1-甲基-3-(硫氰酸基甲基)苯 | 37141-50-7

• 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: 1-甲基-3-(硫氰酸基甲基)苯
• 英文名称: 3-methylbenzyl thiocyanate
• 英文别名: 1-methyl-3-(thiocyanatomethyl)benzene；1-methyl-3-thiocyanomethylbenzene；3-methyl-1-(thiocyanatomethyl)benzene；3-Methyl-benzylthiocyanat；Thiocyansaeure-(3-methyl-benzylester)；α-Thiocyanato-m-xylol；3-Methyl-1-thiocyanatomethyl-benzol；Thiocyansaeure-m-tolubenzylester；m-Tolubenzylrhodanid；m-methylbenzyl thiocyanate；(3-methylphenyl)methyl thiocyanate
• CAS: 37141-50-7
• 化学式: C₉H₉NS
• mdl: MFCD00019767
• 分子量: 163.243
• InChiKey: NSGWUGKMTAEVPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-甲基-3-(硫氰酸基甲基)苯 在 苯 作用下， 生成 benzoyl dithiocarbimidoic acid benzyl ester-(3-methyl-benzyl ester)
  参考文献：
  名称：

  Wheeler; Johnson, American Chemical Journal, 1901, vol. 26, p. 202

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基苄基氯 在 乙醇 、 sodium ethanolate 作用下， 生成 1-甲基-3-(硫氰酸基甲基)苯
  参考文献：
  名称：

  v.Braun; May; Michaelis, Justus Liebigs Annalen der Chemie, 1931, vol. 490, p. 189,200

  摘要：

  DOI：

文献信息

• AIBN-initiated direct thiocyanation of benzylic sp³ C–H with <i>N</i>-thiocyanatosaccharin
  作者：Di Wu、Yongjie Duan、Kun Liang、Hongquan Yin、Fu-Xue Chen

  DOI：10.1039/d1cc04302a

  日期：——

  Direct thiocyanations of benzylic compounds have been implemented. Here, a new strategy, involving a free radical reaction pathway initiated by AIBN, was used to construct the benzylic sp3 C–SCN bond. In this way, the disadvantage of other strategies involving introducing leaving groups in advance to synthesize benzyl thiocyanate compounds was overcome. The currently developed protocol also involved

  已经实施了苄类化合物的直接硫氰化。在这里，涉及由 AIBN 引发的自由基反应途径的新策略用于构建苄型 sp 3 C-SCN 键。通过这种方式，克服了其他涉及提前引入离去基团以合成硫氰酸苄酯化合物的策略的缺点。目前开发的协议还涉及使用现成的原材料，并导致高产率（高达 100%），这两者都是合成硫氰酸苄酯的巨大优势。
• Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates
  作者：Chengrong Ding、Guofu Zhang、Lidi Xuan、Yiyong Zhao

  DOI：10.1055/s-0040-1707151

  日期：2020.9

  one-step synthesis of thiocyanates through C–O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative

  开发了一种新的 SO2F2 促进的硫氰化方法，通过以硫氰酸铵为硫氰化剂的容易获得的醇的 C-O 键裂解，一步合成硫氰酸盐。该方法避免使用额外的催化剂，并且各种（杂）芳烃、烯烃和脂肪醇在温和条件下在乙酸乙酯中高效反应，以优异的定量收率提供相应的硫氰酸酯，并具有广泛的官能团兼容性。
• One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF 2 CO 2 Et)
  作者：Lijun Xu、Hongyu Wang、Changwu Zheng、Gang Zhao

  DOI：10.1016/j.tet.2017.08.048

  日期：2017.10

  An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.

  描述了一种用于合成（乙氧基羰基）二氟甲基硫醚的有效的一锅级联方法。在CsF或NaOAc的存在下，以苄基，烯丙基，烷基卤化物或重氮盐为起始原料，与硫氰酸钠和TMS-CF 2 CO 2 Et一起，以中等至良好的收率提供了多种氟代烷基硫代产物。
• Crown ether functionalized magnetic hydroxyapatite as eco‐friendly microvessel inorganic‐organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives
  作者：Maedeh Azaroon、Ali Reza Kiasat

  DOI：10.1002/aoc.4046

  日期：2018.2

  (γ‐Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase‐transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by‐products was observed and the products obtained in pure form without further purification. The

  在本文中，4个催化活性高'，4“-diformyl二苯并-18-冠-6锚定在官能磁铁矿羟基磷灰石（γ-的Fe 2 ö 3制备了一种新的，多用途且可磁回收的催化剂@@ HAp-Crown。它被用作相转移催化剂和分子主体系统，用于水中卤化苄基卤与硫氰酸根，氰化物，叠氮化物和乙酸根阴离子的亲核取代反应。没有观察到形成副产物的证据，并且没有进一步纯化就以纯净形式获得了产物。通过施加磁场，可以轻松地从溶液中去除纳米复合材料，从而实现直接回收和再利用。合成的纳米复合材料通过多种技术进行了表征，如FT-IR，TGA-DTG，EDX，XRD，BET，FE-SEM，TEM和VSM。
• β-Cyclodextrin conjugated magnetic nanoparticles as a novel magnetic microvessel and phase transfer catalyst: synthesis and applications in nucleophilic substitution reaction of benzyl halides
  作者：Ali Reza Kiasat、Simin Nazari

  DOI：10.1007/s10847-012-0207-8

  日期：2013.8

  This paper presents a feasible protocol for the preparation of β-cyclodextrin conjugated Fe3O4 magnetic nanoparticles as an efficient microvessel and host system for nucleophilic substitution reaction of benzyl halides in water. No evidence for the formation of by-product for example isothiocyanate or benzyl alcohol was observed and the products were obtained in pure form without further purification

  本文提出了一种制备 β-环糊精共轭 Fe3O4 磁性纳米粒子的可行方案, 作为一种有效的微血管和宿主系统, 用于苄基卤化物在水中的亲核取代反应。没有观察到形成副产物例如异硫氰酸酯或苯甲醇的证据，并且产物以纯形式获得而无需进一步纯化。FT-IR、XRD、TGA 和SEM 的特征结果表明β-CD 接枝到Fe3O4 纳米颗粒上。通过使用外部磁铁，纳米磁性催化剂可以很容易地从溶液中分离出来，从而可以直接回收和再利用。

表征谱图