5-(4-甲酸苯基)-1H-四唑 | 34114-12-0

• 物质功能分类: 有机原料 - 杂环化合物
• 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-(4-甲酸苯基)-1H-四唑
• 中文别名: 5-(4-甲酸苯基)-1H-四唑,97；4-(1H-四唑-5-基)苯甲酸；5-(4-羧基苯基)-1H-四唑；4-(2H-1,2,3,4-四唑)-苯甲酸；5-(4-甲酸苯基)-1H-四唑,97%
• 英文名称: 4-(1H-tetrazol-5-yl)benzoic acid
• 英文别名: 5-(4-carboxyphenyl)-1H-tetrazole；4-(2H-tetrazol-5-yl)benzoic acid
• CAS: 34114-12-0
• 化学式: C₈H₆N₄O₂
• mdl: MFCD01569290
• 分子量: 190.161
• InChiKey: GEKBULKUEADYRB-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250℃
• 沸点：
  467.5±47.0 °C(Predicted)
• 密度：
  1.518

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  4.1
• 危险性防范说明：
  P240,P210,P241,P264,P280,P302+P352,P370+P378,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险品运输编号：
  1325
• 危险性描述：
  H315,H319,H228
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-(1H-Tetrazol-5-yl)benzoic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-(1H-Tetrazol-5-yl)benzoic acid
Ingredient name:
CAS number: 34114-12-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H6N4O2
Molecular weight: 190.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

5-(4-甲酸苯基)-1H-四唑是一种有机中间体，可通过4-氰基苯甲酸制备。文献报道，它可用于制备自分泌运动因子抑制剂。

制备

将7.15 g（0.11 mol）叠氮化钠和5.88 g（0.11 mol）氯化铵溶解在100 mL无水二甲基亚枫（DMF）中，室温搅拌30分钟。然后，在不断搅拌下加入14.71 g（0.1 mol）4-氰基苯甲酸。将此混合物回流加热至120°C，持续18-20小时。

冷却至室温后，使用200 mL 1 M 盐酸溶液在搅拌下进行酸化处理。过滤形成的白色沉淀，并用连续的等分蒸馏水（3 x 25 mL）洗涤所得产物。最终产物在无水丙酮中重结晶，产率约为90%，得到13.23 g产物。

反应信息

• 作为反应物：
  描述：

  5-(4-甲酸苯基)-1H-四唑 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 77.0h， 生成 [Ru(SCN)(1,10-phenanthroline)₂(4-(1H-tetrazole-5-yl)benzoic acid)]
  参考文献：
  名称：

  Going from green to red electroluminescence through ancillary ligand substitution in ruthenium(ii) tetrazole benzoic acid emitters

  摘要：

  合成、表征、光致发光（PL）和电致发光（EL）性能的新型钌（II）发射体已报道，其基本配体为4-(1H-五氮唑-5-基)苯甲酸（TzBA），辅助配体为2,2'-联吡啶（bpy）、1,10-菲咯啉（phen）和吡啶五氮唑（pyTz）。EL结果表明，Ru(TzBA)的发光依赖于辅助配体，可以通过调节辅助配体使Ru(TzBA)复合物的EL颜色从绿色调至红色。通过DFT计算研究了辅助配体在Ru(TzBA)复合物EL器件中的作用。器件[Ru(TzBA)(bpy)(pyTz)(SCN)]（5）在16 V时具有480 cd m−2的亮度和1.2 cd A−1的最高效率，为五个研究器件中最高值。该器件的开启电压约为6 V。我们提出，当pyTz作为辅助配体引入Ru(TzBA)时，PVK-Ru复合物界面发生了电复合现象。OLED研究表明，作为辅助配体的pyTz在电流生成能力上优于bpy和phen配体，这些配体由发射体（5）引入。

  DOI：

  10.1039/c3tc31350f
• 作为产物：
  描述：

  对氰基苯甲酸 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到5-(4-甲酸苯基)-1H-四唑
  参考文献：
  名称：

  具有出色 C-H 键胺化活性的金属-有机框架

  摘要：

  尽管近年来在 C-H 活化领域取得了重大进展，但开发能够在温和条件下快速、稳定地进行 C-H 键胺化的催化剂仍是一个尚未实现的目标。描述了一种 Mn 基金属有机框架 (CPF-5)，它促进 C-H 键的直接胺化，具有出色的活性。CPF-5 能够以分子间方式功能化 C-H 键，具有无与伦比的催化稳定性，可产生 >10 5的转换。

  DOI：

  10.1002/anie.201709420

文献信息

• Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation
  作者：Zhixiong Ruan、Zhixing Huang、Zhongnan Xu、Shaogao Zeng、Pengju Feng、Ping-Hua Sun

  DOI：10.1007/s11426-020-9938-9

  日期：2021.5

  The installation of azoles via C-H/N-H cross-coupling is significantly underdeveloped, particularly in benzylic C-H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C-H bonds enabled by electrooxidation is described, which proceeds in an undivided cell under mild, catalyst- and

  唑类的安装通过由于对外部化学氧化剂的要求以及控制位点和化学选择性的挑战，CH / NH交叉偶联显着欠发达，特别是在苄基CH偶氮化反应中。在本文中，描述了通过电氧化实现的苄基CH键的后期偶氮化，其在温和，无催化剂和无化学氧化剂的反应条件下在未分格的电池中进行。该策略可选择性地在伯，仲，甚至具有挑战性的叔苄基位置上实现CH偶氮化。我们的方法具有非凡的合成效用，其突出的特点是易于扩展，不引起产品过度氧化，并具有适用范围广的有价值的官能团。该方法可直接用于在高度官能化的药物分子上安装苄基和唑基。
• 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。
• Microwave Synthesis of 5-Substituted 1<i>H</i>-Tetrazoles Catalyzed by Bismuth Chloride in Water
  作者：Adiel Coca、Liana Feinn、Joshua Dudley

  DOI：10.1080/00397911.2014.989451

  日期：2015.4.18

  Abstract Bismuth chloride was used to catalyze the [2 + 3] cycloaddition between sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles. A number of 5-substituted 1H-tetrazoles were synthesized in water or isopropanol/water mixtures using microwave heating. Good yields were obtained for these reactions when heated for 1 h at 120–160 °C in a 3:1 isopropanol/water mixture. A few of the

  摘要 氯化铋用于催化叠氮化钠与芳基腈、脂肪腈和乙烯基腈之间的[2+3]环加成反应。使用微波加热在水或异丙醇/水混合物中合成了许多 5-取代的 1H-四唑。当在 3:1 的异丙醇/水混合物中在 120–160 °C 下加热 1 小时时，这些反应获得了良好的产率。一些反应性较低的腈类需要更长的反应时间才能获得良好的产率。图形概要
• NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
  申请人：Bischoff Alexander

  公开号：US20100160323A1

  公开（公告）日：2010-06-24

  The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为硬脂酰辅酶A去饱和酶抑制剂的哌嗪衍生物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• [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。