4-氨基-5-乙基-4H-[1,2,4]噻唑-3-硫醇 | 20939-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氨基-5-乙基-4H-[1,2,4]噻唑-3-硫醇
• 中文别名: 4-氨基-5-乙基-4H-3-巯基-1,2,4-三唑
• 英文名称: 4-amino-5-ethyl-1,2,4-triazole-3-thione
• 英文别名: 4-amino-5-ethyl-4H-1,2,4-triazole-3-thiol；4-amino-3-ethyl-1H-1,2,4-triazole-5-thione
• CAS: 20939-16-6
• 化学式: C₄H₈N₄S
• mdl: MFCD00128485
• 分子量: 144.2
• InChiKey: NHJQUZUFQOQBNE-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C (decomp)(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  213.7±23.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

SDS

Name:	4-Amino-5-ethyl-4h-1 2 4-triazole-3-thiol 97% Material Safety Data Sheet
Synonym:
CAS:	20939-16-6

Section 1 - Chemical Product MSDS Name:4-Amino-5-ethyl-4h-1 2 4-triazole-3-thiol 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
20939-16-6	4-Amino-5-ethyl-4H-1,2,4-triazole-3-th	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 20939-16-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 184 - 186 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H8N4S
Molecular Weight: 144

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 20939-16-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Amino-5-ethyl-4H-1,2,4-triazole-3-thiol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 20939-16-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20939-16-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20939-16-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-氨基-5-乙基-4H-[1,2,4]噻唑-3-硫醇 在 一水合肼 作用下， 以 乙醇 为溶剂， 以80%的产率得到4-Amino-3-hydrazino-5-ethyl-1,2,4-triazol
  参考文献：
  名称：

  DNA cleavage and antimicrobial studies of 17-membered schiff base macrocyclic triazoles: synthesis and spectroscopic approach

  摘要：

  我们用新衍生的生物活性配体（LI-LIV）合成了一系列新型的 17 元络合物 [MLCl2]（M = Co2+、Ni2+ 和 Cu2+）。这些配体是通过 3-取代-4-氨基-5-肼基-1,2,4-三唑与双（邻苯二甲酸）乙二胺前体缩合合成的。通过元素分析、红外光谱、EPR、电子光谱研究、电导率、磁性、热和电化学研究，提出了这些配合物的结构。所有络合物都能溶于 DMF 和 DMSO，并且是非电解质。通过琼脂和马铃薯葡萄糖琼脂扩散法，对所有这些希夫碱及其复合物进行了抗菌（大肠杆菌、金黄色葡萄球菌、伤寒沙门氏菌和绿脓杆菌）和抗真菌（黑曲霉、黄曲霉和克拉多孢霉）活性筛选。DNA 裂解研究是通过琼脂糖凝胶电泳技术进行的。

  DOI：

  10.1007/s10847-010-9794-4
• 作为产物：
  描述：

  potassium 2-propionylhydrazinecarbodithioate 在 一水合肼 作用下， 以 水 为溶剂， 反应 3.0h， 生成 4-氨基-5-乙基-4H-[1,2,4]噻唑-3-硫醇
  参考文献：
  名称：

  含有1,2,4-三唑作为有效酪氨酸酶抑制剂的曲酸衍生物的合成及生物学评价。

  摘要：

  通过5-羟基-2-的亲核取代反应，合成了一系列5-取代的-3- [5-羟基5-吡喃-2-基-甲基巯基] -4-氨基-1,2,4-三唑衍生物。评价了具有5-取代的-3-巯基-4-氨基-1,2,4-三唑的氯甲基-4H-吡喃-4-酮及其对蘑菇酪氨酸酶的抑制作用。结果表明，大多数合成的化合物显示出显着的抑制活性。具体而言，5-（4-氯苯基）-3- [5-羟基-4-吡喃-2-基-甲基巯基] -4-氨基-1,2,4-三唑（6j）表现出最强的酪氨酸酶抑制活性IC50值为4.50 +/- 0.34微米。化合物（6j）的动力学研究表明，该化合物对酪氨酸酶的抑制作用属于竞争性抑制剂。同时，还讨论了结构-活性关系。

  DOI：

  10.1111/cbdd.12577
• 作为试剂：
  描述：

  丙酸 、 硫代卡巴肼 在 4-氨基-5-乙基-4H-[1,2,4]噻唑-3-硫醇 、 乙醚 作用下， 以 乙醚 为溶剂， 反应 17.5h， 生成 4-氨基-5-乙基-4H-[1,2,4]噻唑-3-硫醇
  参考文献：
  名称：

  Triazolobenzocycloalkylthiadiazine derivatives

  摘要：

  小说三唑基苯并环烷基噻二嗪，其制备方法，以及作为中枢神经系统抗抑郁药物的用途。

  公开号：

  US03954983A1

文献信息

• Dimethylformamide Catalyzed Synthesis of Novel Heterocycles-Their Characterization and Antimicrobial Evaluation
  作者：Vijay V. Dabholkar、Sunil R. Patil、Rajesh V. Pandey

  DOI：10.1002/jhet.1073

  日期：2013.3

  Indandione 1 was brominated to yield 2‐bromoIndandione 2, which further reacted with substituted thiocarbamides, carbamides, 2‐aminothiophenols, 2‐aminophenol, and triazole to furnished 3‐substituted aniline‐2‐thia‐4‐aza‐6,7‐benzo‐8‐oxo‐bicyclo[3.3.0]‐1(5),3‐octadiene 3, 3‐substituted aniline‐2‐oxa‐4‐aza‐6,7‐benzo‐8‐oxo‐bicyclo[3.3.0]‐1(5),3‐octadiene 4, 2‐Thia‐5‐aza‐9‐oxo‐3,4‐(3′‐substituted) benzo‐7

  茚满二酮1溴化生成2-溴茚满二酮2，后者进一步与取代的硫代氨基甲酸酯，脲，2-氨基硫酚，2-氨基苯酚和三唑反应生成3取代的苯胺-2-二硫杂-4-氮杂-6,7-苯并呋喃。 -8-氧代双环[3.3.0] -1（5），3-辛二烯3，3-取代的苯胺-2-氧杂-4-氮杂-6,7-苯并-8-氧代-双环[3.3.0 ] -1（5），3-辛二烯4，2 -Thia-5-氮杂-9-oxo-3,4-（3'-取代）苯并-7,8-苯并双环[4.3.0] -1 （6）壬烯5，2-氧杂-5-氮杂-9-氧代（3,4） - （7,8） -二苯并-二环[4.3.0] -1（6）壬烯6，3'-取代-（1'，2'，4'）triazolo [5,6-b] [indeno（2,3-e）]-1,3,4-噻二嗪7， 分别。根据光谱技术阐明了化合物的结构，进一步筛选了具有代表性的化合物的抗菌活性。
• 1,2,4-三唑硫醚衍生物及其晶体结构与应用
  申请人：湖南大学

  公开号：CN110156704B

  公开（公告）日：2023-06-09

  本发明公开了结构式Ⅰ所示的1,2,4‑三唑硫醚衍生物及其药学上可接受的盐，晶体结构、及药物组合物以及其在制备流感病毒神经氨酸酶抑制剂中的应用：其中，R选自：氢、2‑OH、3‑OH、4‑OH、2,4‑(OH)2、2,3,4‑(OH)3、2‑COOH、4‑COOH、2‑OH‑3‑OCH3、3‑OH‑4‑OCH3或4‑OH‑3‑OCH3；R1选自：C1～C2烷基、C3～C5直链烷基或C3～C5支链烷基、苄基、4‑硝基苄基、4‑氰基苄基或羧甲基；Y选自：H、C1～C2烷基、C3～C7直链或C3～C7支链烷基；Z选自：H、氟、氯、溴、碘、甲基、乙基、氨基、甲氧基或羟基。
• Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives
  作者：Ru-Yi Jin、Chu-Yue Zeng、Xu-Hua Liang、Xiao-Hong Sun、Yuan-Fa Liu、Yan-Yan Wang、Sha Zhou

  DOI：10.1016/j.bioorg.2018.06.030

  日期：2018.10

  antifungal activity than triadimefon. Meanwhile, the antibacterial activity assay also indicated compound 2a exhibited excellent antibacterial activities comparable to chloramphenicol. The SAR manifested no substitution at position 5 of the triazole ring caused an increase in activity, and 3-phenoxy phenyl group introduced in 1,2,4-triazole scaffold can enhance the antibacterial activity. The DFT calculation

  已经设计并合成了一系列1,2,4-三唑希夫碱（2a-2d，2f-2h和3a-3h）。根据其光谱数据和元素分析证实了标题化合物的结构。筛选所有目标化合物的体外抗真菌活性和抗菌活性。被测化合物中的两种（2a和2b）对大多数真菌表现出显着的抗真菌活性，尤其是化合物2a比三唑酮显示出更好的抗真菌活性。同时，抗菌活性测定还表明化合物2a表现出与氯霉素相当的优异抗菌活性。SAR显示在三唑环的5位上没有取代引起活性增加，并且在1,2,4-三唑支架中引入的3-苯氧基苯基可以增强抗菌活性。
• Design, Synthesis, and Antifungal Activities of Novel 1,2,4-Triazole Schiff Base Derivatives
  作者：Ruyi Jin、Jingli Liu、Guanghui Zhang、Jiajia Li、Shuan Zhang、Hui Guo

  DOI：10.1002/cbdv.201800263

  日期：2018.9

  With the aim to find new compounds with high antifungal activity, 21 4‐amino‐5‐substituted‐1,2,4‐triazole Schiff bases (2a – 2g, 3a – 3g, and 4a – 4g) were designed and synthesized. Their antifungal activities against Pythium solani, Gibberlla nicotiancola, Fusarium oxysporium f. sp. niveum, Gibberlla saubinetii, Alternaria iycopersici, Phytophthora capsici, Physalospora piricola, Cercospora arachidicola

  为了寻找具有高抗真菌活性的新化合物，设计并合成了21个4-氨基-5-取代-1,2,4-三唑席夫碱（2a-2g、3a-3g和4a-4g）。它们对 Pythium solani、Gibberlla nicotiancola、Fusarium oxysporium f 的抗真菌活性。sp. niveum, Gibberlla saubinetii, Alternaria iycopersici, Phytophthora capsici, Physalopora piricola, Cercospora arachidicola hori 和 Fusarium oxysporium f。sp. 黄瓜进行了测试，部分化合物表现出优异的抗真菌活性。这项研究为进一步研究抗真菌剂提供了有用的信息。
• Syntheses and crystal structures of four new organotin complexes with Schiff bases containing triazole
  作者：Hai-Xia Yu、Jian-Fang Ma、Guo-Hai Xu、Shun-Li Li、Jin Yang、Ying-Ying Liu、Yan-Xiang Cheng

  DOI：10.1016/j.jorganchem.2006.05.002

  日期：2006.8

  4-triazole-5-thione (HL4). Compounds 1–4 were characterized by elemental analysis, IR spectra and their structures were determined by single-crystal X-ray diffraction methods. Complexes 1–3 show similar structures containing a Sn4O4 ladder skeleton in which each of the exo tin atoms is bonded to the N atom of a corresponding thione-form deprotonated ligand. Complex 4 shows a mononuclear structure in which the tin atom

  四种新的有机锡配合物，即[（Bu 2 Sn）2 O（EtO）（L1）] 2（1），[（Bu 2 Sn）2 O（EtO）（L2）] 2（2），[（Bu 2 Sn）2 O（EtO）（L3）] 2（3）和[Ph 3 Sn（L4）]·0.5H 2 O（4），是通过Bu 2 SnO和Ph 3 SnOH与4-苯基亚氨基氨基反应制得的。3-甲基1,2,4-三唑-5-硫酮（HL1），4-糠醛亚氨基-3-甲基-1,2,4-三唑-5-硫酮（HL2），4-（2-噻吩亚氨基）- 3-乙基1,2,4-三唑-5-硫酮（HL3）和4-（3,5-二-叔丁基水杨基亚氨基）-3-乙基-1,2,4-三唑-5-硫酮（HL4）。化合物1 - 4进行了表征通过元素分析，红外光谱和其结构经单晶X-射线衍射方法测定的。配合物1 - 3示出具有Sn类似结构4 ø 4，其中每个所述的梯子骨架外的锡原子键合到相应的硫酮形式配体去质子化的N原子