5-巯基-1-(对甲氧基苯基)四氮唑 | 13980-76-2

• 物质功能分类: 有机原料
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-巯基-1-(对甲氧基苯基)四氮唑
• 中文别名: 5-巯基-1-(4-甲氧苯基)-1H-四唑；1,2-二氢-1-(4-甲氧基苯基)-5H-四唑-5-硫酮；5-疏基-1-(4-甲氧基苯基)-1H-四唑
• 英文名称: 1-(4-methoxyphenyl)-1H-tetrazole-5-thiol
• 英文别名: 1-(4-methoxyphenyl)-2H-tetrazole-5-thione
• CAS: 13980-76-2
• 化学式: C₈H₈N₄OS
• mdl: MFCD01321180
• 分子量: 208.244
• InChiKey: UFALKIBIWOKBDL-UHFFFAOYSA-N

物化性质

• 熔点：
  156-160°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  81.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  4.1
• 危险品运输编号：
  UN 1325
• 海关编码：
  2933990090
• 危险类别码：
  R11
• 储存条件：
  室温且干燥环境下使用。

SDS

5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 1
Flammable solids
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Hazard statements Flammable solid
Precautionary statements:
[Prevention] Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Use explosion-proof electrical/ventilating/lighting equipment.
Wear protective gloves/eye protection/face protection.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole
Components:
Percent: >98.0%(T)
CAS Number: 13980-76-2
Synonyms: 1-(4-Methoxyphenyl)-1H-tetrazole-5-thiol
Chemical Formula: C8H8N4OS

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Explosion risk in case of fire. Fight fire remotely due to the risk of explosion.
from the chemical: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Keep containers cool by
spraying with water. Eliminate all ignition sources if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Be careful not to cause leakage, overflow, or dispersion. Steam should not be
generated unnecessarily. Keep away from heat/sparks/open flame/hot surfaces. -No
smoking. Take measures to prevent the build up of electrostatic charge. Use
explosion-proof equipment. Avoid shock and friction. Wash hands and face before
breaks and immediately after handling the product.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Be sure not to give the container unexpected impacts, such as falling down or falling
off.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Very pale yellow
Odour: No data available

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous May explosively decompose on heating, shock, friction, etc.
reactions:
Conditions to avoid: Heat, Spark, Open flame, Static discharge, Shock, Friction
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities and an expert of disposal. You may be able
to dissolve or mix material with a combustible solvent and little by little burn in a chemical incinerator equipped with
an afterburner and scrubber system. If a large amount of the substance is burned at a time, an explosion may
occur. Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: 4.1: Flammable solid.
UN-No: 1325

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Section 14. TRANSPORT INFORMATION
Proper shipping name: Flammable solid, organic, n.o.s.
Packing group: II

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-巯基-1-(对甲氧基苯基)四氮唑 在 咪唑 、 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 106.0h， 生成 (R)-1-[1-(tert-butyldiphenylsiloxy)pentan-3-yl]-4-(4-methoxyphenyl)-1H-tetrazol-5-(4H)-thione
  参考文献：
  名称：

  5-Mercaptotetrazoles as Synthetic Equivalents of Nitrogen-Contaning Functional Groups. The Case of the Organocatalytic Enantioselective aza-Michael Reaction

  摘要：

  5-Mercaptotetrazoles have been identified as useful and versatile Michael donors in enantioselective amine-catalyzed aza-Michael reactions with alpha,beta-unsaturated aldehydes, showing excellent behavior as N-nucleophiles instead of their usual trend to react as S-nucleophiles. In addition several unprecedented chemical modifications on the tetrazolothione moiety have been carried out leading to the enantioselective preparation of different compounds incorporating nitrogen-containing functionalities such as oxazinimines, formamidines, ureas and isoureas.

  DOI：

  10.1021/ol102892f
• 作为产物：
  描述：

  N-(4-methoxyphenyl)-1,2,3,4-thiatriazol-5-amine 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5-巯基-1-(对甲氧基苯基)四氮唑
  参考文献：
  名称：

  Cowper; Astik; Thaker, Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1087 - 1088

  摘要：

  DOI：

文献信息

• 1-Substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their isosteric analogs: A new class of selective antitubercular agents active against drug-susceptible and multidrug-resistant mycobacteria
  作者：Galina Karabanovich、Jaroslav Roh、Tomáš Smutný、Jan Němeček、Petr Vicherek、Jiřina Stolaříková、Marcela Vejsová、Ida Dufková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek

  DOI：10.1016/j.ejmech.2014.05.069

  日期：2014.7

  In this work, a new class of highly potent antituberculosis agents, 1-substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their oxa and selanyl analogs, is described. The minimal inhibitory concentration (MIC) values reached 1 μM (0.36–0.44 μg/mL) against Mycobacterium tuberculosis CNCTC My 331/88 and 0.25–1 μM against six multidrug-resistant clinically isolated strains of M. tuberculosis

  在这项工作中，描述了一类新型的高效抗结核药，即1-取代的5-[（3,5-二硝基苄基）硫烷基] -1 H-四唑及其氧杂和硒基类似物。最小抑菌浓度（MIC）值达到了1μM（0.36-0.44微克/毫升）对结核分枝杆菌CNCTC我八十八分之三百三十一和0.25-1μM针对六个多药耐药性临床分离菌株的结核分枝杆菌。这些化合物的抗分枝杆菌作用具有高度特异性，因为它们对所研究的所有八种细菌菌株和八种真菌菌株均无效。此外，这些化合物在四种哺乳动物细胞系中均表现出较低的体外毒性（IC 50 > 30μM）。我们还检查了化合物的结构-活性关系，特别是硝基基团的数量和位置，四唑和苄基部分之间的连接基以及四唑本身对抗分枝杆菌活性的影响。在不对分枝杆菌活性产生负面影响的情况下，四唑上取代基R 1的相对较高的变异性可进一步优化毒性，并进一步优化1-取代的5-[（3,5-二硝基苄基）硫烷基]-的ADME性质。 1 H-四唑化合物。
• Discovery of quinazoline derivatives as a novel class of potent and in vivo efficacious LSD1 inhibitors by drug repurposing
  作者：Zhonghua Li、Tingting Qin、Zhongrui Li、Xuan Zhao、Xinhui Zhang、Taoqian Zhao、Nian Yang、Jinxin Miao、Jinlian Ma、Zhenqiang Zhang

  DOI：10.1016/j.ejmech.2021.113778

  日期：2021.12

  remarkable capacity to inhibit colony formation, suppress migration and induce apoptosis of MGC803 cells. Furthermore, in MGC-803 xenograft mouse model, 5k treatment resulted in significant reduction in tumor size by 81.6% and 96.1% at dosages of 40 and 80 mg/kg/d, respectively. Our findings indicate that erlotinib-based analogs provide a novel structural set of LSD1 inhibitors with potential for further

  组蛋白赖氨酸特异性去甲基化酶 1 (LSD1) 是一种重要的表观遗传调节剂，并以不同的方式参与恶性转化和肿瘤发病机制。因此，LSD1的抑制为癌症治疗提供了一个有吸引力的治疗靶点。基于药物再利用策略，我们筛选了我们内部针对 LSD1 的化学库，发现 EGFR 抑制剂厄洛替尼（一种 FDA 批准的肺癌药物）对 LSD1 的效力较低（IC 50  = 35.80 μM）。在此，我们报告了我们进一步的药物化学努力，以获得高度水溶性的厄洛替尼类似物5k (>100 mg/mL)，其对 LSD1 的抑制活性显着增强 (IC 50  = 0.69 μM) 以及更高的特异性。在 MGC-803 细胞中，5k抑制 LSD1 的去甲基化，表明其对酶的细胞活性。此外，5k具有显着的抑制集落形成、抑制迁移和诱导MGC803细胞凋亡的能力。此外，在 MGC-803 异种移植小鼠模型中，5k治疗导致肿瘤大小分别在 40
• Novel ligands for the hisb10 zn2+ sites of the r-state insulin hexamer
  申请人：——

  公开号：US20030229120A1

  公开（公告）日：2003-12-11

  Novel ligands for the HisB10 Zn 2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R-态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• [EN] PHAMACEUTICAL PREPARATIONS COMPRISING INSULIN<br/>[FR] PREPARATIONS PHARMACEUTIQUES CONTENANT DE L'INSULINE
  申请人：NOVO NORDISK AS

  公开号：WO2006005683A1

  公开（公告）日：2006-01-19

  Novel preparations comprising ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer wherein the ligand is extended by protamine that are capable of prolonging the ac­tion of insulin preparations.

  新型制剂包括配体，用于R-态胰岛素六聚体的HisB10 Zn2+位点，其中配体通过精氨酸延长，能够延长胰岛素制剂的作用。
• Stabilised insulin compositions
  申请人：Kaarsholm Christian Niels

  公开号：US20050065066A1

  公开（公告）日：2005-03-24

  The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the His B10 Zn 2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.

  本发明提供了包含胰岛素和新型配体的药物组合物，用于R-态胰岛素六聚体的His B10 Zn2+位点。由此制备的药物具有改善的物理和化学稳定性。

表征谱图