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2-Iodoxybenzoic acid (IBX) is an organic compound used in organic synthesis as an oxidizing agent. This periodinane is especially suited to oxidize alcohols to aldehydes. IBX is prepared from 2-iodobenzoic acid, potassium bromate, and sulfuric acid. Frigerio and co-workers have also demonstrated, in 1999 that potassium bromate may be replaced by commercially available Oxone. One of the main drawbacks of IBX is its limited solubility; IBX is insoluble in many common organic solvents. In the past, it was believed that IBX was shock sensitive, but it was later proposed that samples of IBX were shock sensitive due to the residual potassium bromate left from its preparation. Commercial IBX is stabilized by carboxylic acids such as benzoic acid and isophthalic acid.

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dbo:abstract
  • Kyselina jodoxybenzoová (zkráceně IBX) je organická sloučenina používaná v organické syntéze jako oxidační činidlo. Používá se na oxidace alkoholů na aldehydy. IBX se připravuje z , bromičnanu draselného a kyseliny sírové. Bromičnan draselný lze nahradit lépe dostupným hydrogenperoxosíranem. Nevýhodou této sloučeniny je její špatná rozpustnost; IBX je ve většině běžných organických rozpouštědel nerozpustná. V minulosti byla IBX považována za citlivou na náraz, ovšem zjistilo se, že tato citlivost vzorků IBX byla pravděpodobně způsobena zbytky bromičnanu draselného z její přípravy. Komerčně prodávané vzorky IBX jsou stabilizovány karboxylovými kyselinami. například benzoovou nebo isoftalovou. (cs)
  • 2-Iodoxybenzoic acid (IBX) is an organic compound used in organic synthesis as an oxidizing agent. This periodinane is especially suited to oxidize alcohols to aldehydes. IBX is prepared from 2-iodobenzoic acid, potassium bromate, and sulfuric acid. Frigerio and co-workers have also demonstrated, in 1999 that potassium bromate may be replaced by commercially available Oxone. One of the main drawbacks of IBX is its limited solubility; IBX is insoluble in many common organic solvents. In the past, it was believed that IBX was shock sensitive, but it was later proposed that samples of IBX were shock sensitive due to the residual potassium bromate left from its preparation. Commercial IBX is stabilized by carboxylic acids such as benzoic acid and isophthalic acid. (en)
  • 2-Iodoxybenzoesäure ist eine chemische Verbindung aus der Gruppe der hypervalenten Iodverbindungen. (de)
  • L'acide 2-iodoxybenzoïque ou IBX est un composé organique utilisé comme réactif oxydant en synthèse organique. Ce periodinane est particulièrement adapté pour oxyder des alcools en aldéhydes. L'un des principaux inconvénients de l'IBX est sa solubilité limitée : il est insoluble dans de nombreux solvants organiques courants. Dans le passé, l'IBX a été cru sensible aux chocs, mais il a ensuite été démontré que des échantillons d'IBX sont sensibles aux chocs en raison du bromate de potassium résiduel, issu de la synthèse. L'IBX commercial (SIBX:Stabilized IBX) est stabilisé par des acides carboxyliques tels que l'acide benzoïque et l'acide isophtalique. L'acide 2-iodylbenzoïque, ortho Ph(I(=O)2),(COOH), est un tautomère de l'acide 2-iodoxybenzoïque. L'acidité de l'IBX qui a été mesurée dans l'eau (pKa=2,4) et le DMSO (pKa=6,65), est connue pour affecter les réactions chimiques, par exemple les oxydations accompagnées de réactions d'isomérisation catalysées par les acides. (fr)
  • 2-ヨードキシ安息香酸(2-ヨードキシあんそくこうさん、英: 2-iodoxybenzoic acid)は、有機合成化学で使われる酸化剤である。IBX または IBX acid の略称で呼ばれる。この超原子価ヨウ素化合物は、温和な条件下ではたらく酸化剤であり、特にアルコールを酸化してアルデヒドに変える目的に適している。 (ja)
  • Ácido 2-iodoxibenzoico ou IBX é um composto orgânico usado em síntese orgânica como um agente oxidante. Este periodinano é especialmente usado para oxidar álcoois a aldeídos. IBX é preparado de ácido 2-iodobenzoico, bromato de potássio e ácido sulfúrico. Frigerio e colaboradores também demonstraram, em 1999, que bromato de potássio pode ser substituído por Oxone disponível comercialmente. Uma das principais desvantagens do IBX é a sua solubilidade limitada. IBX é insolúvel na maioria dos solventes orgânicos comuns. No passado, acreditava-se que o IBX era sensível ao choque, mas foi mais tarde proposto que as amostras de IBX eram sensíveis ao choque devido ao bromato de potássio residual deixado na sua preparação. IBX comercial é estabilizado por ácidos carboxílicos tais como o ácido benzoico e ácido isoftálico. (pt)
  • 2-Иодоксибензойная кислота (IBX) — органическое соединение, соединение гипервалентного иода. В органической химии широко применяется как окислитель, а также в качестве реагента в . (ru)
  • 2-碘酰基苯甲酸(IBX)是典型的,在有机合成中用作氧化剂,用于将醇氧化为醛。 (zh)
dbo:alternativeName
  • 1-Hydroxy-1λ3,2-benziodoxol-3(1H)-one 1-oxide (en)
dbo:iupacName
  • 1-Hydroxy-1λ5,2-benziodoxole-1,3-dione (en)
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  • IBXAcid.png (en)
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  • correct (en)
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  • correct (en)
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rdfs:comment
  • 2-Iodoxybenzoic acid (IBX) is an organic compound used in organic synthesis as an oxidizing agent. This periodinane is especially suited to oxidize alcohols to aldehydes. IBX is prepared from 2-iodobenzoic acid, potassium bromate, and sulfuric acid. Frigerio and co-workers have also demonstrated, in 1999 that potassium bromate may be replaced by commercially available Oxone. One of the main drawbacks of IBX is its limited solubility; IBX is insoluble in many common organic solvents. In the past, it was believed that IBX was shock sensitive, but it was later proposed that samples of IBX were shock sensitive due to the residual potassium bromate left from its preparation. Commercial IBX is stabilized by carboxylic acids such as benzoic acid and isophthalic acid. (en)
  • 2-Iodoxybenzoesäure ist eine chemische Verbindung aus der Gruppe der hypervalenten Iodverbindungen. (de)
  • 2-ヨードキシ安息香酸(2-ヨードキシあんそくこうさん、英: 2-iodoxybenzoic acid)は、有機合成化学で使われる酸化剤である。IBX または IBX acid の略称で呼ばれる。この超原子価ヨウ素化合物は、温和な条件下ではたらく酸化剤であり、特にアルコールを酸化してアルデヒドに変える目的に適している。 (ja)
  • 2-Иодоксибензойная кислота (IBX) — органическое соединение, соединение гипервалентного иода. В органической химии широко применяется как окислитель, а также в качестве реагента в . (ru)
  • 2-碘酰基苯甲酸(IBX)是典型的,在有机合成中用作氧化剂,用于将醇氧化为醛。 (zh)
  • Kyselina jodoxybenzoová (zkráceně IBX) je organická sloučenina používaná v organické syntéze jako oxidační činidlo. Používá se na oxidace alkoholů na aldehydy. IBX se připravuje z , bromičnanu draselného a kyseliny sírové. Bromičnan draselný lze nahradit lépe dostupným hydrogenperoxosíranem. Nevýhodou této sloučeniny je její špatná rozpustnost; IBX je ve většině běžných organických rozpouštědel nerozpustná. V minulosti byla IBX považována za citlivou na náraz, ovšem zjistilo se, že tato citlivost vzorků IBX byla pravděpodobně způsobena zbytky bromičnanu draselného z její přípravy. (cs)
  • L'acide 2-iodoxybenzoïque ou IBX est un composé organique utilisé comme réactif oxydant en synthèse organique. Ce periodinane est particulièrement adapté pour oxyder des alcools en aldéhydes. L'un des principaux inconvénients de l'IBX est sa solubilité limitée : il est insoluble dans de nombreux solvants organiques courants. Dans le passé, l'IBX a été cru sensible aux chocs, mais il a ensuite été démontré que des échantillons d'IBX sont sensibles aux chocs en raison du bromate de potassium résiduel, issu de la synthèse. L'IBX commercial (SIBX:Stabilized IBX) est stabilisé par des acides carboxyliques tels que l'acide benzoïque et l'acide isophtalique. (fr)
  • Ácido 2-iodoxibenzoico ou IBX é um composto orgânico usado em síntese orgânica como um agente oxidante. Este periodinano é especialmente usado para oxidar álcoois a aldeídos. IBX é preparado de ácido 2-iodobenzoico, bromato de potássio e ácido sulfúrico. Frigerio e colaboradores também demonstraram, em 1999, que bromato de potássio pode ser substituído por Oxone disponível comercialmente. Uma das principais desvantagens do IBX é a sua solubilidade limitada. IBX é insolúvel na maioria dos solventes orgânicos comuns. No passado, acreditava-se que o IBX era sensível ao choque, mas foi mais tarde proposto que as amostras de IBX eram sensíveis ao choque devido ao bromato de potássio residual deixado na sua preparação. IBX comercial é estabilizado por ácidos carboxílicos tais como o ácido ben (pt)
rdfs:label
  • Kyselina jodoxybenzoová (cs)
  • 2-Iodoxybenzoesäure (de)
  • 2-Iodoxybenzoic acid (en)
  • Acide 2-iodoxybenzoïque (fr)
  • 2-ヨードキシ安息香酸 (ja)
  • 2-Иодоксибензойная кислота (ru)
  • Ácido 2-iodoxibenzoico (pt)
  • 2-碘酰基苯甲酸 (zh)
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