5-(3-吡啶基)-1,3,4-噁二唑-2-硫醇 | 3690-46-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硫醇盐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(3-吡啶基)-1,3,4-噁二唑-2-硫醇
• 中文别名: 5-(3-吡啶基)-1,3,4-二唑-2-硫醇
• 英文名称: 5-(3-pyridinyl)-1,3,4-oxadiazol-2-thiol
• 英文别名: 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-thiol；5-(3-pyridyl)-1,3,4-oxadiazole-2-thiol；5-pyridin-3-yl-3H-1,3,4-oxadiazole-2-thione
• CAS: 3690-46-8
• 化学式: C₇H₅N₃OS
• mdl: MFCD00139080
• 分子量: 179.202
• InChiKey: QBLWWQDTKCIRSW-UHFFFAOYSA-N

物化性质

• 熔点：
  231 °C (dec.)
• 沸点：
  274.9±32.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  78.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S26,S39
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险品运输编号：
  3259
• 危险性描述：
  H302,H315,H318,H335
• 储存条件：
  室温

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 5-(3-Pyridyl)-1,3,4-oxadiazole-2-thiol
CAS-No. : 3690-46-8
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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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)
Serious eye damage (Category 1)
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 respiratory system and skin. Risk of serious damage to eyes.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H318 Causes serious eye damage.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves/ eye protection/ face protection.
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.
R37/38 Irritating to respiratory system and skin.
R41 Risk of serious damage to eyes.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S39 Wear eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 5-(3-Pyridinyl)-1,3,4-oxadiazole-2(3H)-thione
Formula : C7H5N3OS
Molecular Weight : 179,2 g/mol
Component Concentration
5-(3-pyridyl)-1,3,4-oxadiazole-2-thiol
CAS-No. 3690-46-8 -

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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
Face shield and safety glasses 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
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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: 231 °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- no data available
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
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 eye burns.
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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  5-(3-吡啶基)-1,3,4-噁二唑-2-硫醇 在 potassium phosphate 、 methyloxirane 作用下， 以 水 为溶剂， 生成 5-(pyridin-3-yl)-1,3,4-oxadiazole-2(3H)-one
  参考文献：
  名称：

  环氧丙烷辅助在水中一锅，串联合成取代的1,3,4-恶二唑-2（3 H）-ones

  摘要：

  已经开发了通过新颖的一锅式，串联方式和环氧丙烷辅助合成取代的1,3,4-恶二唑-2（3 H）-one衍生物的方法。从3个分子中分别获得5个取代的1,3,4-恶二唑-2（3 H）-one和3,5-个取代的1,3,4-恶二唑-2（3 H）-one酰基肼，二硫化碳和环氧丙烷的三组分反应，以及酰基hy嗪，二硫化碳，环氧丙烷和有机卤化物的四组分反应。在磷酸钾的存在下，以水为溶剂进行反应，以良好至优异的产率提供预期的产物。

  DOI：

  10.1016/j.tet.2012.07.004
• 作为产物：
  描述：

  烟酸乙酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 5-(3-吡啶基)-1,3,4-噁二唑-2-硫醇
  参考文献：
  名称：

  新型5-取代的1,3,4-恶二唑曼尼希碱和双曼尼希碱作为酮醇酸还原异构酶抑制剂的合成及生物活性。

  摘要：

  方便地以高收率方便地合成了一系列新颖的5-取代的1,3,4-恶二唑曼尼希碱和双曼尼希碱。通过IR，（1）H NMR，（13）C NMR和元素分析对它们的结构进行表征。初步的生物测定结果表明，某些化合物对几种试验植物真菌显示出良好的体外杀真菌活性。其中一些对甘蓝型油菜表现出显着的除草活性，对水稻酮醇-酸还原异构酶（KARI）的体外抑制活性极好。在14种新化合物中，8c，8d和8m显示出有效的KARI抑制活性，Ki值分别为（0.96±0.42），（3.86±0.49）和（3.10±0.71）μmol/ L，与IpOHA相当。这些化合物可能是新型的KARI抑制剂，需要进一步研究。

  DOI：

  10.1016/j.bmcl.2016.08.059

文献信息

• 含哌嗪的1,3,4-噁二唑Mannich碱类化合物 及制备与应用
  申请人：南开大学

  公开号：CN105541748B

  公开（公告）日：2017-09-12

  本发明公开了一类含哌嗪的1,3,4‑噁二唑Mannich碱类化合物及制备与应用。本发明化合物具有如通式I和II所示的结构式，式中 R1和R2具有权利要求1所定义。本发明的通式I和通式II化合物具有高效的KARI酶抑制活性，也具有较高的除草活性，特别是对双子叶植物油菜活性显著。同时还具有一定的杀菌活性，对黄瓜枯萎病菌、花生褐斑病菌、苹果轮纹病菌、小麦纹枯病菌、番茄早疫病菌和小麦赤霉病菌等有离体抑制活性，尤其是对小麦纹枯病菌效果显著。本发明适用于对KARI酶活性的高效抑制，以及对各种作物上草害和菌害的综合防治。
• Synthesis of New Bis-pyrazolines Endowed with Potent Antifungal Activity against Candida albicans and Aspergillus niger
  作者：Belgin Sever、Mehlika Dilek Altintop、Ahmet Özdemir

  DOI：10.2174/1570180817999201008155247

  日期：2021.2.26

  need to identify potent antifungal agents capable of combating IFIs. Pyrazolines are one such class of therapeutically active agents that could be considered to fulfill this need. Objective: In this context, this paper aims to identify two new series of bis-pyrazolines endowed with potent antifungal activity against Candida albicans and Aspergillus niger. Methods: Two new series of bis-pyrazolines (4a-i

  背景：由于侵袭性真菌感染（IFI）的病例数量不断增加，迫切需要确定能够与IFI对抗的有效抗真菌剂。吡唑啉是可以被认为满足这种需要的一类此类治疗活性剂。 目的：在此背景下，本文旨在确定两个新的双吡唑啉类，它们具有对白色念珠菌和黑曲霉的有效抗真菌活性。 方法：通过高效且通用的合成方法合成了两个新的双吡唑啉系列（4a-i，5a-e）。使用肉汤微稀释法筛选化合物对白色念珠菌和黑曲霉的抗真菌作用。用MTT法测定它们对NIH / 3T3小鼠胚胎成纤维细胞的细胞毒性作用。在羊毛甾醇14的活性位点进行了分子对接研究
• Synthesis of novel indole derivatives containing double 1,3,4-oxadiazole moiety as efficient bactericides against phytopathogenic bacterium Xanthomonas oryzae
  作者：Kun Tian、Xiao-Qin Li、Li Zhang、Yi-Yuan Gan、Jiao Meng、Shou-Qun Wu、Jin-Lin Wan、Yang Xu、Chao-Ting Cai、Gui-Ping Ouyang、Zhen-Chao Wang

  DOI：10.1007/s11696-018-0555-y

  日期：2019.1

  derivatives containing double 1,3,4-oxadiazole moiety was designed, synthesized and evaluated for their antibacterial activities in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that most of title compounds exhibited excellent antibacterial activities against rice bacterial pathogen Xanthomonas oryzae (Xoo). For example, compounds 7d, 7h, 7i

  摘要设计，合成了一系列含有双1,3,4-恶二唑部分的新型吲哚衍生物，并对其体外抗菌活性进行了评估。这些化合物通过1 H NMR，13 C NMR和HRMS进行了充分表征。生物测定结果表明，大多数标题化合物对水稻细菌病原体米黄单胞菌（Xanthomonas oryzae，Xoo）均表现出优异的抗菌活性。例如，化合物7d，7h，7i，7j，7k，7l和7m具有最大有效浓度的一半（EC 50）值分别为52.31、54.12、40.65、38.80、51.13、52.75和50.66 µg / mL，优于商品化的比美噻唑（BMT）（85.18 µg / mL）。实验结果证明，带有双1,3,4-恶二唑单元的吲哚衍生物有望成为开发新型农用杀菌剂以对抗致病菌Xoo的候选物。 图形概要
• Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents
  作者：Mohamed Ayman El-Zahabi、Helmy Sakr、Khaled. El-Adl、Mohamed Zayed、Adel S. Abdelraheem、Sally I. Eissa、Hazem Elkady、Ibrahim H. Eissa

  DOI：10.1016/j.bioorg.2020.104218

  日期：2020.11

  12 to 76.91 µM). The most active compounds were further evaluated for their in vitro immunomodulatory activities via estimation of human tumor necrosis factor alpha (TNF-α), human caspase-8 (CASP8), human vascular endothelial growth factor (VEGF), and nuclear factor kappa-B P65 (NF-κB P65) in HCT-116 cells. Thalidomide was used as a positive control. Compounds 33h and 42f showed a significant reduction

  沙利度胺及其类似物是免疫调节药物，可抑制某些与癌症相关的炎性介质的产生。在目前的工作中，设计并合成了一系列新的沙利度胺类似物以获得新的有效抗肿瘤免疫调节剂。评估合成的化合物对四种癌细胞系（HepG-2，HCT-116，PC3和MCF-7）的细胞毒性活性。化合物33 ħ，33我，42 ˚F和42 ħ表现出较强的效力针对与IC所有测试的细胞系中50个值范围从14.63到49.90μM比得上的沙利度胺（IC 50值范围从32.12到76.91 µM）。通过评估人类肿瘤坏死因子α（TNF-α），人类caspase-8（CASP8），人类血管内皮生长因子（VEGF）和核因子kappa-B ，进一步评估了活性最高的化合物的体外免疫调节活性。P 65（NF-κB P 65）中的HCT-116细胞。沙利度胺用作阳性对照。化合物33 ħ和42 ˚F显示出TNF-α一个显著减少。此外，化合物33 i和42 f
• Unfused heterobicycles as amplifiers of phleomycin. VII. Some triazolyl-, thiadiazolyl- and oxadiazolyl-pyridines and related pyrimidines
  作者：DJ Brown、WB Cowden

  DOI：10.1071/ch9831469

  日期：——

  Syntheses are described for several 4-(1',2',4'-triazol-3'yl)pyridines, 3-and 4-(1',3',4'-thiadiazol-2'-yl)-pyridines, 3- and 4-(1',3',4'-oxadiazol-2'-yl)pyridines, 5-(1',3',4'-thiadiazol-2'-yl)pyrimidines and 5-(1',3',4'-oxadiazol-2'-yl)pyrimidines, all provided with a β-dimethylaminoethylthio side chain at the 5-position of the five-membered ring. The activities of these compounds as amplifiers of phleomycin-G against an in vitro culture of Escherichia coli B are tabulated and discussed.

  介绍了 几种 4-(1',2',4'-三唑-3'-基)吡啶的合成、 3-和 4-(1',3',4'-噻二唑-2'-基)吡啶、 3 和 4-(1',3',4'-噁二唑-2'-基)吡啶、5-(1',3',4'-噻二唑-2'-基)嘧啶 和 5-(1',3',4'-噁二唑-2'-基)嘧啶、 所有这些 在五聚体的 5 位上有一个 β-二甲基氨基乙硫基侧链。 五元环的 5 位。这些化合物作为 对大肠杆菌 B 的体外培养的活性。