benzyl(methyl)aminoboron dichloride | 33441-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl(methyl)aminoboron dichloride
• 英文别名: dichloro(benzylmethylamino)borane；Me(PhCH2)NBCl2；Benzyl-methyl-amino-dichlorboran；Methylbenzylaminodichlorboran；N-dichloroboranyl-N-methyl-1-phenylmethanamine
• CAS: 33441-75-7
• 化学式: C₈H₁₀BCl₂N
• 分子量: 201.891
• InChiKey: RWAVZCFZTAQPDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  benzyl(methyl)aminoboron dichloride 在 甲基溴化镁 作用下， 以65%的产率得到N-Methyl-benzylamino-dimethylboran
  参考文献：
  名称：

  Niedenzu, K.; Beyer, H.; Dawson, J. W., Chemische Berichte, 1963, vol. 96, p. 2653 - 2656

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基苄胺 在 三氯化硼 、 三乙胺 作用下， 生成 benzyl(methyl)aminoboron dichloride
  参考文献：
  名称：

  Niedenzu,K. et al., Chemische Berichte, 1963, vol. 96, p. 2653 - 2656

  摘要：

  DOI：

文献信息

• Stabilization of tris(trifluoromethyl)borane in complexes with primary, secondary and tertiary amines. Crystal and molecular structure of (CF3)3B·NHEt2 and (CF3)3B·NH2Et
  作者：D.J. Brauer、H. Bürger、F. Dörrenbach、B. Krumm、G. Pawelke、W. Weuter

  DOI：10.1016/0022-328x(90)87281-h

  日期：1990.3

  by-products in the preparations of II and VI, respectively. Reactions of I, II and VII with KOH yield the corresponding salts K[(CF3)3B·NMe2] (IX), K[(CF3)3B·NEt2] (X) and K[(CF3)3B·NHEt] (XI). IX and X react with CH3I, CH3OSO2CF3 and allyl bromide to yield the tertiary amine adducts (CF3)3B·NR1R2R3, R1R2R3Me (XII), R1R2Me, R3C3H5 (XIII), R1R2Et, R3Me (XIV), R1R2Et, R3C3H5 (XV). The structure

  各种加合物（CF 3）3 ·B·NHR 1 - [R 2未知游离路易斯酸的三（三氟甲基）硼烷与仲胺已被选自Cl制备2 BNR 1 - [R 3通过与亲核三氟甲基化和随后的质子化，R 1 R 2 Me（I）中，R 1 R 2 Et（II）中，R 1 + R 2 C 5 ħ 10（III）中，R 1 R 2 cyclo-C 6 H ^ 11（IV）中，R 1 我，R 2CH 2博士（V）中，R 1 Me，R 2 t卜（VI）。伯胺衍生物（CF 3）3 ·B·NH 2 - [R 1，R 1 Et（VII）和Me（VIII），已经分离作为副产物在分别II和VI的制剂。I，II和VII与KOH的反应生成相应的盐K [（CF 3）3 B·NMe 2 ]（IX），K [（CF 3）3 B·NEt 2 ]（X）和K [（CF 3）3 B·NHEt]（XI）。IX和X与CH 3 I，CH
• The first 1,3,2-diazabora-[3]ferrocenophanes – molecular structures and dynamic behaviour in solution
  作者：Bernd Wrackmeyer、Elena V. Klimkina、Heidi E. Maisel、Wolfgang Milius、Max Herberhold

  DOI：10.1016/j.ica.2003.09.039

  日期：2004.4

  Abstract Dilithiated 1,1′-bis(trimethylsilylamino)ferrocene (1) reacts with aminoboron dihalides (2) X2B-N(R′)R [X=Br, R′=R=Et (2a); X=Cl, R′=Me, R=CH2Ph (2b), X=Cl, R′=Et, R=Ph (2c)] to give 2-amino-1,3,2-diazabora-[3]ferrocenophanes (3a–c) for the first time. The steric constraints exerted by the [3]ferrocenophane unit and the presence of the N-SiMe3 groups cause rather different B–N bonding situations

  摘要二片化的1,1'-双（三甲基硅烷基氨基）二茂铁（1）与氨基硼二卤化物（2）反应X2B-N（R'）R [X = Br，R'= R = Et（2a）; X = Cl，R'= Me，R = CH2Ph（2b），X = Cl，R'= Et，R = Ph（2c）]产生2-氨基-1,3,2-二氮杂硼烷-[3]二茂铁（3a–c）第一次。在这些三（氨基）硼烷中，[3]二茂铁硼烷单元施加的空间约束和N-SiMe3基团的存在会导致完全不同的B–N键合情况。硼原子可以在三个氮原子之间进行BN（pp）π键的选择：在3a和3b的情况下，它分别比NE-SiMe3基团更喜欢NEt2和N（Me）CH2Ph基团，而在在图3c中，N（Et）Ph基团似乎是较弱的π供体。这可以从对3a和3c进行的X射线结构分析以及3a-3c的低温1H，13C和29Si NMR光谱得出结论。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.4, 4.9.3, page 181 - 204
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.4, 4.4.2.3.3, page 126 - 130
  作者：

  DOI：——

  日期：——
• (Dimethylamino)borylene and Related Complexes of Electron-Rich Metal Fragments: Generation of Nucleophile-Resistant Cations by Spontaneous Halide Ejection
  作者：David A. Addy、Nicholas Phillips、Glesni A. Pierce、Dragoslav Vidovic、Tobias Krämer、Dibyendu Mallick、Eluvathingal D. Jemmis、Gill Reid、Simon Aldridge

  DOI：10.1021/om201144e

  日期：2012.2.13

  Spontaneous halide ejection from a three-coordinate Lewis acid has been shown to offer a remarkable new route to cationic metal complexes featuring a linear, multiply bonded boron-donor Ligand. The exploitation of electron-rich [CpM(PR3)(2)] fragments within boryl systems of the type LnMB(hal)NR2 leads to the spontaneous formation in polar solvents of chemically robust borylene complexes, [LnM(BNR2)](+), with exceptionally low electrophilicity and short M-B bonds. This is reflected by M-B distances (ca. 1.80 angstrom for FeB systems) which are more akin to alkyl-/aryl-substituted borylene complexes and, perhaps most strikingly, by the very low exothermicity associated with the binding of pyridine to the two-coordinate boron center (Delta H = -7.4 kcal mol(-1), cf. -40.7 kcal mol(-1) for BCl3). Despite the strong pi electron release from the metal fragment implied by this suppressed reactivity and by such short M-B bonds, the barrier to rotation about the Fe=B bond in the unsymmetrical variant [CpFe(dmpe)(BNC6H4OMe-4}Me)](+) is found to be very small (ca. 2.9 kcal mol(-1)). This apparent contradiction is rationalized by the orthogonal orientations of the HOMO and HOMO-2 orbitals of the [CpML2](+) fragment, which mean that the M-B pi interaction does not fall to zero even in the highest energy conformation.