4-(4-Bromo-3-nitrophenyl)pyridine | 101681-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(4-Bromo-3-nitrophenyl)pyridine
• CAS: 101681-35-0
• 化学式: C₁₁H₇BrN₂O₂
• 分子量: 279.093
• InChiKey: SVVBPESGFYBQFN-UHFFFAOYSA-N

物化性质

• 沸点：
  363.1±32.0 °C(Predicted)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Bromo-3-nitrophenyl)pyridine 在 N-甲基吡咯烷酮 、 盐酸 、 sodium methylate 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 5-(4-pyridinyl)benzothiazol-2(3H)-thione
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193
• 作为产物：
  描述：

  4-(4-amino-3-nitrophenyl)-pyridine 在 氢溴酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以77%的产率得到4-(4-Bromo-3-nitrophenyl)pyridine
  参考文献：
  名称：

  rosoxacin 2-氮杂类似物的合成

  摘要：

  2-硝基-4-（4-吡啶基）苯胺（4）在氢溴酸中的重氮化反应得到相应的溴衍生物5，将其用氰化亚铜处理，得到苄腈衍生物6，该苄腈衍生物6随后转化为2-硝基苯乙酮衍生物9。还原9，然后将所得胺10重氮化，得到7-（4-吡啶基）肉桂醇-4（1H）-一（11），其随后转化为1-乙基-1,4-二氢-4-氧代- 7-（4-吡啶基）cinnoline-3-羧酸（14）分三步。

  DOI：

  10.1002/jhet.5570280408

文献信息

• RANKEN, P. F.
  作者：RANKEN, P. F.

  DOI：——

  日期：——
• US4554352A
  申请人：——

  公开号：US4554352A

  公开（公告）日：1985-11-19
• An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones
  作者：Baldev Singh、Patrick O. Pennock、George Y. Lesher、Edward R. Bacon、Donald F. Page

  DOI：10.3987/com-92-6193

  日期：——

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.
• Synthesis of 2-aza analog of rosoxacin
  作者：Baldev Singh

  DOI：10.1002/jhet.5570280408

  日期：1991.6

  Diazotization of 2-nitro-4-(4-pyridinyl)aniline (4) in hydrobromic acid gave the corresponding bromo derivative 5 which was treated with cuprous cyanide to give the benzonitrile derivative 6 which in turn was converted to 2-nitroacetophenone derivative 9. Reduction of 9 followed by diazotization of the resulting amine 10 gave 7-(4-pyridinyl)cinnolin-4(1H)-one (11) which was subsequently converted to

  2-硝基-4-（4-吡啶基）苯胺（4）在氢溴酸中的重氮化反应得到相应的溴衍生物5，将其用氰化亚铜处理，得到苄腈衍生物6，该苄腈衍生物6随后转化为2-硝基苯乙酮衍生物9。还原9，然后将所得胺10重氮化，得到7-（4-吡啶基）肉桂醇-4（1H）-一（11），其随后转化为1-乙基-1,4-二氢-4-氧代- 7-（4-吡啶基）cinnoline-3-羧酸（14）分三步。