4-Dimethylaminopyridine (original) (raw)
4-ثنائي ميثيل أمينو البيريدينيوم هو مركب كيميائي عضوي له الصيغة C7H10N2، ويوجد على شكل بلورات بيضاء. يرمز للمركب اختصاراً DMAP.
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| dbo:abstract | 4-ثنائي ميثيل أمينو البيريدينيوم هو مركب كيميائي عضوي له الصيغة C7H10N2، ويوجد على شكل بلورات بيضاء. يرمز للمركب اختصاراً DMAP. (ar) 4-dimethylaminopyridin (DMAP), známý také jako N,N-dimethyl-4-pyridinamin je derivát pyridinu s chemickým vzorcem (CH3)2NC5H4N. Využívá se jako báze a nukleofilní katalyzátor v organické syntéze. Díky mezomernímu efektu NMe2 skupiny je bazičtější než pyridin. Využívá se jako katalyzátor acylací alkoholů a aminů, především terciárních, aromatických nebo stericky bráněných. Katalyzuje také silylace a tricylace alkoholů a přímou syntézu esterů z alkoholů a kyselin v přítomnosti dicyklohexylkarbodiimidu (Steglichova esterifikace). (cs) 4-(Dimethylamino)pyridin (Abk.: DMAP oder 4-DMAP) ist ein substituiertes Pyridin. (de) 4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This colourless solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe2 substituent. Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement, Staudinger synthesis of β-lactams and many more. Chiral DMAP analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxiliary type amides. (en) La 4-diméthylaminopyridine ou DMAP est un dérivé de la pyridine avec une fonction diméthylamine en position para et de formule (CH3)2NC5H4N. Ce solide incolore est un catalyseur nucléophile utile dans un grand nombre de réactions comme des estérifications avec des anhydrides, la réaction de Baylis-Hillman, des hydrosilylations, des tritylations, l'estérification de Steglich, la (en) de β-lactames et encore beaucoup d'autres. Des analogues chiraux de la DMAP sont utilisés dans des expériences de (en), principalement, des alcools secondaires et d'auxiliaires d'Evans de type amide. (fr) 4-ジメチルアミノピリジン (4-Dimethylaminopyridine) は様々な有機合成反応で触媒として用いられる求核剤、強塩基である。4-(ジメチルアミノ)ピリジン、N,N-ジメチル-4-アミノピリジンとも呼ばれ、DMAP（ディーマップ）と略称される。利用例として酸無水物のエステル化、ベイリス・ヒルマン反応、シリル化、トリチル化、シュテークリヒ転位、シュタウディンガー反応などが挙げられる。 (ja) 4-dimethylaminopyridine (doorgaans afgekort tot DMAP) is een organische verbinding met als brutoformule C7H10N2. De stof komt voor als een kleurloze tot witte vaste stof, die slechts matig oplosbaar is in water. De verbinding wordt veelvuldig ingezet als nucleofiele katalysator bij tal van organische reacties. 4-dimethylaminopyridine wordt hierbij gebruikt in aanwezigheid van een andere organische basen, zoals tri-ethylamine, pyridine, imidazool, DABCO of DBU. (nl) 4-Dimetilaminopiridina (DMAP) é um catalisador nucleofílico o qual catalisa uma variedade de reações. Por exemplo esterificações com anidridos, reação de Baylis-Hillman, , tritilação, o , de β-lactamas e muitas mais. (pt) 4-Диметиламинопиридин (ДМАП, DMAP) — органическое соединение, производное пиридина. Используется в органическом синтезе как катализатор ацилирования аминов и спиртов, конденсации в присутствии , а также и тритилирования спиртов. (ru) 4-二甲氨基吡啶（DMAP）是一个吡啶衍生物，为无色至淡黄色晶体，是有机合成中应用很广的万能超亲核的酰化反应催化剂。 (zh) |
| dbo:alternativeName | DMAP (en) N,N-Dimethyl-4-aminoazabenzene (en) N,N-Dimethyl-4-aminopyridine (en) N,N-dimethyl-4-aminoazine (en) 4-Dimethylaminopyridine (en) 4-(Dimethylamino)azabenzene (en) 4-(Dimethylamino)azine (en) 4-(Dimethylamino)pyridine (en) |
| dbo:iupacName | N,N-Dimethylpyridin-4-amine (en) Dimethyl(pyridin-4-yl)amine (en) Dimethyl(pyridin-4-yl)azane (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/4-Dimethylaminopyridine_chemical_structure.png?width=300 |
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| dbp:author | B. Neises (en) W. Steglich (en) |
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| dbp:iupacnames | Dimethylamine (en) Dimethylazane (en) N,N-Dimethylpyridin-4-amine (en) |
| dbp:othernames | 4 (xsd:integer) DMAP (en) N,N-Dimethyl-4-aminoazabenzene (en) N,N-Dimethyl-4-aminopyridine (en) N,N-dimethyl-4-aminoazine (en) |
| dbp:pin | N,N-Dimethylpyridin-4-amine (en) |
| dbp:prep | cv7p0093 (en) |
| dbp:title | Esterification of Carboxylic Acids with Dicyclohexylcarbodiimide/4-Dimethylaminopyridine: tert-Butyl Ethyl Fumarate (en) |
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| dbp:year | 1990 (xsd:integer) |
| dct:subject | dbc:Catalysts dbc:Dimethylamino_compounds dbc:Reagents_for_organic_chemistry dbc:Aminopyridines |
| gold:hypernym | dbr:Derivative |
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| rdfs:comment | 4-ثنائي ميثيل أمينو البيريدينيوم هو مركب كيميائي عضوي له الصيغة C7H10N2، ويوجد على شكل بلورات بيضاء. يرمز للمركب اختصاراً DMAP. (ar) 4-dimethylaminopyridin (DMAP), známý také jako N,N-dimethyl-4-pyridinamin je derivát pyridinu s chemickým vzorcem (CH3)2NC5H4N. Využívá se jako báze a nukleofilní katalyzátor v organické syntéze. Díky mezomernímu efektu NMe2 skupiny je bazičtější než pyridin. Využívá se jako katalyzátor acylací alkoholů a aminů, především terciárních, aromatických nebo stericky bráněných. Katalyzuje také silylace a tricylace alkoholů a přímou syntézu esterů z alkoholů a kyselin v přítomnosti dicyklohexylkarbodiimidu (Steglichova esterifikace). (cs) 4-(Dimethylamino)pyridin (Abk.: DMAP oder 4-DMAP) ist ein substituiertes Pyridin. (de) La 4-diméthylaminopyridine ou DMAP est un dérivé de la pyridine avec une fonction diméthylamine en position para et de formule (CH3)2NC5H4N. Ce solide incolore est un catalyseur nucléophile utile dans un grand nombre de réactions comme des estérifications avec des anhydrides, la réaction de Baylis-Hillman, des hydrosilylations, des tritylations, l'estérification de Steglich, la (en) de β-lactames et encore beaucoup d'autres. Des analogues chiraux de la DMAP sont utilisés dans des expériences de (en), principalement, des alcools secondaires et d'auxiliaires d'Evans de type amide. (fr) 4-ジメチルアミノピリジン (4-Dimethylaminopyridine) は様々な有機合成反応で触媒として用いられる求核剤、強塩基である。4-(ジメチルアミノ)ピリジン、N,N-ジメチル-4-アミノピリジンとも呼ばれ、DMAP（ディーマップ）と略称される。利用例として酸無水物のエステル化、ベイリス・ヒルマン反応、シリル化、トリチル化、シュテークリヒ転位、シュタウディンガー反応などが挙げられる。 (ja) 4-dimethylaminopyridine (doorgaans afgekort tot DMAP) is een organische verbinding met als brutoformule C7H10N2. De stof komt voor als een kleurloze tot witte vaste stof, die slechts matig oplosbaar is in water. De verbinding wordt veelvuldig ingezet als nucleofiele katalysator bij tal van organische reacties. 4-dimethylaminopyridine wordt hierbij gebruikt in aanwezigheid van een andere organische basen, zoals tri-ethylamine, pyridine, imidazool, DABCO of DBU. (nl) 4-Dimetilaminopiridina (DMAP) é um catalisador nucleofílico o qual catalisa uma variedade de reações. Por exemplo esterificações com anidridos, reação de Baylis-Hillman, , tritilação, o , de β-lactamas e muitas mais. (pt) 4-Диметиламинопиридин (ДМАП, DMAP) — органическое соединение, производное пиридина. Используется в органическом синтезе как катализатор ацилирования аминов и спиртов, конденсации в присутствии , а также и тритилирования спиртов. (ru) 4-二甲氨基吡啶（DMAP）是一个吡啶衍生物，为无色至淡黄色晶体，是有机合成中应用很广的万能超亲核的酰化反应催化剂。 (zh) 4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This colourless solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe2 substituent. (en) |
| rdfs:label | 4-ثنائي ميثيل أمينو البيريدينيوم (ar) 4-Dimethylaminopyridin (cs) 4-(Dimethylamino)pyridin (de) 4-Dimethylaminopyridine (en) 4-Diméthylaminopyridine (fr) 4-ジメチルアミノピリジン (ja) 4-dimethylaminopyridine (nl) 4-dimetilaminopiridina (pt) 4-Диметиламинопиридин (ru) 4-二甲氨基吡啶 (zh) |
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