CAS: 837364-89-3; 2,4-Difluoro-5-Iodopyridine

该化合物是卤化的丙烯衍生物,其特点是其独特的替代模式,以2,4和5个位置的氟和碘原子为主,该化合物是有机合成的多用途中间体,特别是在诸如铃木-宫浦或松冈竹草交配等交叉反应中,因为碘分质的反活性.用电镀氟原子在核分裂性芳烃替代反应中提高了其效用,使选择性功能化成为可能.其稳定性和明确界定的再活动对于制药和农用化学应用来说是有价值的,因为需要精确的结构修改.该化合物通常在惰性条件下处理,以保持其完整性.

英文名称2,4-Difluoro-5-Iodopyridine
中文名称2,4-二氟-5-碘吡啶
IUPAC名称2,4-difluoro-5-iodopyridine
其它别名Pyridine, 2,4-Difluoro-5-Iodo-; 2,4-Difluoro-5-Iodo-Pyridine
CAS编号837364-89-3
MFCD编号:MFCD09029864
EINECS号:809-997-4
分子式:C5H2F2IN分子量:240.98
产品CID: 1825574
产品分类有机原料→分子砌块→芳杂环类化合物→吡啶类化合物

相似结构搜索
InChIKey: GTAAUJUZQSTFHD-UHFFFAOYSA-N
InChI=1S/C5H2F2IN/c6-3-1-5(7)9-2-4(3)8/h1-2H
计算化学: 氢键受体数1.0氢键供体数*可旋转键数*

相似化合物

837364-88-2 685517-67-3 171197-80-1

MSDS等安全信息

GHS符号GHS07
危险类别急性毒性类别4(吸入)
急性毒性类别4(经皮)
急性毒性类别4(经口)
特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2A
警示词Warning
危险描述H332 |吸入有害.
H312 |皮肤接触有害.
H302 |吞咽有害.
H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

欧盟法规

C&L通报

上下游产品

合成工艺路线路线简述

837364-88-2 = 837364-89-3
反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,-75 °C; 30 Min,-75 °C1.2 Solvents: Water
标题:Regiochemically Flexible Substitutions Of Di-,Tri-,And Tetrahalopyridines: The Trialkylsilyl Trick
作者:Schlosser,Manfred; Et Al
参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(7) 页码:2494-2502]

837364-88-2 = 837364-89-3
反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; -70 °C1.2 Solvents: Water
标题:Rerouting Nucleophilic Substitution From The 4-Position To The 2- Or 6-Position Of 2,4-Dihalopyridines And 2,4,6-Trihalopyridines: The Solution To A Long-Standing Problem
作者:Schlosser,Manfred; Et Al
参考文献:Organic Letters 日期:2005 卷标:7(1) 页码:127-129]

837364-98-4 = 837364-89-3
反应条件:1.1 Reagents: Copper Sulfate Solvents: Water; 25 Min,Reflux2.1 Reagents: Diisopropylamine,Butyllithium Solvents: Tetrahydrofuran,Hexane; -100 °C; 45 Min,-100 °C2.2 Reagents: Iodine Solvents: Tetrahydrofuran; 15 Min,-75 °C2.3 Reagents: Sodium Sulfite Solvents: Water; -75 °C3.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,-75 °C; 30 Min,-75 °C3.2 Solvents: Water
标题:Regiochemically Flexible Substitutions Of Di-,Tri-,And Tetrahalopyridines: The Trialkylsilyl Trick
作者:Schlosser,Manfred; Et Al
参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(7) 页码:2494-2502]

837364-95-1 = 837364-89-3
反应条件:1.1 Reagents: Hydrazine Solvents: Tetrahydrofuran; 2 H,50 °C2.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 2 H,25 °C3.1 Reagents: Copper Sulfate Solvents: Water; 25 Min,Reflux4.1 Reagents: Diisopropylamine,Butyllithium Solvents: Tetrahydrofuran,Hexane; -100 °C; 45 Min,-100 °C4.2 Reagents: Iodine Solvents: Tetrahydrofuran; 15 Min,-75 °C4.3 Reagents: Sodium Sulfite Solvents: Water; -75 °C5.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,-75 °C; 30 Min,-75 °C5.2 Solvents: Water
标题:Regiochemically Flexible Substitutions Of Di-,Tri-,And Tetrahalopyridines: The Trialkylsilyl Trick
作者:Schlosser,Manfred; Et Al
参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(7) 页码:2494-2502]

3512-17-2 + 994-30-9 = 837364-89-3
反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; 45 Min,-100 °C1.2 45 Min,-75 °C2.1 Reagents: Hydrazine Solvents: Tetrahydrofuran; 2 H,50 °C3.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 2 H,25 °C4.1 Reagents: Copper Sulfate Solvents: Water; 25 Min,Reflux5.1 Reagents: Diisopropylamine,Butyllithium Solvents: Tetrahydrofuran,Hexane; -100 °C; 45 Min,-100 °C5.2 Reagents: Iodine Solvents: Tetrahydrofuran; 15 Min,-75 °C5.3 Reagents: Sodium Sulfite Solvents: Water; -75 °C6.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,-75 °C; 30 Min,-75 °C6.2 Solvents: Water
标题:Regiochemically Flexible Substitutions Of Di-,Tri-,And Tetrahalopyridines: The Trialkylsilyl Trick
作者:Schlosser,Manfred; Et Al
参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(7) 页码:2494-2502]

34941-90-7 = 837364-89-3
反应条件:1.1 Reagents: Diisopropylamine,Butyllithium Solvents: Tetrahydrofuran,Hexane; -100 °C; 45 Min,-100 °C1.2 Reagents: Iodine Solvents: Tetrahydrofuran; 15 Min,-75 °C1.3 Reagents: Sodium Sulfite Solvents: Water; -75 °C2.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,-75 °C; 30 Min,-75 °C2.2 Solvents: Water
标题:Regiochemically Flexible Substitutions Of Di-,Tri-,And Tetrahalopyridines: The Trialkylsilyl Trick
作者:Schlosser,Manfred; Et Al
参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(7) 页码:2494-2502]

837364-90-6 = 837364-89-3
反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; -75 °C1.2 Reagents: Iodine2.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; -70 °C2.2 Solvents: Water
标题:Rerouting Nucleophilic Substitution From The 4-Position To The 2- Or 6-Position Of 2,4-Dihalopyridines And 2,4,6-Trihalopyridines: The Solution To A Long-Standing Problem
作者:Schlosser,Manfred; Et Al
参考文献:Organic Letters 日期:2005 卷标:7(1) 页码:127-129]

837364-97-3 = 837364-89-3
反应条件:1.1 Reagents: Iodine Chloride2.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; -70 °C2.2 Solvents: Water
标题:Rerouting Nucleophilic Substitution From The 4-Position To The 2- Or 6-Position Of 2,4-Dihalopyridines And 2,4,6-Trihalopyridines: The Solution To A Long-Standing Problem
作者:Schlosser,Manfred; Et Al
参考文献:Organic Letters 日期:2005 卷标:7(1) 页码:127-129]

837364-96-2 = 837364-89-3
反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 2 H,25 °C2.1 Reagents: Copper Sulfate Solvents: Water; 25 Min,Reflux3.1 Reagents: Diisopropylamine,Butyllithium Solvents: Tetrahydrofuran,Hexane; -100 °C; 45 Min,-100 °C3.2 Reagents: Iodine Solvents: Tetrahydrofuran; 15 Min,-75 °C3.3 Reagents: Sodium Sulfite Solvents: Water; -75 °C4.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,-75 °C; 30 Min,-75 °C4.2 Solvents: Water
标题:Regiochemically Flexible Substitutions Of Di-,Tri-,And Tetrahalopyridines: The Trialkylsilyl Trick
作者:Schlosser,Manfred; Et Al
参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(7) 页码:2494-2502

📜2,4,6-三氟吡啶置于正丁基锂,四丁基氟化铵,一水合肼,Copper(II) Sulfate,Lithium Diisopropyl Amide体系中,用四氢呋喃,正己烷,水作为反应溶剂,化学反应 5.92H,反应生成 2,4-二氟-5-碘吡啶
参考文献:Rerouting Nucleophilic Substitution From The 4-Position To The 2-Or 6-Position Of 2,4-Dihalopyridines And 2,4,6-Trihalopyridines: The Solution To A Long-Standing Problem
标题:Rerouting Nucleophilic Substitution From The 4-Position To The 2-Or 6-Position Of 2,4-Dihalopyridines And 2,4,6-Trihalopyridines: The Solution To A Long-Standing Problem
摘要:2,4-Difluoro-,2,4,6-Trifluoro-,And 2,3,4,6-Tetrafluoropyridine Undergo Nucleophilic Substitution Preferentially If Not Exclusively At The 4-Position. However,After The Introduction Of A Trialkylsilyl Group At C-3 Or C-5,The Halogen At The 6-(2-)Position Is Displaced Selectively. This Synthetically Valuable Regiocontrol Can Also Be Realized With Other Halopyridines Such As 2,4-Dichloro-And 2,4,6-Trichloropyridine.
DOI:10.1021/ol047826G

海关参考信息

2933310010-吡啶
2939800000-其他生物碱
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合成参考文献

参考文献:10.1055/s-0029-1218810
摘要:Schlosser M, Ruzziconi R. Nucleophilic Substitutions of Nitroarenes and Pyridines: New Insight and New Applications. Synthesis. 2010 Jun 02;2010(13):2111–23. doi: 10.1055/s-0029-1218810.