N,N'-二甲基-N,N'-二亚硝基乙二胺 | 13256-12-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N'-二甲基-N,N'-二亚硝基乙二胺
• 英文名称: 1,2-bismethylnitrosaminoethane
• 英文别名: N,N'-dimethyl-N,N'-dinitroso-ethylenediamine；N,N'-Dimethyl-N,N'-dinitroso-aethylendiamin；N,N'-Dimethyl-N,N'-dinitroso-1,2-diamino-aethan；N,N'-dimethyl-N,N'-dinitro-ethylendiamine；2,5-Dinitroso-2,5-diazahexan；Dimethyldinitrosoethylenediamine；N-methyl-N-[2-[methyl(nitroso)amino]ethyl]nitrous amide
• CAS: 13256-12-7
• 化学式: C₄H₁₀N₄O₂
• 分子量: 146.149
• InChiKey: YHIARNFLMZPJGR-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  265.75°C (rough estimate)
• 密度：
  1.3494 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 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：
  65.3
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N,N'-二甲基-N,N'-二亚硝基乙二胺 在 palladium on activated charcoal 氢气 作用下， 生成 1-methyl-1-[2-(1-methylhydrazino)ethyl]hydrazine
  参考文献：
  名称：

  Gol'din,G.S. et al., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 1644 - 1648

  摘要：

  DOI：
• 作为产物：
  描述：

  亚硝基二甲胺 生成 N,N'-二甲基-N,N'-二亚硝基乙二胺
  参考文献：
  名称：

  1, 4, 5, 6-Tetrahydro-?-tetrazin-Derivate

  摘要：

  1, 4, 5, 6‐Tetrahydro‐ν‐tetrazin‐DerivateThe title compounds 2 and 13 are readily available from α‐lithiated N‐alkyl‐nitrosoamines 1 (see Tables 1 and 2) which decompose at − 73° to yield the N‐oxides 2. The ESR. spectra of two derivatives 1 are recorded (Fig. 1), and tentative mechanisms are proposed for the head to head dimerizations (la‐ 3‐ 4‐ 5‐ 2a and Scheme 1). Coupling of lithionitrosoamines with iodine (‐6) and alternative decomposition routes of representatives of this class of organometallics with special substitution [equations (2)‐(5)] are reported.The structures of the tetrazines are established by spectroscopic data [ESCA] (Fig. 2), IR., UV., 1H‐ (cf. Fig. 9) and 13C‐NMR., PE. (Scheme 2), by an X‐ray analysis of 2a (Fig. 4‐8 and Table 3), and by the chemical reactions. The crystal structure of 2a is a twisted boat with non planar terminal nitrogen atoms which reflects the electron repulsion in the 4‐atom‐6‐electron NNNN‐system. Comparisons are made with 2‐tetrazenes, the open chain analogues of 13, wherever possible. Raney‐Ni reductions of 2 or 13 gives diamines 14 to which is assigned the d, l‐configuration through the 1H‐NMR. spectra of the aminals 7 and 15. Neither the oxides 2 nor the tetrazines 13 undergo cycloaddition reactions [equation (6) and Section 4].Compound 2a is dimerized to the bis (nitrosoamino)‐2‐tetrazene 18 by treatment with acid, ZnII, CuI or iodomethane. 2a is oxidized at nitrogen to the ethylene diamine derivative 6a (through 20, with H2O2), or at the CH2‐groups of the ring to give oxo‐N‐oxide 21 (with MnO2 or the ring contracted oxo‐tetrazoline‐N‐oxide 22 (with KMnO4).Pyrolysis or photolysis of the dimethyl tetrahydrotetrazine 13a furnishes the trimer 26 of N‐methylimine, but no diazetidine 27. Silver and mercury complexes 29 are obtained from 13a, while Cr(CO)5. THF does not furnish a complex as with azocompounds, but rather replaces N2 in 13a by CO (→ 28). Oxidation with permanganate converts 13a into the oxalic acid derivative 30 with unchanged tetrazine structure.

  DOI：

  10.1002/hlca.19780610512

文献信息

• Nitric oxide reactivity of copper(ii) complexes of bidentate amine ligands: effect of substitution on ligand nitrosation
  作者：Moushumi Sarma、Biplab Mondal

  DOI：10.1039/c2dt11082b

  日期：——

  Three copper(II) complexes with bidentate ligands L1, L2 and L3 [L1, N,N/-dimethylethylenediamine; L2, N,N/-diethylethylenediamine and L3, N,N/-diisobutylethylenediamine], respectively, were synthesized as their perchlorate salts. The single crystal structures for all the complexes were determined. The nitric oxide reactivity of the complexes was studied in acetonitrile solvent. The formation of thermally

  具有双齿配体L 1，L 2和L 3 [ L 1，N，N /-二甲基乙二胺的三个铜（II）配合物；分别合成了L 2，N，N，N /-二乙基乙二胺和L 3，N，N，N /-二异丁基乙二胺。确定了所有配合物的单晶结构。配合物的一氧化氮反应性进行了研究。乙腈溶剂。热不稳定[形成Cu II -NO]与在乙腈中的溶液的一氧化氮的复合物的反应中间体中观察到铜（还原之前II）中心铜（我）。发现减少是由于在配体的仲胺位点同时发生亚硝基化。分离并表征了所有亚硝化产物。发现单亚硝化产物和二亚硝化产物的产率之比取决于存在于配体骨架中的N-取代。
• Boyer, Joseph H.; Kumar, Govindarajulu; Pillai, T. Perumal, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1751 - 1754
  作者：Boyer, Joseph H.、Kumar, Govindarajulu、Pillai, T. Perumal

  DOI：——

  日期：——
• Gol'din,G.S. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 1177 - 1179
  作者：Gol'din,G.S. et al.

  DOI：——

  日期：——
• Schneider, Chemische Berichte, 1895, vol. 28, p. 3073
  作者：Schneider

  DOI：——

  日期：——
• BOYER J. H.; KUMAR G.; PILLAI T. P., J. CHEM. SOC. PERKIN TRANS.,(1986) N 10, 1751-1754
  作者：BOYER J. H.、 KUMAR G.、 PILLAI T. P.

  DOI：——

  日期：——