cas 110-51-0, Borane-pyridine complex | Articles data

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Substitution of the laser borane: Anti -B18H22 with pyridine: A structural and photophysical study of some unusually structured macropolyhedral boron hydrides
Reaction of anti-B18H221 with pyridine in neutral solvents gives sparingly soluble B16H18-3′,8′-Py23a as the major product (ca. 53%) and B18H20-6′,9′-Py22 (ca. 15%) as the minor product, with small quantities of B18H20-8′-Py 4 (ca. 1%) also being formed. The three new compounds 2, 3a and 4 are characterized by single-crystal X-ray diffraction analyses and by multinuclear multiple-resonance NMR spectroscopy. Compound 2 is of ten-vertex nido:ten-vertex arachno two-atoms-in-common architecture, long postulated for a species with borons-only cluster constitution, but previously elusive. Compound 3a is of unprecedented ten-vertex nido:eight-vertex arachno two-atoms-in-common architecture. The single-crystal X-ray diffraction analysis for the picoline derivative B16H18(NC5H4Me)23b, similarly obtained, is also presented. B18H20Py 4 is also previously unreported but is of known ten-vertex nido:ten-vertex nido two-atoms-in-common architecture of anti configuration, but now with the pyridine ligand positioned differently to other reported examples of B18H20L compounds. Factors behind the remarkably low solubility of 3a and 3b are elucidated in terms of electrostatic potential (ESP) calculations, polarity, and van der Waals complementarities. In view of contemporary developing high interest in the fluorescent properties of macropolyhedral boron-containing species, a detailed assessment of the photophysical characteristics of 3a and 4 is also presented. In contrast to the thermochromic fluorescence of 2 (from 620 nm brick-red at room temperature to 585 nm yellow at 8 K, quantum yield 0.15), compound 3a is only weakly phosphorescent in the yellow region (590 nm, quantum yield 0.01), whereas compound 4 exhibits no luminescence. The far more photoactive nature of compound 2 is associated with S1 excited-state minima structures that differ from each other only by the relative rotational positions of the pyridine substituents on its disubstituted ten-vertex {arachno-B10Py2}-subcluster. The wavelength and relative intensity of fluorescence from these structures depends on the rotational positions of the pyridine ligands, which in turn are influenced by temperature and/or rotational inhibition in the solid-state.
Londesborough, Michael G. S.,Dolansky, Ji?í,Jelínek, Tomá?,Kennedy, John D.,Císa?ová, Ivana,Kennedy, Robert D.,Roca-Sanjuán, Daniel,Francés-Monerris, Antonio,Lang, Kamil,Clegg, William
p. 1709 - 1725
(2018)
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Reactions of the Octahydrotriborate(1-) Anion, -, with Some Complexes of Cobalt(I), Cobalt(II), Rhodium(I), and Iridium(I), and the Characterization of the 'Borallyl' Complex III(η3-B3H7)(CO)H(PPh3)2>
The octahydrotriborate(1-) anion, -, reacts with amine and tertiary phosphine complexes of cobalt(I) and cobalt(II) halides to give arachno-triborane-ligand adducts, B3H7L, together with B2H4L2 and BH3L (where L = pyridine or tertiary phosphine).A similar reaction occurs with trans-I(CO)Cl(PPh3)2> and with I(CO)Cl(PPh3)2>.The latter complex also yields the novel 'borallyl' compound III(η3-B3H7)(CO)H(PPh3)2> which may also be described as a nido-iridatetraborane, .The spectroscopic properties and structure of this compound are discussed.The - ion does not react with I(CO)(dppe)2>+ but I(dppe)2>+ is converted into IIIH2(dppe)2>+ (dppe = Ph2PCH2CH2PPh2).
Greenwood, Norman N.,Kennedy, John D.,Reed, David
p. 196 - 200
(1980)
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Chemistry of boranes. XV. Synthesis of diborane from boric oxide
A direct synthesis of diborane from boric oxide has been achieved by hydrogenation of the oxide in the presence of aluminum and aluminum trichloride. Very pure diborane is obtained from this reaction in 40-50% conversions at temperatures above 150° and hydrogen pressures of 750 atm. This hydrogenation is believed to proceed through an aluminum chlorohydride intermediate. Amine boranes, aminoboranes, and borazines were obtained directly from boric oxide when the hydrogenation was effected in the presence of secondary or tertiary alkylamines.
Ford,Kalb,Mcclelland,Muetterties
p. 1032 - 1035
(1964)
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Crown-ether-catalysed synthesis of amine borane and amine trideuterioborane adducts from NaBH4-NaBD4 in ether
Amine borane and amine trideuterioborane adducts have been obtained in good yield by the crown-ether-catalysed reaction of R3N*HCl with NaBH4 and NaBD4 in ether.The absence of isotopic exchange in the reaction with NaBD4 is demonstrated by IR and 11B and
Kampel, V.,Warshawsky, A.
p. 15 - 18
(1994)
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Kikugawa,Kawase
p. 1279
(1977)
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Matrix Isolation Study of the Reactions of B2H6 with Pyridine, Pyrrole, and Pyrrolidine: Spectroscopic Characterization of C4H9N*BH3 and C4H8N=BH2
The products of the pyrolytic reaction of B2H6 with pyrrole, pyrrolidine, and pyridine have been isolated in argon matrices at 14 K and characterized by infrared spectroscopy.For the B2H6/C4H9N system, complex formation was observed at temperatures between ambient and 200 deg C and the subsequent H2 elimination product H2B=NC4H8 at pyrolysis temperatures above 50 deg C.The B=N stretching frequency (1486 cm-1) and local density functional calculations done in upport of the experiments both support substantial double-bond character for the boron-nitrogen bond.The reaction of B2H6 with pyridine led to formation of the H3B*NC5H5 complex only, while copyrolysis of B2H6 with pyrrole led to no reaction even when a pyrolysis temperature of 380 deg C was employed.This result is best understood in terms of the role of thenitrogen lone pair in the aromaticity of the pyrrole ring.
Carpenter, John D.,Ault, Bruce S.
p. 11397 - 11401
(1993)
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Catalytic Reactions of Metalloporphyrins. 1. Catalytic Modifikation of Borane Reduction of Ketone with Rhodium(III) Porphyrin as Catalyst
(Octaethyl- or tetraphenylporphyrinato)rhodium(III) chloride shows an efficient catalysis in the aerobic reduction of ketone with NaBH4 in THF, BH4- + 2R1R2C=O + O2 ->2R1R2CHOH + BO2-.The initial step in the catalytic cycle is the rate-determining complexation of BH4- with RhIII porphyrin (RhIII + BH4- -> RhIII-BH4) followed by a rapid borane transfer from the adduct to ketone to give dialkoxyborane and hydridorhodium species (RhIII-BH4 + 2R1R2C=O -> Rh-H + HB(O-CHR1R2)2).In the subsequent step, the Rh-H species undergoes oxidation with O2 back to RhIII with concomitant "hydrolisis" of dialkoxyborane to alcohol (Rh-H + O2 + HB(O-CHR1R2)2 -> RhIII + 2R1R2CHOH + BO2-).Essentially, autorecycling RhIII and Rh-H act as a "borane" generator and proton source, respectively, in a catalytic manner.Furthermore, the RhIII-BH4 complex capable of transferring borane to ketone lacks what is characteristic of free borane, i.e., facile oxidation with O2 and ready hydrolysis with H2O.Thus, the present system provedes a highly efficient, catalytic modification of synthetic reactions of borane in the presence of oxygen.
Aoyama, Yasuhiro,Fujisawa, Takeshi,Watanabe, Takamichi,Toi, Hiroo,Ogoshi, Hisanobu
p. 943 - 947
(1986)
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Amine-boranes bearing borane-incompatible functionalities: Application to selective amine protection and surface functionalization
The first general open-flask synthesis of amine-boranes with inexpensive and readily available reagents, such as sodium borohydride, sodium bicarbonate, water, and the desired amines is described. Even amines bearing borane-reactive functionalities, such as alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, and nitro are well tolerated. Some of these novel amine-boranes represent stable molecules containing potentially incompatible electrophilic and nucleophilic centers in proximity. This convenient scalable synthesis provides a novel class of organic ligands for surface functionalization, as demonstrated by the formation of self-assembled layers of thiol- and alkoxysilane-bearing amine-boranes on gold and silica surfaces, respectively.
Veeraraghavan Ramachandran,Kulkarni, Ameya S.,Zhao, Yan,Mei, Jianguo
p. 11885 - 11888
(2016)
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Brown et al.
p. 325,328
(1942)
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Reactivity of Decaborane(14) with Pyridine: Synthesis and Characterization of the First 6,6-Substituted Isomer of nido-B10H14, 6,6-(C5H5N)2B10H12, and Application of (11)B-(11)B Double-Quantum NMR Spectroscopy
In the low-temperature reaction of B10H14 with C5H5N, a new product, identified as arachno-6,6-(C5H5N)2B10H12, was formed in high yield and purity. The proposed 6,6-L2B10H12 compound represents the first known report of this decaborane substitution pattern. The formation of an asymmetric 6,6-(C5H5N)2B10H12 isomer was unexpected on the basis of literature precedent describing the synthesis and structural elucidation of numerous 6,9-L2B10H12 species (where L = Lewis base). The observed reaction sequence in the formation of the 6,6-(C5H5N)2B10H12 compound proceeded through an initially observed (H.C5H5N](1+)[B10H13](1-) intermediate. In addition to the formation of the 6,6-isomer, the synthesis of the 6,9-(C5H5N)2B10H12 isomer is also reported from the reflux of nido-B10H14 in pyridine. Refluxing the 6,6-(pyridine)2B10H12 isomer in pyridine was also found to convert this isomer into the 6,9-isomer. Both isomers were characterized by (11)B NMR, FTIR, UV-vis, mass spectroscopic, and elemental analyses. The structure of the 6,6-isomer was established by 2D (11)B-(11)B COSY NMR data and by the first application of a pure phase (11)B-(11)B 2Q correlation NMR (double-quantum) experiment to the elucidation of a borane cluster framework. This latter NMR technique was very successful ingreatly simplifying the NMR assignments of the 6,6-substituted decaborane cluster species and should be a very powerful tool in cluster structure elucidation in general.
Cendrowski-Guillaume, Sophie M.,O'Loughlin, Jennifer L.,Pelczer, Istvan,Spencer, James T.
p. 3935 - 3941
(1995)
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Coordination Chemistry of Borane in Solution: Application to a STING Agonist
Equilibrium constants were determined for ligand exchange reactions of borane complexes with various oxygen, sulfur, nitrogen, and phosphorus nucleophiles in solution, and a binding affinity scale was built spanning a range of 12 orders of magnitude. While the Keq are minimally dependent on the solvent, the rate of ligand exchange varies significantly. The fastest and slowest rates were observed in THF and CDCl3, respectively. Moreover, the ligand exchange rate differs in a very broad range depending on stability of the starting complex. Binding of BH3 was found to be much more sensitive to steric factors than protonation. Comparing nitrogen bases having equal steric properties, a linear correlation of BH3 binding affinity vs. Br?nsted acidity was found. This correlation can be used to quickly estimate the BH3 binding affinity of a substrate if pKa is known. Kinetic studies suggest the ligand exchange to occur as a bimolecular SN2 reaction unless other nucleophilic species were present in the reaction mixture.
Lemaire, Sébastien,Zhdanko, Alexander,van der Worp, Boris A.
(2022/04/09)

Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- And phosphine-boranes
A highly versatile synthesis of amine-boranes via carbonyl reduction by sodium borohydride is described. Unlike the prior bicarbonate-mediated protocol, which proceeds via a salt metathesis reaction, the carbon dioxide-mediated synthesis proceeds via reduction to a monoformatoborohydride intermediate. This has been verified by spectroscopic analysis, and by using aldehydes and ketones as the carbonyl source for the activation of sodium borohydride. This process has been used to produce borane complexes with 1°-, 2°-, and 3°-amines, including those with borane reactive functionalities, heteroarylamines, and a series of phosphines.
Hamann, Henry J.,Lin, Randy,Veeraraghavan Ramachandran, P.
supporting information
p. 16770 - 16774
(2021/12/08)

Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor
Supramolecular catalysts emulate the mechanism of enzymes to achieve large rate accelerations and precise selectivity under mild and aqueous conditions. While significant strides have been made in the supramolecular host-promoted synthesis of small molecules, applications of this reactivity to chemoselective and site-selective modification of complex biomolecules remain virtually unexplored. We report here a supramolecular system where coencapsulation of pyridine-borane with a variety of molecules including enones, ketones, aldehydes, oximes, hydrazones, and imines effects efficient reductions under basic aqueous conditions. Upon subjecting unprotected lysine to the host-mediated reductive amination conditions, we observed excellent ?-selectivity, indicating that differential guest binding within the same molecule is possible without sacrificing reactivity. Inspired by the post-translational modification of complex biomolecules by enzymatic systems, we then applied this supramolecular reaction to the site-selective labeling of a single lysine residue in an 11-amino acid peptide chain and human insulin.
Morimoto, Mariko,Cao, Wendy,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean
supporting information
p. 2108 - 2114
(2021/02/06)

Synthesis of Cationic Silaamidinate Germylenes and Stannylenes and the Catalytic Application for Hydroboration of Pyridines
The N-heterocyclic germylenes and stannylenes LSi(NAr)2EX (L = PhC(NtBu)2, Ar = 2,6-iPr2C6H3; E = Ge, Sn; X = Cl, CF3SO3, BPh4) supported by the bulky silaamidinate ligand [LSi(NAr)2]- have been synthesized and fully characterized. The germylene triflate LSi(NAr)2GeOTf (3b) and dimeric borate [LSi(NAr)2Ge]2ClBPh4 (3a) enabled highly regio- and chemoselective catalytic hydroboration of pyridines and may represent the most active catalytic system for the transformation. DFT calculations disclosed that the cationic germylene [LSi(NAr)2Ge]+ with a low-lying LUMO energy initiated the catalytic process. In contrast, the analogous amidinate germylene triflates are almost inactive, indicating the silaamidinate ligand is essential for the stabilization of cationic species.
Hu, Chaopeng,Zhang, Jianying,Yang, Hao,Guo, Lulu,Cui, Chunming
supporting information
p. 14038 - 14046
(2021/09/28)

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics
The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.
García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.
supporting information

(2022/01/04)

Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones
Although transition-metal-catalyzed B-H bond insertion of carbenes into stable borane adducts has emerged as a promising method for organoborane synthesis, all the diazo compounds used to date as carbene precursors have had an electron-withdrawing group to stabilize them. Herein, we report a protocol for rhodium-catalyzed B-H bond insertion reactions of unstabilized diazo compounds generated in situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried out on a gram scale. It also enabled one-pot transformation of a carbonyl group to a boryl group enantioselectively. The B-H bond insertion products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.
Pang, Yue,He, Qiao,Li, Zi-Qi,Yang, Ji-Min,Yu, Jin-Han,Zhu, Shou-Fei,Zhou, Qi-Lin
supporting information
p. 10663 - 10668
(2018/09/06)

The role of ammonia in promoting ammonia borane synthesis
Ammonia promotes the synthesis of pure ammonia borane (AB) in excellent yields from sodium borohydride and ammonium sulfate in tetrahydrofuran under ambient conditions. An examination of the influence of added ammonia reveals that it is incorporated into the product AB, contrary to its perceived function as a catalyst or a co-solvent. Mechanistic studies point to a nucleophilic attack by ammonia on ammonium borohydride with concurrent dehydrogenation to yield AB.
Ramachandran, P. Veeraraghavan,Kulkarni, Ameya S.
p. 16433 - 16440
(2016/10/31)

Open-Flask Synthesis of Amine-Boranes via Tandem Amine-Ammonium Salt Equilibration-Metathesis
An amine-ammonium salt equilibration-metathesis sequence provides high-purity amine-boranes in excellent yields from sodium borohydride in refluxing reagent-grade tetrahydrofuran in an open flask.
Ramachandran, P. Veeraraghavan,Kulkarni, Ameya S.
supporting information
p. 5618 - 5620
(2015/06/25)

Nucleophilic displacement of ammonia from ammonia borane for the preparation of alkylamine-, pyridine- and phosphine-boranes
A near quantitative and safe preparation of a series of aliphatic amine- and phosphine-boranes from ammonia borane (AB) in refluxing THF has been achieved by exploiting the volatility of ammonia. A one-pot preparation of lithium aminoborohydrides from AB has also been described.
Veeraraghavan Ramachandran,Kulkarni, Ameya S.
p. 26207 - 26210
(2014/07/08)

Metal tetrahydroborates and tetrahydroborato metallates, 30 [1]. Alkoxo-substituted alkali metal tetrahydroborates: Studies in solution and structures in the solid state
Reactions of MBH4 (M = Li, Na, K) with tBuOH, Ph3COH, PhOH, F5C6OH, and 2,4-tBu2C6H 3OH in THF in a 1:1 ratio were followed by 11B NMR spectroscopy. No M[H2B(OR)2] species could be detected, but minor amounts of M[H3BOR] and larger amounts of M[HB(OR) 3]. In the reaction of LiBH4 with 2,4-tBu 2C6H3OH also a fair proportion of (RO) 2BH was generated. The perfluorophenolato borane (F5C 6O)2BH·THF was prepared from the phenol and BH 3·THF in THF solution. It is unstable to disproportionation. Compound (C6F5O)3B·THF was isolated and its crystal structure determined. Reaction of LiBH4 with F 5C6OH in hexane generated a solid that proved to be Li[H2B(OC6F5)2]. It is unstable in THF. On the other hand, 2,2′-dihydroxydiphenyl in the presence of secondary amines reacts to give Li[C12H8O 2B(NR2)2] (3-5). Li[B(O2C 12H8)2], 2, is formed when HN(tBu)Ph is used as a secondary amine. The unstable phthalatoborane H{C6H 4[C(O)O]2}BH·THF (7), is stabilized as its pyridine adduct (phth)BH·py (8). 7 reacts with 3 equivalents of LitBu to give [Li(HBtBu)3] (11), isolated as its tris(THF) solvate. Analogously, 7 reacts with LiNMePh to produce compound Li[HB(NMePh)3] (10). Similarly, 7 and NaOtBu (molar ratio 1:3) give access to Na[HB(OtBu) 3] (9). In attempts to grow single crystals, specimens resulting from a hexane solution showed that partial hydrolysis has occurred to give Na[HB(OtBu)3]·Na[(tBuO)2BO]·Na[tBuOB(O)H], which crystallizes as a centrosymmetric dimer. While catecholborane when treated with LitBu in THF and DME gave access to (dme)2Li[catB(tBu) 2], 12 (dme)2, several compounds were observed when Li piperidide was used as nucleophile. Amongst these, the most interesting one was (dme)(THF)Li2(cat)(catBH), 13 (dme)THF, the crystal structure of which was determined. In all cases where the borate species carried OR groups the O atoms of the RO or PhO group coordinate with the alkali metal cation. DFT calculations for the series of anions H4-nBXn- showed that HBX3- is the most stable species for X = F, OH, NH2. This confirms experimental results.
Knizek, J?rg,N?th, Heinrich,Warchhold, Markus
p. 1079 - 1093
(2008/09/19)

Synthesis of N-substituted derivatives of the hypho-(amine)(amino)B8H11 system
The chemistry of the hypho-(amine)(amino)B8H11 system is developed by the synthesis of several derivatives by three routes. [(Et2HN)B8H11NEt2] (4), characterised by single-crystal X-ray work, is prepared from the reaction between B9H13(SMe2) and Et2NH. Methylation of [(EtH2N)B8H11NHEt] (1) using NaH and MeI gives, successively, [(EtMeHN)B8H11NHEt] (5), [(EtMe2N)B8H11NHEt] (6) and [(EtMe2N)B8H11NMeEt] (7). Alternatively, a displacement reaction with NHEt2 on (1) or on [(MeH2N)B8H11NHMe] (2) yields [(Et2HN)B8H11NHEt] (8) or [(Et2HN)B8H11NHMe] (9), and a displacement on (1) with pyridine yields [(C5H5N)B8H11NHEt] (10). Phosphine-containing derivatives [(Ph3P)B8H11NHEt] (11) and [(PhMe2P)B8H11NHEt] (12) can be isolated from interaction of (1) with PPh3, [RhCl(PPh3)3] or [PtCl2(PMe2Ph)2].
D?rfler, Udo,Bauer, Claudia,Gabel, Detlef,Rath, Nigam P.,Barton, Lawrence,Kennedy, John D.
p. 215 - 222
(2007/10/03)

Metal tetrahydridoborates and tetrahydridoborato metalates. 23.1 amine solvates of lithium and sodium tetrahydridoborate
A series of amine solvates of LiBH4 and NaBH4 have been prepared and characterized by IR and NMR spectroscopy as well as by X-ray single-crystal structure determinations. LiBH4 crystallizes from pyridine as LiBH4·3(py), 1, in which the BH4 anion acts as a bidentate ligand. However, in the structure of LiBH4·3py*, 2 (py* = p-benzylpyridine), a tridentate But group is observed. In contrast, LiBH4·2(coll), 3 (coll = 2,4,6-trimethylpyridine, collidine), possesses only a bidentate tetrahydridoborate group, while a tridentate BH) group is present in monomeric LiBH4·PMDTA, 4 (PMDTA = pentamethyldiethylenetriamine). In contrast, NaBH4·PMDTA, 6, is dimeric in the solid state: three of the four H atoms of each BH4 group coordinate to the Na atoms; two form a double bridge to two Na atoms while the third one is bonded only to one Na center. LiBH4·TMTA, 5 (TMTA = trimethylhexahydrotriazine), is also dimeric; however, only two of the nitrogen atoms of the TMTA ligand coordinate to Li. The BH4 groups bridge the two Li centers each with one H atom coordinating to two Li atoms, and two bind to a single Li atom. A totally different situation exists for NaBH4·TMTCN, 7 (TMTCN = trimethyltriazacyclononane), which is tetrameric in the crystal. Only one hydrogen atom of the BH4 group functions as a hydride bridge and binds to three Na centers. The molecule contains a Na4B4 heterocubane core. Thus, the different modes of the interaction of the BH4 groups with the alkali metal atoms are determined by the number of donor atoms from the neutral amine ligand and the size of the cation. No definitive conclusion as to the structure of the amine solvates can be derived from IR and/or 11B NMR spectra for the solution state. The crystallographic data are as follows. 1: a = 10.9939(5) A?, b = 9.9171(4) A?, c = 14.8260(8) A?, β= 94.721(3)°, V = 1611.0(1) A?3, monoclinic, space group P2(1)/n, Z = 4, R1= 0.0823. 2: a = 10.121(1) A?, b = 12.417(2) A?, c = 13.462(3) A?, α = 83.189(2)°, β = 86.068(3)°, γ = 69.166(4)°, V = 1369.3(5) A?3, triclinic, space group P1?, Z = 2, R1 = 0.0689. 3: a = 28.527(3) A?, b = 10.858(1) A?, c = 11.319(1) A?, V = 3505.7(6) A?3, orthorhombic, space group Fdd2, Z = 8, R1 = 0.0502. 4: a = 7.591(3) A?, b = 15.325(6) A?, c = 8.719(4) A?, β = 99.80(2)°, V = 999.5(7) A?3, monoclinic, space group P2(1)/c, Z = 4, R1 = 0.0416. 5: a = 14.68(1) A?, b = 11.830(7) A?, c = 16.960(8) A?, V = 2946(3) A?, orthorhombic, space group P2(1)2(1)2(1), Z = 8, R1 = 0.0855. 6: a = 9.993(2) A?, b = 10.008(3) A?, c = 14.472(4) A?, β= 93.55(2)°, V = 1444.6(7) A?3, monoclinic, space group P2(1)/n, Z = 4, R1 = 0.0455. 7: cubic, a = b = c = 13.859(5) A?, V = 2662(2) A?3, cubic, space group I4?3m, Z = 8, R1 = 0.0871.
Giese, Hans-Hermann,Habereder, Tassilo,N?th, Heinrich,Ponikwar, Werner,Thomas, Steffen,Warchhold, Marcus
p. 4188 - 4196
(2008/10/08)

Molecular addition compounds. 9. Effect of structure on the reactivities of representative borane-amine complexes in typical reactions such as hydrolysis, hydroboration, and reduction
A number of borane-amine complexes with widely different structural features in the amine portion was prepared and their reactivities toward typical B-H reactions, such as hydrolysis, hydroboration of 1-octene, and reduction of cyclohexanone, were studied. BH3-amine complexes containing an N-phenyl group are hydrolyzed by neutral hydroxylic solvents, while others require a strong acid medium for the hydrolysis. In hydroboration, BH3-N-phenylamine complexes react rapidly with 1-octene in THF at 25°C, while all other types require refluxing THF or toluene for reaction. Again, BH3-N-phenylamine complexes reduce cyclohexanone in THF at 25°C at reasonable rates, while others require acetic acid solvent or mineral or Lewis acids to achieve the desired reduction. Thus, among such borane-amine addition compounds, the BH3-N-phenylamines emerge as unique hydroborating and reducing agents. The results of the present study provide insights into the mechanisms of the hydroboration and reduction reactions. The rates of hydroboration of alkenes with BH3-amine complexes are inversely related to the stability of the adduct, arguing for a prior dissociation of the adduct, followed by the reaction of BH3 with the alkene. The reduction of cyclohexanone with BH3-amine complex in THF proceeds by an analogous dissociation mechanism. In acetic acid or in the presence of mineral or Lewis acids, a bimolecular attack of the BH3-amine complex on the protonated carbonyl group has been considered to be the most viable mechanistic pathway. However, this does not account for the effect of acids on hydrolytic behavior. Consequently, caution is urged in considering possible interpretation of the acid-enhanced reactions of amine-boranes.
Brown, Herbert C.,Murray, Leo T.
p. 2746 - 2753
(2008/10/08)

The Reaction between Sulfur or Carbon Disulfide Respectively, and Sodium Borohydride in Amines. Two New Methods for the Preparation of Alkylamine Boranes, R3-nHnN-BH3
Sodium borohydride reacts with sulfur in ammonia, primary, secondary or tertiary amines with hydrogen evolution to give the corresponding amine boranes, R3-nHnN-BH3.The reaction of sodium borohydride with carbon disulfide in the presence of a tertiary amine yields compounds R3N-BH3.The formulation of these reactions has been established by 11B and 1H NMR. - Keywords: Amine Boranes
Binder, Herbert,Diamantikos, Wassilios
p. 203 - 207
(2007/10/02)

Hexamethylenetetramine-borane adducts
The four possible borane adducts of hexamethylenetetramine (hexamine) were prepared, three of which being hitherto unknown. Synthesis and purification procedures were worked out so that pure samples were available for chemical studies. Pyrolysis of the tetraadduct when controlled proceeded with rearrangement by hydride migration to form dimethylaminoborane derivatives. The adducts were not amenable to borane cation formation; those two cations eventually prepared, (CH2)6N4BH2py+ and (CH2)6N4BH2P(CH3) 3+, were not very stable.
Riley, Marvin D.,Miller, Norman E.
p. 707 - 710
(2008/10/08)

Lewis acid-base reactions among dimethylaminoboron hydrides
The dimethylaminoboron hydrides related to diborane form a system of Lewis acids and bases, the interconversion of which can be described as addition or removal of BH3 groups. The first-stage action of [(CH3)2N]3B to remove BH3 from (CH3)3N· BH3 is not appreciably reversible, but the second stage, in which [(CH3)2N]2BH and (CH3)3N·BH3 form 2(CH3)2NBH2 and (CH3)3N, is reversible with ΔF° = 13.95 - 0.0330T kcal. Our base·(CH3)2NB2H5 adducts show vapor-phase dissociation increasing in the order pyridine, (CH3)3P, 2-methylpyridine, (CH3)3N; and (CH3)2PH·(CH3)2NB 2H5 fails to exist in the vapor phase but forms a partially dissociated liquid. All five of these adducts on heating react further to form (CH3)2NBH2 and base·BH3, without reversal. The adducts CH3PH2·(CH3)2NB 2H5 and (CH3)2PCF3·(CH3) 2NB2H5 are still more easily dissociated, and their conversion to BH3 complexes and (CH3)2NBH2 is reversible with ΔF° = 10.61 - 0.0268T and 6.59 - 0.01943T kcal., respectively. It is quite apparent that diborane is a much stronger Lewis acid than (CH3)2NB2H5.
Burg, Anton B.,Sandhu, Jagtar S.
p. 1467 - 1472
(2008/10/08)

Water‐promoted, open‐flask synthesis of amine‐boranes: 2‐methylpyridine‐borane (2‐picoline‐borane)
A procedure yielding 2‐methylpyridine‐borane as a white solid is presented. Sodium borohydride and powdered sodium bicarbonate are added into a single‐necked, air‐dried round‐bottomed flask with a Teflon‐coated, egg‐shaped magnetic stir bar. A discussion on amine‐boranes, reductive amination with aldehyde bisulfites and carbohydrates, and metathesis of metal borohydrides with alkylammonium salts concludes the chapter.
Kulkarni, Ameya S.,Ramachandran, P. Veeraraghavan
(2018/11/21)

Chemical Properties

Appearance/Colour :clear to slightly hazy colorless to amber liquid
Melting Point: 10-11 °C(lit.)
Boiling Point: 1575 ℃
Flash Point:21 °C
Density: 0.92 g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 22.8mmHg at 25°C
Refractive Index: 1.530 - 1.532
Sensitive: Air & Moisture Sensitive
BRN: 3674913
PSA: 3.88000
LogP: -0.89740

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Chemical Properties

Appearance/Colour :clear to slightly hazy colorless to amber liquid

Melting Point: 10-11 °C(lit.)

Boiling Point: 1575 ℃

Flash Point:21 °C

Density: 0.92 g/cm³

Storage Temp.:2-8°C

Vapor Pressure: 22.8mmHg at 25°C

Refractive Index: 1.530 - 1.532

Sensitive: Air & Moisture Sensitive

BRN: 3674913

PSA: 3.88000

LogP: -0.89740

Global suppliers and manufacturers of 110-51-0total 106 suppliers on LookChem

Article Database

110-51-0

Articles about 110-51-0Total 25 be found

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Chemical Properties

Appearance/Colour :clear to slightly hazy colorless to amber liquid

Melting Point: 10-11 °C(lit.)

Boiling Point: 1575 ℃

Flash Point:21 °C

Density: 0.92 g/cm3

Storage Temp.:2-8°C

Vapor Pressure: 22.8mmHg at 25°C

Refractive Index: 1.530 - 1.532

Sensitive: Air & Moisture Sensitive

BRN: 3674913

PSA: 3.88000

LogP: -0.89740

Global suppliers and manufacturers of 110-51-0total 106 suppliers on LookChem

Density: 0.92 g/cm³