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吡嗪

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吡嗪
IUPAC名
Pyrazine
别名 对二嗪、1,4-二嗪
识别
CAS号 290-37-9  ✓
PubChem 9261
ChemSpider 8904
SMILES
InChI
EINECS 206-027-6
ChEBI 30953
性质
化学式 C4H4N2
摩尔质量 80.09 g·mol−1
外观 白色晶体
密度 1.031
熔点 52 °C(325 K)
沸点 115 °C(388 K)
溶解性 易溶
危险性
警示术语 R:R11-R36/37/38
安全术语 S:S16-S26-S36
NFPA 704
NFPA 704.svg
2
2
0
 
闪点 55 ºC
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

吡嗪bǐqín(Pyrazine,C4H4N2)是1,4位含两个杂氮原子的杂环化合物。与嘧啶哒嗪互为同分异构体。具有较弱的芳香性,与吡啶类似。不易发生亲电取代反应,但易和亲核试剂反应。在自然界中,其纯品很少存在,但其结构存在于叶酸之中,组成其中的蝶呤部分。工业上则用乙醇胺在气相催化的条件下脱氢制取。

其衍生物有较多应用,如二苯并吡嗪是重要的染料,吩嗪(phenazine)以具有抗肿瘤,抗菌和利尿的性质而著称。而 四甲基吡嗪被报道可以捕捉超氧阴离子,并减少人体有粒细胞的氮氧化物产生[1]

合成

很多方法可以合成吡嗪和它的衍生物,有些方法已经很古老了。

2-氯苯乙酮与氨反应,可以生成氨基酮,之后脱水氧化为吡嗪。[2]

参见

  1. ^ Life Sciences, 2003, 72, 2465-2472, DOI: http://dx.doi.org/10.1016/S0024-3205(03)00139-5
  2. ^ Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol (p 563-564) W. Staedel, L. Rügheimer doi:10.1002/cber.187600901174 Berichte der deutschen chemischen Gesellschaft Volume 9, Issue 1 , Pages 563 - 564 1876
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吡嗪
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