Bronopol

Base Information

• Chemical Name: Bronopol
• CAS No.: 52-51-7
• Deprecated CAS: 133248-96-1,179733-60-9,1135443-73-0,179733-60-9
• Molecular Formula: C3 H6BrNO4
• Molecular Weight: 199.989
• Hs Code.: HYSICAL AND CHEMICAL PROPERTIES PHYSICAL
• European Community (EC) Number: 200-143-0
• ICSC Number: 0415
• NSC Number: 141021
• UN Number: 3241
• UNII: 6PU1E16C9W
• DSSTox Substance ID: DTXSID8024652
• Nikkaji Number: J1.911I
• Wikipedia: Bronopol
• Wikidata: Q2462902
• NCI Thesaurus Code: C77031
• RXCUI: 1114345
• Metabolomics Workbench ID: 67431
• ChEMBL ID: CHEMBL1408862
• Mol file: 52-51-7.mol

Synonyms:2-bromo-2-nitro-1,3-propanediol;bronopol;bronosol

Chemical Property of Bronopol

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 1.45E-06mmHg at 25°C
• Melting Point: 130- 133°C
• Refractive Index: 1.574
• Boiling Point: 358 °C at 760 mmHg
• PKA: 12.02±0.10(Predicted)
• Flash Point: 170.3 °C
• PSA: 86.28000
• Density: 2.018 g/cm³
• LogP: -0.13790
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: H2O: soluble100mg/mL, clear, colorless to faintly yellow
• Water Solubility.: 25 g/100 mL (22 ºC)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 198.94802
• Heavy Atom Count: 9
• Complexity: 107
• Transport DOT Label: Flammable Solid

Purity/Quality:

98% ^*data from raw suppliers

Bronopol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn,N
• Statements: 21/22-37/38-41-50
• Safety Statements: 26-37/39-61-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C(C(CO)([N+](=O)[O-])Br)O
• Recent EU Clinical Trials: Clinical Evaluation of TRUE TEST? Panel 3.2 Allergens: Bronopol and Disperse Blue 106 Dose Response Study
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is corrosive to the eyes. The substance is irritating to the skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: Bronopol, a formaldehyde releaser, was reported as an allergen in dairy workers. In a recent case report, bronopol was contained in a lubricant jelly used for ultrasound examination and caused contact dermatitis in a veterinary surgeon.
• Uses: 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. First synthesized in 1897, 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. It 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.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.https://www.ulprospector.comhttps://www3.epa.gov
• Therapeutic Function: Antiseptic
• Biological Functions: Bronopol, 2-bromo-2-nitropropan-1,3-diol, is an aliphatic halogenonitro compound with potent antibacterial activity but limited activity against fungi(Guthrie, 1999).Its activity is reduced somewhat by 10% serum and to a greater extent by sulphydryl compounds, but is unaffected by 1% polysorbate or 0.1% lecithin. It has a half-life of about 96 daysat pH 8 and 25oC (Toler, 1985). Bronopol is most stable under acid conditons;the initial decomposition appears to involve the liberation of formaldehyde and the formulation of bromonitroethanol. A secondorder reaction involving bronopol and formaldehyde occurs simultaneously to produce 2-hydro-xymethyl-2-nitro-1,3-propanediol, which itself decomposes with the loss of formaldehyde. Bronopol has been employed extensively as a preservative for pharmaceuticalandcosmetic products.However, its use to preserve products containing secondary amines should be avoided as the by-product of this reaction is nitrosoamine which is carcinogenic. Details of the microbiological activity,chemical stability,toxicology and uses of bronopol are documented by Bryce et al. (1978),Croshaw & Holland (1984)，Toler (1985) and Rossmorc and Sondossi (1988). Dcnyer and Wallhausser (1990) have provided useful information about bronopol, the typical in-use concentration of which is 0.01-0.1% w/v. Sulphhydryl compounds act as appropriate neutralizers inpreservative efficacy tests.

Technology Process of Bronopol

There total 13 articles about Bronopol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

→ 2-bromo-2-nitro-1,3-propanediol (52-51-7)

Guidance literature:

Reference yield: 88.6%

Sodium; 3-hydroxy-2-[(Z)-hydroxyimino]-propionate → 2-bromo-2-nitro-1,3-propanediol (52-51-7)

Guidance literature:

With bromine; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1007/BF01431611

Reference yield: 85.0%

C3H5Cl2NO2 → 2-bromo-2-nitro-1,3-propanediol (52-51-7)

Guidance literature:

With water; phosphorus pentabromide; In ethanol; at 60 ℃; for 48h; under 0 Torr;

upstream raw materials:

formaldehyd

bromonitromethane

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

nitromethane

Downstream raw materials:

bis-(N-p-tolyl-benzimidoyl)-disulfane

bis-(N-[1]naphthyl-benzimidoyl)-disulfane

2-bromo-2-nitro-1-ethanol

bromopicrin

Refernces

• 1、 Fedorov,Golovina,Arakcheeva,Trofimova,Atovmyan. "New reaction of the sodium salt of 2-nitroethanol. X-ray analysis of the sodium salt of 2-oxo-3-hydroxypropionic acid oxime, 2-bromo-2-nitropropane-1,3-diol, and the model 2,2-dinitropropane-1,3-diol". . p. 1157 - 1161. Retrieved 1996.
• 2、 -. "A PROCESS FOR THE PREPARATION OF BRONOPOL". Page/Page column 22-24. . Retrieved 2009/10/21.