2-硝基丙三醇 | 620-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 中文名称: 2-硝基丙三醇
• 英文名称: glycerol 2-nitrate
• 英文别名: propylene glycol 2-nitrate；Glycerol 2-mononitrate；glycerol mononitrate；2-mononitroglycerin；Glyceryl 2-nitrate；Glycerol-2-nitrat；Glycerol-2-nitrate；1,3-dihydroxypropan-2-yl nitrate
• CAS: 620-12-2
• 化学式: C₃H₇NO₅
• mdl: MFCD01075379
• 分子量: 137.092
• InChiKey: QYZBMMOLPVKAPU-UHFFFAOYSA-N

物化性质

• 熔点：
  54°C
• 沸点：
  251.89°C (rough estimate)
• 密度：
  1.4000
• 闪点：
  2℃
• 溶解度：
  乙腈（可溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2920909090
• WGK Germany：
  2

反应信息

• 作为反应物：
  描述：

  2-硝基丙三醇 生成 [2S-[2α,3&#x3B2(2'S*,3'S*)]]-2,2'-二(3,4-二羟基苯基)-2,2',3,3'-四氢-3',5,5',7,7'-五羟基[3,8'-联-4H-1-苯并吡喃]-4,4'-二酮
  参考文献：
  名称：

  Will, Chemische Berichte, 1908, vol. 41, p. 1120

  摘要：

  DOI：
• 作为产物：
  描述：

  [2S-[2α,3&#x3B2(2'S*,3'S*)]]-2,2'-二(3,4-二羟基苯基)-2,2',3,3'-四氢-3',5,5',7,7'-五羟基[3,8'-联-4H-1-苯并吡喃]-4,4'-二酮 在 水 作用下， 生成 2-硝基丙三醇
  参考文献：
  名称：

  Study of nitration equilibrium in the glycerin-aqueous nitric acid system. 1. Dependence of the equilibrium constants of nitration reactions on the temperature, acidity of the medium, and structure of the nitrated compound

  摘要：

  The equilibrium constants of seven sequential-parallel reactions of conversion of glycerin into glycerin trinitrate in aqueous HNO3 were measured. The effect of the acidity of the medium on the equilibrium nitration constants is correlated with processes of protonation of glycerin and its nitrates. The equilibrium nitration constants are higher for primary hydroxides than for secondary hydroxides, and they decrease in both series in going from glycerin to its dinitrates.

  DOI：

  10.1007/bf00961477

文献信息

• NO donors. Part 18: Bioactive metabolites of GTN and PETN—Synthesis and vasorelaxant properties
  作者：Kathrin Lange、Andreas Koenig、Carolin Roegler、Andreas Seeling、Jochen Lehmann

  DOI：10.1016/j.bmcl.2008.04.057

  日期：2009.6

  The vasodilators glyceryl trinitrate (GTN) and pentaerythrityl tetranitrate (PETN) are supposed to be degraded in vivo to the lower nitrates PETriN, PEDN, PEMN, 1,2-GDN, 1,3-GDN, 1-GMN, and 2-GMN. We synthesized these bioactive metabolites as reference compounds for pharmacokinetic studies. The use of HPLC-methods for monitoring the stepwise reduction of PETN to lower nitrates and the syntheses of the glyceryl dinitrates proved advantageous. Furthermore, we measured the vasorelaxant properties of all metabolites by performing organ bath experiments with porcine pulmonary arteries. In general, the vasodilator potency increases with the number of nitrate moieties in the compound. (C) 2009 Published by Elsevier Ltd.
• Study of nitration equilibrium in the glycerin-aqueous nitric acid system. 2. Changes in ?H and ?S in the nitration reaction
  作者：A. I. Kazakov、E. P. Kirpichev、G. V. Lagodzinskaya、L. P. Andrienko、N. G. Yunda、A. M. Korolev、Yu. I. Rubtsov、G. B. Manelis、L. T. Eremenko

  DOI：10.1007/bf00961478

  日期：1990.8

  The real enthalpies of seven sequential-parallel reactions of nitration of glycerin into glycerin trinitrate were found by combination of the heats of the reactions obtained by the thermochemical method and with the equation for the isobar of the chemical reaction, and the standard enthalpies of formation of glycerin nitrates were calculated with them. The difference in the enthalpies of nitration with respect to different positions in glycerin and its nitrates basically determines the difference in the corresponding equilibrium constants of the nitration reactions.
• 230. Nitric esters. Part I. Characterisation of the isomeric glycerol dinitrates
  作者：I. Dunstan、J. V. Griffiths、S. A. Harvey

  DOI：10.1039/jr9650001319

  日期：——
• Reduction of Nitroglycerin with Elemental Iron:  Pathway, Kinetics, and Mechanisms
  作者：Seok-Young Oh、Daniel K. Cha、Byung J. Kim、Pei C. Chiu

  DOI：10.1021/es0354667

  日期：2004.7.1

  Nitroglycerin (NG) is a nitrate ester used in dynamites, propellants, and medicines and is therefore a common constituent in propellant-manufacturing and pharmaceutical wastewaters. In this study we investigated the reduction of NG with cast iron as a potential treatment method. NG was reduced stepwise to glycerol via 1,2- and 1,3-dinitroglycerins (DNGs) and 1- and 2-mononitroglycerins (MNGs). Nitrite was released in each reduction step and was further reduced to NH4+. Adsorption of NG and its reduction products to cast iron was minimal. A reaction pathway and a kinetic model for NG reduction with cast iron were proposed. The estimated surface area-normalized reaction rate constants for NG and NO2- were (1.65 +/- 0.30) x 10(-2) (L(.)M(-2.)h(-1)) and (0.78 +/- 0.09) x 10(-2) (L(.)M(-2.)h(-1)), respectively. Experiments using dialysis cell with iron and a graphite sheet showed that reduction of NG to glycerol can be mediated by graphite. However, reduction of NO2- mediated by graphite was very slow. NG and NO2- were also found to reduce to glycerol and NH4+ by Fe2+ in the presence of magnetite but not by aqueous Fe2+ or magnetite alone. These results indicate that in a cast iron-water system NG may be reduced via multiple mechanisms involving different reaction sites, whereas nitrite is reduced mainly by iron and/ or adsorbed Fe2+. The study demonstrates that iron can rapidly reduce NG to innocuous and biodegradable end products and represents a new approach to treat NG-containing wastewaters.
• Laufen; Leitold, Arzneimittel-Forschung/Drug Research, 1988, vol. 38, # 1, p. 103 - 105
  作者：Laufen、Leitold

  DOI：——

  日期：——