5,6-二氯苯并[c][1,2,5]噻二唑 | 17821-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 中文名称: 5,6-二氯苯并[c][1,2,5]噻二唑
• 英文名称: 5,6-dichloro-2,1,3-benzothiadiazole
• 英文别名: 5,6-Dichlor-<2,1,3>benzothiadiazol；5,6-Dichlor-benz-2,1,3-thiadiazol；5,6-Dichlor-2,1,3-benzothiadiazol；5,6-dichloro-benzo[1,2,5]thiadiazole；5,6-Dichlor-benzo[1,2,5]thiadiazol；5,6-Dichlorobenzo[c][1,2,5]thiadiazole
• CAS: 17821-93-1
• 化学式: C₆H₂Cl₂N₂S
• mdl: MFCD00277454
• 分子量: 205.067
• InChiKey: FANYVGCAISPJSX-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  288.0±20.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 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
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole
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: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole
CAS number: 17821-93-1

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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: C6H2Cl2N2S
Molecular weight: 205.1

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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, 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

5,6-二氯苯并[C][1,2,5]噻二唑是一种用于研究的化合物。

反应信息

• 作为反应物：
  描述：

  5,6-二氯苯并[c][1,2,5]噻二唑 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 溴 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 5,6-dichloro-4,7-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  苯并噻二唑对共轭聚合物中卤化影响的综合研究

  摘要：

  近年来，卤化有机半导体材料的兴起导致有机光伏电力转换效率的显着提高。但是，卤原子对光电，结构和光伏性能的影响尚未完全了解。特别地，由于不同的物理化学性质，使用氯原子代替氟原子的聚合物的设计仍然需要合理化。在本文中，我们不仅改变了卤素原子的数量，还改变了它们的性质，研究了一系列4种卤代D–A电子给体共聚物。使用非卤代聚合物作为参考，对这些新聚合物进行了深入的实验和理论研究，使我们能够合理化这些化学修饰的影响。特别是，我们发现，在这一系列聚合物中，结构特性和共混形态主要受卤素性质的影响。我们还证明，沿聚合物主链合理地减少氟原子的数量可以是改善薄膜加工条件，同时将效率保持在可接受水平的好策略。

  DOI：

  10.1021/acs.macromol.9b01760
• 作为产物：
  描述：

  4,5-二氯邻苯二胺 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以53 %的产率得到5,6-二氯苯并[c][1,2,5]噻二唑
  参考文献：
  名称：

  苯并杂二唑类受体单体上的分子内钯催化剂转移及催化剂转移抑制剂的发现

  摘要：

  在 Suzuki-Miyaura 偶联反应和t Bu 3 PPd 预催化剂的缩聚反应中，分子内催化剂转移发生在二溴苯并三唑上，但不是发生在二溴苯并噻二唑上。此外，苯并噻二唑的添加干扰了二溴亚苯基与苯基硼酸酯的偶联反应中的催化剂转移，其中催化剂转移在不存在任何添加剂的情况下发生。

  DOI：

  10.1002/chem.202301242

文献信息

• Synthesis of Novel Halogenated Heterocycles Based on o-Phenylenediamine and Their Interactions with the Catalytic Subunit of Protein Kinase CK2
  作者：Maria Winiewska-Szajewska、Agnieszka Monika Maciejewska、Elżbieta Speina、Jarosław Poznański、Daniel Paprocki

  DOI：10.3390/molecules26113163

  日期：——

  Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER-stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma

  蛋白激酶CK2是高度多效性蛋白激酶，能够磷酸化数百种蛋白底物。它涉及许多细胞功能，包括细胞活力，凋亡，细胞增殖和存活，血管生成或ER应激反应。由于发现CK2活性在包括癌症在内的许多病理状态中受到干扰，因此它成为该药的有吸引力的靶标。已经开发了许多低质量的ATP竞争性抑制剂，其中大多数已被卤化。我们测试了六种系列卤代杂环配体的结合，这些配体衍生自可商购的4,5-二卤代苯-1,2-二胺。选择这些配体系列以使支架作用与直接归因于卤素原子存在的疏水相互作用分离。最初使用计算机分子对接技术来测试每种配体在CK2的ATP结合位点结合的能力。将HPLC衍生的配体疏水性数据与通过小体积差示扫描荧光法（nanoDSF）评估的结合亲和力进行比较。我们确定了三个有希望的配体支架，其中两个尚未被描述为CK2抑制剂，但可能导致有效的CK2激酶抑制剂。已经确定了在nanoDSF分析中被鉴定为最有前途的八种化合物对CK
• Formation and rearrangement of adducts from benzyne and substituted 2,1,3-benzoselenadiazoles
  作者：Martin R. Bryce、Colin D. Reynolds、Peter Hanson、John M. Vernon

  DOI：10.1039/p19810000607

  日期：——

  substituted 2,1,3-benzoselenadiazoles. Some of these adducts rearrange either thermally or photochemically to give 2-(2-pyridyl)phenyl selenocyanates (7), which are reduced to 2-phenylpyridine derivatives (6) or hydrolysed to give ultimately, diselenides (9). The crystal structure of one benzyne adduct (2b) is reported and the mechanism of its rearrangement discussed.

  通过将苯炔加到取代的2,1,3-苯并硒基二唑上，已制备了一系列5-（1,2-苯并硒唑-3-基）戊二烯腈衍生物（2）。这些加合物中的一些通过热或光化学重排得到2-（2-吡啶基）苯基硒氰酸酯（7），将其还原为2-苯基吡啶衍生物（6）或水解得到最终的二硒化物（9）。报告了一种苯并加合物（2b）的晶体结构，并讨论了其重排机理。
• Chlorination <i>vs.</i> fluorination: a study of halogenated benzo[<i>c</i>][1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging
  作者：Daize Mo、Li Lin、Pengjie Chao、Hanjian Lai、Qingwen Zhang、Leilei Tian、Feng He

  DOI：10.1039/d0nj00700e

  日期：——

  Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor–acceptor (D–A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are

  红色/近红外有机染料在生物应用中变得越来越普遍。然而，设计具有长波长发射，大斯托克斯频移和高荧光量子效率的这些染料仍然是非常艰巨的任务。在这项工作中，基于不同氯化/氟化苯并[ c]的五个供体-受体（D-A）红色/近红外荧光团[ c设计并合成了[1,2,5]噻二唑单元。在这项研究中探索的光物理，理论计算和电化学性质已经证明，引入氯原子将导致较低的HOMO能级，更强的空间位阻和相对较低的溶液量子产率。当制造有机点时，与氟化点相比，氯化点显示出更高的荧光量子产率，更大的斯托克斯位移和更好的光稳定性。标记A549细胞后，所有的氯化/氟化点均显示出高红色发射强度。所有这些结果表明，苯并[ c]的卤素原子的细微变化。] [1,2,5]噻二唑单元是调节这些材料的光物理性质的独特方法，也为设计用于细胞成像应用的高效红/近红外分子提供了良好的指导。
• [EN] 1,3-DITHIOLO[5,6-F]BENZO-2,1,3-THIADIAZOLE OR 1,3-DITHIOLO[6,7-G]QUINOXALINE BASED ORGANIC SEMICONDUCTORS<br/>[FR] SEMI-CONDUCTEURS ORGANIQUES À BASE DE 1,3-DITHIOLO [5,6-F] BENZO -2,1,3-THIADIAZOLE OU 1,3-DITHIOLO [6,7-G] QUINOXALINE
  申请人：MERCK PATENT GMBH

  公开号：WO2018041768A1

  公开（公告）日：2018-03-08

  The invention relates to novel organic semiconducting (OSC) compounds containing one or more 1,3-dithiolo[5,6-f]benzo-2,1,3-thiadiazole ("DTBTz") or 1,3-dithiolo[6,7-g]quinoxaline ("DTQ") units or derivatives thereof, to methods for their preparation and educts or intermediates used therein, to compositions and formulations containing them, to the use of the compounds and compositions as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photodetectors (OPD), organic field effect transistors (OFET) and organic light emitting diodes (OLED), and to OE devices comprising these compounds or compositions.

  该发明涉及包含一个或多个1,3-二硫代[5,6-f]苯并-2,1,3-噻二唑（"DTBTz"）或1,3-二硫代[6,7-g]喹喔啉（"DTQ"）单元或其衍生物的新型有机半导体（OSC）化合物，以及其制备方法、用于制备的底物或中间体，包含它们的组合物和配方，将这些化合物和组合物作为有机半导体在有机电子（OE）设备中的使用，特别是在有机光伏（OPV）设备、钙钛矿基太阳能电池（PSC）设备、有机光探测器（OPD）、有机场效应晶体管（OFET）和有机发光二极管（OLED）的制备中的使用，以及包含这些化合物或组合物的OE设备。
• NMDA Receptor Antagonists for Neuroprotection
  申请人：Liotta Dennis C.

  公开号：US20090253710A1

  公开（公告）日：2009-10-08

  Provided are compounds, pharmaceutical compositions and methods of treatment or prophylaxis of disorders associated with NMDA receptor activity, including neuropathic pain, stroke, traumatic brain injury, epilepsy, and related neurologic events or neurodegeneration. Compounds are of the general Formula I, or a pharmaceutically acceptable salt, ester, prodrug or derivative thereof are provided: wherein: each (L) k -Ar 1 is a substituted or unsubstituted, mono or bicyclic aryl or heteroaryl; W is a bond, alkyl, or alkenyl; X is a bond, NR 1 or O and each R 1 and R 2 is independently H, alkyl, alkenyl or aralkyl or R 1 and R 2 taken together form a 5-8 membered ring; R 3− R 6 are selected from certain specific substituents or a carbonyl; Y is a bond, O, S, SO, SO 2 , CH 2 , NH, N(alkyl), or NHC(═O); and Z is OH, NR 6 R 7 , NR 8 SO 2 (alkyl), NR 8 C(O)NR 6 R 7 , NR 8 C(O)O(alkyl), NR 8 -dihydrothiazole, or NR 8 -dihydroimidazole or wherein Z can fuse with Ar 2 to form selected heterocycles.

  提供了与NMDA受体活性相关的疾病治疗或预防的化合物、制药组合物和方法，包括神经病理性疼痛、中风、创伤性脑损伤、癫痫和相关的神经事件或神经退行性疾病。提供了通式I的化合物或其药学上可接受的盐、酯、前药或衍生物: 其中：每个（L）k-Ar1是取代或未取代的、单环或双环芳基或杂环芳基；W是键、烷基或烯基；X是键、NR1或O，每个R1和R2是独立的H、烷基、烯基或芳基烷基，或R1和R2共同形成5-8成员环；R3-R6选自特定的取代基或羰基；Y是键、O、S、SO、SO2、CH2、NH、N（烷基）或NHC（═O）；Z是OH、NR6R7、NR8SO2（烷基）、NR8C（O）NR6R7、NR8C（O）O（烷基）、NR8-二氢噻唑或NR8-二氢咪唑，或Z可以与Ar2融合形成选择的杂环。