3-氯-1,2-苯并异噻唑-1,1-二氧化物 | 567-19-1

• 物质功能分类: 有机原料 - 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: 3-氯-1,2-苯并异噻唑-1,1-二氧化物
• 中文别名: 3-氯-1,2-苯并噻唑1,1-二氧化物
• 英文名称: 3-chloro-1,2-benzisothiazole 1,1-dioxide
• 英文别名: 3-chlorobenzo[d]isothiazole 1,1-dioxide；Pseudosaccharin chloride；3-chloro-1,2-benzothiazole 1,1-dioxide
• CAS: 567-19-1
• 化学式: C₇H₄ClNO₂S
• mdl: MFCD00835585
• 分子量: 201.633
• InChiKey: VBEJRJPHNPIURV-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C
• 沸点：
  377.1±25.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)
• 稳定性/保质期：
  本品为无色固体，熔点范围为143～145℃，不溶于水，但能溶解于二氯乙烷、甲苯等溶剂中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 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：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934991000
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P280,P301+P312+P330,P305+P351+P338+P310,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H318
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Chloro-benzo[d]isothiazole 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: 3-Chloro-benzo[d]isothiazole 1,1-dioxide
CAS number: 567-19-1

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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: C7H4ClNO2S
Molecular weight: 201.6

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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, hydrogen chloride, 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

化学性质： 本品为无色固体，熔点在143～145℃之间，不溶于水，但能溶解于二氯乙烷、甲苯等有机溶剂中。

用途： 3-氯-1,2-苯并异噻唑-1,1-二氧化物是杀菌剂烯丙苯噻唑的中间体。

生产方法： 其制备过程为：将糖精置于反应釜内，加入溶剂，并以DMF作为催化剂，再加入氯化亚砜。随后加热回流数小时后冷却，蒸去剩余的氯化亚砜和溶剂，即可得到成品。此外，氯化剂也可以选用光气或三氯化磷等其他试剂。

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
  1,2-苯并噻唑1,1-二氧化物	benzo[d]isothiazole 1,1-dioxide	5669-05-6	C7H5NO2S	167.188

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1,2-苯并异噻唑-3-胺 1,1-二氧化物	3-amino-1,2-benzisothiazole 1,1-dioxide	7668-28-2	C7H6N2O2S	182.203
  3-甲基-1,2-苯并噻唑1,1-二氧化物	3-methylbenzo[d]isothiazole-1,1-dioxide	34989-82-7	C8H7NO2S	181.215
  3-苯基-1,2-苯并噻唑1,1-二氧化物	3-phenylbenzo[d]isothiazole-1,1-dioxide	53440-57-6	C13H9NO2S	243.286
  N-甲基-1,2-苯并异噻唑-3-胺1,1-二氧化物	3-Methyl-amino-1,2-benzisothiazol-1,1-dioxid	7677-47-6	C8H8N2O2S	196.23
  3-肼基-1,2-苯并异噻唑 1,1-二氧化物	3-hydrazinylbenzoisothiazole-1,1-dioxide	6635-42-3	C7H7N3O2S	197.217
  3-甲氧基-1,2-苯并噻唑1,1-二氧化物	3-(methoxy)-1,2-benzisothiazole 1,1-dioxide	18712-14-6	C8H7NO3S	197.214
  N,N-二甲基-1,2-苯并异噻唑-3-胺 1,1-二氧化物	N,N-dimethyl-1,2-benzothiazol-3-amine 1,1-dioxide	22716-43-4	C9H10N2O2S	210.257
  3-乙氧基-1,2-苯并噻唑1,1-二氧化物	3-ethoxy-benzo[d]isothiazole 1,1-dioxide	18712-15-7	C9H9NO3S	211.241
  ——	3-(4-(trifluoromethyl)phenyl)benzo[d]isothiazole 1,1-dioxide	124401-05-4	C14H8F3NO2S	311.284
  ——	N-(1,1-dioxo-1,2-benzisothiazol-3-yl)ethylamine	7677-48-7	C9H10N2O2S	210.257

反应信息

• 作为反应物：
  描述：

  3-氯-1,2-苯并异噻唑-1,1-二氧化物 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 7-thia-8-azabucyclo[4.2.0]octa-1,3,5-triene 7,7-dioxide
  参考文献：
  名称：

  在固体氩气中分离的新型四唑-糖基共轭物的结构和光化学

  摘要：

  摘要 复合基质分离 FTIR 和理论 DFT/B3LYP/6-311++G(3df,3pd) 研究了新型合成的四唑-糖基共轭物 2-[1-(1 H-tetrazol-5-yl)ethyl]-进行了 1,2-benzisothiazol-3(2 H )-one 1,1-dioxide [1-TE-BZT]。在气相中，在室温下，该化合物以六种异构形式（1 H 互变异构体的四种构象异构体和 2 H 互变异构体的两种构象异构体）的混合物形式存在。根据理论计算，构象异构体 1 H 是最稳定的，三种最稳定形式之间的相对能量低于 4 kJ mol -1 。这些构象异构体受益于稳定的分子内氢键样相互作用，涉及四唑环的 1 H 和糖基部分的羰基氧。研究了 1-TE-BZT 在固氩中的光化学和理论 DFT/B3LYP/6-311++G(3df, 3pd) 计算也有助于分配实验波段。在用 λ = 275 nm

  DOI：

  10.1016/j.molstruc.2012.04.081
• 作为产物：
  描述：

  邻甲酸甲酯苯磺酰胺 在 盐酸 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-氯-1,2-苯并异噻唑-1,1-二氧化物
  参考文献：
  名称：

  新型3-(烷基/芳氨基)苯并[d]异噻唑1,1-衍生物的合成、表征及抗菌评价

  摘要：

  糖精核长期以来被认为是医学的重要组成部分。合成了一系列拟糖胺衍生物（7a-j）并检查了其抗菌活性。在测试所有化合物后，发现化合物7b、7f、7g、7i和7j对大肠杆菌、金黄色葡萄球菌和枯草芽孢杆菌菌株最有效。该化合物的 MIC 为 4.6 至 16.1 μM。此外，化合物7f和7i对大肠杆菌和枯草芽孢杆菌表现出优异的活性，MIC值分别为4.6和4.7 μM。化合物 7b 和 7i 被发现对所有三种细菌都有活性。在 10 μM 浓度下观察到对大肠杆菌、金黄色葡萄球菌和枯草芽孢杆菌的区域抑制作用分别为 7b 的 0.9、1.8、3.9 和 7i 的分别为 1.0、1.8 和 2.0 cm。

  DOI：

  10.13005/ojc/370405
• 作为试剂：
  描述：

  哌啶 、 苯亚磺酸 在 三乙胺 、 3-氯-1,2-苯并异噻唑-1,1-二氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到1-(苯基亚硫酰基)哌啶
  参考文献：
  名称：

  Furukawa, Mitsuru; Ohkawara, Tadashi; Noguchi, Yoshihide, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 134 - 141

  摘要：

  DOI：

文献信息

• Molecular structure of nitrogen-linked methyltetrazole-saccharinates
  作者：Amin Ismael、José António Paixão、Rui Fausto、Maria Lurdes S. Cristiano

  DOI：10.1016/j.molstruc.2012.04.018

  日期：2012.9

  0737 A, α = 96.517°, β = 107.543°, γ = 99.989°; Z = 2), 1-methyltetrazole-saccharinate units assume the most stable configuration for the isolated molecule, (1H)-1-methytetrazole iminosaccharin tautomeric form (1MTIS), with the N C spacer linking the two heterocycles. On the other hand, neat crystalline 2-methyl derivative units (space group P 1 ¯ , a = 7.8010 A, b = 8.6724 A, c = 9.4984 A, α = 114.083°

  摘要 利用 X 射线晶体学、红外和拉曼光谱研究了结晶相中氮连接的 1-和 2-甲基四唑糖精的分子结构，并辅以在 DFT(B3LYP)/6-31 上进行的量子化学计算。 ++G(d,p) 孤立分子的理论水平。在纯结晶固体中（空间群 P 1¯ , a = 6.9763 A, b = 8.3097 A, c = 10.0737 A, α = 96.517°, β = 107.543°, γ = 99.989°; Z = 2-甲基四唑），1-甲基四唑-糖精单位假定分离分子的最稳定构型，(1H)-1-甲基四唑亚氨基糖精互变异构形式 (1MTIS)，NC 间隔基连接两个杂环。另一方面，纯结晶 2-甲基衍生单元（空间群 P 1¯ , a = 7.8010 A, b = 8.6724 A, c = 9.4984 A, α = 114.083°, β = 107.823°, γ = 93.080°；Z = 2)
• Pyrazolopyrimidines as therapeutic agents
  申请人：Abbott Laboratories

  公开号：US20020156081A1

  公开（公告）日：2002-10-24

  The present invention provides compounds of Formula I, 1 including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R 2 , and R 3 are defined as described herein.

  本发明提供了公式I的化合物，包括其药学上可接受的盐和/或前药，其中G、R2和R3的定义如本文所述。
• SYNTHESIS AND REACTION OF 3-(ALKYLTHIO)- 1,2-BENZISOTHIAZOLE 1,1-DIOXIDES AS AN ODORLESS CRYSTALLINE EQUIVALENT OF THIOLS
  作者：Katsuhiko Inomata、Hiroyuki Yamada、Hiroshi Kotake

  DOI：10.1246/cl.1981.1457

  日期：1981.10.5

  It was found that sodium salt of 1,2-benzisothiazol-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide, which very smoothly produced the corresponding alkanethiol by the reaction with piperidine in almost quantitative yield.

  发现 1,2-苯并异噻唑-3(2H)-硫酮 1,1-二氧化物（硫糖精）的钠盐容易与卤代烷反应，得到 3-（烷硫基）-1,2-苯并异噻唑 1,1-二氧化物，通过与哌啶反应以几乎定量的产率非常顺利地产生相应的烷硫醇。
• Synthesis and Antileishmanial Activity of 1,2,4,5-Tetraoxanes against Leishmania donovani
  作者：Lília I. L. Cabral、Sébastien Pomel、Sandrine Cojean、Patrícia S. M. Amado、Philippe M. Loiseau、Maria L. S. Cristiano

  DOI：10.3390/molecules25030465

  日期：——

  A chemically diverse range of novel tetraoxanes was synthesized and evaluated in vitro against intramacrophage amastigote forms of Leishmania donovani. All 15 tested tetraoxanes displayed activity, with IC50 values ranging from 2 to 45 µm. The most active tetraoxane, compound LC140, exhibited an IC50 value of 2.52 ± 0.65 µm on L. donovani intramacrophage amastigotes, with a selectivity index of 13.5. This compound reduced the liver parasite burden of L. donovani-infected mice by 37% after an intraperitoneal treatment at 10 mg/kg/day for five consecutive days, whereas miltefosine, an antileishmanial drug in use, reduced it by 66%. These results provide a relevant basis for the development of further tetraoxanes as effective, safe, and cheap drugs against leishmaniasis.

  一系列新型四氧杂环己烷类化合物在体外对利什曼原虫（Leishmania donovani）巨噬细胞内阿马斯蒂果形态进行了合成和评价。所有15种测试的四氧杂环己烷类化合物均显示出活性，IC50值范围为2至45 µm。其中最活性的四氧杂环己烷类化合物LC140，在L. donovani巨噬细胞内阿马斯蒂果上表现出IC50值为2.52 ± 0.65 µm，选择性指数为13.5。该化合物通过腹腔注射每天10 mg/kg，连续五天治疗后，将感染利什曼原虫的小鼠肝脏寄生虫负担减少了37％，而目前使用的抗利什曼病药物米尔托芬辛则将其减少了66％。这些结果为进一步开发四氧杂环己烷类化合物作为有效、安全和廉价的利什曼病药物提供了重要依据。
• In Vitro Assessment of Antimicrobial, Antioxidant, and Cytotoxic Properties of Saccharin–Tetrazolyl and –Thiadiazolyl Derivatives: The Simple Dependence of the pH Value on Antimicrobial Activity
  作者：Luís M. T. Frija、Epole Ntungwe、Przemysław Sitarek、Joana M. Andrade、Monika Toma、Tomasz Śliwiński、Lília Cabral、M. Lurdes S. Cristiano、Patrícia Rijo、Armando J. L. Pombeiro

  DOI：10.3390/ph12040167

  日期：——

  The antimicrobial, antioxidant, and cytotoxic activities of a series of saccharin–tetrazolyl and –thiadiazolyl analogs were examined. The assessment of the antimicrobial properties of the referred-to molecules was completed through an evaluation of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values against Gram-positive and Gram-negative bacteria and yeasts. Scrutiny of the MIC and MBC values of the compounds at pH 4.0, 7.0, and 9.0 against four Gram-positive strains revealed high values for both the MIC and MBC at pH 4.0 (ranging from 0.98 to 125 µg/mL) and moderate values at pH 7.0 and 9.0, exposing strong antimicrobial activities in an acidic medium. An antioxidant activity analysis of the molecules was performed by using the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, which showed high activity for the TSMT (N-(1-methyl-2H-tetrazol-5-yl)-N-(1,1-dioxo-1,2-benzisothiazol-3-yl) amine, 7) derivative (90.29% compared to a butylated hydroxytoluene positive control of 61.96%). Besides, the general toxicity of the saccharin analogs was evaluated in an Artemia salina model, which displayed insignificant toxicity values. In turn, upon an assessment of cell viability, all of the compounds were found to be nontoxic in range concentrations of 0–100 µg/mL in H7PX glioma cells. The tested molecules have inspiring antimicrobial and antioxidant properties that represent potential core structures in the design of new drugs for the treatment of infectious diseases.

  一系列邻苯磺酰胺-四唑基和-噻二唑基类似物的抗菌、抗氧化和细胞毒活性进行了研究。通过评估最小抑制浓度（MIC）和最小杀菌浓度（MBC）值来完成对所述分子的抗菌性质的评估，针对革兰氏阳性和革兰氏阴性细菌以及酵母。对四种革兰氏阳性菌株在pH 4.0、7.0和9.0下的MIC和MBC值进行审查，结果显示在pH 4.0下MIC和MBC的值较高（范围从0.98到125 µg/mL），在pH 7.0和9.0下的值适中，表明在酸性介质中具有强大的抗菌活性。通过使用DPPH（2,2-二苯基-1-苯基肼）方法对分子的抗氧化活性进行分析，结果显示TSMT（N-(1-甲基-2H-四唑-5-基)-N-(1,1-二氧-1,2-苯并异噻唑-3-基)胺，7）衍生物的活性较高（90.29%，与正丁基羟基甲苯醌阳性对照61.96%相比）。此外，对邻苯磺酰胺类似物的一般毒性在一个溴虾模型中进行了评估，显示毒性值微乎其微。反过来，在对细胞存活能力进行评估时，发现所有化合物在H7PX胶质瘤细胞中的浓度范围为0-100 µg/mL时均无毒性。经测试的分子具有令人鼓舞的抗菌和抗氧化性质，代表了设计用于治疗传染病的新药物的潜在核心结构。