dimethylaminoethyldimethylammonium trifluoromethanesulfonate | 1236158-28-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: dimethylaminoethyldimethylammonium trifluoromethanesulfonate
• 英文别名: [temeda][TfO]
• CAS: 1236158-28-3
• 化学式: CHF₃O₃S*C₆H₁₆N₂
• 分子量: 266.285
• InChiKey: DUIOMOKAVMULFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.85
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  sodium iodide 、 tin(II) iodide 、 dimethylaminoethyldimethylammonium trifluoromethanesulfonate 以 丙酮 为溶剂， 生成 、
  参考文献：
  名称：

  Iodostannate mit polymeren Anionen: (Me3PhN)4∞2[Sn3I10], [Me2HN-(CH2)2-NMe2H]2∞1[Sn3I10] und [Me2HN-(CH2)2-NMe2H]∞2[Sn3I8]

  摘要：

  The polymeric iodostannate anions in (Me3PhN)(4 infinity)(2)[Sn3I10] (1) and [Me2HN-(CH2)(2)-NMe2H](2)-(1)(infinity)[Sn3I10] (2) consist of Sn3I12-trioctahedra, which share four common iodine atoms with adjacent units to form infinite layers in 1 and polymeric chains in 2. In the anion of [Me2HN-(CH2)(2)-NMe2H](infinity)(2)[Sn3I8] (3) distorted SnI6 octahedra sharing common edges and vertices form a two-dimensional network.(Me3PhN)(4 infinity)(2)[Sn3I10] (1): Space group C2/c (No. 15), a = 2406.9(2), b = 968.26(7), c = 2651.7(2) pm, beta = 111.775(9), V = 5735.9(8) . 10(6) pm(3); [Me2HN-(CH2)(2)-NMe2H](2 infinity)(1) [Sn3I10] (2): Space group P2(1)/n (No. 14), a = 1187.2(1), b = 1554.4(1), c = 1188.9(1) pm, beta =116.620(8), V=1961.4(3) . 10(6) pm(3); [Me2HN-(CH2)(2)-NMe2H](infinity)(2)[Sn3I8] (3). Space group P2(1)/c (No. 14), a = 1098.9(2), b = 803.93(7), c = 1571.5(2) pm, beta =102.96(1), V=1352.9(2) . 10(6) pm(3).

  DOI：

  10.1002/1521-3749(200107)627:7<1454::aid-zaac1454>3.0.co;2-7
• 作为产物：
  描述：

  四甲基乙二胺 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 20.0~68.0 ℃ 、140.0 kPa 条件下， 反应 74.0h， 生成 dimethylaminoethyldimethylammonium trifluoromethanesulfonate
  参考文献：
  名称：

  Reactivity of Ortho-Palladated Benzamides toward CO, Isocyanides, and Alkynes. Synthesis of Functionalized Isoindolin-1-ones and 4,5-Disubstituted Benzo[c]azepine-1,3-diones

  摘要：

  Aryl palladium complexes [Pd{C6H4C(O)NRR'-2}I(tmeda)] [NRR' = NH2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N',N'-tetramethylethylenediamine] are prepared by oxidative addition of the corresponding 2-iodophenylbenzamides to Pd(dba)(2) ([Pd-2(dba)(3)]center dot dba; dba = dibenzylideneacetone) in the presence of tmeda. Cationic cyclometalated derivatives [Pd{'2C,O-C6H4C(O)NRR'-2}(tmeda)]TfO (2ac) are obtained by iodide abstraction from the appropriate complex 1 with AgTfO, while the deprotonation of the amide function of 1a or 1b with KOtBu gives the neutral amidate complexes [Pd{'2C,N-C6H4C(O)NR-2}(tmeda)] [R = H (3a), Me (3b)]. Complexes 2a,b and 3a,b react with CO under mild conditions to yield phthalimide (4a) or N-methylphthalimide (4b), whereas the reactions of derivatives 1c and 2c with CO are very slow and give N-1,N-1,N-2,N-2-tetramethylphthalamide and phthalic anhydride. The reaction of 1b with 1 equiv of XyNC (Xy = 2,6-dimethylphenyl) or tBuNC affords Pd(0), (tmedaH)I, and 3-(2,6-dimethylphenylimino)-2-methylisoindolin-1-one (5b) or 3-(tert-butylimino)-2-methylisoindolin-1-one (5b'), respectively, while complex 1c reacts with 3 equiv of XyNC to give trans-[Pd{C('NXy)C6H4C(O)NMe2-2}I(CNXy)(2)] (6). The seven-membered palladacycles [Pd{'2C,O-C(X)'C(X')C6H4C(O)NRR'-2}(tmeda)]TfO [NRR' = NH2 and X = Ph, X' = Me (7a); NRR' = NHMe and X = Ph, X' = Me (7b), X = X' = Ph (8b), Et (9b), CO2Me (10b), X = CO2Me, X' = Ph (11b), X = CO2Et, X' = Ph (12b); NRR' = NMe2 and X = X' = Ph (8c), Et (9c)] are obtained from the reactions of 2ac with alkynes. Treatment of complexes 7a, 7b, 8b, and 9b with CO at room temperature gives the corresponding 2H-benzo[c]azepine-1,3-diones (14), resulting from the insertion of a molecule of CO into the PdC bond followed by a CN reductive coupling. In contrast, the reactions of 11b or 12b with CO in the presence of residual water or 2 equiv of ROH (R = Me, Et) lead to 2-methyl-3-phenylisoindolin-1-one derivatives (15), resulting from a CO insertion followed by an intramolecular aza-Michael addition of the NHMe moiety to the activated vinyl group and subsequent hydrolysis or alcoholysis of the acylPd bond. The neutral complex [Pd('2C,O-C14H13O5)(tmeda)] (18) was synthesized by reacting the cationic derivative 10b with NaOMe in MeOH. Depalladation of 18 gives (E)-4-[methoxy(methoxycarbonyl)methylene]-2-methylisoquinoline-1,3(2H,4H)-dione (19).

  DOI：

  10.1021/om4006406

文献信息

• Nonhumidified Intermediate Temperature Fuel Cells Using Protic Ionic Liquids
  作者：Seung-Yul Lee、Atsushi Ogawa、Michihiro Kanno、Hirofumi Nakamoto、Tomohiro Yasuda、Masayoshi Watanabe

  DOI：10.1021/ja102367x

  日期：2010.7.21

  In this paper, the characterization of a protic ionic liquid, diethylmethylammonium trifluoromethanesulfonate ([dema][TfO]), as a proton conductor for a fuel cell and the fabrication of a membrane-type fuel cell system using [dema][TfO] under nonhumidified conditions at intermediate temperatures are described in detail. In terms of physicochemical and electrochemical properties, [dema][TfO] exhibits high activity for fuel cell electrode reactions (i.e., the hydrogen oxidation reaction (HOR) and oxygen reduction reaction (ORR)) at a Pt electrode, and the open circuit voltage (OCV) of a liquid fuel cell is 1.03 Vat 150 degrees C C, as has reported in ref 27. However, diethylmethylammonium bis(trifluoromethane sulfonyl)amide ([dema][NTf2]) has relatively low HOR and ORR activity, and thus, the OCV is ca. 0.7 V, although [dema][NTf2] and [dema][TfO] have an identical cation ([dema]) and similar thermal and bulk-transport properties. Proton conduction occurs mainly via the vehicle mechanism in [dema][TfO] and the proton transference number (t(+)) is 0.5-0.6. This relatively low t(+) appears to be more disadvantageous for a proton conductor than for other electrolytes such as hydrated sulfonated polymer electrolyte membranes (t(+) = 1.0). However, fast proton-exchange reactions occur between ammonium cations and amines in a model compound. This indicates that the proton-exchange mechanism contributes to the fuel cell system under operation, where deprotonated amines are continuously generated by the cathodic reaction, and that polarization of the cell is avoided. Six-membered sulfonated polyimides in the diethylmethylammonium form exhibit excellent compatibility with [dema][TfO]. The composite membranes can be obtained up to a [dema][TfO] content of 80 wt % and exhibit good thermal stability, high ionic conductivity, and mechanical strength and gas permeation comparable to those of hydrated Nafion. H-2/O-2 fuel cells prepared using the composite membranes can successfully operate at temperatures from 30 to 140 degrees C under nonhumidified conditions, and a current density of 250 mA cm(-2) is achieved at 120 degrees C. The protic ionic liquid and its composite membrane are a possible candidate for an electrolyte of a H-2/O-2 fuel cell that operates under nonhumidified conditions.