5-(4-氨基苯基)-1,3,4-二唑-2(3H)-硫酮 | 32058-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-氨基苯基)-1,3,4-二唑-2(3H)-硫酮
• 英文名称: 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-(4-aminophenyl)-1,3,4-oxadiazol-2-thiol；5-(4-aminophenyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 32058-82-5
• 化学式: C₈H₇N₃OS
• 分子量: 193.229
• InChiKey: FIGMOSDEYMCQLX-UHFFFAOYSA-N

物化性质

• 熔点：
  235 °C (dec.)
• 沸点：
  320.0±44.0 °C(Predicted)
• 密度：
  1.53±0.1 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)：
  1.3
• 重原子数：
  13
• 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：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 5-(4-Aminophenyl)-1,3,4-oxadiazole-2-thiol
CAS-No. : 32058-82-5

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 5-(4-Aminophenyl)-1,3,4-oxadiazole-2(3H)-thione
2-(4-Aminophenyl)-1,3,4-oxadiazole-5-thione
Formula : C8H7N3OS
Molecular Weight : 193,23 g/mol
Component Concentration
5-(4-Aminophenyl)-1,3,4-oxadiazole-2-thiol
CAS-No. 32058-82-5 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 235 °C - dec.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 0,874
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(4-氨基苯基)-1,3,4-二唑-2(3H)-硫酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 1-methyl-3-(4-(5-(methylthio)-1,3,4-oxadiazol-2-yl)phenyl)thiourea
  参考文献：
  名称：

  THE LITTLE MOLECULE COMPOUND WHICH USED FOR PROMOTING THE STEM CELLS HYPERPLASIA AND THE USE THEREOF

  摘要：

  该发明提供了能够加速干细胞增殖的小分子化合物及其用途。这些化合物在干细胞增殖机制研究中发挥着重要作用。该发明还涉及这些化合物及相关化合物在制备干细胞增殖加速剂和加速干细胞增殖的药物中的用途。该发明还涉及这些化合物在制备用于治疗由功能细胞丧失或损伤引起的各种疾病的药物中的用途。由干细胞创伤引起的疾病包括与神经系统细胞退化或损伤有关的疾病、血液系统疾病、与心血管细胞丧失或损伤有关的疾病、皮肤烧伤等。

  公开号：

  US20120053214A1
• 作为产物：
  描述：

  potassium;N-[(4-aminobenzoyl)amino]carbamodithioate 在 盐酸 作用下， 以 水 为溶剂， 生成 5-(4-氨基苯基)-1,3,4-二唑-2(3H)-硫酮
  参考文献：
  名称：

  Ultrasound-assisted, one-pot, three-component synthesis and antibacterial activities of novel indole derivatives containing 1,3,4-oxadiazole and 1,2,4-triazole moieties

  摘要：

  摘要 通过超声辐照，以4-氨基-5-(1H-吲哚-3-基)-4H-[1,2,4]三唑-3-硫醇(8)和2-巯基-5-取代的-1,3,4-噁二唑(5a–m)为原料，高效合成了十三种新型吲哚衍生物。与传统方法和微波方法相比，产率提高到82–93%，反应时间缩短到15–35分钟。这些新化合物的结构通过光谱数据和元素分析得到表征。合成的化合物中有两种(10f和10l)对金黄色葡萄球菌和大肠杆菌显示出优异的活性，因此值得进一步研究。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.pdf

  DOI：

  10.1016/j.crci.2015.09.005

文献信息

• Synthesis and Evaluation of Antimicrobial Activity of New Imides and Schiff Bases Derived from Ethyl -4-Amino Benzoate
  作者：Wurood S. Ahmed、Ammar A. Razzak Mahmood、Redha I. Al-Bayati

  DOI：10.13005/ojc/340533

  日期：2018.10.20

  Candida albicans). Among the synthesized derivatives, compound (15) displayed a moderate to potent antibacterial activity, against different (Gram positive and Gram negative) bacteria, and also showed a slight to moderate antifungal activity. keywords: Antimicrobial, Imides, Schiff base, Synthesis, 1,3,4-Oxadiazole derivatives.

  从原料4-氨基苯甲酸乙酯获得了一系列双取代的1,3,4-恶二唑衍生物，包括：酰亚胺和席夫碱，通过与4-氨基苯甲酰肼（1）反应，将其转化为相应的4-氨基苯并酰肼（1）。在无水乙醇中的水合肼。由（1）合成了两个恶二唑母核，第一个核5-（4-氨基苯基）1,3,4-恶二唑-2-胺（2），第二个是5-（4-氨基苯基）-1 ，3，4-恶二唑-2-硫酮（3）。化合物（2）在室温下将（1）的甲醇溶液与溴化氰（CNBr）和碳酸氢钠（NaHCO3）搅拌得到。尽管在（KOH）存在下通过将（1）与CS 2回流来合成化合物（3），但是所产生的酰肼钾盐通过用10％HCl酸化而进行环化。同时，通过将（2）或（3）与酸酐热熔融合成环酰亚胺衍生物（4-6）和（10-12），而通过以下方法合成Schiffs碱衍生物（7-9）和（13-15）常规方法涉及在酸性介质中（使用冰醋酸）将（2）或（3）与不同的芳族醛回流。新的衍生物已
• Inhibitory growth evaluation and apoptosis induction in MCF-7 cancer cells by new 5-aryl-2-butylthio-1,3,4-oxadiazole derivatives
  作者：Rashmin Khanam、Kamal Ahmad、Iram I. Hejazi、Ibrar A. Siddique、Vikash Kumar、Abdul Roouf Bhat、Amir Azam、Fareeda Athar

  DOI：10.1007/s00280-017-3414-6

  日期：2017.11

  regulation of apoptotic signaling pathways may lead to cancer formation. Subsequently, the synthesis of effective chemotherapeutic agents that can induce apoptosis in tumor cell has emerged as a significant approach in cancer drug discovery. METHODS The goal of this work is to develop a potential antitumor agent exerting significant inhibitory effects on cancer cell and low cytotoxicity, for which we focused

  背景技术癌症已经成为全球健康问题之一，并且它是威胁生命的疾病，其特征在于细胞不受限制地生长。尽管化学疗法的管理取得了各种进步，但是由于高毒性，副作用和发展的耐药性，目前的抗癌药物如阿霉素，天冬酰胺酶，甲氨蝶呤，长春新碱的使用仍然受到限制。凋亡是关键的细胞过程，凋亡信号通路的调控不当可能导致癌症形成。随后，可以在肿瘤细胞中诱导凋亡的有效化学治疗剂的合成已成为癌症药物发现中的重要方法。方法这项工作的目的是开发一种潜在的抗肿瘤药物，该药物对癌细胞具有显着的抑制作用，且细胞毒性低，为此，我们将重点放在1,3,4-恶二唑的结构特征上，因为它是现代药物化学中的优先支架，并具有抑制可能与实现细胞永生和致癌作用有关的生长因子，酶和激酶的能力。结果体外MTT筛选试验显示化合物5-氨基苯基-2-丁基硫代-1,3,4-恶二唑（5e）对MCF-7癌细胞表现出最高的抑制作用，IC50值为10.05±1.08 µM，
• Study of Some Alkanes Thermodynamic Parameters Using New Liquid Crystals Containing Sulfur as Stationary Phases
  作者：Mebrouk Djedid、Mokhtar Benalia、Fouad Ferkous、Asma Boudaoud、Ammar Al-Dujaili

  DOI：10.13005/ojc/310214

  日期：2015.6.20

  have liquid crystalline character in their composition comprise aromatic molecules. Furthermore there are few jobs that replace this type of molecules by inhomogeneous molecules that have LC character. We will replace the aromatic rings by units of 1,3,4-oxadiazole and study the effects of these new components of the transition temperatures and the Thermodynamic characteristics of n- alkanes in these

  组成中具有液晶特性的大多数合成化合物都包含芳族分子。此外，很少有工作可以用具有LC特性的非均质分子替代这种类型的分子。我们将用1,3,4-恶二唑单元取代芳环，并研究这两个液相中过渡温度的这些新成分的影响以及正构烷烃的热力学特性。已经通过反相气相色谱法进行了研究。GC获得的转变温度与DSC发现的转变温度非常吻合。根据参数“ b”和相关的热力学量来解释结果。
• Synthesis, Structural Analysis, and Screening of Some Novel 5-Substituted Aryl/Aralkyl-1,3,4-Oxadiazol-2-Yl 4-(Morpholin-4-Ylsulfonyl)Benzyl Sulfides As Potential Antibacterial Agents
  作者：Aziz-ur-Rehman、Samreen Gul、Muhammad Athar Abbasi、Khadija Nafeesa、Muhammad Nadeem Akhtar、Irshad Ahmad、Saira Afzal

  DOI：10.1080/10426507.2014.965816

  日期：2015.7.3

  GRAPHICAL ABSTRACT Abstract A series of new 5-substituted aryl/aralkyl-1,3,4-oxadiazol-2-yl 4-(morpholin-4-ylsulfonyl)benzyl sulfides 6a–k were synthesized by converting multifarious aryl/aralkyl organic acids 1a–k successively into corresponding esters 2a–k, hydrazides 3a–k, and 5-substituted aryl/aralkyl-1,3,4-oxadiazole-2-thiols 4a-k. Finally, the target compounds, 6a–k were prepared by stirring

  图形摘要 摘要 通过转化多种芳基/芳烷基有机酸 1a，合成了一系列新的 5-取代芳基/芳烷基-1,3,4-恶二唑-2-基 4-(吗啉-4-基磺酰基)苄基硫化物 6a-k -k 依次转化为相应的酯 2a-k、酰肼 3a-k 和 5-取代的芳基/芳烷基-1,3,4-恶二唑-2-硫醇 4a-k。最后，通过在 N,N 存在下搅拌 5-取代-1,3,4-恶二唑-2-硫醇与 4-(4-(溴甲基)苯磺酰基) 吗啉 (5) 制备目标化合物 6a-k -二甲基甲酰胺 (DMF) 和氢化钠 (NaH)。通过光谱技术阐明了新合成化合物的结构。此外，
• N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents
  作者：M. A. Abbasi、M. S. Ramzan、Aziz-ur-Rehman、S. Z. Siddiqui、S. A. A. Shah、M. Hassan、S.-Y. Seo、M. Ashraf、B. Mirza、H. Ismail

  DOI：10.1134/s106816201806002x

  日期：2018.11

  2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles

  亲电子试剂 2-溴-N-(5-甲基-1,3-噻唑-2-基)乙酰胺是通过 5-甲基-1,3-噻唑-2-胺和溴乙酰溴在水性介质。在平行方案中，一系列（未）取代的苯甲酸依次转化为相应的酯、酰肼，然后转化为 1,3,4-恶二唑杂环核。亲电子试剂与上述 1,3,4-恶二唑偶联以获得目标双杂环。通过IR、EI-MS、1H NMR和13C NMR对合成的化合物进行结构分析。这些分子的酶抑制研究是针对四种酶进行的，即乙酰胆碱酯酶、丁酰胆碱酯酶、α-葡萄糖苷酶和脲酶。这些化合物与相应酶的相互作用通过他们的计算机研究得到认可。而且，