6-氟-2(3h)-苯并噻唑酮肼酮 | 78364-55-3

• 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-氟-2(3h)-苯并噻唑酮肼酮
• 中文别名: 6-氟-2-肼基苯并噻唑；6-氟-2-肼基-1,3-苯并噻唑
• 英文名称: 1-(6-fluorobenzo[d]thiazol-2-yl)hydrazine
• 英文别名: 6-fluoro-2-hydrazinobenzothiazole；6-fluorobenzothiazol-2-ylhydrazine；6-fluoro-2-hydrazinylbenzo[d]thiazole；(6-fluoro-1,3-benzothiazol-2-yl)hydrazine
• CAS: 78364-55-3
• 化学式: C₇H₆FN₃S
• mdl: MFCD04448803
• 分子量: 183.209
• InChiKey: QODXZESJVXQCSC-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C(Solv: ethanol (64-17-5))
• 沸点：
  351.1±44.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  -20°C下，应避免光照并储存在惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(6-Fluorobenzo[d]thiazol-2-yl)hydrazine
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: 1-(6-Fluorobenzo[d]thiazol-2-yl)hydrazine
CAS number: 78364-55-3

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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, refrigerated.
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: C7H6FN3S
Molecular weight: 183.2

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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, hydrogen fluoride, 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

反应信息

• 作为反应物：
  描述：

  6-氟-2(3h)-苯并噻唑酮肼酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 1-(6-fluorobenzothiazol-2-yl)-6-phenyl-3-(p-tolyl)-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridine
  参考文献：
  名称：

  Multi-component solvent-free versus stepwise solvent mediated reactions: Regiospecific formation of 6-trifluoromethyl and 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines

  摘要：

  A simple and efficient regiospecific synthesis of 6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines has been achieved in excellent yields via a three-component reaction between 2-hydrazinobenzothiazoles, alpha-cyanoacetophenones and trifiuoromethyl-beta-diketones under solvent-free conditions. This method was found to be more convenient than the classical stepwise solvent mediated process, which furnished not only the opposite regioisomer i.e. 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines (50-60%) but also an undesired amide, 5-acetylamino-1-(benzothiazol-2'-yl)-3-phenyl-1H-pyrazole as a side product. The structure of the two regioisomers was established with certainty on the basis of rigorous analysis of H-1, C-13, F-19-NMR spectral data and (H-1-C-13) gs-HMQC, (H-1-C-13) gs-HMBC experiments. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.04.007
• 作为产物：
  描述：

  1-(4-氟苯基)-2-硫脲 在 盐酸 、 溴 、 一水合肼 作用下， 以 乙二醇 为溶剂， 生成 6-氟-2(3h)-苯并噻唑酮肼酮
  参考文献：
  名称：

  具有抗糖尿病作用的新型胡椒碱衍生物作为PPAR-γ激动剂

  摘要：

  胡椒碱是负责黑胡椒辛辣的生物碱。在这项研究中，从分离胡椒碱胡椒L.碱性条件下进行水解，得到胡椒酸和用作前体进行含有苯并噻唑部分20个胡椒碱衍生物的合成。通过OGT试验评估所有苯并噻唑衍生物的抗糖尿病潜力，然后在STZ诱导的糖尿病模型中评估活性衍生物。观察到二十种新型胡椒碱类似物中有九种（5b，6a-h）与罗格列酮（标准品）相比，具有明显更高的抗糖尿病活性。此外，评估了这些活性衍生物作为PPAR-γ激动剂的作用，证明了其作用机理。还研究了服用活性衍生物后对体重，脂质过氧化和肝毒性的影响，以进一步确立这些衍生物作为治疗糖尿病副作用较小的先导分子。

  DOI：

  10.1111/cbdd.12760

文献信息

• Ferulic acid and benzothiazole dimer derivatives with high binding affinity to β-amyloid fibrils
  作者：Seong Rim Byeon、Yun Jung Jin、Soo Jeong Lim、Ji Hoon Lee、Kyung Ho Yoo、Kye Jung Shin、Seung Jun Oh、Dong Jin Kim

  DOI：10.1016/j.bmcl.2007.04.079

  日期：2007.7

  New ferulic acid and benzothiazole dimer derivatives were synthesized and evaluated by in vitro competition assay using [(125)I]TZDM for their specific binding affinities to Abeta fibrils. In particular, 4a showed the most excellent binding affinity (K(i)=0.53 nM), compared to PIB (K(i)=0.77 nM), for benzothiazole binding sites of Abeta(1-42) fibrils. This result suggests a possibility of a potential

  合成了新的阿魏酸和苯并噻唑二聚体衍生物，并通过体外竞争试验使用[（125）I] TZDM评估了它们与Abeta原纤维的特异性结合亲和力。特别地，与PIB（K（i）= 0.77 nM）相比，4a对Abeta（1-42）原纤维的苯并噻唑结合位点显示出最优异的结合亲和力（K（i）= 0.53 nM）。该结果表明潜在的AD诊断探针用于检测Abeta原纤维的可能性。
• Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles
  作者：Navin B. Patel、Imran H. Khan、Smita D. Rajani

  DOI：10.1002/ardp.201000061

  日期：2010.11

  In this study, we report the antimycobacterial and antimicrobial evaluation of newly synthesized 3‐(3‐pyridyl)‐5‐(4‐methoxyphenyl)‐4‐(N‐substituted‐1,3‐benzothiazol‐2‐amino)‐4H‐1,2,4‐triazole 6a–j in good yields. All the synthesized compounds have been established by elemental analysis, IR, 1H NMR, 13C‐NMR and Mass spectral data. In‐vitro antimycobacterial activity was carried out against (Mycobacterium

  在这项研究中，我们报告了新合成的 3-(3-吡啶基)-5-(4-甲氧基苯基)-4-(N-取代的-1,3-苯并噻唑-2-氨基)-4H-的抗分枝杆菌和抗菌评价1,2,4-三唑 6a – j 收率良好。所有合成的化合物均已通过元素分析、IR、1H NMR、13C-NMR和质谱数据确定。使用Lowenstein-Jensen培养基对（结核分枝杆菌）H37Rv菌株进行体外抗分枝杆菌活性，对两种革兰氏阳性菌（金黄色葡萄球菌、化脓性链球菌）、两种革兰氏阴性菌（大肠杆菌、假单胞菌）物种（白色念珠菌、黑曲霉、棒状曲霉）使用肉汤微量稀释法。化合物 2e、6a、6g、6h、
• Pharmacological evaluation and characterizations of newly synthesized 1,2,4-triazoles
  作者：Navin B. Patel、Imran H. Khan、Smita D. Rajani

  DOI：10.1016/j.ejmech.2010.06.031

  日期：2010.9

  multistep synthesis sequence beginning with ethyl nicotinoate 3 which on treatment with hydrazine hydrate yields nicotinoyl hydrazide 4. Intermolecular cyclisation of 4 with 4-methylbenzoic acid in presence of phosphorous oxy chloride affords 2-(3-pyridyl)-5-(4-methylphenyl)-1,3,4-oxadiazole 5. Condensation of 5 with various substituted 2-hydrazino benzothiazole 2a–j results in 3-(3-pyridyl)-5-(4-meth

  通过获得三唑类似物。从烟酸乙酯3开始的多步合成序列 ，在用水合肼处理时产生烟酰酰肼4。在氯氧化磷存在下，用4-甲基苯甲酸将4进行分子间环化，得到2-（3-吡啶基）-5-（4-甲基苯基）-1,3,4-恶二唑5。5与各种取代的2-肼基苯并噻唑2a – j缩合，生成3-（3-吡啶基）-5-（4-甲基苯基）-4-（N-取代-1,3-苯并噻唑-2-氨基）-4 H -1,2,4-三唑6a – j类似物。所有化合物均已通过元素分析，IR，1 H NMR，13 C NMR和质谱数据进行了表征。使用Lowenstein-Jensen培养基对结核分枝杆菌H 37 Rv菌株进行了体外抗结核活性，并采用肉汤微量稀释法对各种细菌和真菌进行了抗菌活性。化合物2e，6a，6b，6c，6d，6g，6h和6i作为有希望的抗菌药物出现。还观察到有希望的抗微生物剂已被证明是更好的抗结核药。与利福平相比，化合物6j显示出更好的抗结核活性。
• Anti-HIV, antimycobacterial and antimicrobial studies of newly synthesized 1,2,4-triazole clubbed benzothiazoles
  作者：Navin B. Patel、Imran H. Khan、Christophe Pannecouque、Erik De Clercq

  DOI：10.1007/s00044-012-0129-4

  日期：2013.3

  In an attempt to synthesize pharmacologically active molecules, we report here the synthesis and in vitro anti-HIV, antimycobacterial and antimicrobial activity of various series of 3-(3-pyridyl)-5-(4-substitutedphenyl)-4-(N-substituted-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole. The anti-HIV activity of the title compounds was evaluated as selective human immunodeficiency virus type-1 and -2 (HIV-1

  在试图合成药理学活性分子，我们在这里报告的合成和体外抗HIV，各种系列3-（3-吡啶基）的抗分支杆菌的和抗微生物活性-5-（4-取代苯基）-4-（ñ -取代的-1,3-苯并噻唑-2-氨基）-4 H -1,2,4-三唑。评价了标题化合物的抗HIV活性，包括选择性的1型和2型人类免疫缺陷病毒（HIV-1，HIV-2 RT）抑制剂，使用Lowenstein-Jensen琼脂法的针对H 37 Rv的抗结核活性以及针对H 37 Rv的抗菌活性。某些细菌和真菌菌株采用肉汤微稀释法。FTIR，1 H-NMR，13C-NMR和质谱数据以及元素分析。
• The reaction of aryl and heteroarylhydrazines with aryl-trifluoromethyl β-diketones
  作者：Shiv P. Singh、Vinod Kumar、Ranjana Aggarwal、Jose Elguero

  DOI：10.1002/jhet.5570430428

  日期：2006.7

  We report the results obtained when five aromatic or heteroaromatic hydrazines react with six β-diketones bearing trifluoromethyl and aryl substituents. Forty-two compounds have been isolated corresponding to two isomeric trifluoromethyl pyrazoles and the intermediate 5-CF3, 5-OH pyrazolines. The results have provided useful information for establishing the mechanism of the synthesis of pyrazoles.

  我们报告了当五个芳香族或杂芳香族肼与六个带有三氟甲基和芳基取代基的β-二酮反应时获得的结果。四十二个化合物已被分离出对应于两个同分异构的三氟甲基吡唑和中间体5-CF 3，5-OH吡唑啉。该结果为建立吡唑的合成机理提供了有用的信息。