4-氯-2-硝基苯胺 | 89-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-2-硝基苯胺
• 中文别名: 红色基3GL；1-氨基-4-氯-2-硝基苯；邻硝基对氯苯胺；P-氯-0-硝基苯胺；2-硝基-4-氯苯胺；2-氨基-5-氯硝基苯；对氯邻硝基苯胺；红贝司3GL
• 英文名称: 4-Chloro-2-nitroaniline
• 英文别名: 4-chloro-2-nitro-benzenamine；2-nitro-4-chloroaniline
• CAS: 89-63-4
• 化学式: C₆H₅ClN₂O₂
• mdl: MFCD00007836
• 分子量: 172.571
• InChiKey: PBGKNXWGYQPUJK-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  本品具有高毒性，其毒性接近对硝基苯胺。有关其毒性和防护方法的更多信息，请参考对硝基苯胺的相关内容。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

14C标记的4-氯-2-硝基苯胺（CNA）在雄性F344大鼠体内的处置和代谢进行了研究，研究包括口服或静脉（iv）给药。发现CNA的胃肠道吸收几乎是完全的，并且在研究的剂量范围内（0.788-78.8微摩尔/千克）不受剂量的影响。无论是口服还是静脉给药后，CNA迅速分布到全身组织，并未表现出对任何特定组织的明显亲和力。[14C]CNA通过代谢和尿液排泄迅速清除，在粪便中也有少量的排泄。在大鼠体内，CNA的全身半衰期大约为1小时，3天内体内的放射性活性几乎完全清除。已知的致癌物和CNA的潜在代谢物，4-氯邻苯二胺，在给予CNA后的大鼠组织或排泄物中未被检测到。大约70%的剂量以CNA单一代谢物的硫酸盐结合物形式出现在尿液中。剩余的剂量以七种额外代谢物和少量母体化合物的形式被排泄。CNA衍生的放射性活性几乎不具有生物积累的潜力，并且没有证据表明在研究的剂量范围内CNA的吸收、分布、代谢或排泄机制会饱和。

The disposition and metabolism of 14C-labeled 4-chloro-2-nitroaniline (CNA) was studied in male F344 rats following oral or intravenous (iv) administration. The gastrointestinal absorption of CNA was found to be near complete and was not affected by the dose in the range studied (0.788-78.8 mumol/kg). Following either oral or iv administration, CNA was rapidly distributed throughout the tissues and showed no marked affinity for any particular tissue. [14C]CNA was rapidly cleared by metabolism and excretion in urine and to a lesser extent in feces. The whole-body half-life of CNA in the rat was approximately 1 hr, and clearance of radioactivity from the body was near complete in 3 d. The known carcinogen and potential metabolite of CNA, 4-chloro-o-phenylenediamine, was not detected in rat tissues or excreta following administration of CNA. Approximately 70% of the dose was detected in urine as a sulfate conjugate of a single metabolite of CNA. The remainder of the dose was excreted in the form of seven additional metabolites and a trace of the parent compound. CNA-derived radioactivity had little potential for bioaccumulation, and there was no evidence for saturation of any mechanism involved in the absorption, distribution, metabolism, or excretion of CNA in the dose range studied.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

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

毒理性

• 医疗监测

对暴露人员的嘴唇、舌头和指甲床进行常规检查，以观察是否有发绀的迹象。/保护/那些患有贫血、心血管或肺部疾病的人员免受暴露。

Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

慢性毒性：长期暴露可能导致恶心和呕吐，高剂量暴露会导致昏迷。局部影响：过度暴露的症状可能包括头痛、眩晕、疲劳、恶心和呕吐。特定效应：可能包括中到重度的红斑（发红）和中度水肿（皮肤隆起），恶心，呕吐，头痛。

/SIGNS AND SYMPTOMS/ Chronic toxicity: Chronic exposure may cause nausea and vomiting, higher exposure causes unconsciousness. Local effects: Symptoms of overexposure may be headache, dizziness, tiredness, nausea and vomiting. Specific effects: May include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, headache.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

有害物质信息/ 通过吸入、皮肤接触和吞咽有害。 ... 对眼睛有严重损害的风险

/OTHER TOXICITY INFORMATION/ Harmful by inhalation, in contact with skin and if swallowed. ... Risk of serious damage to eyes

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

遗传毒性/研究了4-氯-2-硝基苯胺（4C2NA）和2-氯-4-硝基苯胺（2C4NA）对离体大鼠肝细胞的毒性，这些细胞暴露于这些异生物质1-3小时，浓度为0.2和/或2 mM。两个浓度中较高的一个似乎显著地诱导了细胞活性的统计学显著损失（与对照组相比，p小于0.01）...此外，两种氯硝基苯胺都产生了肝细胞和微粒体损伤，表现为LDH和G-6-Pase活性的显著变化（p小于0.01）。暴露于2 mM的4C2NA和/或2C4NA 3小时后，显著耗尽了细胞内GSH池（分别为13 mM/10(6)和10 mM/10(6)细胞；p小于0.01）。...

/GENOTOXICITY/ The toxicity of 4-chloro-2-nitroaniline (4C2NA) and 2-chloro-4-nitroaniline (2C4NA) was investigated on isolated rat hepatocytes following 1-3 hours of exposure to 0.2 and/or 2 mM of these xenobiotics. The higher of the two concentrations appeared to induce a statistically significant loss of cellular viability (p less than 0.01 compared to control) ... Furthermore, both chloronitroanilines produced an hepatocellular and microsomal damage demonstrated by conspicuous changes in LDH and G-6-Pase activities (p less than 0.01). The exposure to 2 mM of both 4C2NA and/or 2C4NA produced a marked depletion of the intracellular pool of GSH after 3 hours (13 mM/10(6) and 10 mM/10(6) cells, respectively; p less than 0.01). ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

14C标记的4-氯-2-硝基苯胺（CNA）在雄性F344大鼠体内的分布和代谢进行了研究，这些大鼠通过口服或静脉注射（iv）给药。发现CNA的胃肠道吸收几乎是完全的，并且在此研究范围内剂量（0.788-78.8微摩尔/千克）对吸收没有影响。无论是口服还是静脉注射给药后，CNA迅速分布到各个组织中，并没有显示出对任何特定组织的明显亲和力。[14C]CNA通过代谢和尿液排泄迅速清除，在粪便中也有少量的排泄...

The disposition and metabolism of 14C-labeled 4-chloro-2-nitroaniline (CNA) was studied in male F344 rats following oral or intravenous (iv) administration. The gastrointestinal absorption of CNA was found to be near complete and was not affected by the dose in the range studied (0.788-78.8 mumol/kg). Following either oral or iv administration, CNA was rapidly distributed throughout the tissues and showed no marked affinity for any particular tissue. [14C]CNA was rapidly cleared by metabolism and excretion in urine and to a lesser extent in feces...

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  本品应密封保存在阴凉干燥处，并避免阳光直射。 采用胶合板桶或纸板桶内衬塑料袋包装，每桶重35公斤或50公斤。请将其存放在阴凉通风的地方，并注意防止曝晒和雨淋。搬运过程中，请按有毒化学品的规定进行存储和运输。

制备方法与用途

制备方法

以2,5-二氯硝基苯与液氨为原料，先进行加压氨解和结晶，然后过滤、干燥而得。具体原料消耗定额如下：2,5-二氯硝基苯（工业品）1167kg/t、液氨（工业品）230kg/t、氨水（工业品）2420kg/t。

合成制备方法

同样以2,5-二氯硝基苯与液氨为原料，先进行加压氨解和结晶，然后过滤、干燥而得。具体原料消耗定额如下：2,5-二氯硝基苯（工业品）1167kg/t、液氨（工业品）230kg/t、氨水（工业品）2420kg/t。

用途简介

冰染染料色基主要用于制备大红色淀、嫩黄10G色淀等有机颜料和染料。它可作为棉、粘胶织物的印染显色剂，同时也适用于丝绸和涤纶织物的印染。

用途

冰染染料色基用于制备大红色淀、嫩黄10G色淀等有机颜料和染料。主要用于棉、粘胶织物的印染显色，也可应用于丝绸和涤纶织物的印染。

反应信息

• 作为反应物：
  描述：

  4-氯-2-硝基苯胺 在 苯胺 作用下， 生成 N-phenyl-glycine-(4-chloro-2-nitro-anilide)
  参考文献：
  名称：

  吐根糖浆中吐根生物碱头孢烯和依米丁在大鼠体内的生物转化。

  摘要：

  在大鼠中研究了吐根糖浆的主要活性成分头孢喹啉和依米丁的代谢。Cephaeline-6'-O-glucuronide 被发现是 cephaeline 的胆汁代谢物。观察到 Cephaeline (6'-O-demethylemetine) 和 9-O-demethylemetine 是 emetine 的酶水解胆汁代谢物。Cephaeline 与葡糖苷酸结合，而 emetine 去甲基化为 cephaeline 和 9-0-demethylemetine，之后可能与葡糖苷酸结合。在给予含有氚 (3H) 的吐根糖浆后 48 小时内，从大鼠身上收集尿液、粪便和胆汁——标记的头孢烯或依米丁。通过薄层色谱法 (TLC) 或高效液相色谱法 (HPLC) 分离和量化代谢物。3H-头孢烯的胆汁和尿排泄率为 57。分别为剂量的 5% 和 16.5%。Cephaeline-6'-O-glucuronide 占胆道放射性的

  DOI：

  10.1007/bf03190402
• 作为产物：
  描述：

  2,5-二氯硝基苯 在 NH₂ 作用下， 生成 4-氯-2-硝基苯胺
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3
• 作为试剂：
  描述：

  2,4-bis(methylsulfonyl)pyridine 、 4-氯-2-硝基苯胺 、 potassium carbonate 在 4-氯-2-硝基苯胺 、 Brine 、 Sodium sulfate-III 、 silica gel 、 甲醇 、 二氯甲烷 作用下， 以 N,N-二甲基甲酰胺 、 乙酸乙酯 为溶剂， 反应 0.5h， 以to afford 864 mg of N-(4-chloro-2-nitrophenyl)-2-(methylsulfonyl)pyridin-4-amine as an orange solid (yield was 44.0%) and 294 mg of N-(4-chloro-2-nitrophenyl)-4-(methylsulfonyl)pyridin-2-amine (yield was 15.0%)的产率得到N-(4-chloro-2-nitrophenyl)-2-(methylsulfonyl)pyridin-4-amine
  参考文献：
  名称：

  NOVEL AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION

  摘要：

  本发明提供了具有下列一般式的新化合物：其中R1、R2、R3、R4、R5、W和X如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。

  公开号：

  US20160159794A1

文献信息

• Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives
  作者：Satish A. Dake、Dnyaneshwar S. Raut、Kiran R. Kharat、Rooth S. Mhaske、Satish U. Deshmukh、Rajendra P. Pawar

  DOI：10.1016/j.bmcl.2011.02.039

  日期：2011.4

  Ionic liquid ethyl ammonium nitrate is used as an excellent catalyst and solvent for three-component one-pot reaction of an aldehydes, amines and diethylphosphite to form novel α-aminophosphonates at room temperature. Among the various catalysts, the preparation of ethyl ammonium nitrate is an environmental friendly, cost effective and recyclable catalyst. Compounds 4b, 4c, 4d, 4f and 4j were found

  离子液体硝酸乙基铵用作醛，胺和亚磷酸二乙酯的三组分一锅反应在室温下形成新的α-氨基膦酸酯的极佳催化剂和溶剂。在各种催化剂中，硝酸乙基铵的制备是环境友好的，成本有效的和可回收的催化剂。发现化合物4b，4c，4d，4f和4j对病原微生物更有效。而化合物4a，4g，4h和4j抑制活性大肠杆菌NCIM 2645和伤寒沙门氏菌的生长NCIM2501。发现化合物4j对A549和SK-MEL2人黑素瘤细胞系具有良好的抗增殖作用。
• Highly chemoselective reduction of nitroarenes over non-noble metal nickel-molybdenum oxide catalysts
  作者：Haigen Huang、Xueguang Wang、Xu Li、Chenju Chen、Xiujing Zou、Weizhong Ding、Xionggang Lu

  DOI：10.1039/c6gc03141b

  日期：——

  Chemoselective reduction of nitroarenes is an important transformation for the production of arylamines, which are the primary intermediates in the synthesis of pharmaceuticals, agrochemicals and dyes. Heterogeneous non-noble metal nickel-molybdenum...

  硝基芳烃的化学选择性还原是生产芳胺的重要转变，芳胺是合成药物，农药和染料的主要中间体。非均质非贵金属镍钼合金
• Palladium nanoparticles stabilized by aqueous vesicles self-assembled from a PEGylated surfactant ionic liquid for the chemoselective reduction of nitroarenes
  作者：Zhu-bing Xu、Guo-ping Lu、Chun Cai

  DOI：10.1016/j.catcom.2017.04.051

  日期：2017.8

  can be applied for stabilizing palladium nanoparticles, which prove to be an efficient catalytic system for chemoselective hydrogen transfer of nitroarenes using hydrazine hydrate as a hydrogen source. The particle sizes of vesicles are decreased with the increase of ionic liquid's concentrations and relatively small particle sizes are beneficial to the reduction. Moreover, the aqueous catalytic system

  由聚乙二醇化表面活性剂离子液体水溶液自组装的囊泡可用于稳定钯纳米颗粒，这被证明是使用肼水合物作为氢源进行硝基芳烃化学选择性氢转移的有效催化体系。囊泡的粒径随着离子液体浓度的增加而减小，相对小的粒径有利于减小。而且，水性催化体系通过简单的萃取仍停留在反应器中，并且无需进一步处理即可重复使用。
• Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs
  作者：Jia-wei Zhang、Guo-ping Lu、Chun Cai

  DOI：10.1016/j.catcom.2016.05.023

  日期：2016.9

  Highly dispread Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes (CTH) using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with

  合成了高度分散的Ni-Co双金属纳米颗粒（Ni-Co BMNPs），并使用水合肼作为氢供体，将其作为有效的催化剂用于硝基芳烃（CTH）的化学选择性转移加氢。在高TOF的温和条件下，无需任何添加剂，BMNP即可有效催化还原反应。与相应的单组分催化剂相比，可以显着提高活性，筛选出Ni-Co BMNPs的最佳组成，事实证明这对选择性和收率都至关重要。Ni-Co BMNP的出色性能归因于BMNPs表面活性位点的改善分散性（与Ni NPs相比）以及电子从钴到镍的转移。
• Phenoxypiperidines and analogs thereof useful as histamine H3 antagonists
  申请人：Mutahi W. Mwangi

  公开号：US20070167435A1

  公开（公告）日：2007-07-19

  Disclosed are compounds of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein: M is CH or N; U and W are each CH, or one of U and W is CH and the other is N; X is a bond, alkylene, —C(O)—, —C(N—OR 5 )—, —C(N—OR 5 )—CH(R 6 )—, —CH(R 6 )—C(N—OR 5 )—, —O—, —OCH 2 —, —CH 2 O— or —S(O) 0-2 —; Y is —O—, —(CH 2 ) 2 —, —C(═O)—, —C(═NOR 7 )— or —SO 0-2 —; Z is a bond, optionally substituted alkylene or alkylene interrupted by a heteroatom or heterocyclic group; R 1 is optionally substituted alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heterocycloalkyl, or benzimidazolyl or a derivative thereof; R 2 is optionally substituted alkyl, alkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl; and the remaining variables are as defined in the specification; compositions and methods for treating an allergy-induced airway response, congestion, diabetes, obesity, an obesity-related disorder, metabolic syndrome and a cognition deficit disorder using said compounds, alone or in combination with other agents.

  揭示了以下化合物的结构式或其药学上可接受的盐或溶剂，其中：M为CH或N；U和W分别为CH，或者U和W中的一个为CH，另一个为N；X为键，烷基，—C(O)—，—C(N—OR5)—，—C(N—OR5)—CH(R6)—，—CH(R6)—C(N—OR5)—，—O—，—OCH2—，—CH2O—或—S(O)0-2—；Y为—O—，—(CH2)2—，—C(═O)—，—C(═NOR7)—或—SO0-2—；Z为键，可选择地取代的烷基或被杂原子或杂环基中断的烷基；R1为可选择地取代的烷基，环烷基，芳基，芳基烷基，杂芳基，杂环烷基或苯并咪唑基或其衍生物；R2为可选择地取代的烷基，烯基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基或杂环烷基；其余变量如规范中所定义；使用这些化合物，单独或与其他药剂联合使用，治疗由过敏引起的气道反应、充血、糖尿病、肥胖症、与肥胖有关的疾病、代谢综合征和认知缺陷障碍的组合物和方法。

表征谱图