2,6-二硝基甲苯 | 606-20-2

• 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: 2,6-二硝基甲苯
• 中文别名: 2-甲基-1,3-二硝基苯
• 英文名称: 2,6-Dnt
• 英文别名: 2,6-Dinitrotoluene；2-methyl-1,3-dinitrobenzene；1-methyl-2,6-dinitrobenzene
• CAS: 606-20-2
• 化学式: C₇H₆N₂O₄
• mdl: MFCD00007158
• 分子量: 182.136
• InChiKey: XTRDKALNCIHHNI-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C
• 沸点：
  285 °C
• 密度：
  1.2833 g/cm3(Temp: 111 °C)
• 物理描述：
  2,6-dinitrotoluene appears as yellow to red solid or heated liquid with a slight odor. Solidifies in cool water. Solid and liquid sink in water. (USCG, 1999)
• 颜色/状态：
  Yellow rhombic crystals
• 气味：
  Slight odor
• 闪点：
  207 °C c.c.
• 溶解度：
  In water, 204 mg/L at 25 °C
• 蒸汽密度：
  6.28 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  5.67X10-4 mm Hg at 25 °C
• 分解：
  285 °C
• 燃烧热：
  -8099 Btu/lb = -4499 cal/g = -188.3x10(+5) J/kg
• 折光率：
  Index of Refraction: 1.479
• 解离常数：
  pKa = 1.80
• 保留指数：
  1416;1385;1401;1415;1392;1392
• 稳定性/保质期：

  一、基本性质

  能随水蒸气挥发。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

接触二硝基甲苯的工人水解尿液中含有2,4-和2,6-DNT、2,4-和2,6-二硝基苯甲酸、2,4-和2,6-二硝基苄醇、2-氨基-4-硝基苯甲酸以及2-(N-乙酰基)氨基-4-硝基苯甲酸。...个别受试者尿液中2,4-和2,6-DNT代谢物的百分比从79%到93%不等。

Hydrolyzed urine from workers exposed to dinitrotoluene contained 2,4- and 2,6-DNT, 2,4- and 2,6-dinitrobenzoic acid, 2,4- and 2,6-dinitrobenzyl alcohol, 2-amino-4-nitrobenzoic acid, and 2-(N-acetyl)amino-4-nitrobenzoic acid. ... The percentages of 2,4- and 2,6-DNT metabolites in the urine of individual subjects ranged from 79% to 93%.

来源:Hazardous Substances Data Bank (HSDB)

代谢

二硝基甲苯在大鼠体内的生物活化被认为通过以下过程发生：甲基团通过细胞色素P450依赖途径被氧化成醇；苯甲醇与葡萄糖酸酸结合并随胆汁排出体外。肠道微生物菌群水解葡萄糖苷酸并还原一个硝基团，形成可以重新从肠道吸收的氨基硝基苄醇。氨基团通过肝酶氧化成羟胺并与硫酸盐结合。硫酸酯的分解产生一个高度亲电子的硝基正离子（或碳正离子），它可以与DNA和其他生物亲核物质反应。

Bioactivation of dinitrotoluene in the rat is thought to occur by the following processes: The methyl group is oxidized to an alcohol by a cytochrome p450 dependent pathway; the benzyl alcohol is conjugated with glucoronic acid and excreted in the bile. Intestinal microflora hydrolyze the glucuronide and reduce one nitro group, forming an aminonitrobenzyl alcohol which can be readsorbed from the intestine. The amino group oxidized to an hydroxylamine by hepatic enzymes and conjugated with sulfate. Decomposition of the sulfate ester yields a highly electrophilic nitrenium (or carbonium) ion which can react with DNA and other biological nucleophiles.

来源:Hazardous Substances Data Bank (HSDB)

代谢

从一家二硝基甲苯制造厂的工人身上收集了72小时的尿液样本。通过气相色谱/质谱(GC/MS)分析样本中的2,4-和2,6-DNT及其假定代谢物。接触二硝基甲苯的工人尿液中含有2,4-和2,6-DNT、2,4-和2,6-二硝基苯甲酸、2,4-和2,6-二硝基苄基葡萄糖醛酸苷、2-氨基-4-硝基苯甲酸和N-(乙酰)氨基-4-硝基苯甲酸。这些代谢物的排泄在工作班次接近结束时达到高峰，但在第二天开始工作前降至低浓度或无法检测到的水平。计算出的尿液总二硝基甲苯相关物质消除的半衰期从1.0-2.7小时不等，个别代谢物的半衰期从0.8-4.5小时不等。最丰富的代谢物是2,4-二硝基苯甲酸和2-氨基-4-硝基苯甲酸，它们共同占检测到的二硝基甲苯代谢物的74-86%。

Urine specimens were collected over 72 hr from workers at a dinitrotoluene manufacturing plant. Samples were analyzed for 2,4- and 2,6-DNT and putative metabolites by GC/MS. Urine from workers exposed to dinitrotoluene contained 2,4- and 2,6-DNT, 2,4- and 2,6-dinitrobenzoic acid, 2,4-and 2,6-dinitrobenzyl glucuronide, 2-amino-4-nitrobenzoic acid and N-(acetyl)amino-4-nitrobenzoic acid. Excretion of these metabolites peaked near the end of the workshift, but declined to low or undetectable concentrations by the start of work the following day. The calculated half-times for elimination of total dinitrotoluene-related material detected in urine ranged from 1.0-2.7 hr, and those of individual metabolites from 0.8-4.5 hr. The most abundant metabolites were 2,4-dinitrobenzoic acid and 2-amino-4-nitrobenzoic acid, collectively accounting for 74-86% of the dinitrotoluene metabolites detected.

来源:Hazardous Substances Data Bank (HSDB)

代谢

研究了Fischer 344大鼠体内和离体灌流肝脏中肝致癌物2,6-二硝基甲苯（2,6-DNT）的代谢和排泄。给药（10 mg/kg）后72小时内，尿液排泄占剂量的半数。（14）C-2,6-DNT的尿液排泄中，2,6-二硝基苯甲酸、2,6-二硝基苄醇葡萄糖苷酸和2-氨基-6-硝基苯甲酸占了95%。72小时内，粪便排泄占剂量的五分之一。在离体灌流大鼠肝脏的灌洗液和胆汁中，2,6-二硝基苄醇葡萄糖苷酸是主要的代谢物。雄性大鼠肝脏对2,6-二硝基苄醇葡萄糖苷酸的胆汁排泄量是雌性大鼠的3.3倍和8.6倍，分别对应20和70 uM （14）C 2,6-DNT的灌流。胆汁流量没有观察到性别依赖性差异。在雄性大鼠肝脏中，与肝大分子共价结合的（14）C是雌性大鼠的两倍。2,6-二硝基苄醇葡萄糖苷酸胆汁排泄量减少可能解释了雌性大鼠肝脏中共价结合的（14）C较少。2,6-DNT的观察结果与2,4-DNT的观察结果相似，表明这两种异构体都由肝脏代谢，在胆汁中排泄，被肠道微生物群脱结合并进一步代谢，然后可能被运输回肝脏进行额外的代谢，并与肝脏的内源性成分共价结合。

The metabolism and excretion of the hepatocarcinogen 2,6-DNT was investigated in Fischer 344 rats in vivo and in isolated perfused livers. Urinary excretion accounted for half of the dose (10 mg/kg) 72 hr after administration of (14)C-2,6-DNT. 2,6-Dinitrobenzoic acid, 2,6-dinitrobenzyl alcohol glucuronide, and 2-amino-6-nitrobenzoic acid accounted for 95% of the urinary (14)C. Fecal excretion accounted for 1/5 of the dose in 72 hr. 2,6-Dinitrobenzyl alcohol glucoronide was the major metabolite found in the perfusate and bile of isolated perfused rat livers. Biliary excretion of 2,6-dinitrobenzyl alcohol glucoronide by livers from male rats was 3.3 and 8.6-fold that of female rats on perfusion with 20 and 70 uM (14)C 2,6-DNT, respectively. No sex-dependent differences in biliary flow rates were observed. Twice as much (14)C was found to be covalently bound to hepatic macromolecules in male than female rat livers in vivo. Decreased biliary excretion of 2,6-dinitrobenzyl alcohol glucoronide may account for the lesser amount of (14)C found to be covalently bound in female rat livers. Observations with 2,6-DNT parallel those made with 2,4-DNT, suggesting that both isomers are metabolized by the liver, excreted in the bile, deconjugated and further metabolized by the intestinal microflora, and transported back to the liver for, perhaps, additional metabolism and covalent binding to an endogenous component of the liver.

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,6-二硝基甲苯（2,6-DNT）的代谢主要发生在肝脏，同时肠道微生物也有作用。口服化合物后，氧化和还原的代谢物都会通过尿液排出体外。在肝脏中，细胞色素P450的氧化代谢占主导地位，生成二硝基苯甲醇，这种物质要么转化为葡萄糖苷酸结合物，要么进一步氧化成二硝基苯甲酸。二硝基苯甲醇葡萄糖苷酸部分排入胆汁，随后在肠道微生物的作用下发生代谢，并进行肠肝循环（硝基还原酶）。因此，2,6-DNT似乎首先在肝脏代谢，代谢物排入胆汁；胆汁中的代谢物在水解后在肠道进一步代谢；代谢物重新吸收并循环回到肝脏后，其中一部分（2-氨基-6-硝基苄基）被肝酶氧化成羟胺。羟胺然后通过肝磺基转移酶与硫酸盐结合。不稳定的N-硫酸酯会分解，形成亲电的硝基正离子，它能与细胞亲核物质如DNA反应。胆汁中可以检测到2,6-二硝基苯甲醇葡萄糖苷酸、2-氨基-6-硝基甲苯和2,6-二硝基苯甲醛。也可以找到一些2,6-二硝基苯甲醇和2-氨基-6-硝基苄醇的含量。（L276）

The metabolism of 2,6-DNT occurs in the liver and also in the intestine by microflora. Both oxidized and reduced metabolites are excreted in the urine after oral administration of the compound. Oxidative metabolism by cytochrome P450 predominates in the liver, leading to the formation of dinitrobenzyl alcohol which is either converted to glucuronide conjugate or further oxidized to dinitrobenzoic acid. Dinitrobenzyl alcohol glucuronide is partially excreted into the bile, followed by metabolism by gut microflora and enterohepatic cycling (nitroreductase). Thus, 2,6-DNT appears to be first metabolized by the liver with the metabolites being excreted into the bile; the biliary metabolites are hydrolyzed and further metabolized in the intestine; after reabsorption and circulation back to the liver, a portion of the metabolites (2-amino-6-nitrobenzyl) are oxidized to a hydroxylamine by hepatic enzymes. The hydroxylamine is then conjugated with sulfate by hepatic sulfotransferase. The unstable N-sulfate decomposes to form an electrophilic nitrenium ion, which can react with cellular nucleophiles such as DNA. 2,6-Dinitrobenzyl alcohol glucuronide, 2-amino-6-nitrotoluene, and 2,6-dinitrobenzaldehyde can be detected in the bile. Some amounts of 2,6-dinitrobenzylalcohol and 2-amino-6nitrobenzyl alcohol can also be found. (L276)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

二硝基甲苯可能通过其代谢物将铁(II)氧化成铁(III)，从而将氧合血红蛋白转化为高铁血红蛋白。高水平的高铁血红蛋白通过分解代谢被移除，导致贫血的发展。二硝基甲苯的一些代谢物也从胆汁返回到肝脏，在那里胺基团通过细胞色素P-450的N-羟基化形成不稳定的硫酸盐共轭物。硫酸盐共轭物降解成碳正离子或硝基正离子。这些离子与肝大分子（DNA、RNA）共价结合，导致突变，进而形成肝肿瘤。它们还与肺和肠道的DNA结合。

Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia. Some metabolites of dinitrotoluene are also transported back from the bile to the liver, where the amine group is N-hydroxylated by cytochrome P-450 to form an unstable sulfate conjugate. The sulfate conjugate is degraded into carbonium or nitrenium ions. These ions covalently bind to hepatic macromolecules (DNA, RNA), leading to mutations and subsequently liver tumors. They also bind to DNA of the lung and the intestine. (L276)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

评估：对于2,6-二硝基甲苯对人类致癌性的证据不足。对于2,6-二硝基甲苯对实验动物致癌性的证据充分。总体评估：2,6-二硝基甲苯可能对人类具有致癌性（2B组）。

Evaluation: There is inadequate evidence in humans for the carcinogenicity of ... 2,6-dinitrotoluene. There is sufficient evidence in experimental animals for the carcinogenicity of ... 2,6-dinitrotoluene. Overall evaluation: ... 2,6-Dinitrotoluene /is/ possibly carcinogenic to humans (Group 2B).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3：已确认对动物有致癌性，但对人类的相关性未知。/二硝基甲苯/

A3: Confirmed animal carcinogen with unknown relevance to humans. /Dinitrotoluene/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：2,6-二硝基甲苯

IARC Carcinogenic Agent:2,6-Dinitrotoluene

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

在给A品系小鼠进行2,6-DNT的腹腔注射和口服给药后，研究了其在体内的分布和消除情况。在一个为期30周的生物检测中，总腹腔注射剂量为600、1500或3000 mg/kg，或总口服剂量为1200、3000或6000 mg/kg，尿液是腹腔注射和口服给予的^(3)H标记的2,6-DNT消除的主要途径，1、10和100 mg/kg腹腔注射剂量分别有87.6%、55.2%和49.1%在4小时内排出。口服给药后相应的排出量分别为33.6%、25.2%和24.3%，在8小时后增加到53.7%、53.5%和48.6%。2,6-DNT在各组织（血液、肝脏、肾脏、肺、小肠和大肠）中的分布没有显示出在任何腹腔注射或口服剂量下的优先摄取或保留。放射性物质在肝脏中的终末半衰期分别为1、10和100 mg/kg腹腔注射剂量后的1.11、0.95和1.16小时。

After ip and oral administration of 2,6-DNT, the distribution and elimination were determined in strain A mice. In a 30 wk bioassay and at total ip doses of 600, 1500, or 3000 mg/kg, or total oral doses of 1200, 3000, or 6000 mg/kg, the urine was the major route of elimination of both ip and orally administered (3)H-labeled 2,6-DNT, with 87.6, 55.2 and 49.1% of ip doses of 1, 10 and 100 mg/kg, respectively, excreted within 4 hr. The corresponding amounts excreted after oral administration were 33.6, 25.2 and 24.3%, which increased to 53.7, 53.5 and 48.6% after 8 hr. The distribution of 2,6-DNT in various tissues (blood, liver, kidneys, lungs, small and large intestine) showed no evidence for preferential uptake or retention at any of the ip or po doses. Terminal half-lives of radioactive material in the liver were 1.11, 0.95 and 1.16 hr after ip doses of 1, 10 and 100 mg/kg, respectively.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S36/37,S45,S456,S53,S61
• 危险类别码：
  R48/22,R52/53,R45,R23/24/25,R62,R68
• WGK Germany：
  3
• RTECS号：
  XT1925000
• 海关编码：
  2904203000
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3454 6.1/PG 2

SDS

第一部分：化学品名称

制备方法与用途

制备方法

由邻硝基甲苯经混酸硝化而得。生产过程与2,4-二硝基甲苯相同。

合成制备方法

由邻硝基甲苯经混酸硝化而得。生产过程与2,4-二硝基甲苯相同。

用途简介

主要用于医药、染料、涂料及其他精细化工品的合成。

用途

工业上大多应用2,4-二硝基甲苯和2,6-二硝基甲苯的混合物，经还原为2,6/2,4-二氨基甲苯，然后经光气化生产甲苯二异氰酸酯（TDI）。也可用于其他有机合成。

反应信息

• 作为反应物：
  描述：

  2,6-二硝基甲苯 在 ammonium sulfide 、 potassium phosphate 、 二氟化氢钾 、 三氯异氰尿酸 、 硫酸 、 溴 、 十六烷基三甲基溴化铵 、 四丁基硫酸氢铵 、 palladium diacetate 、 乙酸酐 、 镍 、 二异丁基氢化铝 、 一水合肼 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 3-戊酮 、 potassium hydroxide 、 sodium hydroxide 、 zinc(II) chloride 、 lithium hexamethyldisilazane 、 sodium nitrite 、 三环己基膦 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 异丙醇 、 甲苯 为溶剂， 生成 奈米利塞
  参考文献：
  名称：

  C–H功能化在磷脂酰肌醇3-激酶Delta抑制剂Nemiralisib的聚合反应中的应用

  摘要：

  本文介绍了一种改进的可扩展方法，用于生产nemiralisib（一种磷脂酰肌醇-3-激酶δ抑制剂）。结合三个连续的催化反应，包括钯催化的C–H功能化和铱催化的硼化反应，显着简化并缩短了合成顺序。修订后的路线已在多千克规模的中试工厂中成功实施，以交付大于100千克的产品。

  DOI：

  10.1021/acs.oprd.0c00486
• 作为产物：
  描述：

  2,6-Dinitro-benzyl-Anion 在 sodium perchlorate 、 溶剂黄146 作用下， 生成 2,6-二硝基甲苯
  参考文献：
  名称：

  Broensted catalysis of the fading reaction of flash-produced transients from 2,6-dinitrotoluene

  摘要：

  DOI：

  10.1021/ja01037a003

文献信息

• [EN] INHIBITORS OF KRAS G12C<br/>[FR] INHIBITEURS DE K-RAS G12C
  申请人：ARAXES PHARMA LLC

  公开号：WO2015054572A1

  公开（公告）日：2015-04-16

  Compounds having activity as inhibitors of G12C mutant KRAS protein are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, tautomer, prodrug or stereoisomer thereof, wherein R1, R2a, R3a, R3b, R4a, R4b, G1, G2, L1, L2, m1, m2, A, B, W, X, Y, Z and E are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, are also provided.

  提供了作为G12C突变KRAS蛋白抑制剂活性的化合物。这些化合物具有以下结构（I）：或其药用可接受的盐、互变异构体、前药或立体异构体，其中R1、R2a、R3a、R3b、R4a、R4b、G1、G2、L1、L2、m1、m2、A、B、W、X、Y、Z和E如本文所定义。还提供了与制备和使用这些化合物相关的方法，包括含有这些化合物的药物组合物以及调节G12C突变KRAS蛋白活性以治疗癌症等疾病的方法。
• Selective Partial Hydrogenation of Dinitrobenzenes to Nitroanilines Catalyzed by Ru/C
  作者：Jie Hou、Yonghuan Ma、Yuhan Li、Fang Guo、Lianhai Lu

  DOI：10.1246/cl.2008.974

  日期：2008.9.5

  Ru/C was found to be a highly effective catalyst for the selective partial hydrogenation of a range of dinitrobenzenes to their corresponding nitroanilines with excellent selectivity under mild conditions. Furthermore, the effect from other substitute groups of dinitrobenzenes on partial hydrogenation was also explored in this study.

  发现Ru/C是一种高效的催化剂，在温和条件下对一系列二硝基苯进行选择性部分氢化，得到相应的高选择性硝基苯胺。此外，本研究还探讨了二硝基苯的其他取代基对部分氢化的影响。
• Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems
  作者：Keith Smith、Mohammad Hayal Alotaibi、Gamal A. El-Hiti

  DOI：10.3998/ark.5550190.p008.527

  日期：——

  Various nitration systems comprising nitric acid, acid anhydride and zeolite Hβ in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite H system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole)

  描述了在不存在溶剂的情况下包含硝酸、酸酐和沸石Hβ的各种硝化系统。已经开发出甲苯与硝酸、丙酸酐和沸石 H 系统的直接双硝化，以 98% 的产率得到 2,4-二硝基甲苯，2,4:2,6-二硝基甲苯的比例为 123:1。该系统还硝酸盐活化的单取代苯（苯甲醚和苯乙醚）和适度活化的单取代苯（乙苯和丙苯），主要生成 2,4-二硝基衍生物。沸石可以回收、再生和再利用，其产率与使用新鲜沸石时的产率几乎相同。
• NITRATION OF AROMATIC COMPOUNDS ON SOLID CATALYSTS
  作者：Tomasz Miłczak、Jarosław Jacniacki、Janusz Zawadzki、Monika Malesa、Wincenty Skupiński

  DOI：10.1081/scc-100000197

  日期：2001.1

  o-Xylene, phenol and toluene were nitrated with 100% nitric acid on MoO3/SiO2, WO3/SiO2, TiO2/SiO2, and TiO2–WO3/SiO2 systems. Phenol and toluene were nitrated with yields higher than 90%, and the 10% and 15% MoO3/SiO2 catalysts were most active in the nitration of o-xylene. The most active catalysts exhibited the para-position selectivity of nitration.

  邻二甲苯、苯酚和甲苯在 MoO3/SiO2、WO3/SiO2、TiO2/SiO2 和 TiO2-WO3/SiO2 系统上用 100% 硝酸硝化。苯酚和甲苯硝化的产率高于90%，其中10%和15%的MoO3/SiO2催化剂对邻二甲苯的硝化活性最强。最活跃的催化剂表现出硝化的对位选择性。
• A Practical Approach of Continuous Processing to High Energetic Nitration Reactions in Microreactors
  作者：Shahriyar Taghavi-Moghadam、Gerhard Panke、Thomas Schwalbe、Wolfgang Stirner、Gregor Wille

  DOI：10.1055/s-2003-42491

  日期：——

  safe and expedient conduct of high energetic reactions and potentially hazardous chemistry. Apart from handling benefits (such as minimised problems inthe scale-up process), reactions in microreactors proceed under precisely controlled conditions providing improved yields and product quality compared to the batch procedure. In this paper, the potential of this technology is exemplarily determined in

  微反应器中的连续处理代表了一种安全和方便地进行高能反应和潜在危险化学的新方法。除了处理优势（例如放大过程中的问题最小化）外，微反应器中的反应在精确控制的条件下进行，与分批程序相比，提供了更高的产率和产品质量。在本文中，该技术的潜力示例性地确定在药物相关中间体 1-甲基-3-丙基-1H-吡唑-5-羧酸 (1) 的关键硝化中。进一步的基本硝化示例证明了危险的 H 2 SO 4 / HNO 3 混合物在 2-甲基吲哚 (4) 和吡啶-N-氧化物 (6) 甚至爆炸性乙酰硝酸酯 Ac 2 O/HNO 3 的硝化中的处理没有问题（甲苯硝化，

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