2,4,6-三硝基甲苯 | 118-96-7

• 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: 2,4,6-三硝基甲苯
• 中文别名: 三硝基甲苯；2-甲基-1,3,5-三硝基苯；1-甲基-2,4,6-三硝基苯；梯恩梯
• 英文名称: 2,4,6-Trinitrotoluene
• 英文别名: 2-methyl-1,3,5-trinitrobenzene；TNT；trinitrotoluene
• CAS: 118-96-7
• 化学式: C₇H₅N₃O₆
• mdl: MFCD00041875
• 分子量: 227.133
• InChiKey: SPSSULHKWOKEEL-UHFFFAOYSA-N

物化性质

• 物理描述：
  Trinitrotoluene appears as an explosive solid. Primary hazard is from effects of a blast. Not designed to produce significant fragmentation or throw projectiles. May explode under exposure to intense heat or fire.
• 颜色/状态：
  Monoclinic rhombohedra from alc; commercial crystals (needles) are yellow
• 气味：
  Odorless
• 沸点：
  240 °C (explodes)
• 熔点：
  80.1 °C
• 闪点：
  explodes
• 溶解度：
  115 mg/L (at 23 °C)
• 密度：
  1.654 at 20 °C/4 °C
• 蒸汽密度：
  7.85 (Air = 1)
• 蒸汽压力：
  8.02X10-6 mm Hg at 25 °C
• 分解：
  May explosively decompose on shock, friction, or concussion. Explodes on heating to 240 °C.
• 电离电位：
  10.59 eV
• 保留指数：
  1704 ;1693
• 稳定性/保质期：

  1. 稳定性：稳定。

  2. 禁配物：强氧化剂、氨、胺类等。

  3. 避免接触的条件：受热、摩擦、震动、撞击。

  4. 聚合危害：不聚合。

  5. 分解产物：氮氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 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：
  138
• 氢给体数：
  0
• 氢受体数：
  6

ADMET

代谢

2,4,6-三硝基甲苯（TNT）在大鼠、小鼠、兔和狗体内的代谢进行了研究，通过口服、皮肤或气管内给药单一剂量的（14）C-环标记化合物。在所有物种中，TNT都被广泛代谢；放射性主要通过尿液以葡萄糖苷酸结合物的形式排出。大多数代谢物是还原产物，包括2-和4-羟基胺以及2-和4-单氨基二硝基和2,6-和4,6-二氨基一硝基衍生物。偶尔会检测到微量的TNT、三硝基苯甲醇和三硝基苯甲酸。

The metabolism of 2,4,6-trinitrotoluene (TNT) was studied in rats, mice, rabbits, and dogs following oral, dermal, or intratracheal admin of single doses of (14)C-ring labeled compound. TNT was extensively metabolized in all species; radioactivity was excreted in urine primarily as the glucuronide conjugates. Most metabolites were reduction products including the 2- and 4-hydroxylamine and 2- and 4-monoaminodinitro and 2,6- and 4,6-diaminomononitro derivatives. Trace quantities of TNT, trinitrobenzyl alcohol, and trinitrobenzoic acid were detected occasionally.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在1x10-4到1x10-3克水平上，2,6-二硝基-4-氨基甲苯，即TNT的主要已知代谢物，在弹药工人的尿样中被发现。

At levels of 1x10-4 to 1x10-3 g 2,6-dinitro-4-aminotoluene, the major known metabolite of TNT, was found in urine samples of munitions workers.

来源:Hazardous Substances Data Bank (HSDB)

代谢

TNT在动物和人类中经历氧化和还原代谢。硝基团通过中间的羟基胺还原为胺。甲基团可以被氧化成醇和酸，两者都可以与葡萄糖酸结合并在尿液中排出。在喂食TNT的兔子的尿液中发现了4-氨基-2,6-二硝基甲苯（4-A）、6-氨基-2,4-二硝基甲苯和4-羟基氨基-2,6-二硝基甲苯（4-HA）。

TNT undergoes both oxidative and reductive metabolism in animals and humans. The nitro groups are reduced through intermediate hydroxylamines to amines. The methyl group can be oxidized to an alcohol and an acid, both of which can be conjugated with glucuronic acid and excreted in the urine. 4-Amino-2,6-dinitrotoluene (4-A), 6- amino-2,4-dinitrotoluene, and 4-hydroxylamino-2,6- dinitrotoluene (4-HA) were found in the urine of rabbits fed TNT.

来源:Hazardous Substances Data Bank (HSDB)

代谢

TNT本身以及2-氨基-4,6-二硝基甲苯（2-A）、4-A和2,4-二氨基-6-硝基甲苯在大鼠口服TNT后的尿液中被发现。4-HA和4-A在喂食TNT的狗的尿液中被发现。4-A、2-A、羟基氨基二硝基甲苯和二氨基硝基化合物在接触TNT的军火工人的尿液中被发现。

TNT itself as well as 2-amino-4,6- dinitrotoluene (2-A), 4-A, and 2,4-diamino-6- nitrotoluene were found in the urine of rats given TNT orally. 4-HA and 4-A were found in the urine of dogs fed TNT. 4-A, 2-A, hydroxylaminodinitrotoluenes, and diaminonitro compounds were found in the urine of TNT-exposed munitions workers.

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,4,6-三硝基甲苯会通过吸入或摄入迅速而完全地进入人体，但通过皮肤进入的速度较慢。一旦2,4,6-三硝基甲苯进入血液，它就会传输到人体的所有器官。当它到达肝脏时，它会分解并转变为多种不同的物质，例如4-氨基二硝基甲苯、2-氨基二硝基甲苯和2,4-二氨基-6-硝基甲苯。这些物质大多数在血液中循环，直到它们到达肾脏。在24小时内，进入人体的几乎所有2,4,6-三硝基甲苯都会分解并通过尿液排出体外。

2,4,6-Trinitrotoluene rapidly and completely enters the body through inhalation or ingestion, but more slowly through the skin. Once 2,4,6-trinitrotoluene is in the blood, it travels throughout the body to all of the organs. When it reaches the liver, it breaks down and changes into several different substances, such as 4-aminodinitrotoluene, 2-aminodinitrotoluene and 2,4-diamino-6-nitrotoluene. Most of these substances travel in the blood until they reach the kidneys. Almost all of the 2,4,6-trinitrotoluene that enters the body breaks down and leaves the body in the urine within 24 hours. (L132)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

2,4,6-三硝基甲苯（TNT）是相对于NADPH的竞争性抑制剂，以及相对于L-精氨酸的非竞争性抑制剂。它结合到eNOS的P450还原酶结构域，并通过将电子从正常的催化途径转移出来，抑制L-瓜氨酸的形成。TNT的还原产生反应性氧种（ROS），如超氧阴离子（O2.-）和过氧化氢（H2O2）。超氧阴离子的过度产生与氧化应激介导的白内障诱导有关。eNOS活性的抑制以浓度依赖性方式发生。（A110，A111）

2,4,6-Trinitrotoluene is a competitive inhibitor with respect to NADPH and a noncompetitive inhibitor with respect to L-arginine. It binds to the P450 reductase domain of the eNOS and suppresses l-citrulline formation by shunting electrons away from the normal catalytic pathway. The reduction of TNT then produces reactive oxygen species (ROS), such as superoxide (O2.−), and hydrogen peroxide (H2O2). The overproduction of superoxide is associated with oxidative stress-mediated induction of cataracts. The inhibition of the eNOS activity occurs in a concentration-dependent manner. (A110, A111)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

分类：C；可能的人类致癌物。分类依据：人类致癌性的证据不足。在雌性Fischer 344大鼠中观察到了膀胱乳头状瘤和癌。在Salmonella中，无论是否经过代谢激活，都观察到了致突变活性。人类致癌性数据：无。动物致癌性数据：有限。

CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Evidence of human carcinogenicity is inadequate. Urinary bladder papilloma and carcinoma were observed in female Fischer 344 rats. Mutagenic activity was observed in Salmonella with and without metabolic activation. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Limited.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：对于2,4,6-三硝基甲苯对人类致癌性的证据不足。对于2,4,6-三硝基甲苯对实验动物致癌性的证据也不足。总体评估：2,4,6-三硝基甲苯对人类致癌性无法分类（第3组）。

Evaluation: There is inadequate evidence in humans for the carcinogenicity of 2,4,6-trinitrotoluene. There is inadequate evidence in experimental animals for the carcinogenicity of 2,4,6-trinitrotoluene. Overall evaluation: 2,4,6-Trinitrotoluene is not classifiable as to its carcinogenicity to humans (Group 3).

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：2,4,6-三硝基甲苯

IARC Carcinogenic Agent:2,4,6-Trinitrotoluene

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：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

三硝基甲苯（TNT）吸收在两个炸药工厂的工人中被评估，通过测量尿液中二硝基氨基甲苯代谢物的浓度。大气中浓度的范围是静态样品中0.02-5.73毫克/立方米，个人样品中<0.01至0.71毫克/立方米。在换班后尿样中，二硝基氨基甲苯的平均浓度为9.7毫克/升（标准差=7.9，n=219）。TNT在暴露期间被迅速吸收。在清除TNT代谢物的速率方面，个体之间存在很大差异。尽管在某些情况下，暴露后第二天早晨采集的样品中代谢物的浓度更高，但整体而言，换班前样品中的每日平均尿总二硝基氨基甲苯浓度低于换班后样品。在工作场所外17天收集的尿样中仍可检测到二硝基氨基甲苯的水平（平均0.06毫克二硝基氨基甲苯/升），这表明一部分TNT或其代谢物会缓慢排泄。

Trinitrotoluene (TNT) absorption was assessed in workers at two explosives factories by measuring urinary concentrations of dinitroaminotoluene dinitroaminotoluene metabolites. The range of atmospheric concentrations was 0.02-5.73 mg/cu m in static samples and <0.01 to 0.71 mg/cu m in personal samples. In postshift urine samples, the mean concentration of dinitroaminotoluene was 9.7 mg/l (standard deviation= 7.9, n= 219). TNT was shown to be absorbed rapidly during the exposure period. A wide variation among individuals in the rate of clearance of TNT metabolites was seen. For the group as a whole the daily mean urinary total dinitroaminotoluene concentrations in preshift samples were lower than those in postshift samples although in some cases higher concentrations of metabolites were seen in samples taken the morning after exposure. Urine samples collected after 17 days away from the workplace still showed detectable levels of dinitroaminotoluene (mean 0.06 mg dinitroaminotoluene/l) indicating that a proportion of TNT or its metabolites is slowly excreted.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

对接触2,4,6-三硝基甲苯的工人进行了两次调查。空气中的2,4,6-三硝基甲苯浓度发现为0.6至4.0毫克/立方米。尿液中的2,6-二硝基-4-氨基甲苯排出量分别为2.5毫克/升和6.5毫克/升。

... Two surveys of 2,4,6-trinitrotoluene-exposed workers /were performed/. Air concentrations of 2,4,6-trinitrotoluene were found to range from 0.6 to 4.0 mg/cu m. The urinary excretion of 2,6-dinitro-4-aminotoluene was 2.5 and 6.5 mg/L, respectively.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

2,4,6-三硝基甲苯（TNT）的分布和代谢在口服、皮肤或气管内给药单剂量的14-C-环标记化合物后在大鼠、小鼠、兔和狗身上进行了研究。研究目的是确定可能的种属和性别差异作为给药途径的函数，作为设计慢性研究的依据。TNT通过所有给药途径在所有物种中均被吸收，其中气管内给药后吸收最为广泛。皮肤吸收在兔中最高，其次是小鼠、大鼠和狗。口服吸收的种属差异无法准确评估。排泄主要在尿液中，较少在粪便中。还注意到广泛的胆汁排泄。女性的血液和组织水平通常高于男性。

The disposition and metabolism of 2,4,6-trinitrotoluene (TNT) was studied in rats, mice, rabbits, and dogs following oral, dermal, or intratracheal administration of single doses of 14-C-ring labeled compound. The objective was to determine possible species and sex differences as a function of route of admin as a rationale for the design of chronic studies. TNT was absorbed in all species by all routes of admin with the most extensive absorption occurring after intratracheal instillation. Dermal absorption was the highest in rabbits followed by mice, rats, and dogs. Species differences in the rate of oral absorption could not be accurately assessed. Excretion was primarily in urine and to a lesser extent in feces. Extensive biliary excretion was also noted. Blood and tissue levels in females were generally higher than in males.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

该物质可以通过吸入其气溶胶、通过皮肤接触以及摄入进入人体。

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S26,S35,S36/37,S45,S61
• 危险品运输编号：
  0209
• 海关编码：
  2904204000
• 危险类别：
  1.1D
• 危险品标志：
  E,N,T,Xn,F,B
• 危险类别码：
  R2

SDS

第一部分：化学品名称

制备方法与用途

制备方法

用甲苯与混酸（硝酸和硫酸）进行硝化制得。甲苯经硝化制得粗品TNT，再精制除去杂质即可。

合成制备方法

同样地，用甲苯与混酸（硝酸和硫酸）进行硝化制得粗品TNT，再精制除去杂质即可。

用途简介

除了直接用作炸药外，TNT还是许多炸药及其中间体的原料。其爆炸力较苦味酸略小，但使用较为安全，可以单独使用或与其他炸药混合使用。TNT与RDX混熔制成的炸药广泛用于炮弹、航弹等。此外，TNT还用于制造染料、医药品和作为试剂等。

用途

1. 除了直接用作炸药外，TNT还是许多炸药及其中间体的原料。其爆炸力较苦味酸略小，但使用较为安全，可以单独使用或与其他炸药混合使用。TNT与RDX混熔制成的炸药广泛用于炮弹、航弹等。
2. 用于制造染料、医药品和作为试剂等。[26]

反应信息

• 作为反应物：
  描述：

  2,4,6-三硝基甲苯 在 盐酸 、 N-氯代丁二酰亚胺 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 78.0h， 生成 (E)-N,N-dimethyl-2-(2-(morpholinosulfonyl)-4,6-dinitrophenyl)ethenamine
  参考文献：
  名称：

  Synthesis of 6-nitro-4-sulfanyl-1H-indole derivatives from 2,4,6-trinitrotoluene

  摘要：

  The synthesis of 6-nitro-4-sulfanyl-1H-indoles from 2,4,6-trinitrotoluene (TNT) is described. The first step is the nucleophilic substitution of an ortho-nitro group with a thiol to give the corresponding sulfide. The latter were transformed into the corresponding enamines upon treatment with dimethylformamide dimethyl acetal (DMF DMA). The enamines were converted into the indoles applying the Batcho Leimgruber synthetic protocol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.107
• 作为产物：
  描述：

  4-硝基甲苯 在 poly(vinyl imidazole)sulfonic acid nitrate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 2,4,6-三硝基甲苯
  参考文献：
  名称：

  [PVI-SO3H]NO3作为新型离子标记聚合硝化剂在制备高能材料中的应用

  摘要：

  本文合成并充分表征了聚(乙烯基咪唑)磺酸硝酸盐[PVI-SO3H]NO3。然后，它被用于制备含能材料。

  DOI：

  10.1039/d1ra00651g
• 作为试剂：
  描述：

  2,2'-(1,2-肼二亚基)二[3-乙基-2,3-二氢-6-苯并噻唑磺酸 在 盐酸 、 2,4,6-三硝基甲苯 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  用于检测各种硝基炸药的增强型比色化学传感器

  摘要：

  介绍了一种用于检测多种硝基炸药的简单快速的比色化学传感器。该方法的基础是二氧化氮将无色ABTS氧化成其强烈的蓝绿色自由基阳离子ABTS +，它可以通过以下两种方法之一从硝基炸药中产生：（i）消化极少量的用碱性氢氧化物炸药，产生亚硝酸根阴离子，在酸性介质中产生二氧化氮，或（ii）通过硝基炸药的热分解而直接产生二氧化氮。在这些过程中，二氧化氮起催化中间体的作用，从而提高了检测效率。

  DOI：

  10.1016/j.tetlet.2012.10.095

文献信息

• Efficient Palladium(0) supported on reduced graphene oxide for selective oxidation of olefins using graphene oxide as a ‘solid weak acid’
  作者：Xi Gao、Jianhao Zhou、Xinhua Peng

  DOI：10.1016/j.catcom.2019.01.020

  日期：2019.3

  Selective oxidation of olefin derivatives to ketones has made innovative development over palladium(0) supported on reduced graphene oxide. Compared to traditional Wacker oxidation, the novel method offers an economical and environment-friendly option by using graphene oxide (GO) as a ‘solid weak acid’ instead of classical homogeneous catalysts like H2SO4 and CF3COOH. X-ray diffraction, X-ray photoelectron

  烯烃衍生物选择性氧化为酮的方法已在还原性氧化石墨烯上负载的钯（0）上取得了创新性的发展。与传统的Wacker氧化相比，该新方法通过使用氧化石墨烯（GO）作为“固体弱酸”，而不是像H 2 SO 4和CF 3 COOH这样的经典均相催化剂，提供了一种经济且环保的选择。Pd 0 / RGO的X射线衍射，X射线光电子能谱，扫描电子显微镜和透射电子显微镜图像表明，在还原的氧化石墨烯的薄片结构上产生了纳米级的Pd颗粒。在最佳条件下，最多可以制备44种结构不同的酮，并具有优异的收率。
• [EN] OXAZOLIDINONE DERIVATES N-SUBSTITUTED BY A TRICYCLIC RING, FOR USE AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES D'OXAZOLIDINONES N-SUBSTITUES PAR UN NOYAU TRICYCLIQUE, DESTINES A ETRE UTILISES EN TANT QU'AGENTS ANTIBACTERIENS
  申请人：WARNER LAMBERT CO

  公开号：WO2004069245A1

  公开（公告）日：2004-08-19

  Compounds of formula (I) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compounds of formula (I) as disclosed herein can be used in a variety of applications including use as antibacterial P is a tricyclic ring system as defined in claiml.

  公式（I）的化合物及其制备方法已被披露。进一步披露了制备公式（I）生物活性化合物的方法，以及包含公式（I）化合物的药用可接受组合物的方法。本文披露的公式（I）化合物可用于各种应用，包括用作抗菌剂P是在权利要求1中定义的三环环系统。
• [EN] PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'ACIDE PYRIDIN-3-YLE ACÉTIQUE UTILISÉS EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK NO 5 LTD

  公开号：WO2018127800A1

  公开（公告）日：2018-07-12

  Disclosed are compounds of Formula I, including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS. (I)

  公开了公式I的化合物，包括药用可接受的盐、包含这些化合物的药物组合物、制备这些化合物的方法，以及它们在抑制HIV整合酶和治疗HIV或艾滋病感染者中的用途。
• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS DE LIAISON À UNE OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2013058809A1

  公开（公告）日：2013-04-25

  Compounds are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.

  披露了一些化合物，可用于治疗由于或与在眼睛中积累的有毒视觉循环产物有关的眼科疾病，例如干性成人黄斑变性，以及由于或与突变视蛋白的错误折叠和/或视蛋白的错误定位有关的疾病。还描述了这些化合物单独或与其他治疗剂联合使用的组合物，以及使用这些化合物和/或组合物的治疗方法。还披露了合成这些药剂的方法。
• [EN] 8-AZA TETRACYCLINE COMPOUNDS<br/>[FR] COMPOSÉS DE 8-AZA TÉTRACYCLINE
  申请人：TETRAPHASE PHARMACEUTICALS INC

  公开号：WO2010129055A1

  公开（公告）日：2010-11-11

  The present invention is directed to a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The variables for Structural Formula I are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula I and its therapeutic use.

  本发明涉及一种由结构式（I）表示的化合物或其药用盐。结构式I的变量在此定义。还描述了包括结构式I化合物的药物组合物及其治疗用途。

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