The 1,2-isomer forms first upon the reaction of decarborane and acetylene. ( N.B. A series of seven BODIPYs functionalized with ortho-carborane groups at the 8(meso) or 3/5(α) position were synthesized and characterized by NMR, HRMS, HPLC, and in the cases of 2b and 5b, by X-ray analysis.The BODIPYs exhibited low dark toxicity and phototoxicity toward human glioma T98G cells, and their cellular uptake varied significantly, with 5b accumulating the most and 7 the least. : The carboranes are electron-deficient molecules in which the bonding electrons are shared by three or more atoms. Due to it being extremely strong acid, it is categorized as "Super Acid". Electron deficient boron cage compounds with one or more carbon atoms as a ligand in the borane framework. Med. Carboryne, or 1,2-dehydro-o-carborane, is an unstable derivative of ortho-carborane with the formula B 10 C 2 H 10. Carborane acid was first discovered and synthesized by Professor Christopher Reed and his colleagues in 2004 at the University of California, Riverside. Carborane has a pH value of -18. It converts quantitatively to . The general formula of carboranes is represented by C2BnHn + 2, in which n is an integer; carboranes with n ranging from 3 to 10 have been characterized. Hazard Codes: Xn. Carborane has a pH value of-18. A carboryne compound was first generated in 1990 starting from o-carborane. The compound resembles and is isolobal with benzyne. The generic structure of a carborane acid. The previous record-holder, fluorosulphuric acid, is so corrosive that it would . Computed by OEChem 2.1.5 (PubChem release 2019.06.18) 2.2 Molecular Formula C4H2B10O4 Computed by PubChem 2.1 (PubChem release 2019.06.18) 2.3 Other Identifiers 2.3.1 CAS 50571-15-8 European Chemicals Agency (ECHA) 2.3.2 European Community (EC) Number 635-457- European Chemicals Agency (ECHA) 2.4 Synonyms 2.4.1 Depositor-Supplied Synonyms When heated to decomposition it emits toxic vapors of B. Ortho-carboranes are prepared by the reaction of acetylenes, including both mono and disubstituted alkynes, with B 10 H 12 L 2, which is generated, often in situ, from decaborane (B 10 H 14) and a weak Lewis base (L=CH 3 CN, RSR, R 3 N) , .Reactions are typically performed in acetonitrile or in toluene heated to . The icosahedral charge-neutral closo-carboranes, 1,2-, 1,7-, and 1,12-C 2 B 10 H 12 (respectively ortho-, meta-, and para-carborane in the informal nomenclature) are particularly stable and are commercially available. The structural geometries of various closo -carboranes and nido -carboranes are given in Tables 1 and 2, respectively. m-Carborane 98%; CAS Number: 16986-24-6; EC Number: 241-065-7; Synonyms: 1,7-Dicarbadodecaborane(12); find Sigma-Aldrich-379182 MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich carborane acids h (cxb 11 y 5 z 6 ) (x, y, z = h, alk, f, cl, br, cf 3 ) are a class of superacids, some of which are estimated to be at least one million times stronger than 100% sulfuric acid in terms of their hammett acidity function values (h 0 ≤ -18) and possess computed pk a values well below -20, establishing them as some of the strongest … Icosahedral carborane anions such as CHB11Cl11- are amongst the least coordinating, most chemically inert anions known. The monomeric form is metastable when condensed, but eventually polymerizes to give a structure with the acid proton bridging between carborane units. Because of their multicenter bonding (in which a pair of bonding electrons binds more than two atoms, as in 3-center-2-electron bonds), borane molecules were previously called "electron . The hydrogen atoms on the C2 unit in the parent o -carborane are missing. Table 1. Like pH, H 0 is a measure of acidity; lower values of H 0 mean higher protonating power. Risk Statements about 1,2-Dicarbadodecaborane (12) (CAS No.16872-09-6): R22:Harmful if swallowed. m-Carborane-9-thiol Synonym(s) : 9-Mercapto-1,7-dicarbadodecaborane (12), 1,7-Dicarba- closo -dodecaborane-9-yl-thiol Empirical Formula (Hill Notation) : C 2 H 12 B 10 S List of Superacids Acidity is indicated by the Hammett acidity function, H 0 . Decaborane, also called decaborane(14), is the borane with the chemical formula B10H14. m-Carborane 98%; CAS Number: 16986-24-6; EC Number: 241-065-7; Synonyms: 1,7-Dicarbadodecaborane(12); find Sigma-Aldrich-379182 MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich Carborane has a pH value of -18. Borane is a homologous sequence of inorganic boron-hydrogen compounds and their derivatives. Icosahedral carboranes. Moderately toxic by ingestion, inhalation, and subcutaneous routes. Prior to carborane acid's discovery, the long-standing record of "strongest acids as single isolable compounds" was held by the two superacids, fluorosulfonic acid and trifluoromethanesulfonic acid, with pK a s of −14 and −16 respectively. Carboranes larger than 14 vertexes containing only carbon and boron in the skeletal framework have not been prepared, but Zhang et al. The general formula of carboranes is represented by C2BnHn + 2, in which n is an integer; carboranes with n ranging from 3 to 10 have been characterized. 50571-15-8. The carborane acid H (CHB 11Cl 11) was shown to be monomeric in the gas phase, with the acidic proton (shown in red) bound to Cl (12) and secondarily bonded to Cl (7). The first carboranes were produced in the 1950s, but the results were not declassified and published until 1962-63. Chem., 20, 4830 (2012); H (carborane), are superacids ( i.e. The degree of the acid can be judged from the fact that it can easily consume plastic and glass. Carborane acids H(CXB 11 Y 5 Z 6 ) (X, Y, Z = H, Alk, F, Cl, Br, CF 3 ) are a class of superacids, some of which are estimated to be at least one million times stronger than 100% sulfuric acid in terms of their Hammett acidity function values (H 0 ≤ -18) and possess computed pK a values well below -20, establishing them as some of the strongest known Brønsted acids.wikipedia The disclosure also provides a catalyst system (20) comprising a plurality of active catalyst complex species (34) formed by combination of a Lewis acid (24), an initiator (22) and a polymorphogenate (26 . Boranes is the name given to compounds with the formula B x H y and related anions. stability, chemical resistance, low surface energy, and electric property, fluoropolymers have been widely uti- . Carborane has a pH value of-18. The carborane superacids may be considered the world's strongest solo acid, as fluoroantimonic acid is actually a mixture of hydrofluoric acid and antimony pentafluoride. m-Carborane-1-carboxylic Acid is used as a reactant or reagent in the synthetic preparation of ortho-carbaborane indomethacin pharmacophores as selective COX-2 enzyme inhibitors. o-Carborane-1-carboxylic Acid is a versatile reactant used in the iridium catalyzed regioselective cage boron alkenylation via direct cage B-H activation. The compound resembles and is isolobal with benzyne. In this work, we report the synthesis of the nido-carborane-substituted ruthenium complexes and the substituent effects of nido-carboranes on the optical properties. Carboryne, or 1,2-dehydro-o-carborane, is an unstable derivative of ortho-carborane with the formula B 10 C 2 H 10. The compound H (CHB 11 Cl 11) is a superacid, forming an isolable salt with protonated benzene, C 6 H + 7. Russell N. Grimes, in Carboranes (Third Edition), 2016 11.5.2 15- to 20-Vertex Carboranes. Because of their multicenter bonding (in which a pair of bonding electrons binds more than two atoms, as in 3-center-2-electron bonds), borane molecules were previously called "electron . Product Name: M-carborane CAS: 16986-24-6 The Molecular formula of M-carborane (CAS NO.16986-24-6): C 2 H 12 B 10 The Molecular Weight of M-carborane (CAS NO.16986-24-6): 144.23 The Molecular Structure of M-carborane (CAS NO.16986-24-6): Melting Point: 272 °C Water Solubility: insoluble Appearance: White crystalline powder or flakes ZINC169821083. stronger than 100% H SO ). o-Carborane Safety Profile. The first carboranes were produced in the 1950s, but the results were not declassified and published until 1962-63. m-Carborane-9-thiol Synonym(s) : 9-Mercapto-1,7-dicarbadodecaborane (12), 1,7-Dicarba- closo -dodecaborane-9-yl-thiol Empirical Formula (Hill Notation) : C 2 H 12 B 10 S The compound, called a carborane acid, is the first 'superacid' that can be stored in a bottle, say its creators. Many such boranes are known. It was reported last year that the carborane superacid H-(CHB 11 F 11) (see Fig. Chemsrc provides 1,2-dilithio-o-carborane(CAS#:22220-85-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. A series of seven BODIPYs functionalized with ortho-carborane groups at the 8(meso) or 3/5(α) position were synthesized and characterized by NMR, HRMS, HPLC, and in the cases of 2b and 5b, by X-ray analysis.The BODIPYs exhibited low dark toxicity and phototoxicity toward human glioma T98G cells, and their cellular uptake varied significantly, with 5b accumulating the most and 7 the least. m-Carborane-1,7-dicarboxylic acid, AldrichCPR Unlike fluorosulfuric acid and fluoroantimonic acid, the carborane acids are so noncorrosive that they may be handled with bare skin. Chemical Formula: H(CHB 11 F 11) H o value:-18 pK a value: -20. Unlike fluorosulfuric acid and fluoroantimonic acid, the carborane acids are so noncorrosive that they may be handled with bare skin. See also Azaborane Heteroborane Metallacarboranes Fluorinated carborane acid is the only acid capable of protonating CO 2 to produce [H(CO 2) 2] +. Articles of 1,2-dilithio-o-carborane are included as well. The H on the carbon in carborane is a weak acid and relatively active. A unique aspect of carborane chemistry is that the carbon and boron vertices have orthogonal reactivities. The hydrogen atoms on the C2 unit in the parent o -carborane are missing. They are also amongst the least basic, so their conjugate acids, H(carborane . Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO 3 F. It is one of the strongest acids commercially available. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. It is also used in the preparation of o-Carbaborane indomethacin pharmacophores as selective COX-2 inhibitors. The synthesis of ortho-carborane was first reported in 1963 by two groups , . Boranes are the common name for a class of synthetic boron hydrides with the formula B x H y (borane formula). Fluoroantimonic Acid Formula Fluoroantimonic acid has a chemical formula as H2FSbF6 and it is the strongest known acid with a Hammett acidity function, H0 of -28. Med. References: Scholz, M., et al. This white crystalline compound is one of the principal boron hydride clusters, both as a reference structure and as a precursor to other boron hydrides. It is easy to deproton with strong basic The structure of the polymer is shown in the formula (I), wherein the formula represents carborane group; p and q are natural numbers between 3 and 16; R1, R2, R3 and R4 are selected from hydrogen, substituted or unsubstituted C1-20 alkyl, cycloalkyl, alkenyl, alkynyl or aryl; m is a number between 0 and 100, except for 0; n is a number between . attention by solvent-free sealant and adhesive formula- . carborane, any member of a class of organometallic compounds containing carbon (C), boron (B), and hydrogen (H). The medical applications of carboranes have been explored. References: Scholz, M., et al. Molecular formulas of a few closo -carboranes and their corresponding structural geometry Table 2. 1) was synthesized and that its primacy of the strength over all other known superacids was confirmed 1.This is an extremely sensitive to moisture solid which was prepared by a treatment of the [(C 2 H 5) 3 Si-H-Si(C 2 H 5) 3][CHB 11 F 11] compound with the anhydrous HCl. A carboryne compound was first generated in 1990 starting from o-carborane. have calculated the cage geometries and stabilities of C 2 B n-2 H n species for n = 13 to 20 and conclude, interestingly, that C 2 B 15 H 17 is the most . AKOS024340907. Carborynes. Like pH, H 0 is a logarithmic scale. Acidity scale measurements indicate that H (CHB 11 Cl 11 ) is the strongest pure Brønsted acid presently known, surpassing triflic. Carborane acids are one of the strongest groups of superacids known to humans, few of which are considered to have a Hammett acidity function value as low as -18, that's more than a million times stronger acidity level than pure (100% . It is toxic and volatile, with a foul odor. The carborane superacids may be considered the world's strongest solo acid, as fluoroantimonic acid is actually a mixture of hydrofluoric acid and antimony pentafluoride. Carborane acid: H(CHB 11 X 11)-18.0: The carborane shown on the left is fluorinated; chlorinated carboranes are also superacids, but with lower acidity. The carborane superacids may be considered theworld's strongest solo acid, as fluoroantimonicacid is actually a mixture of hydrofluoric acid andantimony pentafluoride. The disclosure provides for a process and polymerization system to produce isoolefin polymers (72) utilizing polymorphogenates (16, 26) in the catalyst system to control polydispersity (MWD). m-Carborane-1,7-dicarboxylic acid. : Bioorg. It is a tetrahedral molecule and is closely related to sulfuric acid, H 2 SO 4, substituting a fluorine atom for one of the hydroxyl groups.It is a colourless liquid, although commercial samples are often yellow. C-functionalized carboranes represent a source of boron for boron neutron capture therapy. A superacid is defined as a substance that has a higher H + chemical potential than 100% pure sulfuric acid. It protonates fullerene, C 60. The three common isomers are o-carborane, m-carborane and p-carborane 1The structure could be polyhedral or open cage. Although they have few practical applications, the boranes exhibit structures and bonding that differs strongly from the patterns seen in hydrocarbons. The generic structure of a carborane acid. strongest acid yet gentlest. Most common are those with 1 to 12 boron atoms. Carborane acids are one of the strongest groups of superacids known to humans, few of which are considered to have a Hammett acidity function value as low as -18, that's more than a million times stronger acidity level than pure (100% . Borane is a homologous sequence of inorganic boron-hydrogen compounds and their derivatives. The CH groups in the carboranes are weakly acidic (p Ka ( ortho )=22.0, p Ka ( meta )=25.6, p Ka ( para =26.8)) [42], [43], and can be readily deprotonated generating nucleophiles. Boranes are the common name for a class of synthetic boron hydrides with the formula B x H y (borane formula). Chemical Formula: H(CHB 11 F 11) H o value:-18 pK a value: -20. : Bioorg. Carborane is the only acid capable of protonating C 60 without side reactions. 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