3-氨基-5-苯基异噻唑 | 2825-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-氨基-5-苯基异噻唑
• 英文名称: 3-Amino-5-phenyl-isothiazol
• 英文别名: 5-Phenylisothiazol-3-amine；5-phenyl-1,2-thiazol-3-amine
• CAS: 2825-34-5
• 化学式: C₉H₈N₂S
• 分子量: 176.242
• InChiKey: VLQBYPSKWKIMPS-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C
• 沸点：
  269.8±38.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-amino-4-bromo-5-phenylisothiazole	90792-75-9	C9H7BrN2S	255.138
  ——	4-bromo-3-hydrazinyl-5-phenylisothiazole	1187734-02-6	C9H8BrN3S	270.153

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-amino-4-bromo-5-phenylisothiazole	90792-75-9	C9H7BrN2S	255.138
  ——	1,1-dimethyl-3-(5-phenyl-3-isothiazolyl)urea	——	C12H13N3OS	247.321
  3-氯-5-苯基异噻唑	3-Chlor-5-phenyl-isothiazol	19983-39-2	C9H6ClNS	195.672

反应信息

• 作为反应物：
  描述：

  3-氨基-5-苯基异噻唑 在 nitrosonium tetrafluoroborate 作用下， 以 溶剂黄146 、 丙酸 为溶剂， 生成 5-phenyl-isothiazole-3-diazonium; tetrafluoroborate
  参考文献：
  名称：

  Goerdeler,J.; Roegler,M., Chemische Berichte, 1970, vol. 103, p. 112 - 122

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基丙炔腈 在 sodium sulfide 、 sodium hypochlorite 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 以65%的产率得到3-氨基-5-苯基异噻唑
  参考文献：
  名称：

  The synthesis of 3-amino-5-arylisothiazoles from propynenitriles

  摘要：

  A new synthesis of 3-amino-5-arylisothiazoles is reported. The reaction is operationally simple, utilises readily synthesised propynenitriles as starting materials and is tolerant of a range of functional groups. The optimised reaction conditions can also be used with 3-chloropropenenitriles in place of propynenitriles. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.01.042

文献信息

• Process for the production of urea derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US04183856A1

  公开（公告）日：1980-01-15

  Urea derivatives of the formula ##STR1## (wherein Ar represents a residue of 5- or 6-membered heteroaromatic ring; R represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sup.1 represents a C.sub.1 -C.sub.6 alkyl group; and R.sup.2 represents a C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.1 -C.sub.6 alkoxy group) are produced by reacting an amine of the formula Ar--NH--R (wherein Ar and R have the significance given above) with a carbamoyl halogenide of the formula ##STR2## (wherein X represents a halogen atom, and R.sup.1 and R.sup.2 have the significance given above) in the presence of a Lewis acid in an inert solvent.

  根据上述描述，通过在惰性溶剂中在路易斯酸存在下，将式Ar--NH--R（其中Ar和R具有上述所述意义）的胺与式##STR2##（其中X代表卤素原子，R.sup.1和R.sup.2具有上述所述意义）的氨基甲酰卤化物反应，可以制备式##STR1##的尿素衍生物。
• Isothiazoles. Part XV. 5-Nitroisothiazoles
  作者：R. J. A. Walsh、K. R. H. Wooldridge

  DOI：10.1039/p19720001247

  日期：——

  3-Methyl-5-nitroisothiazole has been prepared from diazotised 5-amino-3-methylisothiazole and sodium nitrite. Oxidation gave the 3-carboxylic acid, which was converted into the amide, nitrile, aldehyde, and derivatives. Treatment of 3,5-dichloroisothiazole-4-carbonitrile with sodium nitrite gave 3-chloro-5-hydroxyisothiazole-4-carbonitrile.

  3-甲基-5-硝基异噻唑是由重氮化的5-氨基-3-甲基异噻唑和亚硝酸钠制得的。氧化得到3-羧酸，将其转化为酰胺，腈，醛和衍生物。用亚硝酸钠处理3，5-二氯异噻唑-4-腈，得到3-氯-5-羟基异噻唑-4-腈。
• The conversion of isothiazoles into pyrazoles using hydrazine
  作者：Heraklidia A. Ioannidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.041

  日期：2009.8

  The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazoie 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 degrees C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5'-Diphenyl-3,3'-biisothiazole-4,4'-dicarbonitrile 78 reacts with hydrazine to give 5,5'-diphenyl-3,3'-bi(1H-pyi-azole)-4,4'-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenytisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbontrile 83 and 3-amino-lmethyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed. (C) 2009 Elsevier Ltd. All rights reserved.
• Goerdeler,J.; Mittler,W., Chemische Berichte, 1963, vol. 96, p. 944 - 954
  作者：Goerdeler,J.、Mittler,W.

  DOI：——

  日期：——
• Herbicidal sulfonamides
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0083975B1

  公开（公告）日：1987-11-19