2-(dichloroamino)butane | 52615-83-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(dichloroamino)butane
• 英文别名: N,N-dichloro-2-butanamine；N,N-Dichloro-2-butanimine；N,N-dichloro-s-butylamine；sec-butyl-dichloro-amine；sec-Butyl-dichlor-amin；N.N-Dichlor-sek.-butylamin；N,N-dichlorobutan-2-amine
• CAS: 52615-83-5
• 化学式: C₄H₉Cl₂N
• 分子量: 142.028
• InChiKey: WVLVUELTZUJOMD-UHFFFAOYSA-N

物化性质

• 熔点：
  -32.5--31.5 °C
• 沸点：
  106.2-106.7 °C(Press: 15 Torr)
• 密度：
  1.116 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(dichloroamino)butane 在 硝酸 、 乙酸酐 作用下， 生成 (+/-)-sec-butyl-nitro-amine
  参考文献：
  名称：

  Smart; Wright, Canadian Journal of Research, Section B: Chemical Sciences, 1948, vol. 26, p. 286,290

  摘要：

  DOI：
• 作为产物：
  描述：

  仲丁胺 在 calcium hypochlorite 、 氨 作用下， 以 水 为溶剂， 生成 2-(dichloroamino)butane
  参考文献：
  名称：

  Direct determination of chlorination products of organic amines using membrane introduction mass spectrometry

  摘要：

  Direct analysis of organic chloramines in low concentrations in aqueous solutions is achieved by membrane introduction mass spectrometry. Tandem mass spectrometry allows structures of the chlorination products to be determined and shows that nitrogen chlorination occurs for aliphatic amines and ring chlorination for aniline. Monochlorination of aniline occurs mainly at the ortho position, while dichlorination yields 20-35% diortho and 80-65% ortho-para substitution products. Depending on the reaction conditions, the actual chlorination reagent can be chloramine, hypochlorous acid, and possibly chlorine. The high ortho chlorination yields of aniline are explained by a mechanism in which chlorination occurs first at the nitrogen atom with subsequent intramolecular rearrangement to the ortho position in analogy to rearrangement of the nitro group in N-nitro aromatic amines. Using flow injection analysis procedures, it is possible to follow in an on-line fashion reactions that yield (or remove) organic chloramines at sub parts per million levels.

  DOI：

  10.1021/ac00017a025

文献信息

• Kinetics of the formation, decomposition, and disproportionation reactions of<i>N</i>-chlorobutylamines
  作者：Juan M. Antelo、Florencio Arce、Marí C. Castro、Juan Crugeiras、Juan C. Pérez-Moure、Pilar Rodríguez

  DOI：10.1002/kin.550270709

  日期：1995.7

  AbstractThe formation ofN‐chlorobutylamines is a reaction of order one with respect to hypochlorite and amine, and order −1 with respect to OH−. Kinetic studies show thatN‐chlorobutylamines undergo decomposition in basic aqueous media, and disproportination (with formation ofN,N‐dichloramines) in acidic media, mechanisms are put forward for both these processes. © 1995 John Wiley & Sons, Inc.
• Reactions of N , N -dichloroalkylamines with solid base as studied by FTIR combined with DFT calculations
  作者：T. Egawa、M. Ito、S. Konaka

  DOI：10.1016/s0022-2860(00)00822-x

  日期：2001.1

  Products of vacuum gas-solid reactions of N,N-dichloroalkylamines with KOH have been identified by FTIR spectroscopy and DFT calculations. It has been found that the reactions consist of elimination of two Cl atoms accompanied with migration of an H atom, a ring carbon or a methyl group from the alpha -carbon to the N atom and unstable imines with a C=N double bond are formed. (C) 2001 Elsevier Science B.V. All rights reserved.
• Molecular Structure of 2-Butanimine, an Unstable Imine, as Studied by Gas Electron Diffraction Combined with MP2 and DFT Calculations
  作者：Toru Egawa、Shigehiro Konaka

  DOI：10.1021/jp004184f

  日期：2001.3.1

  The molecular structure of 2-butanimine (C(4)H-3-C(3)H-2-C(2)(-C(5)H-3)=N(1)H) was determined by means of gas electron diffraction. The sample of 2-butanimine, an unstable imine, was prepared by vacuum gas-solid reaction of N,N-dichloro-2-butanamine ((C2H5)(CH3)CH-NCl2) and KOH in a glass column. The column temperature and sample pressure were optimized by measuring FTIR spectra of the reaction products in a separate experiment. The results of MP2 and DFT calculations were used as supporting information. The coexistence of the ((E)-sp and (E)-ac conformers was assumed. The structural parameters (r(g) and angle (alpha)) obtained for the (E)-sp conformer are as follows: r(C=N) 1.285(3) Angstrom; [r(C-C)] = 1.514(2) Angstrom; [r(C-H)] = 1.113(3) Angstrom; r(N-H)=1.046 Angstrom (dependent); angleN=C-C(3)=115.8(5)degrees; angleN=C-C(5)=125.0(5)degrees; angleC-C-C(4)=115.2(12)degrees; angleC-C(4)-H=113.5(14)degrees; angleC=N-H=109.3 (assumed). Angle brackets denote averaged values, and parenthesized Values are the estimated limits of error (3 sigma) referring to the last significant digit. The dihedral angle, phi NCCC, of the (E)-ac conformer was assumed to be 117.6 degrees. The abundance of the (E)sp conformer was determined to be 60 +/- 10% at room temperature
• Direct determination of chlorination products of organic amines using membrane introduction mass spectrometry
  作者：T. Kotiaho、M. J. Hayward、R. G. Cooks

  DOI：10.1021/ac00017a025

  日期：1991.9.1

  Direct analysis of organic chloramines in low concentrations in aqueous solutions is achieved by membrane introduction mass spectrometry. Tandem mass spectrometry allows structures of the chlorination products to be determined and shows that nitrogen chlorination occurs for aliphatic amines and ring chlorination for aniline. Monochlorination of aniline occurs mainly at the ortho position, while dichlorination yields 20-35% diortho and 80-65% ortho-para substitution products. Depending on the reaction conditions, the actual chlorination reagent can be chloramine, hypochlorous acid, and possibly chlorine. The high ortho chlorination yields of aniline are explained by a mechanism in which chlorination occurs first at the nitrogen atom with subsequent intramolecular rearrangement to the ortho position in analogy to rearrangement of the nitro group in N-nitro aromatic amines. Using flow injection analysis procedures, it is possible to follow in an on-line fashion reactions that yield (or remove) organic chloramines at sub parts per million levels.
• Smart; Wright, Canadian Journal of Research, Section B: Chemical Sciences, 1948, vol. 26, p. 286,290
  作者：Smart、Wright

  DOI：——

  日期：——