolinone in spin finish.
Synthesis and characterization of 5-substituted 1,3-diazacyclohexane derivatives
Analytic validation of an infrared milk urea assay and effects of sample acquisition factors on milk urea results.
Development and testing of a microbiological assay to detect residual effects of disinfectant on hard surfaces.
A Saprolegnia parasitica challenge system for rainbow trout: assessment of Pyceze as an anti-fungal agent for both fish and ova.
Patch testing with preservatives, antimicrobials and industrial biocides. Results from a multicentre study.
A method for quantification of formaldehyde in the presence of formaldehyde donors in skin-care products.
Efficacy of three prevention strategies against legionella in cooling water systems.
A study on the stability of bronopol in bronopol lotion by ion-paired reversed-phase high performance liquid chromatography.
Reactions to formaldehyde and formaldehyde releasers in a standard series.
Rapid ultraviolet spectrophotometric determination of bronopol: application to raw material analysis and kinetic studies of bronopol degradation.
Determination of 2-ethylhexyl 4-(N-methyl-N-nitrosamino) benzoate in commercial sunscreens and cosmetic products.
Patch testing with preservatives at St John's from 1982 to 1993.
Mordant factors that affect the fluorescence and counting of somatic cells by instruments.
Frequency of sensitization to 13 common preservatives in Switzerland. Swiss Contact Dermatitis Research Group.
Effect of hydroxypropyl-beta-cyclodextrin on the antimicrobial action of preservatives.
The diurnal variation of urea in cow's milk and how milk fat content, storage and preservation affects analysis by a flow injection technique.
Diazolidinyl urea: incidence of sensitivity, patterns of cross-reactivity and clinical relevance.
[Antimicrobial conservation of some cosmetics].
A laboratory apparatus for the generation and biocide efficacy testing of Legionella biofilms.
A survey of formaldehyde in shampoos and skin creams on the Danish market.
[The effect of aging of milk samples on the accuracy of infrared analysis of milk composition].
[Comparison of the effectiveness of Milkofix, a preservative preparation, with traditional preservative agents in the determination of somatic cell count in milk samples using a fluoro-optic-electronic method].
[Testing Milkofix, a new preservative preparation for milk samples used for infrared analysis of milk components. II. Verification of its preservative effects in relation to infrared analysis].
[Tests of Milkofix, a new preservative preparation for milk samples used for infrared analysis of milk components. I. Verification of its bacteriostatic and bacteriocidal effects and its interference effects].
Decreased biocide susceptibility of adherent Legionella pneumophila.
Evaluation of an indirect ELISA for the detection of antibodies to bovine leukaemia virus in milk and serum.
[Contact allergies to recently introduced preservatives].
N-nitrosoalkanolamines in cosmetics.
Effects of biocidal treatments to inhibit the growth of legionellae and other microorganisms in cooling towers.
Mortality in calves associated with the feeding of milk containing bronopol.
An unusual case of allergic contact dermatitis in a veterinary surgeon.
Contact allergy to Bronopol.
[Isolation of Legionella spp. from cooling tower water and the effect of microbicides].
Antibacterial action of 2-bromo-2-nitropropane-1,3-diol (bronopol).
Chemical stability and microbiological reply of preservative systems in cosmetics: a direct correlation.
Milk tester's dermatitis.
Dehydroacetic acid sodium salt stability in cosmetic preservative mixtures.
[Current contact allergens].
[Contact allergy to the preservative bronopol].
[Quantitative determination of the protein content of milk by ultraviolet spectrophotometry. 3. Determination of proteins in preserved milk samples].
[Distribution and metabolism of 2-bromo-2-nitropropane-1,3-diol (bronopol)].
Biocidal control of legionellae.
2,3,5-Triphenyltetrazolium chloride as a novel tool in germicide dynamics.
Reactions to Quaternium 15, Bronopol and Germall 115 in a standard series.
Milk recorder dermatitis.
Contact dermatitis due to Bronopol.
Mode of action of the antimicrobial compound 5-bromo-5-nitro-1,3-dioxane (bronidox).
Preservative stability and preservative systems.
Dynamics of disinfection of selected preservatives against Escherichia coli.
Study of the fate of Bronopol and the effects of antioxidants on N-nitrosamine formation in shampoos and skin creams.
Bronopol allergic contact dermatitis.
Allergic contact dermatitis to 2-bromo-2-nitropropane-1,3-diol in a hydrophilic ointment.
Allergic contact dermatitis in two machinists.
[Allergy to preservatives].
The effect of pH, temperature and certain media constituents on the stability and activity of the preservative, bronopol.
Potassium fluxes on hyperosmotic shock and the effect of phenol and bronopol (2-bromo-2-nitropropan-1,3-diol) on deplasmolysis of Pseudomonas aeruginosa.
Cosmetic ingredients and their safety assessment. Reports issued by the Cosmetic Ingredient Review.
Cosmetic dermatitis. Part II. Reactions to some commonly used preservatives.
The biotransformation and disposition of bronopol following topical and intravenous administration to rats.
2-Nitro-2-bromopropan-1,3-diol (bronopol) and UV-rays.
[Study of the disinfectant action of a mixture of chlorhexidine and bronopol].
2-Bromo-2-nitropropane-1,3-diol as a nitrosating agent for diethanolamine: a model study.
A method for studying the activity of preservatives and its application to bronopol.
Hygiene in the prevention of udder infections. VI. Comparative efficacy of a teat dip under experimental and natural exposure to mastitis pathogens.
Hygiene in the prevention of udder infections. IV. Evaluation of teat dips with excised cows' teats.
Dermal sensitization potential of 2-bromo-2-nitropropane-1,3-diol (Bronopol).
The percutaneous absorption and disposition of the antibacterial agent bronopol in rats and rabbits.
The metabolism of the antibacterial agent bronopol (2-bromo-2-nitropropane-1,3-diol) given orally to rats and dogs.
The pain aggression induced by bronopol in the rat.
Some aspects of the mode of action of the antibacterial compound bronopol (2-bromo-2-nitropropan-1,3-diol).
SOME PROPERTIES OF BRONOPOL, A NEW ANTIMICROBIAL AGENT ACTIVE AGAINST PSEUDOMONAS AERUGINOSA.

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
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(IUPAC):	Periodic Table of the Elements
FDA Indirect Additives used in Food Contact Substances:	View
CHEBI:	View
CHEMBL:	View
KEGG (GenomeNet):	C13034
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2905.59.9000
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: •trade name: onyxide 500 •formulation types registered: pelletedtableted, crystalline, soluble concentrateliquid, soluble concentratesolid. •tradename: bronotak •powder for dry application.

Suppliers

BOC Sciences	Connect Chemicals
Covalent Chemical	ECSA Chemicals
Glentham Life Sciences	Kingyoung Bio Technical
Nanjing Jiancheng Chemical	Penta International
Shiva Chemicals and Pharmaceuticals	Sigma-Aldrich: Aldrich
TCI AMERICA	Universal Preserv-A-Chem Inc.
Glentham Life Sciences Ltd	Penta International Corporation

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	199.98861694336
Boiling Point	358 to 359°C @ 760 mm Hg
Flash Point TCC Value	170.3 °C TCC
logP (o/w)	1.15 est
Solubility
water, 2.50E+05 mg/L @ 22 °C (exp)	Yes

Potential Uses

Applications	indirect food additives: adhesives and components of coatings
Other purposes	Preservatives
Cosmetic purposes	Preservatives

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 180 mg/kg "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 5, Pg. 30, 1976. intravenous-rat LD50 37.40 mg/kg Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977. intraperitoneal-rat LD50 26 mg/kg Journal of the Society of Cosmetic Chemists. Vol. 29, Pg. 3, 1978. oral-mouse LD50 270 mg/kg Pesticide Manual. Vol. 9, Pg. 103, 1991. intravenous-mouse LD50 48 mg/kg Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977. intraperitoneal-mouse LD50 15.50 mg/kg Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 11(1), Pg. 73, 1977. oral-dog LD50 250 mg/kg "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 5, Pg. 30, 1976. intraperitoneal-mouse LD50 15500 ug/kg Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 11(1), Pg. 73, 1977. intravenous-rat LD50 37400 ug/kg Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
Dermal Toxicity:
subcutaneous-rat LD50 170 mg/kg SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 1029, 1974. skin-rat LD50 1600 mg/kg "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A542, Pg. 1984. subcutaneous-mouse LD50 116 mg/kg Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977. skin-mouse LD50 4750 mg/kg Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
Inhalation Toxicity:
inhalation-rat LC50 > 5000 mg/m3 Pesticide Manual. Vol. 9, Pg. 103, 1991. inhalation-rat LC50 > 5000 mg/m3/6H Pesticide Manual. Vol. 9, Pg. 103, 1991.

Safety in use information

Category:
indirect food additives: adhesives and components of coatings
Recommendation for 2-bromo-2-nitro-1,3-propane diol usage levels up to:
	not for fragrance use.

Recommendation for 2-bromo-2-nitro-1,3-propane diol flavor usage levels up to:
	not for flavor use.