1-bromo-2-nitrosooxy-ethane | 10311-10-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-bromo-2-nitrosooxy-ethane
• 英文别名: nitrous acid 2-bromo-ethyl ester；2-Bromoethyl nitrite
• CAS: 10311-10-1
• 化学式: C₂H₄BrNO₂
• 分子量: 153.963
• InChiKey: SYZPTPSXWHUACV-UHFFFAOYSA-N

物化性质

• 沸点：
  119.8±23.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-2-nitrosooxy-ethane 在 盐酸 、 sodium perchlorate 作用下， 生成 2-溴乙醇
  参考文献：
  名称：

  Iglesias, Emilia; Garcia-Rio, Luis; Leis J. Ramon, Journal of the Chemical Society. Perkin transactions II, 1992, # 10, p. 1673 - 1679

  摘要：

  DOI：
• 作为试剂：
  描述：

  哌啶 在 1-bromo-2-nitrosooxy-ethane 、 异丙胺 作用下， 以 氯仿 为溶剂， 生成 N-亚硝基哌啶
  参考文献：
  名称：

  Nitrosation of Amines in Nonaqueous Solvents. 2. Solvent-Induced Mechanistic Changes

  摘要：

  We studied the nitrosation of amines (pyrrolidine, piperidine, diethylamine, N-methylpiperazine, N,N'-dimethylethylenediamine, and morpholine) by alkyl nitrites (2-bromoethyl nitrite or 2,2-dichloroethyl nitrite) or by N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) in the solvents chloroform, acetonitrile, and dimethyl sulfoxide (DMSO). The mechanism of nitrosation by alkyl nitrites depends on the solvent: in chloroform, all the results were in keeping with formation of a hydrogen-bonded complex between the amine and alkyl nitrite being followed by rate-controlling formation of a tetrahedral intermediate T+/- that rapidly decomposes to afford the final products; in acetonitrile, a situation intermediate between those obtaining in chloroform and cyclohexane results in the [amine] dependence of the first-order pseudoconstant k(0) being qualitatively influenced by temperature and by the identities of both the amine and the alkyl nitrite; in DMSO, the results suggest a mechanism close to the mechanism acting in water. For nitrosation by MNTS, k(0) depended linearly on [amine] in all three solvents. The Grunwald-Winstein coefficients correlating the rate constants k for nitrosation by MNTS in the chloroform, acetonitrile, DMSO, dioxane, dichloromethane, and water were l = 0.12 and m = 0.29. Correlation with the Kamlet-Abboud-Taft equation confirmed that k depends largely on the dipolarity of the solvent and, to a lesser extent, its capacity for hydrogen bonding.

  DOI：

  10.1021/jo9701896

文献信息

• Nitrosation by alkyl nitrites. Part 6. Thiolate nitrosation
  作者：Hanif M. S. Patel、D. Lyn H. Williams

  DOI：10.1039/p29900000037

  日期：——

  differs significantly from the literature value. With simple alkyl nitrites (ethyl, isopentyl, isopropyl and t-butyl) steric effects appear to be the major influences in reactivity, whereas electron-withdrawing substituents in the 2-position greatly increase the rate constants. The reactions of 2,2,2-trichloroethyl nitrite were too fast to measure at all pH values, whereas the reaction of 2,2-dichloroethyl

  以下每种硫醇在25°C的水中在6-13的pH范围内与一定范围内的亚硝酸烷基酯反应，在溶液中生成相应的亚硝酸盐：L-半胱氨酸，N-乙酰基-L-半胱氨酸，L-半胱氨酸甲酯，L-半胱氨酸乙酯，谷胱甘肽和巯基乙酸。速率常数的pH依赖性清楚地表明，反应仅通过硫醇根阴离子RS –发生。对于Ñ乙酰基大号-半胱氨酸和巯基乙酸只有一个RS -物种是可能的和定量动力学分析产率p ķ一个RSH电离的值与文献值非常吻合。对于每种剩余的硫醇，可能有两个硫醇根离子（NH 2 RS –和NH 3 RS –），所有亚硝酸烷基酯的测得的速率常数通常跟随从公开的显微图中获得的总硫醇根离子浓度（作为pH的函数）。 p K a值。通过计算机将动力学结果拟合到浓度曲线的另一种方法是产生通常与文献值相吻合的微观p K a值。L-半胱氨酸是一个例外，其中测得的（p K a）D值（对于NH 2 -RSH→NH 2 RS –）与文献值明显
• Pseudophase Approach to Reactivity in Microemulsions:  Quantitative Explanation of the Kinetics of the Nitrosation of Amines by Alkyl Nitrites in AOT/Isooctane/Water Microemulsions
  作者：L. García-Río、J. R. Leis、J. C. Mejuto

  DOI：10.1021/jp953264u

  日期：1996.1.1

  The kinetics of nitroso group transfer from 2-ethoxyethyl (EEN) and 2-bromoethyl (BEN) nitrite to the secondary amines piperazine (PIP), N-methylbenzylamine (NMBA), and morpholine (MOR) in bis(2-ethylhexyl) sulfosuccinate (AOT)/isooctane (iC(8))/water microemulsions were determined. They are explained quantitatively in terms of a model in which the reagents are distributed among the aqueous, organic, and AOT film surfactant, with the aqueous pseudophase and the surfactant film as the loci of the reaction.
• Garcia-Rio, Luis; Iglesias, Emilia; Leis, J. Ramon, Journal of the Chemical Society. Perkin transactions II, 1993, # 1, p. 29 - 37
  作者：Garcia-Rio, Luis、Iglesias, Emilia、Leis, J. Ramon、Pena, M. Elena、Rios, Ana

  DOI：——

  日期：——
• Stability and nitrosation efficiency of substitutedN-methyl-N-nitrosobenzenesulfonamides
  作者：L. Garc�a-R�o、J. R. Leis、J. A. Moreira、F. Norberto

  DOI：10.1002/(sici)1099-1395(1998100)11:10<756::aid-poc48>3.0.co;2-d

  日期：1998.10

  A series of substituted N-methyl-N-nitrosobenzenesulfonamides [2,4,6-(CH3)(3), 4-CH3O, 4-CH3, 4-Cl and 4-NO2] were synthesized. All of them transfer their nitroso group to N-methylaniline in a quantitative manner, the more reactive being those substituted with electron-withdrawing groups, thus resembling some of the known alkyl nitrites. Studies of their acid denitrosation and base-catalysed hydrolysis demonstrated that the nitrosobenzene-sulfonamides are fairly stable in aqueous media between pH 2 and 11. Their relative stability in aqueous media together with their ability to transfer the nitroso group to nucleophiles suggest their use as excellent alternatives to alkyl nitrites in both neutral and basic media. (C) 1998 John Wiley & Sons, Ltd.
• Iglesias, Emilia, Journal of Chemical Research - Part S, 1995, # 3, p. 98 - 99
  作者：Iglesias, Emilia

  DOI：——

  日期：——