6-硝基-1,2-苯并异噻唑啉-3-酮 1,1-二氧化物 | 22952-24-5

• 物质功能分类: 香精与香料 - 合成香料 - 内酯和含氧杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 6-硝基-1,2-苯并异噻唑啉-3-酮 1,1-二氧化物
• 中文别名: 6-硝基糖精；6-硝基-1,2-苯并异噻唑啉-3-酮1,1-二氧化物
• 英文名称: 6-nitrosaccharin
• 英文别名: 6-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide；6-nitrosaccharine
• CAS: 22952-24-5
• 化学式: C₇H₄N₂O₅S
• mdl: MFCD00110677
• 分子量: 228.185
• InChiKey: HZZFBUZSKAVIOV-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 °C
• 密度：
  1.762±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Nitro-1,2-benzisothiazolin-3-one 1,1-dioxide
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: 6-Nitro-1,2-benzisothiazolin-3-one 1,1-dioxide
CAS number: 22952-24-5

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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.
Store in closed vessels.
Storage:

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H4N2O5S
Molecular weight: 228.2

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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

应用6-硝基-1,2-苯并异噻唑啉-3-酮1,1-二氧化物是一个有机中间体，可通过两步制备得到。该物质可由对硝基甲苯合成，并用于基于空间光诱导电子转移（SPET）的新型探针。

制备 步骤 1

将22.0g (160mmol) 的对硝基甲苯加入53.0mL 氯磺酸中，于60℃反应48小时。冷却至室温后，缓慢倒入碎冰，并用1L乙醚萃取有机相。使用饱和食盐水（共500mL×3次）洗涤合并后的有机相，加入300mL浓氨水加热至50℃，直到乙醚全部挥发。反应液冷却至室温后过滤，用水重结晶两次，得到淡黄色针状晶体12.1g，产率为35%，熔点182-183℃。

步骤 2

将9.0g (900mmol) 的三氧化铬溶解于84.0mL 浓硫酸和67.0mL 去离子水的混合溶剂中，冰浴搅拌至冷却至室温。分批加入4.3g (20mmol) 化合物1，室温下搅拌24小时。反应结束后将反应液倒入碎冰中，过滤得到白色粗产品粉末。粗产品再用10%的NaHCO₃水溶液溶解，过滤除去不溶性杂质，滤液再用5%的HCl酸化，过滤得白色粉末1.8g，产率为40%，熔点209-210℃。

反应信息

• 作为反应物：
  描述：

  6-硝基-1,2-苯并异噻唑啉-3-酮 1,1-二氧化物 在 盐酸 、 tin 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 50.5h， 生成 2-ethyl-6-amino-1,1-dioxo-1λ⁶-benz[d]isothiazol-3-one
  参考文献：
  名称：

  [EN] DISPERSE AZO DYES, A PROCESS FOR THE PREPARATION THEREOF AND THE USE THEREOF
  [FR] COLORANTS AZOÏQUES DISPERSÉS, LEUR PROCÉDÉ DE PRÉPARATION ET UTILISATION

  摘要：

  本发明涉及式（1）的染料，其中A为-CO-且Q为-SO2-或A为-SO2-且Q为-CO-，R1表示C1-C6烷基，苄基，烯丙基，-CnH2n-COOR或-CnH2n-CN，其中n为1至3的数字，R代表氢或C1-C6烷基；X为硝基，氰基或卤素；Y为氢，硝基，氰基或卤素，K为苯，萘，吡唑酮；6-羟基吡啶酮-（2）或乙酰乙酸芳基酰胺系列的偶联组分的基团，以及其制备过程和在染色或印刷半合成和特别是合成亲水性纤维材料，更特别是纺织材料中的使用。

  公开号：

  WO2011072966A1
• 作为产物：
  描述：

  4-硝基甲苯 在 chromium(VI) oxide 、 氯磺酸 、 ammonium hydroxide 、 硫酸 作用下， 以 乙醚 为溶剂， 反应 46.0h， 生成 6-硝基-1,2-苯并异噻唑啉-3-酮 1,1-二氧化物
  参考文献：
  名称：

  某些糖精衍生物对红细胞碳酸酐酶Ⅰ和Ⅱ的体外抑制作用和构效关系。

  摘要：

  在这项研究中，以CO2为底物，研究了一些糖精衍生物对纯化碳酸酐酶I和II的体外抑制作用。结果表明，所有化合物均抑制hCA I和hCA II酶活性。在这些化合物中，发现6-（对-甲苯基硫脲基）糖精（6m）对hCA I活性最强（IC50 = 13.67μM），而6-（间-甲氧基苯基脲基）糖精（6b）是最有效的。 hCA II活性最高的一种（IC50 = 6.54μM）。结构活性关系（SARs）研究表明，一般而言，硫脲衍生物（6v）比尿素衍生物（6a-k）抑制更多的hCA I和hCA II。所有化合物（不包括6c和6r）对hCA II的抑制活性均高于对hCA I的抑制活性。

  DOI：

  10.3109/14756366.2012.757222

文献信息

• A Convenient Synthesis of 2-Methoxycarbonyl-5-iodobenzene Sulfonamide
  作者：Xinhong Cai、Qiulu Chen、Jing Guan、Shunze Gong、Hao Fu、Defeng Xu

  DOI：10.14233/ajchem.2017.20627

  日期：——

  A convenient and concise synthesis of 2-methyl-5-nitrobenzene sulfonamide can be achieved by sulfochlorination and ammoniation with p-nitrotoluene as raw materials for an 81.2 % yield. 6-Aminosaccharin can be produced via oxidation and reduction in a 64.3 % yield and then the iodination using potassium iodide can afford 6-iodosaccharin with a 70.8 % yield. 2-Methoxycarbonyl-5-iodobenzene sulfonamide can be produced via esterification in a 94.1 % yield.

  一种方便简洁的2-甲基-5-硝基苯磺酰胺的合成方法，以对硝基甲苯为原料，通过磺�氯化及氨化得到其产物，产率为81.2％。6-氨基糖精可利用氧化还原法得到，产率为64.3％，再利用碘化钾进行碘化得到6-碘糖精，产率为70.8％。2-甲氧羰基-5-碘苯磺酰胺可利用酯化法得到，产率为94.1％。
• [EN] FURO[3,2-d]PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE FURO[3,2-D]PYRIMIDINE
  申请人：ABBOTT LAB

  公开号：WO2012048222A1

  公开（公告）日：2012-04-12

  The present invention is directed to novel compounds of Formula (I), pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof wherein the variables are defined as herein. The compounds of Formula (I) are useful as kinase inhibitors and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, cancers.

  本发明涉及式(I)的新化合物、药用可接受的盐、生物活性代谢物、前药、外消旋混合物、对映异构体、非对映异构体、溶剂合物和水合物，其中变量如本文所述定义。式(I)的化合物作为激酶抑制剂是有用的，因此可用于治疗某些状况和疾病，特别是炎症状况和疾病以及增殖性障碍和状况，例如癌症。
• Cyclic Secondary Sulfonamides: Unusually Good Inhibitors of Cancer-Related Carbonic Anhydrase Enzymes
  作者：Janina Moeker、Thomas S. Peat、Laurent F. Bornaghi、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm500255y

  日期：2014.4.24

  IX selective ligands is imperative for the development of these agents. Primary sulfonamides are broad specificity inhibitors of CA enzymes, while secondary sulfonamides are generally poor CA inhibitors. However, saccharin, a cyclic secondary sulfonamide, has unusually good inhibition of CA IX (Ki = 103 nM). In this study, we demonstrate that the affinity and selectivity of saccharin for CA IX can

  碳酸酐酶IX（CA IX）是低氧癌症治疗的目标，而CA IX选择性配体的发现对于这些药物的开发至关重要。一级磺酰胺是CA酶的广泛特异性抑制剂，而二级磺酰胺通常是较差的CA抑制剂。但是，糖精（一种环状仲磺酰胺）对CA IX的抑制作用非常好（K i = 103 nM）。在这项研究中，我们证明了糖精对CA IX的亲和力和选择性在与疏水或亲水取代基连接时可以得到进一步调节。亲水性糖缀合物衍生物（12）对CA IX的抑制作用得到改善（K i = 49.5 nM），对主要脱靶CAs的抑制作用非常差（K i > 50 000 nM）与糖精相比。对于CA IX的脱靶CA选择性> 1000倍，对于经典的伯磺酰胺CA抑制剂来说是前所未有的。我们的研究强调了环状仲磺酰胺被用于发现有效的，对癌症有选择性的CA抑制剂的潜力。
• Syntheses of Saccharin and Cyclamate Derivatives Bearing Polymerizable Vinyl Group
  作者：Hiroyoshi Kamogawa、Shuji Yamamoto、Masato Nanasawa

  DOI：10.1246/bcsj.55.3824

  日期：1982.12

  Vinyl monomers containing saccharin or cyclamate residues were synthesized. 6-Acrylamido-, 6-methacrylamido-, 6-(4-styrenesulfonamido)-, and 6-(vinylbenzylamino)saccharins were synthesized from 6-aminosaccharin. N-[2-(4-Styrenesulfonamido)cyclohexyl] and N-[2-(vinylbenzylamino)cyclohexyl]sulfamic acids were synthesized starting with 1,2-cyclohexanediamine via sodium N-(2-aminocyclohexyl)sulfamate.

  合成了含有糖精或甜蜜素残基的乙烯基单体。6-丙烯酰胺-、6-甲基丙烯酰胺-、6-(4-苯乙烯磺酰胺)-和6-(乙烯基苄基氨基)糖精由6-氨基糖精合成。N-[2-(4-苯乙烯磺酰胺基)环己基]和N-[2-(乙烯基苄基氨基)环己基]氨基磺酸以1,2-环己二胺为原料，通过N-(2-氨基环己基)氨基磺酸钠合成。发现由此合成的所有单体都与 N-乙烯基-2-吡咯烷酮聚合或共聚以提供具有悬垂糖精和环己基氨基磺酸盐单元的乙烯基聚合物。
• Visible-light-induced intermolecular aminoselenation of alkenes
  作者：Gong-Qing Liu、Chen-Fan Zhou、Yun-Qian Zhang、Wei Yi、Peng-Fei Wang、Ji Liu、Yong Ling

  DOI：10.1039/d1gc03195c

  日期：——

  An intermolecular aminoselenation of alkenes with sulfonimides and diselenides is achieved via a visible-light-induced three component reaction. A broad variety of aminoselenation products is accessible in good yields with excellent functional group compatibility. Additional features of this new protocol include being additive- and photocatalyst-free and the use of natural sunlight as well as suitability

  烯烃与磺酰亚胺和二硒化物的分子间氨基硒化是通过可见光诱导的三组分反应实现的。种类繁多的氨基硒化产品可以以良好的收率获得，并具有出色的官能团兼容性。这一新协议的其他特点包括无添加剂和光催化剂、使用自然阳光以及适用于改性苯乙烯功能化生物分子。机理研究表明，这种转变是通过一系列自由基加成和亲核取代发生的。