PRODUCTS

2-BROMO-2-NITRO-1,3-PROPANEDIOL (BRONOPOL)

2-Bromo-2-nitro-1,3-propanediol (bronopol) is an organic compound that is used as an antimicrobial.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is a white solid although commercial samples appear yellow.
The first reported synthesis of 2-Bromo-2-nitro-1,3-propanediol (bronopol) was in 1897.

CAS:   52-51-7
MF:   C3H6BrNO4
MW:   199.99
EINECS:   200-143-0

Synonyms
Bronopol 1g [52-51-7];Broken Ball;2-BroMo-2-nitropropane-1;3-diol (Bronopol);Bronopol(2-BroMo-2-nitro-1,3-propanedio1);2-BroMo-2-nitro-1,3-propanediol, 98% 25GR;Bronopol BNPD;Bronopol 0;bronopol;52-51-7;2-Bromo-2-nitro-1,3-propanediol;2-Bromo-2-nitropropane-1,3-diol;Bronosol;Bronocot;Bronidiol;Bronopolu;Bronotak;Lexgard bronopol;Onyxide 500;Bronopolum;1,3-Propanediol, 2-bromo-2-nitro-;2-Nitro-2-bromo-1,3-propanediol;Caswell No. 116A;MFCD00007390;beta-Bromo-beta-nitrotrimethyleneglycol;NSC 141021;Bronopolum [INN-Latin];HSDB 7195;EINECS 200-143-0;UNII-6PU1E16C9W;EPA Pesticide Chemical Code 216400;NSC-141021;BRN 1705868;6PU1E16C9W;DTXSID8024652;CHEBI:31306;AI3-61639;2-Bromo-2-nitropropan-1,3-diol;DTXCID904652;EC 200-143-0;C3H6BrNO4;NCGC00164057-01;Bronopolum (INN-Latin);BRONOPOL (MART.);BRONOPOL [MART.];Bronopolu [Polish];Bioban;Myacide AS;Myacide AS plus;Myacide BT;CAS-52-51-7;Bronopol [INN:BAN:JAN];Myacide Pharma BP;Canguard 409;BNPD;Nalco 92RU093;UN3241;Remain Silver;Remain Gold;Bronopol solution;Gold-Bloc;Soft Tuch;2-Bronopol;Gil Sani-Guard;Bronopol Teat Dip;QM Gold;Ultra-Soft Barrier;2-bromo-2-nitro-propane-1,3-diol;Bronopol (Standard);1,2-Bromo-2-nitropropane-1,3-diol;Medic Booster Barrier;Bronopol (JAN/INN);BRONOPOL [HSDB];BRONOPOL [INN];BRONOPOL [JAN];BRONOPOL [MI];BRONOPOL [VANDF];WLN: WNXE1Q1Q;1, 2-bromo-2-nitro-;2-Bromo-2-nitropropane-1,3-diol (Bronopol);BRONOPOL [WHO-DD];SCHEMBL23260;TDX-84;Bioban BNPD-40 (Salt/Mix);CHEMBL1408862;SCHEMBL16556987;HY-B1217R;LVDKZNITIUWNER-UHFFFAOYSA-;2-Bromo-2-nitropropane-1,3-diol [UN3241] [Flammable Solid];ALBB-031641;HY-B1217;Tox21_112079;Tox21_300126;BDBM50248122;NSC141021;s4553;2-bromanyl-2-nitro-propane-1,3-diol;AKOS003606838;CCG-213823;CS-4699;DB13960;FB01194;AST Inc. PRO-4 BARRIER TEAT DIP;USEPA/OPP Pesticide Code: 216400;NCGC00164057-02;NCGC00164057-03;NCGC00253984-01;AS-11889

2-Bromo-2-nitro-1,3-propanediol (bronopol) was invented by The Boots Company PLC in the early 1960s and first applications were as a preservative for pharmaceuticals.
Due to 2-Bromo-2-nitro-1,3-propanediol (bronopol)'s low mammalian toxicity at in-use levels and high activity against bacteria, especially Gram-negative species, bronopol became popular as a preservative in many consumer products such as shampoos and cosmetics.
2-Bromo-2-nitro-1,3-propanediol (bronopol) was subsequently adopted as an antimicrobial in other industrial environments such as paper mills, oil exploration, and production facilities, as well as cooling water disinfection plants.
2-Bromo-2-nitro-1,3-propanediol (bronopol), a formaldehyde releaser, was reported as an allergen in dairy workers.
In a recent case report, 2-Bromo-2-nitro-1,3-propanediol (bronopol) was contained in a lubricant jelly used for ultrasound examination and caused contact dermatitis in a veterinary surgeon.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is a nitro compound.

2-bromo-2-nitropropane-1,3-diol appears as white crystals.
Ignite easily and burn readily.
May detonate under strong shock.
Decomposes when heated, evolving toxic gases.
Toxic by skin absorption, inhalation or ingestion.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is an antimicrobial preservative that works by forming formaldehyde in cosmetic products.
People exposed to such formaldehyde-releasing ingredients may develop a formaldehyde allergy or an allergy to the ingredient itself.
In the U.S. approximately 20% of cosmetics and personal care products contain a formaldehyde-releaser and the frequency of contact allergy to these ingredients is much higher among Americans compared to studies in Europe.

2-Bromo-2-nitro-1,3-propanediol (bronopol), also known as Bronopol, is a chemical preservative widely used in cosmetics and personal care products.
2-Bromo-2-nitro-1,3-propanediol (bronopol)'s main function is to prevent the growth of bacteria, mold, and fungi, thereby extending the shelf life of various formulations.
2-Bromo-2-nitro-1,3-propanediol (bronopol) appears as a white crystalline powder or solid and is water-soluble, facilitating its incorporation into different cosmetic products like creams, lotions, and shampoos.
2-Bromo-2-nitro-1,3-propanediol (bronopol)'s chemical formula is C3H6BrNO4, and it works effectively over a wide pH range.

2-Bromo-2-nitro-1,3-propanediol (bronopol) is an organic compound which is used as an antimicrobial.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is a white solid although commercial samples appear yellow.
The first cited synthesis of 2-Bromo-2-nitro-1,3-propanediol (bronopol).
1st applications were as a preservative for pharmaceuticals.
Thanks to its low mammalian toxicity (at in-use levels) and high activity against bacteria (especially the troublesome Gram-negative species), 2-Bromo-2-nitro-1,3-propanediol (bronopol) became popular as a preservative in many consumer products such as shampoos and cosmetics.
2-Bromo-2-nitro-1,3-propanediol (bronopol) was subsequently adopted as an antimicrobial in other industrial environments such as paper mills, oil exploration and production facilities, as well as cooling water disinfection plants.

2-Bromo-2-nitro-1,3-propanediol (bronopol) Chemical Properties
Melting point: 130-133 °C(lit.)
Boiling point: 358.0±42.0 °C(Predicted)
Density: 2.0002 (rough estimate)
Refractive index: 1.6200 (estimate)
Fp: 167°C
Storage temp.: Inert atmosphere,Room Temperature
Solubility H2O: soluble100mg/mL, clear, colorless to faintly yellow
pka: 12.02±0.10(Predicted)
Form: Crystals or Crystalline Powder
Color: White to yellow
Odor: odorless
Water Solubility: 25 g/100 mL (22 ºC)
Merck: 14,1447
BRN: 1705868
Stability: Stable. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, strong reducing agents, acid chlorides and anhydrides, moisture.
LogP: 1.150 (est)
CAS DataBase Reference: 52-51-7(CAS DataBase Reference)
NIST Chemistry Reference: 2-Bromo-2-nitro-1,3-propanediol (bronopol)(52-51-7)
EPA Substance Registry System: 2-Bromo-2-nitro-1,3-propanediol (bronopol) (52-51-7)

2-Bromo-2-nitro-1,3-propanediol (bronopol) is a white or almost white crystalline powder; odorless or with a faint characteristic odor.

Appearance
2-Bromo-2-nitro-1,3-propanediol (bronopol) is supplied as crystals or crystalline powder, which may vary from white to pale yellow in colour depending on the grade.
The yellow coloration is due to chelation of iron during the manufacturing process.

Melting point
As a pure material, 2-Bromo-2-nitro-1,3-propanediol (bronopol) has a melting point of about 130 °C.
However, due to its polymorphic characteristics, 2-Bromo-2-nitro-1,3-propanediol (bronopol) undergoes a lattice rearrangement at 100 to 105 °C and this can often be wrongly interpreted as the melting point.
At temperatures above 140 °C, 2-Bromo-2-nitro-1,3-propanediol (bronopol) decomposes exothermically releasing hydrogen bromide and oxides of nitrogen.

Solubility
2-Bromo-2-nitro-1,3-propanediol (bronopol) is readily soluble in water; the dissolution process is endothermic.
Solutions containing up to 28% w/v are possible at ambient temperature.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is poorly soluble in non-polar solvents but shows a high affinity for polar organic solvents.

Uses
First synthesized in 1897, 2-Bromo-2-nitro-1,3-propanediol (bronopol) was primarily used as an effective preservative agent and possesses a wide spectrum of antibacterial activity and inhibits the growth of fungi and yeasts.
2-Bromo-2-nitro-1,3-propanediol (bronopol) can be used in the formulation of a wide variety of cosmetic and personal care products, especially in leave-on and rinse-off shampoos, creams, lotions, rinses and eye makeup to protect the product integrity by preventing or slowing bacterial growth.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is used as a microbiocide/microbiostat in oil field systems, air washer systems, air conditioning/humidifying systems, cooling water systems, papermills, absorbent clays, metal working fluids, printing inks, paints, adhesives and consumer/institutional products.
A formulating technical material is also registered.
2-Bromo-2-nitro-1,3-propanediol (bronopol) has been used as reference standard in ultra performance liquid chromatography (UPLC) coupled to inductively coupled plasma mass spectrometry (UPLC-ICP-MS) method for determination of bromine containing preservatives from cosmetic products.

2-Bromo-2-nitro-1,3-propanediol (bronopol) is used in consumer products as an effective preservative agent, as well as a wide variety of industrial applications (almost any industrial water system is a potential environment for bacterial growth, leading to slime and corrosion problems - in many of these systems bronopol can be a highly effective treatment).
2-Bromo-2-nitro-1,3-propanediol (bronopol) serves as a highly effective chemical preservative with broad applications in various industries.
In cosmetics and personal care products, 2-Bromo-2-nitro-1,3-propanediol (bronopol) prevents the growth of bacteria, mold, and fungi, ensuring product stability and extending shelf life.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is frequently used in formulations like creams, lotions, shampoos, and makeup products.
2-Bromo-2-nitro-1,3-propanediol (bronopol) finds great utility in water-based products due to its water-soluble nature.
However, given 2-Bromo-2-nitro-1,3-propanediol (bronopol)'s potential to cause skin sensitization, its usage in cosmetics is subject to regulatory guidelines and concentration limitations, prioritizing consumer safety and product quality.

The use of 2-Bromo-2-nitro-1,3-propanediol (bronopol) in personal care products (cosmetics, toiletries) has declined since the late 1980s due to the potential formation of nitrosamines.
While 2-Bromo-2-nitro-1,3-propanediol (bronopol) is not in itself a nitrosating agent, under conditions where it decomposes (alkaline solution and/or elevated temperatures) it can liberate nitrite and low levels of formaldehyde and these decomposition products can react with any contaminant secondary amines or amides in a personal care formulation to produce significant levels of nitrosamines (due to the toxicity of these substances, the term 'significant' means levels as low as tens of parts per billion).

Manufacturers of personal care products are therefore instructed by regulatory authorities to avoid the formation of nitrosamines which might mean removing amines or amides from the formulation, removing bronopol from a formulation, or using nitrosamine inhibitors.
2-Bromo-2-nitro-1,3-propanediol (bronopol) has been restricted for use in cosmetics in Canada.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is used in consumer products as an effective preservative agent, as well as a wide variety of industrial applications (almost any industrial water system is a potential environment for bacterial growth, leading to slime and corrosion problems - in many of these systems 2-Bromo-2-nitro-1,3-propanediol (bronopol) can be a highly effective treatment).
The use of 2-Bromo-2-nitro-1,3-propanediol (bronopol) in personal care products (cosmetics, toiletries) has declined since the late 1980s due to the potential formation of nitrosamines.

While 2-Bromo-2-nitro-1,3-propanediol (bronopol) is not in itself a nitrosating agent, under conditions where it decomposes (alkaline solution and/or elevated temperatures) it can liberate nitrite and low levels of formaldehyde and these decomposition products can react with any contaminant secondary amines or amides in a personal care formulation to produce significant levels of nitrosamines (due to the toxicity of these substances, the term 'significant' means levels as low as 10s of parts per billion).
Manufacturers of personal care products are therefore instructed by regulatory authorities to 'avoid the formation of nitrosamines' which might mean removing amines or amides from the formulation, removing Bronopol from a formulation, or using nitrosamine inhibitors.

Pharmaceutical Applications
2-Bromo-2-nitro-1,3-propanediol (bronopol) is used as an antimicrobial preservative either alone or in combination with other preservatives in topical pharmaceutical formulations, cosmetics, and toiletries; the usual concentration is 0.02% w/v.

Production Methods
2-Bromo-2-nitro-1,3-propanediol (bronopol) is synthesized by the reaction of nitromethane with paraformaldehyde in an alkaline environment, followed by bromination.
After crystallization, 2-Bromo-2-nitro-1,3-propanediol (bronopol) powder may be milled to produce a powder of the required fineness.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is produced by the bromination of di(hydroxymethyl)nitromethane, which is derived from nitromethane by a nitroaldol reaction.
World production increased from the tens of tonnes in the late 1970s to current estimates in excess of 5,000 tonnes.
Production today is the business of low cost producers, mainly in China.

Contact allergens
2-Bromo-2-nitro-1,3-propanediol (bronopol) is a preservative sometimes considered as a formaldehyde releaser.
2-Bromo-2-nitro-1,3-propanediol (bronopol) was reported to be an allergen in cosmetics, cleaning agents, dairy workers, and a lubricant jelly used for ultrasound examination.
Fire may produce irritating and/or toxic gases.
Contact may cause burns to skin and eyes.
Contact with molten substance may cause severe burns to skin and eyes.
Runoff from fire control may cause pollution.
In 2005–2006, 2-Bromo-2-nitro-1,3-propanediol (bronopol) was the 15th-most-prevalent allergen in patch tests (3.4%) of people with suspected allergic contact dermatitis.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is used as a substitute for formaldehyde, a disinfectant and preservative, in solvents.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is prevalent in skin and personal care products and topical medications.

Reactivity Profile
Incompatible with strong oxidizing agents, strong bases, strong reducing agents, acid chlorides and acid anhydrides.
2-Bromo-2-nitro-1,3-propanediol (bronopol) is also incompatible with sulfhydryl compounds or with aluminum or iron containers (it is stable in contact with tin or stainless steel).

Manufacturing Process
A mixture of 441 g (3 mols) of calcium chloride dihydrate, 61 g (1 mol) of nitromethane, 163 g (2 mols) of formalin (37% formaldehyde solution) and 470 ml of water was cooled to 0°C and mixed with 5 g of calcium hydroxide while stirring.
The temperature thereby rose to 30°C.
As soon as the temperature had fallen again, a further 32 g of calcium hydroxide (total of 0.5 mol) were added.
The mixture was then cooled to 0°C and with intensive cooling and stirring, 159.8 g (1 mol, 51 ml) of bromine were dropped in at a rate so that the temperature remained at around 0°C.
After the addition was ended, the mixture was stirred for a further 2 hours, when the reaction product separated in crystalline form.
The product was quickly filtered on a suction filter and the crystalline sludge obtained was taken up in 450 ml of ethylene chloride and dissolved at reflux.
Then by addition of magnesium sulfate, undissolved inorganic salts were separated and the solution was slowly cooled whereby 140 g (70% yield) of 2-Bromo-2-nitro-1,3-propanediol (bronopol) precipitated in colorless crystals melting at 123°-124°C.