pentamethylphenylnitromethane | 29328-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: pentamethylphenylnitromethane
• 英文别名: Pentamethyl(nitromethyl)benzene；1,2,3,4,5-pentamethyl-6-(nitromethyl)benzene
• CAS: 29328-77-6
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: XXBZQWFJXCDUQN-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  333.5±11.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  五甲基苯 在 盐酸 、 silver(I) nitrite 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 9.0h， 生成 pentamethylphenylnitromethane
  参考文献：
  名称：

  Direct observation of the kinetic acidities of transient aromatic cation radicals. The mechanism of electrophilic sidechain nitration of the methylbenzenes

  摘要：

  DOI：

  10.1021/ja00188a048

文献信息

• An Interpretation of the Puzzling Dichotomy of the Reaction Modes Observed during the Side-chain Nitration of Alkylaromatics with HNO₃/CH₂Cl₂and HNO₃/(CH₃CO)₂O
  作者：Hitomi Suzuki、Hideki Koide、Yukiko Taki、Eiichi Ohbayashi、Takuji Ogawa

  DOI：10.1246/cl.1987.891

  日期：1987.5.5

  Nitration of substituted pentamethylbenzenes has been carried out under various conditions using the title nitrating systems in order to elucidate the peculiar dependence of the modes of side-chain substitution on the reagent employed; nitrooxylation with HNO3/CH2Cl2 and nitration with HNO3/(CH3CO)2O. Based on the evidence obtained from product variations with substituents, electrochemical nitrodecarboxylation

  已使用标题硝化系统在各种条件下对取代的五甲基苯进行硝化，以阐明侧链取代模式对所用试剂的特殊依赖性；用 HNO3/CH2Cl2 硝化和用 HNO3/(CH3CO)2O 硝化。基于从具有取代基的产物变化、芳基乙酸酯的电化学硝基脱羧和侧链反应初始阶段的 ESR 检查中获得的证据，提出多取代芳烃的侧链取代通过与 HNO3 的杂溶路径发生/CH2Cl2 并通过与 HNO3/(CH3CO)2O 的均裂路径。
• The Preparation of Tetramethylphthalic Anhydride
  作者：Koji Chiba、Eiji Endo、Tokio Sakamoto、Eiji Sato、Ryoichi Fukuhara、Toshiko Kobayashi

  DOI：10.1246/bcsj.49.2614

  日期：1976.9

  The alkaline hydrolysis of bis(nitromethyl)prehnitene (1) with aqueous sodium hydroxide gave almost quantitatively disodium tetramethylphthalate (11). Under milder conditions the sodium salts of tetramethylphthalimide (8), N-hydroxytetramethylphthalimide (10), and 2-hydroxy-3-hydroxyimino-4,5,6,7-tetramethylphthalimide (9) were fo were formed, probably as intermediate products of the above reaction. But, pentamethylphenylnitromethane (14) and bis(nitromethyl)isodurene (15) were not hydrolyzed in an aqueous base. From the above results, it is recognized that the sodium nitronate from 1 is unstable in a different way from general nitronates such as the sodium salt of 14 or 15. It appears that the instability of 1 arises from the two adjacent nitromethyl groups on the benzene ring.

  用氢氧化钠水溶液碱性水解双（硝基甲基）预硝烯（1），几乎可以定量得到四甲基邻苯二甲酸二钠（11）。在较温和的条件下，可能作为上述反应的中间产物，生成了四甲基邻苯二甲酰亚胺（8）、N-羟基四甲基邻苯二甲酰亚胺（10）和 2-羟基-3-羟基亚氨基-4,5,6,7-四甲基邻苯二甲酰亚胺（9）的钠盐。但是，五甲基苯基硝基甲烷（14）和双（硝基甲基）异杜烯（15）在水基中没有水解。从上述结果可以看出，1 的硝酸酯钠盐与 14 或 15 的钠盐等一般硝酸酯钠盐的不稳定性不同。1 的不稳定性似乎是由苯环上两个相邻的硝甲基引起的。
• Intermediate Stages of the Nitration of Hexamethylbenzene to Dinitroprehnitene
  作者：Hitomi Suzuki

  DOI：10.1246/bcsj.43.879

  日期：1970.3

  A syrupy substance formed in quantity during the nitration of hexamethylbenzene to dinitroprehnitene has been found to be a complex mixture of varying amounts, depending markedly on the conditions, of 2,3,4,5,6-pentamethylbenzyl nitrate, 5,6-bis(nitrooxymethyl)-1,2,3,4-tetramethylbenzene, nitropentamethylbenzene, 6-nitro-2,3,4,5-tetramethylbenzyl nitrate, 2,3,4,5,6-pentamethylphenylnitromethane, bis (2,3,4,5,6-pentamethylbenzyl) ether, pentamethylbenzaldehyde, and several other unidentified carbonyl compounds, nitrite esters, and aliphatic nitro compounds. On the basis of the products isolated, a possible path by which hexamethylbenzene can be converted into dinitroprehnitene has been suggested.

  在将六甲基苯硝化成二硝基苯的过程中，发现了一种大量形成的糖浆状物质，它是由 2,3,4,5,6-五甲基苄基硝酸盐、5,6-双(硝基氧甲基)-1,2,3,4-四甲基苯硝基五甲基苯、6-硝基-2,3,4,5-四甲基苄基硝酸盐、2,3,4,5,6-五甲基苯基硝基甲烷、双（2,3,4,5,6-五甲基苄基）醚、五甲基苯甲醛以及其他几种不明羰基化合物、亚硝酸酯和脂肪族硝基化合物。根据分离出的产物，提出了将六甲基苯转化为二硝基苯的可能途径。
• OXIME-SUBSTITUTED AMIDE COMPOUND AND PEST CONTROL AGENT
  申请人：Nissan Chemical Industries, Ltd.

  公开号：US20150210630A1

  公开（公告）日：2015-07-30

  To provide a novel pesticide, especially a fungicide and a nematocide. An oxime-substituted amide compound represented by the formula (I) or its salt, and a pesticide containing it: wherein G 1 is a structure represented by G 1 -1 or the like, G 2 is a structure represented by G 2 -2 or the like: W is an oxygen atom or the like, X 1 is a halogen atom, methyl, trifluoromethyl or the like, each of X 2 , X 3 , X 4 and X 5 is independently a hydrogen atom, a halogen atom or the like, each of Y 1 and Y 3 is independently a halogen atom, cyano, methyl, trifluoromethyl, C 2 -C 6 alkynyl or the like, each of Y 2 and Y 4 is independently a hydrogen atom, a halogen atom or the like, R 1 is C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, (C 1 -C 4 )alkyl substituted with R 18 , C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl or the like, each of R 2 and R 3 is independently a hydrogen atom, methyl or the like, R 4 is a hydrogen atom or the like, R 18 is C 3 -C 6 cycloalkyl, phenyl, phenyl substituted with (Z) m or the like, Z is a halogen atom or the like, and m is an integer of 1, 2 or 3.

  提供一种新型杀虫剂，特别是杀菌剂和线虫杀剂。一种由式(I)或其盐表示的氧肟取代酰胺化合物，以及含有它的杀虫剂：其中G1是由G1-1或类似结构表示的结构，G2是由G2-2或类似结构表示的结构：W是氧原子或类似物，X1是卤素原子，甲基，三氟甲基或类似物，X2，X3，X4和X5中的每个都是独立的氢原子，卤素原子或类似物，Y1和Y3中的每个都是独立的卤素原子，氰基，甲基，三氟甲基，C2-C6炔基或类似物，Y2和Y4中的每个都是独立的氢原子，卤素原子或类似物，R1是C1-C6烷基，C1-C4卤代烷基，(C1-C4)烷基取代R18，C3-C6环烷基，C3-C6烯基或类似物，R2和R3中的每个都是独立的氢原子，甲基或类似物，R4是氢原子或类似物，R18是C3-C6环烷基，苯基，取代(Z)m的苯基或类似物，其中Z是卤素原子或类似物，m是1、2或3的整数。
• Thermal and Photochemical Nitration of Aromatic Hydrocarbons with Nitrogen Dioxide
  作者：E. Bosch、J. K. Kochi

  DOI：10.1021/jo00091a018

  日期：1994.6

  Aromatic hydrocarbons (ArH) are readily nitrated by nitrogen dioxide (NO2) in dichloromethane at room temperature and below (in the dark). The red colors, transiently observed, arise from the metastable precursor complex [ArH, NO+]NO3-, which is formed in the prior disproportionation of nitrogen dioxide induced by the aromatic donor (eq 7). The deliberate irradiation of the diagnostic (red) charge-transfer absorption band (h nu(CT)) of [ArH, NO+] NO3- at low temperatures results directly in aromatic nitration, even at -78 degrees C, where the thermal nitration is too slow to compete. The mechanism of the photochemical (charge-transfer) nitration is established by time-resolved laser spectroscopy to proceed via the aromatic cation radical (ArH.+) formed spontaneously upon the charge-transfer excitation of [ArH, NO+]NO3- in Scheme 1. The related thermal activation of [ArH, NO+]NO3- derives from the adiabatic electron transfer that produces the same radical pair [ArH.+ NO.] as the reactive intermediate in Scheme 3. The close relationship between the thermal/photochemical nitrations with nitrogen dioxide and those conventionally carried out with nitric acid (in the presence of nitrous acid) is delineated by Scheme 4.

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