2,4-dinitrophenylhydrazone of methacrolein | 5077-73-6

• 物质功能分类: 化学试剂 - 有机试剂 - 腙
• 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: 2,4-dinitrophenylhydrazone of methacrolein
• 英文别名: Methacrolein-(2,4-dinitrophenylhydrazon)；methacrolein (2,4-dinitrophenyl)hydrazone；Methacrylaldehyd-(2,4-dinitro-phenylhydrazon)；2-Methyl-acrolein-(2,4-dinitro-phenylhydrazon)；N-(2-methylprop-2-enylideneamino)-2,4-dinitroaniline
• CAS: 5077-73-6
• 化学式: C₁₀H₁₀N₄O₄
• 分子量: 250.214
• InChiKey: TUBWWZMXYOKKNG-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C (dec.)(lit.)
• 沸点：
  402.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 闪点：
  2 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  F,Xi,T
• 安全说明：
  S16,S26,S36,S36/39
• 危险类别码：
  R20/21/22,R36/37/38,R11,R41
• WGK Germany：
  3
• 危险品运输编号：
  UN 1648 3/PG 2
• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 2,4-dinitrophenylhydrazone of methacrolein 以 xylene 为溶剂， 反应 45.0h， 以42%的产率得到3-methyl-6-phenylpyrrolo<3,4-b>pyridine-5,7-dione
  参考文献：
  名称：

  甲基丙烯醛和乙基丙烯醛衍生的酰基hydr的分子内和分子间狄尔斯-阿尔德反应

  摘要：

  已经研究了衍生自甲基丙烯醛或乙基丙烯醛的hydr与末端不饱和N-酰基-N-甲基肼的分子内Diels-Alder反应。发现衍生自N-甲基-N-戊-4-烯丙基肼3b的7b和7c在140℃以上进行分子内[4 + 2]环加成，并分离了吡啶并哒嗪12。相应的腙图8b和图8c从Ñ甲基ñ -戊-4- ynoylhydrazone 4A同样反应，并得到作为最终产物的吡啶13。反应的范围是有限的，如αβ-不饱和醛的其他几种末端不饱和的分子内环加成反应所表明的。然而，这些确实发生了N-苯基马来酰亚胺的分子间[4 + 2]环加成反应。甲基丙烯醛的其他氢化物15。包括苯甲酰hydr和苯,，也与N-苯基马来酰亚胺反应，通过可分离的二氢吡啶16生成吡啶14b。

  DOI：

  10.1016/s0040-4020(01)96054-5
• 作为产物：
  描述：

  2,4-dinitrobenzene-1-diazonium tertafluoroborate 以 氯仿 、 乙腈 为溶剂， 生成 2,4-dinitrophenylhydrazone of methacrolein
  参考文献：
  名称：

  Synthesis of allylazo compounds by reactions of aryldiazonium salts with allylsilanes

  摘要：

  Aryldiazonium tetrafluoroborates react with allylsilanes to yield allylazo compounds. If the allylic carbon attached to the azo group carries hydrogen, tautomerization with formation of hydrazones takes place.

  DOI：

  10.1021/jo00030a001

文献信息

• Quantitative RP-HPLC Determination of Some Aldehydes and Hydroxyaldehydes as Their 2,4-Dinitrophenylhydrazone Derivatives
  作者：Eija Koivusalmi、Elisa Haatainen、Andrew Root

  DOI：10.1021/ac980699f

  日期：1999.1.1

  A high-performance liquid chromatographic (HPLC) method is described for the quantitative determination of some aliphatic aldehydes and beta-hydroxyaldehydes as their 2,4-dinitrophenylhydrazone derivatives. A method is described for the preparation of derivatives for those beta-hydroxyaldehydes where no reference compounds of known purity are available. The detection limit of the method was 4.3-21

  描述了一种高效液相色谱（HPLC）方法，用于定量测定某些脂肪族醛和β-羟基醛的2,4-二硝基苯基hydr衍生物。描述了一种用于制备那些β-羟基醛的衍生物的方法，其中没有已知纯度的参考化合物可用。该方法的检测限为4.3-21.0杯/升，取决于醛。
• METHOD FOR DETECTING ALDEHYDE AND KETONE BY USING THIN LAYER CHROMATOGRAPHY
  申请人：LG CHEM, LTD.

  公开号：EP3686593A1

  公开（公告）日：2020-07-29

  The present invention relates to a method for simultaneously qualitatively and quantitatively analyzing aldehyde and/or ketone compounds in a short time using an optimal TLC plate, proportion of developing solvent, sample amount, and the like. By providing the optimal conditions for using TLC, the analysis result equivalent to a conventional analysis result can be obtained in a shorter time.

  本发明涉及一种利用最佳 TLC 板、显影溶剂比例、样品量等在短时间内同时定性和定量分析醛和/或酮化合物的方法。通过提供使用 TLC 的最佳条件，可在较短时间内获得与传统分析结果相当的分析结果。
• Synthesis of analogs of 1,3-dihydroxyacetone phosphate and glyceraldehyde 3-phosphate for use in studies of fructose-1,6-diphosphate aldolase
  作者：Norbert Bischofberger、Herbert Waldmann、Tohru Saito、Ethan S. Simon、Watson Lees、Mark D. Bednarski、George M. Whitesides

  DOI：10.1021/jo00250a010

  日期：1988.7
• Self- and Cross-Aldol Condensation of Propanal Catalyzed by Anion-Exchange Resins in Aqueous Media
  作者：Sang-Hyun Pyo、Martin Hedström、Stefan Lundmark、Nicola Rehnberg、Rajni Hatti-Kaul

  DOI：10.1021/op200004p

  日期：2011.5.20

  Carbon-carbon bond formation using strong and weak anion-exchange resins as green catalysts for self- and cross-aldol condensation of propanal in aqueous media was investigated. The reaction pathway followed the route of aldol condensation to a beta-hydroxy aldehyde and dehydration to an alpha,beta-unsaturated aldehyde. The resulting products were further converted to hemiacetal, and/or acetal moieties, which were confirmed by FT-IR and NMR. In self-condensation using strong anion-exchange resin, 97% conversion of propanal was achieved with 95% selectivity to 2-methyl-2-pentenal within 1 h using 0.4 g/mL resin at 35 degrees C. The conversion and selectivity using weak anion exchanger was lower. During cross-aldol condensation of propanal with formaldehyde, 3-hydroxy-2-methyl-2-hydroxymethylpropanal was obtained as the main product through first and second cross-condensation followed by hydration reaction in acidic aqueous conditions. The strong anion-exchange resin provided maximal propanal conversion of 80.4% to the product with 72.4% selectivity after 7 h reaction at 35 degrees C and resin concentration of 1.2 g/mL. Using weak anion-exchange resin, the optimal conversion of propanal was 89.9% after 24 h at 0.8 g/mL resin and 35 degrees C, and the main product was 3-hydroxy-2-methylpropanal by first cross-aldol condensation along with relatively minor amounts of methacrolein and 3-hydroxy-2-methyl-2-hydroxymethylpropanal.
• Saprygina; Zlot-skii; Rakhmankulov, Journal of applied chemistry of the USSR, 1987, vol. 60, # 4 pt 2, p. 862 - 866
  作者：Saprygina、Zlot-skii、Rakhmankulov

  DOI：——

  日期：——