异噻唑 | 288-16-4

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 异噻唑
• 中文别名: 1,4-二氮杂二环[2.2.2]辛烷；三乙基二胺
• 英文名称: isothiazol
• 英文别名: isothiazole；1,2-thiazole
• CAS: 288-16-4
• 化学式: C₃H₃NS
• mdl: MFCD00020818
• 分子量: 85.1295
• InChiKey: ZLTPDFXIESTBQG-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C (decomp)(Solv: water (7732-18-5))
• 沸点：
  114°C(lit.)
• 密度：
  1.1566 (rough estimate)
• 溶解度：
  可溶于氯仿、乙酸乙酯
• 最大波长(λmax)：
  242nm(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  3
• 海关编码：
  2934999090
• 包装等级：
  II
• 危险类别：
  3
• 危险性防范说明：
  P210,P233,P264,P280,P370+P378,P303+P361+P353
• 危险品运输编号：
  1993
• 危险性描述：
  H315,H319,H225
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Isothiazole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Isothiazole
CAS number: 288-16-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C3H3NS
Molecular weight: 85.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

异噻唑的应用

异噻唑是一种重要的医药中间体，在医药、杀菌等领域有广泛的应用。

制备过程

在乙腈（176kg）中加入邻碘苯磺酸（1.5kg，5.3mol）和过硫酸氢钾复合盐（132kg，215mol），再加入丙炔醇（15kg，268mol）。将混合物升温至70℃并反应5小时。跟踪反应结束后进行压滤，得到含有丙炔醛的乙腈溶液，中控产品气相纯度>90%。

接着，将该乙腈溶液冷却至-15℃，缓慢加入醋酸（15kg），再缓缓加入硫代硫酸钠（77kg）溶解于水（99kg）中的溶液。反应过程中会剧烈放热，在加完后需保持-5℃搅拌30分钟。过滤所得产物为盐中间体，该中间体的核磁表征如下：1H NMR(D2O): 9.6(1H, d, J=2.8Hz), 7.86(1H, d, J=10Hz), 6.56(1H, dd, J=10Hz)。此中间体不稳定，不宜长时间存放，应及时投入下一步反应。

随后，在0℃下将氨水（60kg）分批加入上述盐中间体中，并在此温度下搅拌2小时，跟踪反应结束后，加入二氯甲烷萃取两次。合并有机相并通过常压蒸馏得到异噻唑。异噻唑是一种具有类似吡啶气味的无色液体，其沸点为114℃。

反应信息

• 作为反应物：
  描述：

  异噻唑 在 溴 、 溶剂黄146 作用下， 反应 6.33h， 以15%的产率得到4-溴异噻唑
  参考文献：
  名称：

  [EN] IMIDAZO [1,5-A]PYRIMIDINYL CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
  [FR] COMPOSÉS IMIDAZO [1,5-A]PYRIMIDINYL CARBOXAMIDE ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES MÉDICAUX

  摘要：

  本发明提供了取代的咪唑[1,5-a]嘧啶基甲酰胺及其相关有机化合物，包含此类化合物的组合物，医疗试剂盒，以及使用此类化合物和组合物治疗医疗障碍的方法，例如，戈谢病，帕金森病，路易体病，痴呆症或多系统萎缩症。本说明书中描述的代表性的取代咪唑[1,5-a]嘧啶基甲酰胺化合物包括取代的2-杂环基-4-烷基-咪唑[1,5-a]嘧啶-8-甲酰胺化合物及其变体。

  公开号：

  WO2017176961A1
• 作为产物：
  描述：

  thiosulfuric acid S-(3-oxo-cis-propenyl) ester; sodium salt 在 氨 作用下， 反应 2.0h， 以60%的产率得到异噻唑
  参考文献：
  名称：

  具有异噻唑并乙烯基侧链的新型1β-甲基卡宾烯的合成和生物学评估。

  摘要：

  描述了在吡咯烷环的C-5位置带有异噻唑并乙烯基的新型1β-甲基碳烯化合物1a，b的合成及其生物学评价。两种化合物均显示出有效且均衡的抗菌活性以及对DHP-1的高稳定性。特别是，与5-异恶唑衍生物2，亚胺培南和美洛培南相比，5-异噻唑衍生物1a表现出出色的DHP-1稳定性和先进的药代动力学特性。

  DOI：

  10.1016/s0960-894x(02)00948-4

文献信息

• Fungicides for the control of take-all disease of plants
  申请人：Monsanto Company

  公开号：US05498630A1

  公开（公告）日：1996-03-12

  A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR.sub.3, --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ; B is --W.sub.m --Q(R.sub.2).sub.3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ; Q is C, Si, Ge, or Sn; W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W is selected from --C(R.sub.3).sub.p H(.sub.2-p), --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--; X is 0 or S; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2; each R and R.sub.2 is independently defined herein; R.sub.3 is C.sub.1 -C.sub.4 alkyl; R.sub.4 is C.sub.1 -C.sub.4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R.sub.7 is C.sub.1 -C.sub.4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R.sub.4 ; or an agronomic salt thereof.

  一种通过施用公式##STR1##的杀菌剂来控制植物全蚀病的方法，其中Z1和Z2为C，并且是苯并噻吩的芳香环的一部分；A从--C(X)-胺中选择，其中胺是未取代的、单取代的或双取代的氨基基团，--C(O)--SR.sub.3，--NH--C(X)R.sub.4和--C(.dbd.NR.sub.3)--XR.sub.7；B为--W.sub.m --Q(R.sub.2).sub.3或从O-甲苯基、1-萘基、2-萘基和9-菲基中选择，每个都可以选择性地用卤素或R.sub.4取代；Q为C、Si、Ge或Sn；W为--C(R.sub.3).sub.p H.sub.(2-p)--；或当Q为C时，W从--C(R.sub.3).sub.p H(.sub.2-p)，--N(R.sub.3).sub.m H(.sub.1-m)--，--S(O)p--和--O--中选择；X为0或S；n为0、1、2或3；m为0或1；p为0、1或2；每个R和R.sub.2在此独立定义；R.sub.3为C.sub.1 -C.sub.4烷基；R.sub.4为C.sub.1 -C.sub.4烷基、卤代烷基、烷氧基、烷硫基、烷基氨基或二烷基氨基；R.sub.7为C.sub.1 -C.sub.4烷基、卤代烷基或苯基，可以选择性地用卤素、硝基或R.sub.4取代；或其农艺学盐。
• TETRAHYDROPYRROLOTHIAZINE COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：US20130261111A1

  公开（公告）日：2013-10-03

  The present invention provides compounds of Formula I: wherein A is selected from the group consisting of; R 1 is H or F; R 2 is H, —CH 2 OH, C 1 -C 3 alkyl, R 3 is H, F, or CN; R 4 is H, F; or CN; and R 5 is H, —CH 3 , or —OCH 3 ; or a pharmaceutically acceptable salt thereof.

  本发明提供了以下式I的化合物： 其中A选自以下组合之一； R1为H或F； R2为H，—CH2OH，C1-C3烷基， R3为H，F或CN； R4为H，F；或CN；和 R5为H，—CH3，或—OCH3； 或其药学上可接受的盐。
• Heteroarylmethylbenzenes
  申请人：Ciba-Geigy Corporation

  公开号：US05246952A1

  公开（公告）日：1993-09-21

  Compounds of formula I ##STR1## wherein Z is thiazolyl or isothiazolyl, and X, R, R.sub.0, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description, have valuable pharmaceutical properties and are effective especially against tumors.

  式I的化合物##STR1##其中Z是噻唑基或异噻唑基，而X、R、R.sub.0、R.sub.1、R.sub.2和R.sub.3如描述中所定义，具有宝贵的药理特性，特别对抗肿瘤有效。
• 一种制备N-甲基噻唑啉-2-酮类化合物的方法
  申请人：苏州波菲特新材料科技有限公司

  公开号：CN103965136B

  公开（公告）日：2016-09-07

  本发明公开了一种制备N‑甲基噻唑啉‑2‑酮类化合物的方法，在惰性气氛中以有机溶剂为反应介质，以铜盐和氧化剂为催化体系，通过氧化甲基化反应将噻唑类化合物氧化为N‑甲基噻唑啉‑2‑酮类化合物。本发明的制备方法反应活性较高，反应条件温和，反应时间短，收率高；且使用的催化剂廉价、低毒、用量少，将多步反应缩短为一步反应，处理简单，有利于产物的纯化；更重要的是避免了剧毒性易挥发的甲基化试剂的使用；本发明公开的催化剂体系对多种反应物具有普适性；本发明原料简单易得，反应过程简单可控，适于工业化生产。
• Estrogen synthetase inhibitors. 2. Comparison of the in vitro aromatase inhibitory activity for a variety of nitrogen heterocycles substituted with diarylmethane or diarylmethanol groups
  作者：C. David Jones、Mark A. Winter、Kenneth S. Hirsch、Nancy Stamm、Harold M. Taylor、Howard E. Holden、James D. Davenport、Eriks V. Krumkalns、Robert G. Suhr

  DOI：10.1021/jm00163a065

  日期：1990.1

  The preparation and in vitro aromatase inhibitory activity of a wide variety of heterocyclic (4,4'-dichlorodiphenyl)methanes and -methanols are described. The choice of the two diaryl-bearing moieties as a vehicle for the evaluation of the heterocycles was made by the comparison of series of imidazole and pyridine-derived compounds with similar pyrimidine compounds reported previously. A structural

  描述了多种杂环（4,4'-二氯二苯基）甲烷和-甲醇的制备和体外芳香酶抑制活性。通过将一系列咪唑和吡啶衍生的化合物与先前报道的类似嘧啶化合物进行比较，从而选择了两个带有二芳基的部分作为评估杂环的载体。还介绍了活性最高的化合物的结构模型。发现包含两个杂环部分的一系列相关化合物的活性与模型一致。评估的许多化合物（包括吡啶，咪唑，嘧啶，吡唑，三唑，噻唑和异噻唑类的代表）在低纳摩尔浓度下均具有EC50抑制芳香酶的能力。

表征谱图