γ-二硝基酚 | 329-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: γ-二硝基酚
• 中文别名: 2,5-二硝基苯酚；γ-二硝基苯酚；2,5-二硝基酚；-二硝基苯酚
• 英文名称: 2,5-dinitrophenol
• 英文别名: 2,5-DNP；2,4-dinitrophenol
• CAS: 329-71-5
• 化学式: C₆H₄N₂O₅
• mdl: MFCD00007108
• 分子量: 184.108
• InChiKey: UWEZBKLLMKVIPI-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C
• 沸点：
  309.6±27.0 °C(Predicted)
• 密度：
  1.650±0.06 g/cm3(Predicted)
• 物理描述：
  2,5-dinitrophenol is a yellow crystalline solid with a sweet musty odor. Sinks and mixes slowly with water. (USCG, 1999)
• 颜色/状态：
  Yellow monoclinic prisms or needles from water, ligand
• 溶解度：
  In water, 385 mg/L at 25 °C
• 蒸汽压力：
  1.22X10-4 mm Hg at 20 °C
• 稳定性/保质期：
  Appear to be stable in acid solution, but are susceptible to decomposition by uv radiation in alkaline solutions. /Dinitrophenols/
• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
• 气味阈值：
  Detection: 2.4 mg/L
• 解离常数：
  pKa = 5.21 at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

ADMET

代谢

2,5-二硝基苯酚的代谢物：2-氨基-5-硝基苯酚，5-氨基-2-硝基苯酚，2,5-二氨基苯酚/来自表格/

Metabolites of 2,5-Dinitrophenol: 2-amino-5-nitrophenol, 5-amino-2-nitrophenol, 2,5-diaminophenol /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,5-二硝基苯酚可能在大肠杆菌中形成2-氨基-5-硝基苯酚和5-氨基-2-硝基苯酚。

2,5-dinitrophenol /forms/ 2-amino-5-nitrophenol and 5-amino-2-nitrophenol probably in Pseudomonas.

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,4-二硝基苯酚（2,4-DNP），2,5-二硝基苯酚（2,5-DNP），2,6-二硝基苯酚（2,6-DNP）在刺激通气量和氧耗方面的效果进行了比较。在所有实验中，通过动脉内输注将1 mg/kg的亚硝基苯酚同分异构体给予氯醛麻醉的狗……2,5-DNP在通气和氧耗方面引起了小幅增加。

2,4-Dinitrophenol (2,4-DNP), 2,5-dinitrophenol (2,5-DNP), 2,6-dinitrophenol (2,6-DNP) were compared with respect to stimulation of ventilation and oxygen consumption. In all experiments, 3-4 mg/kg of 1 dinitrophenol isomer was administered to chloralose anesthetized dogs by intraarterial infusion. ... 2,5-DNP elicited small increments in both ventilation and oxygen consumption.

来源:Hazardous Substances Data Bank (HSDB)

代谢

一项研究对猴子组织中谷胱甘肽-S-转移酶对各种硝基化合物的活性分布以及纯化的猴子肝脏谷胱甘肽-S-转移酶对包括致癌物质在内的各种硝基化合物的作用进行了研究。当使用4-硝基喹啉-N-氧化物（56575）、5-硝基呋喃二缩醛和邻二硝基苯（99650）等化合物作为底物时，肝脏、肾脏和小肠显示出特别高的活性。还使用了包括19种硝基呋喃衍生物在内的52种硝基化合物来测试从猕猴中纯化出的主要酶的亚硝酸盐释放活性。纯化的酶只对邻二硝基苯、4-硝基喹啉-N-氧化物、3,4-二硝基苯甲酸（528450）、对二硝基苯（100254）、2,5-二硝基苯甲酸（610286）、2,5-二硝基酚（329715）、四氯硝基苯和2,4-二硝基苯甲酸（610300）这33种非硝基呋喃衍生物的测试底物显示出活性。

A study was made of the distribution of glutathione-S-transferase activity toward various nitro compounds in monkey tissues and the action of a purified monkey liver glutathione-S-transferase toward various nitro compounds including carcinogenic substances. The liver, kidney and small intestine demonstrated particularly high levels of activity when compounds such as 4-nitroquinoline-N-oxide (56575), 5-nitrofurfural-diacetal and o-dinitrobenzene (99650) were used as substrates. Fifty-two nitro compounds, including 19 nitrofuran derivatives, were also used to test the nitrite releasing activity of the major enzyme purified from rhesus-monkey. The purified enzyme showed activity only toward o-dinitrobenzene, 4-nitroquinoline-N-oxide, 3,4-dinitrobenzoic-acid (528450), p-dinitrobenzene (100254), 2,5-dinitrobenzoic-acid (610286), 2,5-dinitrophenol (329715), tetra-chloronitrobenzene, and 2,4-dinitrobenzoic-acid (610300) of the 33 nitro compounds other than nitrofuran derivatives which were tested as substrates.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。 肾毒素 - 该化学品在职业环境中可能对肾脏有毒。 高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为第二性毒性效应。 其他毒物 - 解偶联剂 皮肤毒素 - 皮肤烧伤。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting. Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect Other Poison - Uncoupler Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

6种二硝基酚在大鼠肝脏线粒体中解偶联磷酸化的相对效力依次递减为：3,5-二硝基酚、2,4-二硝基酚、2,6-二硝基酚、3,4-二硝基酚、2,3-二硝基酚和2,5-二硝基酚。这些酚类化合物的相对效力可能主要取决于它们穿越边界膜的能力以及与通常与能量守恒相关的蛋白质上的阳性位点结合的能力，而不仅仅是它们的相对酸度或脂溶性。

The relative potencies of the 6 dinitrophenols in uncoupling phosphorylation in rat liver mitochondria were in declining order 3,5-dinitrophenol, 2,4-dinitrophenol 2,6-dinitrophenol and 3,4-dinitrophenol and 2,3-dinitrophenol and 2,5-dinitrophenol. The relative potency of these phenolic compounds may be determined primarily by their ability to cross a boundary membrane and to bind to a cationic site on a protein normally associated with energy-conservation, rather than merely by their relative acidity or lipid solubility.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

立即急救：确保已经进行了充分去污。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按训练进行操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。/二硝基酚及其相关化合物/

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Dinitrophenol and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非重复呼吸面罩以10至15升/分钟的速度给予氧气。监测休克并如有必要进行治疗……监测肺水肿并如有必要进行治疗……预期癫痫发作并如有必要进行治疗……对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……在去污染后，用干燥的无菌敷料覆盖皮肤烧伤……在体温过高的情况下，可能需要快速身体降温。水杨酸类药物是禁忌的。/二硝基苯酚及其相关化合物/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination. flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . Rapid body cooling may be necessary in case of hyperthermia. Salicylates are contraindicated. /Dinitrophenol and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于失去意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑对肺水肿进行药物治疗...。监测心率和必要时治疗心律失常...。开始静脉输注0.9%的生理盐水（NS）或乳酸林格氏液（LR）/SRP：“保持开放”，最低流速/。对于脱水和低血压伴有低血容量的症状，谨慎给予液体。如果病人在正常液体容量下出现低血压，考虑使用血管加压药。注意液体过载的迹象...。用安定或劳拉西泮治疗癫痫发作...。如果病人在严重低氧血症、发绀和心脏功能不全且对氧气治疗无反应的情况下出现症状，给予1%亚甲蓝溶液...。使用丙美卡因氢氯化物协助眼部冲洗...。/二硝基酚及其相关化合物/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of 0.9% saline (NS) or lactated Ringer's (LR) /SRP: "To keep open", minimal flow rate/. For dehydration and hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dinitrophenol and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

调查人员研究了二硝基酚同分异构体（包括2,5-二硝基酚）的药代动力学，并显示从小鼠、兔子、豚鼠、大鼠和猴子的血液中消除完全在30小时内完成。

/The investigators/ ... studied the pharmacokinetics of ... dinitrophenol isomers /incl 2,5-dinitrophenol/ and showed that elimination from the blood of mice, rabbits, guinea pigs, rats, and monkeys was complete within 30 hr.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

二硝基化合物的吸收可以通过肺部、肠道或者完好无损的皮肤轻易发生。当这些物质以油性而非水溶性溶液形式应用时，通过皮肤的吸收速率可能会更高。/二硝基化合物/

Absorption of dinitro compounds can take place with ease through the lungs, the gut, or the intact skin. The rate of absorption through skin is likely to be greater when the substances are applied in oily rather than aq soln. /Dinitro cmpd/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 二硝基化合物是持久的黄色染料，能够使暴露的皮肤、头发、羊毛、毛皮和羽毛呈现出明显的黄色或橙色，并且这种染色在几周甚至几个月后仍然明显，尽管有水和天气的作用。这种染色为至少与化学物质的表面接触提供了证据。 /二硝基化合物/

... Dinitro compounds are persistent yellow dye-stuffs, staining exposed skin, hair, wool, fur, and feathers a distinct yellow or orange color which remains obvious for weeks or even months afterwards, despite the action of water and weather. Such staining provides evidence of at least external contact with the chemicals. /Dinitro cmpd/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  T,N
• 安全说明：
  S28,S37,S45,S61
• 危险类别码：
  R23/24/25,R51/53,R33
• WGK Germany：
  3
• RTECS号：
  SL2900000
• 海关编码：
  2908999090
• 包装等级：
  I
• 危险类别：
  4.1
• 危险品运输编号：
  UN 1320 4.1/PG 1

SDS

第一部分：化学品名称

制备方法与用途

制备方法

由间硝基苯酚经硝化而得。将40%的硝酸加热至40℃，慢慢加入间硝基苯酚，在40-60℃下约用3小时加完。然后在50-70℃加热1小时，冷却后倾去稀酸溶液，将固体物粉碎，用冰水洗去酸性，滤干。将所得产物溶于冷乙醇中，其中不溶物为2,5-二硝基酚。

合成制备方法

同样由间硝基苯酚经硝化而得。将40%的硝酸加热至40℃，慢慢加入间硝基苯酚，在40-60℃下约用3小时加完。然后在50-70℃加热1小时，冷却后倾去稀酸溶液，将固体物粉碎，用冰水洗去酸性，滤干。将所得产物溶于冷乙醇中，其中不溶物为2,5-二硝基酚。

用途简介

用于有机合成。在化学分析中用作指示剂，将其70%乙醇溶液配成0.05-0.1%的溶液或用其饱和水溶液作为指示剂，pH变色范围为4.0（无色）-5.8（黄色）。

用途

用于有机合成。在化学分析中用作指示剂，将其70%乙醇溶液配成0.05-0.1%的溶液或用其饱和水溶液作为指示剂，pH变色范围为4.0（无色）-5.8（黄色）。

反应信息

• 作为反应物：
  描述：

  γ-二硝基酚 在 硝酸 作用下， 生成 2，4，6-三硝基间苯二酚，收敛酸
  参考文献：
  名称：

  Bantlin, Chemische Berichte, 1878, vol. 11, p. 2101

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-乙氧基苯基)-4-甲基苯磺酰胺 在 硫酸 、 硝酸 作用下， 生成 γ-二硝基酚
  参考文献：
  名称：

  Reverdin; Roethlisberger, Helvetica Chimica Acta, 1922, vol. 5, p. 313

  摘要：

  DOI：

文献信息

• Switchable Bifunctional Bistate Reusable ZnO–Cu for Selective Oxidation and Reduction Reaction
  作者：Kasturi Sarmah、Subhamoy Mukhopadhyay、Tarun K. Maji、Sanjay Pratihar

  DOI：10.1021/acscatal.8b03785

  日期：2019.1.4

  copper loaded zinc oxide (ZnO–Cu) for its stimuli (O2/light) responsive switchable performance between its reduced (S-1) and oxidized (S-2) state for two antagonistic reactions, namely oxidation of alkyl arenes/heteroarenes to aldehydes/ketones and reduction of nitro arenes/heteroarenes to corresponding amines. The two states of the catalyst showed its switchable performance as highly active and poorly

  在这里，我们公开了利用铜负载的氧化锌（ZnO-Cu）在两个还原反应（即氧化）的还原（S-1）和氧化（S-2）状态之间的刺激（O 2 /光）响应可转换性能。将烷基芳烃/杂芳烃还原为醛/酮，并将硝基芳烃/杂芳烃还原为相应的胺。催化剂的两种状态均显示出其可切换的性能，即用于氧化和还原的高活性和低活性催化剂，并且通过改变刺激（光和O 2 / N 2），两个反应都可以“关闭”和“打开”。）。发现状态之间的转换效率及其相对反应性在各种反应条件下均保持一致，并且无论氧化还原顺序（反之亦然）和反应中使用的底物如何，都保持不变。光催化剂（S-1和S-2）表现出良好的催化活性，多种可重复使用性，广泛的底物范围以及对两种反应均具有合理的官能团耐受性，并在大规模应用中探索了其质量性能。该系统被用于辅助串联催化装置中，用于通过催化状态之间的刺激响应切换而利用氧化和还原反应两者来合成苄胺。
• A Convenient Method to Aniline Compounds Using Microwave-Assisted Transfer Hydrogenation
  作者：Michael Wall、Nicholas Chapman、Benjamin Conway、Fiona O’Grady

  DOI：10.1055/s-2006-939062

  日期：——

  The reduction of mononitro and dinitro aromatic compounds to their aniline analogues using microwave-assisted transfer hydrogenation has been demonstrated. The optimised conditions used, with some examples, are described herein.

  使用微波辅助转移氢化将单硝基和二硝基芳香化合物还原为其苯胺类似物的研究已被证实。在此，描述了经过优化的条件，并附有一些实例。
• Base catalysis in nucleophilic aromatic substitution reactions: evidence for cyclic transition state mechanism over the dimer mechanism in a non-polar aprotic solvent
  作者：Olayinka Banjoko、Chike Ezeani

  DOI：10.1039/p29860000531

  日期：——

  The reactions of X-phenyl 2,4,6-trinitrophenyl ethers [X = 2-NO2, 3-NO2, 4-NO2, 2,4-(NO2)2, 3,4-(NO2)2, 2,5-(NO2)2, and 2,6-(NO2)2] with aniline in benzene display three distinct mechanisms even though all except the 2,6-dinitrophenyl ether are base catalysed. The catalysis of the mononitro-substituted ethers involves two aniline molecules and proceeds at a temperature-independent rate in the temperature

  X -苯基-2,4,6-三硝基苯醚[的反应X = 2-NO 2，3-NO 2，4-NO 2，2,4-（NO 2）2，3,4-（NO 2）2，2,5-（NO 2）2，和2,6-（NO 2）2]与苯胺在苯中的反应显示出三种不同的机理，尽管除2,6-二硝基苯基醚以外的所有碱均被催化。一硝基取代醚的催化反应涉及两个苯胺分子，并且在5–35°C的温度范围内以与温度无关的速率进行，而二硝基取代醚的催化仅涉及一个苯胺分子，并且以与温度无关的速率进行在相同温度范围内。根据涉及过渡状态的四元，六元和八元环的循环机制来解释结果。
• The Alkaline Hydrolysis of Aryl (2<i>E</i>)-3-(4‘-Hydroxyphenylazo)propenoates. A Kinetic Study
  作者：Giorgio Cevasco、Daniele Vigo、Sergio Thea

  DOI：10.1021/jo015795m

  日期：2001.11.1

  alkaline hydrolysis of the title esters, possessing three conjugated pi units between the internal nucleophile (the hydroxyl group) and the reaction center, follows an E1cB mechanism involving the participation of an "extra extended" p-oxo azoketene type intermediate. For the hydrolysis of the 2,4-dinitrophenyl ester kinetic data, activation parameters and trapping of the intermediate are consistent with

  在内部亲核试剂（羟基）和反应中心之间具有三个共轭pi单元的标题酯的碱解遵循E1cB机理，其中涉及“额外扩展的”对-氧代偶氮烯酮型中间体的参与。对于2,4-二硝基苯酯的水解动力学数据，活化参数和中间体的捕集与携带反应通量的解离路径一致。离开基团变化对反应性的影响与所提出的机理一致，并且二极管阵列停流实验也支持了中间体的存在。共轭骨架中sp（2）氮原子的存在有利于解离机理。
• Occurrence of an Elongated <i>p</i>-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl (2<i>E</i>,4<i>E</i>)-5-(4‘-Hydroxyphenyl)pentadienoates
  作者：Giorgio Cevasco、Daniele Vigo、Sergio Thea

  DOI：10.1021/jo0008439

  日期：2000.11.1

  The alkaline hydrolysis of title esters possessing acidic leaving groups follows an E1cB mechanism involving the participation of an "extra extended" p-oxo ketene intermediate. For the hydrolysis of the 2,4-dinitrophenyl ester kinetic data, activation parameters and trapping of the intermediate clearly indicate that the dissociative pathway carries the reaction flux. Break in the Bronsted plot of the

  具有酸性离去基团的标题酯的碱性水解遵循E1cB机理，该机理涉及“超扩展”对-氧代乙烯酮中间体的参与。对于2,4-二硝基苯基酯动力学数据的水解，活化参数和中间体的捕集清楚地表明，解离途径携带了反应通量。表观二阶速率常数与离去基团的pK（a）的布朗斯德图的破坏表明，对于pK（a）大于约6的酯，反应机理从E1cB变为B（Ac）2。

表征谱图