B2(1,2-O2-4-MeC6H3)2 | 186790-63-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: B2(1,2-O2-4-MeC6H3)2
• 英文别名: bis(4-methylcatecholato)diborane(4)；bis(4-methylcatecholate)diborane；B2((4-Me)cat)2；5,5'-Dimethyl-2,2'-bi-1,3,2-benzodioxaborole；5-methyl-2-(5-methyl-1,3,2-benzodioxaborol-2-yl)-1,3,2-benzodioxaborole
• CAS: 186790-63-6
• 化学式: C₁₄H₁₂B₂O₄
• 分子量: 265.869
• InChiKey: BYFRSHMXUKRPCN-UHFFFAOYSA-N

物化性质

• 沸点：
  356.6±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [rhodium(I)chloride(triphenylphosphine)2]1 、 B2(1,2-O2-4-MeC6H3)2 以 二氯甲烷 为溶剂， 生成 [RhCl(BO₂C₆H₃CH₃)2(P(C₆H₅)3)2]
  参考文献：
  名称：

  Clegg, William; Lawlor, Fiona J.; Marder, Todd B., Journal of the Chemical Society, Dalton Transactions, 1998, # 2, p. 301 - 309

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chloro-5-methyl-1,3,2-benzodioxaborole 在 sodium amalgam 作用下， 以 甲苯 为溶剂， 以52%的产率得到B2(1,2-O2-4-MeC6H3)2
  参考文献：
  名称：

  四烷氧基二硼烷（4）试剂的简短合成

  摘要：

  一系列双（儿茶酚基）二硼烷（4）化合物B 2（1,2-O 2 C 6 H 4）2，B 2（1,2-O 2 C 6 H 3 Me-4）2的合成，B 2（1,2-O 2 C 6 H 2 Me 2 -3,5）2，B 2 [1,2-O 2 C 6 H 3 Bu t-4）] 2和B 2 [1,2-O 2 C 6 H 2 Bu t2 -3,5] 2，据报道。这些化合物是通过1％的钠/汞合金与相应的卤代胆硼烷反应而合成的，该卤代胆硼烷是从BCl 3或BBr 3与儿茶酚的反应中纯净形成的。在一个锅，B结合这两个步骤2 [1,2-O 2 C ^ 6 ħ 3卜吨-4）] 2，从制备的BCl 3和4-叔-butylcatechol，和B 2 [1,2-O 2 C 6 H 2 Bu t 2 -3,5] 2由3,5-二-叔丁基邻苯二酚和BBr 3（以克为单位）。双（频哪醇）二硼烷（4）不是由氯频哪一种硼烷与Na /

  DOI：

  10.1021/om0208016

文献信息

• Reaction between rhodium(iii) bisboryls and diborane(4) compounds: evidence for a ς-bond metathesis process
  作者：Todd B. Marder、Nicholas C. Norman、Craig R. Rice、Edward G. Robins

  DOI：10.1039/a606993b

  日期：——

  The rhodium bis(boryl) complex [RhCl(PPh 3 ) 2 B(cat)} 2 ] (cat = 1,2-O 2 C 6 H 4 ) reacts with the diborane(4) compounds B 2 (O 2 R) 2 O 2 R = 1,2-O 2 C 6 H 3 Me-4, 1,2-O 2 C 6 H 2 Bu t 2 -3,5 and dimethyl-L-tartrate [OCH(CO 2 Me)CH(CO 2 Me)O]} affording unsymmetrical metal bis(boryls) [RhCl(PPh 3 ) 2 B(cat)}B(O 2 R)}] and diborane(4) compounds (cat)B–B(O 2 R), one possible mechanism for which involves ς-bond metathesis.

  [RhCl(PPh3)2B(cat)}2]（cat = 1,2-O2C6H4）与二硼烷(4)化合物B2(O2R)2（O2R = 1,2-O2C6H3Me-4、1,2-O2C6H2But2-3,5以及二甲基-L-酒石酸酯[OCH(CO2Me)CH(CO2Me)O]）反应，生成非对称的金属二硼基[RhCl(PPh3)2B(cat)}B(O2R)}]和二硼烷(4)化合物(cat)B–B(O2R)，其中一种可能的机理涉及π键交换。
• Synthesis and reactivity of cobalt boryl complexes
  作者：Christopher J. Adams、R. Angharad Baber、Andrei S. Batsanov、George Bramham、Jonathan P. H. Charmant、Mairi F. Haddow、Judith A. K. Howard、Wai Han Lam、Zhenyang Lin、Todd B. Marder、Nicholas C. Norman、A. Guy Orpen

  DOI：10.1039/b516594f

  日期：——

  The reaction between [Co(PMe3)4] and B2(4-Mecat)2 (4-Mecat = 1,2-O2-4-MeC6H3) or between [Co(PMe2Ph)4] and B2(cat)2 (cat = 1,2-O2C6H4) affords the paramagnetic Co(II) bisboryl complexes [Co(PMe3)3B(4-Mecat)}2] and [Co(PMe2Ph)3B(cat)}2] respectively, both of which have been structurally characterised. ESR data and preliminary diboration and boryl transfer reactivity studies are also presented. The reaction between [CoMe(PMe3)4] and B2(cat)2 affords the Co(I) monoboryl complex [Co(PMe3)4B(cat)}].

  [Co(PMe3)4]与B2(4-Mecat)2（4-Mecat = 1,2-O2-4-MeC6H3）或[Co(PMe2Ph)4]与B2(cat)2（cat = 1,2-O2C6H4）的反应分别产生了顺磁性的Co(II)双硼酸络合物[Co(PMe3)3B(4-Mecat)}2]和[Co(PMe2Ph)3B(cat)}2]，这两种化合物的结构特征已经确定。此外，还提供了ESR数据以及初步的二硼化物和硼酰基转移反应性研究。[CoMe(PMe3)4]与B2(cat)2的反应产生了Co(I)单硼酸络合物[Co(PMe3)4B(cat)}]。
• Gold(0) Nanoparticles for Selective Catalytic Diboration
  作者：Jesus Ramírez、Mercedes Sanaú、Elena Fernández

  DOI：10.1002/anie.200800541

  日期：2008.6.27
• Bis-Catecholate, Bis-Dithiocatecholate, and Tetraalkoxy Diborane(4) Compounds:  Aspects of Synthesis and Electronic Structure
  作者：Fiona J. Lawlor、Nicholas C. Norman、Nigel L. Pickett、Edward G. Robins、Paul Nguyen、Gerry Lesley、Todd B. Marder、Jennifer A. Ashmore、Jennifer C. Green

  DOI：10.1021/ic980425a

  日期：1998.10.5

  The synthesis and characterization of a series of bis-catecholate diborane(4) compounds, B-2(1,2-O2C6H4)(2) (3), B-2(1,2-O-2-3-MeC6H3)(2) (6), B-2(1,2-O-2-4-MeC6H3)(2) (7), B-2(1,2-O-2-4-(BuC6H3)-C-t)(2) (8), B-2(1,2-O-2-3,5-(Bu2C6H2)-C-t)(2) (9), B-2(1,2-O-2-3-MeOC6H3)(2) (10), bis-ditkiocatecholate diborane(3) compounds, B-2(1,2-S2C6H4)(2) (13), B-2(1,2-S-2-4-MeC6H3)(2) (14), and tetraalkoxy diborane(4) compounds, B-2(OCH2CMe2CH2O)(2) (11) and B-2(OCMe2CMe2O)(2) (12) from B-2(NMe2)(4) (1) is described, as are the bis(NHMe2) adducts or 3 and 9, namely [B-2(1,1-O2C6H4)(2)-(NHMe2)(2)] (1) and [B-2(1,2-O-2-3,5-(Bu2C6H2)-C-t)(2)(NHMe2)(2)] (5). The latter two compounds are intermediates in thr formation of 3 and 9 from 1. Compound 1 is synthesized by reductive coupling of BCl(NMe2)(2), which in turn is prepared from reaction of BCl3 with B(NMe2)(3) in a 1:2 stoichiometry. We have also tharacterized [B2Cl4- (NHMe2)(2)] (15) formed from addition of HCl to 1 prior to complete reaction with diols, and the salt, [NH2Me2][B(1,2-O2C6H3)(2)] (16) which arises from addition of catechol to B(NMe2)(3). Thus, any B(NMe2)(3) impurity present after the preparation of 1 needs to be removed by distillation prior to reaction with alcohols. The dimer, [BCl2-(mu-NMe2)](2) (17) has also been characterized. This is formed from reaction of BCl3 with B(NMe2)(3) if a 2:1 rather than 1:2 stoichiometry is used. Photoelectron spectra of 1, 3, 8, 11, and 12 are reported along with those of the corresponding diols, catechol, 4-Bu-t-catechol, 2,2-dimethyl-1,3-propanediol. and pinacol. The ionization energies of the B-2(OR)(4) compounds follow the series 8 < 3 < 12 < 11. Replacement of O for N in the B2N4 framework increases the IE by ca. 1.65 eV, whereas the presence of an aromatic ring rather than an aliphatic chain decreases the IE by ca. 1.50 eV. The presence of electron donating Bu-t-gr oups also decreases the IE.
• A Short Synthesis of Tetraalkoxydiborane(4) Reagents
  作者：Natia R. Anastasi、Karen M. Waltz、Wimali L. Weerakoon、John F. Hartwig

  DOI：10.1021/om0208016

  日期：2003.1.1

  The synthesis of a series of bis(catecholato)diborane(4) compounds, B2(1,2-O2C6H4)2, B2(1,2-O2C6H3Me-4)2, B2(1,2-O2C6H2Me2-3,5)2, B2[1,2-O2C6H3But-4)]2, and B2[1,2-O2C6H2But2-3,5]2, is reported. The compounds have been synthesized by reaction of 1% sodium/mercury amalgam with the corresponding halocatecholboranes, which are cleanly formed from the reaction of BCl3 or BBr3 and catechol. Combining these

  一系列双（儿茶酚基）二硼烷（4）化合物B 2（1,2-O 2 C 6 H 4）2，B 2（1,2-O 2 C 6 H 3 Me-4）2的合成，B 2（1,2-O 2 C 6 H 2 Me 2 -3,5）2，B 2 [1,2-O 2 C 6 H 3 Bu t-4）] 2和B 2 [1,2-O 2 C 6 H 2 Bu t2 -3,5] 2，据报道。这些化合物是通过1％的钠/汞合金与相应的卤代胆硼烷反应而合成的，该卤代胆硼烷是从BCl 3或BBr 3与儿茶酚的反应中纯净形成的。在一个锅，B结合这两个步骤2 [1,2-O 2 C ^ 6 ħ 3卜吨-4）] 2，从制备的BCl 3和4-叔-butylcatechol，和B 2 [1,2-O 2 C 6 H 2 Bu t 2 -3,5] 2由3,5-二-叔丁基邻苯二酚和BBr 3（以克为单位）。双（频哪醇）二硼烷（4）不是由氯频哪一种硼烷与Na /