2-氨基-4,5-二氯苯并噻唑 | 1849-71-4

• 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: 2-氨基-4,5-二氯苯并噻唑
• 英文名称: 4,5-dichloro-1,3-benzothiazol-2-amine
• 英文别名: 4,5-dichloro-benzothiazol-2-ylamine；2-amino-4,5-dichlorobenzothiazole；2-Amino-4,5-dichlor-benzothiazol
• CAS: 1849-71-4
• 化学式: C₇H₄Cl₂N₂S
• mdl: MFCD02093913
• 分子量: 219.094
• InChiKey: GMOFXJZIUQGHTF-UHFFFAOYSA-N

物化性质

• 熔点：
  275-276 °C
• 沸点：
  379.7±45.0 °C(Predicted)
• 密度：
  1.654±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

SDS

Name:	2-Amino-4 5-Dichlorobenzothiazole 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	1849-71-4

Section 1 - Chemical Product MSDS Name:2-Amino-4 5-Dichlorobenzothiazole 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1849-71-4	2-Amino-4,5-dichlorobenzothiazole	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May cause burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1849-71-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 175-180 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H4Cl2N2S
Molecular Weight: 219.0074

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Acids, acid chlorides, acid anhydrides, oxidizing agents, carbon dioxide.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1849-71-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Amino-4,5-dichlorobenzothiazole - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1849-71-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1849-71-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1849-71-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氨基-4,5-二氯苯并噻唑 在 sodium hydroxide 作用下， 生成 3,4-dichloro-2-aminobenzenethiol
  参考文献：
  名称：

  新型有效的醛糖还原酶抑制剂：3,4-二氢-4-氧代-3-[[5-（三氟甲基）-2-苯并噻唑基]甲基] -1-酞嗪乙酸（zopolrestat）和同类物。

  摘要：

  为了设计新型有效的醛糖还原酶抑制剂（ARI），人们寻求了一个新的工作假设，即在醛糖还原酶（AR）酶上具有迄今无法识别的结合位点，该结合位点对苯并噻唑具有很强的亲和力。该假设的首次应用产生了一系列新的3,4-二氢-4-氧代-3-（苯并噻唑基甲基）-1-酞嗪乙酸+ + +酸。该系列的母体（207）是一种有效的人胎盘AR抑制剂（IC50 = 1.9 x 10（-8）M），在糖尿病合并症的急性试验中，口服有效预防山楂醇在大鼠坐骨神经中的蓄积（ ED50 ＝ 18.5mg / kg）。通过药物化学原理（包括与其他药物系列的比喻）优化该线索，导致产生更有效的207同类药物，并最终设计出3，4-二氢-4-氧代-3-[[[5-（三氟甲基）-2-苯并噻唑基]甲基] -1-酞嗪乙酸（216，CP-73,850，zopolrestat）。在体外和体内，Zopolrestat被发现比207更有效。在急性试验中，其针对AR和ED50的IC50分别为3

  DOI：

  10.1021/jm00105a018
• 作为产物：
  描述：

  1-(2,3-二氯苯基)-2-硫脲 在 溴 、 氨 作用下， 以 氯仿 、 水 为溶剂， 生成 2-氨基-4,5-二氯苯并噻唑
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 2H-pyrimido[2,1-b]benzothiazol-2-ones

  摘要：

  4-苯基-2H-嘧啶并[2,1-b]苯并噻唑-2-酮通过2-氨基苯并噻唑与炔酸反应，在定量产率下合成。合成化合物对细菌种类的抗菌活性进行了测试，包括凝固芽孢杆菌、枯草芽孢杆菌、金黄色葡萄球菌和铜绿假单胞菌。合成化合物显示出对微生物具有显著的活性，这可以与其融合的杂环系统相关联。

  DOI：

  10.1007/s11164-010-0211-9

文献信息

• Inhibition of the ubiquitin-proteasome system by an NQO1-activatable compound
  作者：Tatiana A. Giovannucci、Florian A. Salomons、Martin Haraldsson、Lotta H. M. Elfman、Malin Wickström、Patrick Young、Thomas Lundbäck、Jürgen Eirich、Mikael Altun、Rozbeh Jafari、Anna-Lena Gustavsson、John Inge Johnsen、Nico P. Dantuma

  DOI：10.1038/s41419-021-04191-9

  日期：——

  Malignant cells display an increased sensitivity towards drugs that reduce the function of the ubiquitin-proteasome system (UPS), which is the primary proteolytic system for destruction of aberrant proteins. Here, we report on the discovery of the bioactivatable compound CBK77, which causes an irreversible collapse of the UPS, accompanied by a general accumulation of ubiquitylated proteins and caspase-dependent cell death. CBK77 caused accumulation of ubiquitin-dependent, but not ubiquitin-independent, reporter substrates of the UPS, suggesting a selective effect on ubiquitin-dependent proteolysis. In a genome-wide CRISPR interference screen, we identified the redox enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1) as a critical mediator of CBK77 activity, and further demonstrated its role as the compound bioactivator. Through affinity-based proteomics, we found that CBK77 covalently interacts with ubiquitin. In vitro experiments showed that CBK77-treated ubiquitin conjugates were less susceptible to disassembly by deubiquitylating enzymes. In vivo efficacy of CBK77 was validated by reduced growth of NQO1-proficient human adenocarcinoma cells in nude mice treated with CBK77. This first-in-class NQO1-activatable UPS inhibitor suggests that it may be possible to exploit the intracellular environment in malignant cells for leveraging the impact of compounds that impair the UPS.

  恶性细胞对降低泛素蛋白酶体系统（UPS）功能的药物表现出增加的敏感性，UPS是异常蛋白质降解的主要蛋白质系统。在这里，我们报告了生物活化化合物CBK77的发现，它导致UPS的不可逆性崩溃，伴随着泛素化蛋白的普遍积累和caspase依赖的细胞死亡。CBK77导致了依赖泛素而非独立于泛素的UPS报告底物的积累，表明对依赖泛素的蛋白质降解具有选择性影响。在全基因组CRISPR干扰筛选中，我们确定了氧化还原酶NAD(P)H：喹啉醌还原酶1（NQO1）作为CBK77活性的关键介导体，并进一步证明了其作为化合物生物活化剂的作用。通过亲和力基础蛋白质组学，我们发现CBK77与泛素发生共价作用。体外实验显示，CBK77处理后的泛素结合物对去泛素化酶的解聚作用较不敏感。在NQO1-proficient人类腺癌细胞中，用CBK77处理的裸鼠显示了CBK77的体内有效性。这种首创的NQO1活化的UPS抑制剂表明，可能可以利用恶性细胞内部环境来增强影响破坏UPS的化合物的作用。

• Ion channel modulating agents
  申请人：——

  公开号：US20020061914A1

  公开（公告）日：2002-05-23

  The present invention relates to ion channel modulating agents. More particularly, the present invention relates to a particular class of chemical compounds represented by general formula (I) that has proven useful as modulators of SK Ca , IK Ca and BK Ca channels. In further aspects, the present invention relates to the use of these SK/IK/BK channel modulating agents for the manufacture of medicaments, and pharmaceutical compositions comprising the SK/IK/BK channel modulating agents. The SK/IK/BK channel modulating agents of the invention are useful for the treatment or alleviation of diseases and conditions associated with the SK/IK/BK channels.

  本发明涉及离子通道调节剂。更具体地，本发明涉及一类化学化合物，其通用式（I）已被证明作为SKCa、IKCa和BKCa通道的调节剂而具有实用价值。在进一步方面，本发明涉及利用这些SK/IK/BK通道调节剂制造药物，以及包含这些SK/IK/BK通道调节剂的药物组合物。本发明的SK/IK/BK通道调节剂对于治疗或缓解与SK/IK/BK通道相关的疾病和症状是有用的。
• Process for the preparation of 2(3H)-benzothiazolones
  申请人：Hoechst AG

  公开号：US05594145A1

  公开（公告）日：1997-01-14

  The process for the preparation of 2(3H)-benzothiazolones which are optionally substituted on the benzene ring by reacting a 2-aminobenzothiazole which is optionally substituted on the benzene ring with a diazotization agent in the presence of aqueous hydrochloric acid, if appropriate with addition of a chloride, to give a diazonium chloride, reacting the diazonium chloride directly to give a 2-chlorobenzothiazole, which is optionally substituted on the benzene ring, and hydrolyzing the 2-chlorobenzothiazole, without intermediate isolation, at 120.degree.-200.degree. C. under reaction pressure.

  制备2(3H)-苯并噻唑酮的过程，可以通过将一种选择性取代苯环的2-氨基苯并噻唑与重氮化试剂在水盐酸存在下反应，如有必要加入氯化物，以得到重氮化氯化物，直接将重氮化氯化物反应，得到一种选择性取代苯环的2-氯苯并噻唑，然后在120℃-200℃的反应压力下，不经过中间分离，水解2-氯苯并噻唑。
• Dispersionsfarbstoffe
  申请人：CIBA-GEIGY AG

  公开号：EP0271444A2

  公开（公告）日：1988-06-15

  Die neuen Dispersionsfarbstoffe der im Anspruch 1 angegebenen Formel eignen sich insbesondere zum Färben von Textilmaterial aus Polyesterfasern.

  权利要求 1 所述式子的新型分散染料特别适用于涤纶纤维纺织品的染色。
• Magenta dye and thermal transfer material comprising it
  申请人：SONY CORPORATION

  公开号：EP0468380A1

  公开（公告）日：1992-01-29

  A magenta dye of the formula: wherein: A is selected from a group consisting of a methyl group, a methoxy group, an alkylcarbonylamino group, and a hydrogen atom: X1 and X2 are selected from a group consisting of a hydrogen atom, a halogen atom and a nitro group; R1 and R2 are selected from a group consisting of an alkyl group, an alkoxyalkyl group, and an alkoxycarbonyl group, and each is substituted by a group selected from an alkyl group, a hydroxyl group, a halogen atom, and a cyano group; and R3 is an alkyl group. A thermal transfer material is disclosed comprising a support and an ink layer, wherein the ink layer comprises the magenta dye of the formula described hereinabove.

  一种洋红色染料，其式如下 其中 A 选自由甲基、甲氧基、烷基羰基氨基和氢原子组成的组： X1 和 X2 选自由氢原子、卤素原子和硝基组成的组； R1 和 R2 选自烷基、烷氧基烷基和烷氧羰基组成的组，且各自被选自烷基、羟基、卤素原子和氰基的基团取代；以及 R3 是烷基。 本发明公开了一种热转印材料，该材料包括支撑体和墨水层，其中墨水层包括上述式中的洋红色染料。