1-乙基-5-巯基-1,2,3,4-四氮唑 | 15217-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-乙基-5-巯基-1,2,3,4-四氮唑
• 英文名称: 1-ethyl-4,5-dihydro-1H-tetrazole-5-thione
• 英文别名: 1-ethyl-1,4-dihydrotetrazol-5-thione；1-ethyl-1H-tetrazole-5(4H)-thione；1-ethyl-1,4-dihydro-tetrazole-5-thione；1-ethyl-1,4-dihydro-tetrazolethione；1-Aethyl-1,4-dihydro-tetrazolthion；1-ethyl-1,2-dihydro-5H-tetrazole-5-thione；1-ethyl-2H-tetrazole-5-thione
• CAS: 15217-53-5
• 化学式: C₃H₆N₄S
• mdl: MFCD00129973
• 分子量: 130.173
• InChiKey: JLQLTELAOKOFBV-UHFFFAOYSA-N

物化性质

• 熔点：
  43°C
• 沸点：
  109 °C(Press: 1 Torr)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 危险类别码：
  R34
• 海关编码：
  2933990090
• 安全说明：
  S26,S36/37/39,S45
• 储存条件：
  2-8°C

SDS

Name:	1-Ethyl-1h-1 2 3 4-tetraazole-5-thiol 97% Material Safety Data Sheet
Synonym:	1-Ethyl-5-mercaptotetrazol
CAS:	15217-53-5

Section 1 - Chemical Product MSDS Name:1-Ethyl-1h-1 2 3 4-tetraazole-5-thiol 97% Material Safety Data Sheet
Synonym:1-Ethyl-5-mercaptotetrazol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15217-53-5	1-Ethyl-1H-1,2,3,4-tetraazole-5-thiol	97%	239-270-1

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

---

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

---

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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

---

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# 15217-53-5: 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: white - cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C3H6N4S
Molecular Weight: 130

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15217-53-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Ethyl-1H-1,2,3,4-tetraazole-5-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
Shipping Name: CORROSIVE SOLID, N.O.S.*
Hazard Class: 8
UN Number: 1759
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: III

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 15217-53-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15217-53-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15217-53-5 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

制备方法与用途

化学性质：无色液体，主要用于有机合成。

反应信息

• 作为反应物：
  描述：

  1-乙基-5-巯基-1,2,3,4-四氮唑 在 双氧水 、 溶剂黄146 作用下， 以 氯仿 、 水 为溶剂， 反应 0.75h， 以85%的产率得到1-乙基-1H-四唑
  参考文献：
  名称：

  Microwave-assisted oxidation of 1-substituted tetrazole-5-thiones

  摘要：

  DOI：

  10.1134/s1070428010010185
• 作为产物：
  描述：

  异硫氰酸乙酯 在 sodium azide 作用下， 生成 1-乙基-5-巯基-1,2,3,4-四氮唑
  参考文献：
  名称：

  ISOMERIC 5-(SUBSTITUTED)AMINOTHIATRIAZOLE AND 1-SUBSTITUTED-TETRAZOLINETHIONES

  摘要：

  有机异硫氰酸酯与乙醇和水中的叠氮化钠的反应已经被研究。结果表明，水是这种反应更有利的溶剂，可以提供更高的产率和最初更纯的1-取代-四唑-5-硫酮。通过这种方法制备了一系列这些后续化合物。产物的产率似乎取决于异硫氰酸酯取代基的电性质，随着电子给予性质的增加，产率会降低。制备了一系列新的4-取代-硫脲酰胺，并通过重氮化转化为相应的5-(取代)氨基噻三唑。提出并讨论了解释叠氮酸和叠氮离子反应模式差异的理论。5-(取代)氨基噻三唑转化为1-取代-四唑硫酮的基本反应可能涉及一个简单的去排列-排列机制，受到副反应的影响。总结了已知的同分异构体5-(取代)氨基噻三唑和1-取代-四唑硫酮。

  DOI：

  10.1139/v59-015
• 作为试剂：
  描述：

  1-金刚烷醇 、 1-乙基-1,4-二氢-5H-四唑-5-酮 在 1-乙基-5-巯基-1,2,3,4-四氮唑 、 硫酸 作用下， 生成 1-ethyl-3-(1-adamantyl)-1H-tetrazolium-5-olate
  参考文献：
  名称：

  Adamantylazoles: XII. Alkylation of 1-R-tetrazole-5-thiones and 1-R-tetrazol-5-ones with tertiary alcohols in sulfuric acid

  摘要：

  1-R-Substituted tetrazole-5-thiones reacted with adamantan-1-ol in sulfuric acid to give mesoionic 1-R-3-(1-adamantyl)tetrazolium-5-thiolates, isomeric 1-R-5-(1-adamantylsulfanyl)tetrazoles, 1-R-4-(1-adamantyl) tetrazole-5-thiones, and 1-R-3-(1-adamantyl)-5-(1-adamantylsulfanyl)tetrazolium salts. Adamantylation of 1-R-tetrazol-5-ones under analogous conditions afforded only the corresponding mesoionic 1-R-3-(1-adamantyl)tetrazolium-5-olates. Mesoionic 1-R-3-tert-butyltetrazolium-5-thiolates and 1-R-3-tert-butyltetrazolium-5-olates were obtained by alkylation of the same substrates with tert-butyl alcohol in sulfuric acid.

  DOI：

  10.1134/s1070363209100235

文献信息

• 4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines
  申请人：Janssen Pharmaceutica, N.V.

  公开号：US04695575A1

  公开（公告）日：1987-09-22

  4-[(Bicyclic heterocyclyl)methyl and -hetero]-piperidines having antihistaminic and serotonin-antagonistic properties which compounds are useful agents in the treatment of allergic diseases.

  具有抗组胺和抗血清素特性的4-[(双环杂环基)甲基和-杂环]-哌啶类化合物在过敏疾病治疗中是有用的药物。
• Cephalosporin derivatives
  申请人：Rhone-Poulenc Industries

  公开号：US04034090A1

  公开（公告）日：1977-07-05

  New cephalosporin derivatives of the formula: ##STR1## in which either (a) R.sub.1 is hydrogen, acetoxy, azido or heterocyclylthio or heterocyclylcarbonylthio which is (1,3,4-thiadiazol-2-yl)-thio which is unsubstituted or substituted by straight or branched chain C.sub.1-4 alkyl or alkoxy, straight or branched chain C.sub.1-4 alkylthio, straight or branched chain C.sub.1-4 alkylsulphonyl, amino or acetylamino; (1,2,3,4-tetrazol-5-yl)-thio which is unsubstituted or substituted in the 1-position by straight or branched chain C.sub.1-4 alkyl, hydroxy straight or branched chain C.sub.1-4 alkyl, phenyl or hydroxyphenyl, or in the 2-position by straight or branched chain C.sub.1-4 alkyl or hydroxy straight or branched chain C.sub.1-4 alkyl; (1,2,4-triazol-3-yl)-thio, (4-methyl-1,3-thiazol-2-yl)-thio, (3-methyl-1,2,4-thiadiazol-5-yl)-thio or (1,2,3-thiadiazol-4-yl)-carbonylthio, and R.sub.2 is carboxy or a radical of the formula: ##STR2## in which the radical: ##STR3## is a radical which can be easily removed enzymatically, and in which R.sub.3 is hydrogen or straight or branched chain C.sub.1-4 alkyl and R.sub.4 is straight or branched chain C.sub.1-4 alkyl or cyclohexyl; or (b) R.sub.1 is a pyridinio ion and R.sub.2 is a carboxylato ion, and pharmaceutically acceptable non-toxic metal salts thereof and addition salts thereof with nitrogen containing bases possess valuable anti-bacterial properties, showing activity against both Gram-positive and Gram-negative bacteria.

  新型头孢菌素衍生物的通式为：##STR1## 其中，(a) R1为氢、乙酸氧、叠氮或杂环硫或杂环羰基硫，具体为未取代或被直链或支链C1-4烷基或烷氧基、直链或支链C1-4烷基硫、直链或支链C1-4烷基磺酰基、氨基或乙酰氨基取代的(1,3,4-噻二唑-2-基)硫；未取代或1位被直链或支链C1-4烷基、羟基直链或支链C1-4烷基、苯基或羟基苯基取代，或2位被直链或支链C1-4烷基或羟基直链或支链C1-4烷基取代的(1,2,3,4-四唑-5-基)硫；(1,2,4-三唑-3-基)硫、(4-甲基-1,3-噻唑-2-基)硫、(3-甲基-1,2,4-噻二唑-5-基)硫或(1,2,3-噻二唑-4-基)羰基硫，R2为羧基或以下通式所示的基团：##STR2## 其中，##STR3## 是一个可被酶轻易移除的基团，R3为氢或直链或支链C1-4烷基，R4为直链或支链C1-4烷基或环己基；或(b) R1为吡啶鎓离子，R2为羧基离子，以及其药用可接受的非毒性金属盐和与含氮碱形成的加成盐，具有宝贵的抗菌特性，对革兰氏阳性和革兰氏阴性细菌均显示出活性。
• A Facile One-Pot Synthesis of 1-Substituted Tetrazole-5-thiones and 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles from Organic Isothiocyanates
  作者：Sam-Yong Han、Je-Woo Lee、Hee-Jung Kim、Yong-Joo Kim、Soon-W. Lee、Young-Soo Gyoung

  DOI：10.5012/bkcs.2012.33.1.55

  日期：2012.1.20

  Treatments of organic isothiocyanates (R-NCS) with $NaN_3$ in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [$S=CN_4(R)$] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, $NaN_3$, and pyridine in water at room temperature exclusively formed 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

  在水和吡啶的存在下，室温下用$NaN_3$处理有机异硫氰酸酯（R-NCS），得到了相应的多种有机四唑硫酮，[$S=CN_4(R)$]（R = 烷基或芳基）。分离得到的产品为白色或黄色固体，产率良好（76-97%）。通过对其中一个产品的X射线衍射研究，显示了预期的分子结构。此外，还展示了1-取代的5-烷基（或芳基）硫基四唑的一锅法合成。在室温下将烷基或芳基卤化物加入有机异硫氰酸酯、$NaN_3$和吡啶的水溶液中，专门形成了高产率的1-取代的5-烷基（或芳基）硫基四唑（S型衍生物）。
• Carbapenem and penem antibiotics. V. Carbapenem and penem antibiotics. VI. Synthesis and antibacterial activity of 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl 1-methylcarbapenems.
  作者：Mitsuru IMUTA、Hikaru ITANI、Hisao ONA、Yoshinori HAMADA、Shoichiro UYEO、Tadashi YOSHIDA

  DOI：10.1248/cpb.39.663

  日期：——

  chain, are described. The introduction of a methyl substituent at the C-1 position was accomplished by a newly developed procedure using crotyl halides and zinc dust. The 2-hydroxymethyl carbapenems as key intermediates allowed an easy entry into the preparation of title carbapenems.

  描述了具有6-[（（R）-1-羟乙基）侧链的1-甲基卡宾烯，2-杂芳族硫代甲基和2-氨基甲酰氧基甲基衍生物的合成和抗菌活性。通过使用巴豆基卤化物和锌粉的新开发的方法完成在C-1位上的甲基取代基的引入。以2-羟甲基碳青霉烯为主要中间体，可以轻松地制备标题碳青霉烯。
• Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities
  作者：V. Dhayanithi、Syed Shafi、K. Kumaran、Sankar Jai、Venkat Ragavan、Kumar Goud、Suchetha Kumari、Hari Pati

  DOI：10.2298/jsc090421001d

  日期：——

  Several 5-thio-substituted tetrazole derivatives were efficiently synthesized by a three-step process. The substituted tetrazol-5-thiol, namely, 1-benzyl-1H-tetrazol-5-thiol (2) was prepared by refluxing commercially available benzyl isothiocyanate (1) with sodium azide in water. The second step was the synthesis of 1-benzyl-5-[(3-bromopropyl) thio]tetrazole (3) by thio alkylation of tetrazol-5-thiol (2) with 1,3- dibromopropane in tetrahydrofuran. Finally, the 5-thio-substituted tetrazole derivatives 4a-i were prepared by condensation of (3) with the corresponding amine or thiol. The structures of the newly synthesized compounds were characterized by NMR, LC/MS/MS, IR spectral data and elemental analysis. All the synthesized compounds were screened for their antibacterial and antifungal activities.

  通过三步法高效合成了几种 5-硫代四氮唑衍生物。 通过三步法合成。取代的四唑-5-硫醇、 即 1-苄基-1H-四唑-5-硫醇（2）是通过回流 市售的异硫氰酸苄酯（1）与叠氮化钠在水中回流制备而成。 第二步是合成 1-苄基-5-[(3-溴丙基) 硫代]四氮唑（3），方法是将四唑-5-硫醇（2）与 1,3- 二溴丙烷在四氢呋喃中进行硫代烷基化。最后，5-硫代四唑 衍生物 4a-i 的制备方法是将 (3) 与相应的胺或硫醇缩合。 胺或硫醇缩合而制备。新合成化合物的结构通过核磁共振、液相色谱/质谱 通过 NMR、LC/MS/MS、IR 光谱数据和元素分析对新合成化合物的结构进行了表征。对所有 的抗菌和抗真菌活性进行了筛选。 抗真菌活性。