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.
Bronopol undergoes degradation in aqueous medium to form bromonitroethanol from a retroaldol reaction with the liberation of an equimolar amount of formaldehyde. Formaldehyde is a degradation product of bronopol, which may cause sensitization. Bromonitroethanol further decomposes to formaldehyde and bromonitromethane. Bromonitroethanol may also break down to release a nitrite ion and 2-bromoethanol.
Approx. 40% of the topically applied dose of antibacterial agent [(14)C] bronopol([(14)C]BP) was absorbed through the rat skin within 24 hr. Of the applied radioactivity, about 19% was excreted in the urine, feces and expired air. The 24 hr recoveries of (14)C in the urine and expired air were 15 and 2%, respectively, of the dose applied to the skin, and 74 and 9%, respectively, of the dose given intravenously. The TLC of the urines showed three metabolites, but no unchanged [(14)C]BP in both groups. The results suggest that rat skin is quite permeable to bronopol.
Transformation products usually differ in environmental behaviors and toxicological properties from the parent contaminants, and probably cause potential risks to the environment. Toxicity evolution of a labile preservative, bronopol, upon primary aquatic degradation processes was investigated. Bronopol rapidly hydrolyzed in natural waters, and primarily produced more stable 2-bromo-2-nitroethanol (BNE) and bromonitromethane (BNM). Light enhanced degradation of the targeted compounds with water site specific photoactivity. The bond order analysis theoretically revealed that the reversible retroaldol reactions were primary degradation routes for bronopol and BNE. Judging from toxicity assays and the relative pesticide toxicity index, these degradation products (i.e., BNE and BNM), more persistent and higher toxic than the parent, probably accumulated in natural waters and resulted in higher or prolonging adverse impacts. Therefore, these transformation products should be included into the assessment of ecological risks of non-persistent and low toxic chemicals such as the preservative bronopol.
来源:Hazardous Substances Data Bank (HSDB)
代谢
动物体内的主要代谢物已被鉴定为2-硝基丙烷-1,3-二醇。
The major metabolite /in animals/ has been identified as 2-nitropropane-1,3-diol.
The only metabolite identified in urine was BTS 23 913 (2-nitropropane-1,3- diol or desbromo-bronopol), accounting for 45-50% of the radioactivity taken for analyses. The remaining radioactivity was not identified (one radioactive peak and radioactivity not resolved into peaks). Unchanged bronopol was not detected.
While 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. These decomposition products can react with any secondary amines or amides (which may contaminate cosmetic products) to produce significant levels of nitrosamines, which are believed to be carcinogenic. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. Formaldehyde itself is also carcinogenic. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (L962, L643, L1889, A2878, A2879, A2880, A2881, L1893)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
致癌性证据
癌症分类：E组 人类非致癌性证据
Cancer Classification: Group E Evidence of Non-carcinogenicity for Humans
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
无致癌性迹象（未被国际癌症研究机构列名）。
No indication of carcinogenicity (not listed by IARC). (L135)
Bronopol may react to produce nitrosamines, which are believed to be carcinogenic. It also releases formaldehyde, a known human carcinogen. (L962, A2881)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
暴露途径
该物质可以通过吸入其气溶胶、通过皮肤接触以及吞食被身体吸收。
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
Bronopol was rapidly absorbed in animal studies. It may be absorbed via aerosol inhalation, dermal contact, and ingestion. In rats, approximately 40% of the topically applied dose of bronopol was absorbed through the skin within 24 hr. Following oral administration of 1 mg/kg in rats, the peak plasma concentrations of bronopol were reached up to 2 hours post-dosing.
Metabolism studies indicate that bronopol is primarily excreted in the urine. In rats, about 19% of dermally-applied bronopol was excreted in the urine, feces and expired air. Following oral administration of 1 mg/kg radiolabelled bronopol in rats, approximately 81% and 6% of the administered radioactivity was recovered in the urine and expired air, respectively, within a period of 24 hours. Following intravenous administration in rat, the recoveries in the urine and expired air were 74% and 9% of the dose, respectively.
来源:DrugBank
吸收、分配和排泄
分布容积
在大鼠的排泄器官如肾脏、肝脏和肺中检测到 bronopol 的最高浓度。脂肪中的浓度最低。
The highest concentrations of bronopol were detected in the excretory organs of rat such as kidney, liver, and lung. The lowest concentration was in the fat.
来源:DrugBank
吸收、分配和排泄
清除
无数据可用。
No data available.
来源:DrugBank
吸收、分配和排泄
The rat metabolism data for bronopol consist of four separate studies conducted with male and female Sprague-Dawley rats. Animals were treated by gavage with (14)C bronopol (radiochemical purity: >95-100%). In the first study animals received a single dose of 10 mg/kg. The second study employed a higher dose of 50 mg/kg. Doses higher the 50 mg/kg caused respiratory problems and death. The third study's dose was 10 mg/kg (14 daily doses of nonradioactive, 100% pure, bronopol, followed by one dose of (14)C-bronopol). Urine, feces and CO2 were collected for 7 days after dosing, at which time the rats were killed and the tissues examined for radioactivity. Because, irrespective of the dose, most of the administered (14)C was excreted in urine (64-78% in 24 hours and 68-83% in 7 days), urine was used for the identification of metabolites in the fourth study. Feces, CO2 and tissues represented minor routes of excretion of (14)C. Very little (14)C was also detected in the whole blood and plasma. From the results of these four studies... /it was/ concluded that bronopol administered orally was rapidly absorbed and rapidly excreted by the rats of both sexes, with urine being the major route of excretion.
对溴硝醇的大鼠代谢数据包括四项独立研究，使用雌雄 Sprague-Dawley 大鼠进行。实验动物通过灌胃给予 (14)C 溴硝醇（放射性纯度：>95-100%）。在第一项研究中，动物接受了一次性剂量为 10 mg/kg。第二项研究使用了更高的剂量，为 50 mg/kg。剂量超过 50 mg/kg 会导致呼吸问题和死亡。第三项研究的剂量为 10 mg/kg（连续 14 天给予非放射性、100% 纯度的溴硝醇，然后给予一次 (14)C-溴硝醇）。在给药后 7 天内收集尿液、粪便和 CO2，此时处死大鼠并检查组织中的放射性。因为无论剂量如何，大部分给予的 (14)C 都通过尿液排出（24 小时内为 64-78%，7 天内为 68-83%），所以在第四项研究中使用尿液来识别代谢物。粪便、CO2 和组织是 (14)C 排泄的次要途径。在全身血液和血浆中也检测到很少的 (14)C。根据这四项研究的结果...得出结论，口服给予的溴硝醇被大鼠迅速吸收并迅速排出，尿液是主要的排泄途径。
The rat metabolism data for bronopol consist of four separate studies conducted with male and female Sprague-Dawley rats. Animals were treated by gavage with (14)C bronopol (radiochemical purity: >95-100%). In the first study animals received a single dose of 10 mg/kg. The second study employed a higher dose of 50 mg/kg. Doses higher the 50 mg/kg caused respiratory problems and death. The third study's dose was 10 mg/kg (14 daily doses of nonradioactive, 100% pure, bronopol, followed by one dose of (14)C-bronopol). Urine, feces and CO2 were collected for 7 days after dosing, at which time the rats were killed and the tissues examined for radioactivity. Because, irrespective of the dose, most of the administered (14)C was excreted in urine (64-78% in 24 hours and 68-83% in 7 days), urine was used for the identification of metabolites in the fourth study. Feces, CO2 and tissues represented minor routes of excretion of (14)C. Very little (14)C was also detected in the whole blood and plasma. From the results of these four studies... /it was/ concluded that bronopol administered orally was rapidly absorbed and rapidly excreted by the rats of both sexes, with urine being the major route of excretion.
The Diels-Alder cycloadditions of the alpha-acetoxynitroso dienophile in water are reported. The rapid and high yielding synthesis of structurally diverse 3,6-dihydro-1,2-oxazines complements the straightforward elaboration of aminoalcohols obtained from the alpha-acetoxynitroso derivative in anhydrous medium. A rationale for this solvent-dependent product distribution is proposed.
Sodiumethanethiolate in methanol is an efficient reducing agent for gem-bromonitro compounds; treatment of the resultant nitronates with a protic acid or with N-chlorosucccinimide gives high yields of the corresponding nitro or gem-chloronitro compounds, respectively.
Novel 1,3,2-dioxaborinanes of the general formula ##STR1## wherein R.sub.1 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a phenyl group or bromine, Y is a 1-oxy-2-thioethyl group, a 1-oxy-4-thiophenyl group or oxygen, each group Z independently of the others is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl, bicycloalkyl or cycloalkylalkyl group, a phenyl group or a phenylalkyl radical, and n is the number 1 or 2. The compounds possess outstanding biocidal properties.
(∇2ρ(rBCP)), energy parameters-kinetic electron energy density (GBCP), potential electron density (VBCP) and the total electron energy density (HBCP) at the bond critical points (BCP) were analyzed by ‘Atoms in molecules’ AIM theory. The Hirshfeld surface analysis helped in identifying important intermolecular interactions in 2e. Global reactivity descriptors and molecular electrostatic potential for compounds
在 2-取代的 1,3-丙二醇存在下，薯蓣皂苷元衍生物中的环 F 的区域选择性打开，产生了在 C-26 处带有 1,3-二恶烷环的新呋喃坦。这些合成的化合物1e、2a、2b、2c、2d和2e 的结构是在光谱数据的基础上建立的，包括 1D 和 2D NMR 以及 ESI-HRMS。2e (22R,25R)-26-(5-bromo-5-nitro-1,3-dioxanyl)furost-5-en-3-yl acetate 的单晶 X 射线衍射分析不仅有助于结构鉴定，还有助于确定其立体化学。这些化合物的分子几何形状是通过密度泛函理论 (DFT/B3LYP) 使用 6–31 G (d, p) 基组在基态下计算的。使用时间相关密度泛函理论（TD-DFT）计算电子特性，例如 HOMO 和 LUMO 能量。拓扑参数-电子密度（ρBCP），电子密度的拉普拉斯算子（∇2 ρ ( r BCP ))、能量参数-动能电子能量密度
Synthesis, characterization and antimicrobial activity of (5- bromo-5-nitro-2-oxido-1,3,2-dioxaphosphinan-2-yl)amino acid esters
Synthesis of a new series of (5-bromo-5-nitro-2-oxido-1,3,2-
dioxaphosphinan-2-yl)amino acid esters (3a-l) was accomplished via a two step
process, which involves the prior preparation of the monochloride
intermediate (2) and its subsequent reaction with the amino acid esters in
dry tetrahydrofuran in the presence of triethylamine at reflux temperature.
The title compounds (3a-l) structures were established by analytical, IR,
1H-, 13C- and 31P-NMR, and mass spectral data. They exhibited significant
antibacterial and antifungal activity.
