1-苄基-5-甲基-1H-[1,2,3]三唑-4-甲酸 | 54698-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苄基-5-甲基-1H-[1,2,3]三唑-4-甲酸
• 中文别名: 1-苄基-5-甲基-1H-[1,2,3]噻唑-4-羧酸
• 英文名称: 1-benzyl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 1-benzyl-5-methyltriazole-4-carboxylic acid
• CAS: 54698-60-1
• 化学式: C₁₁H₁₁N₃O₂
• mdl: MFCD06411557
• 分子量: 217.227
• InChiKey: WIULYDQJIFTHIK-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C
• 沸点：
  455.0±47.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

SDS

Name:	1-Benzyl-5-methyl-1H-[1 2 3-]triazole-4-carboxylic acid Material Safety Data Sheet
Synonym:
CAS:	54698-60-1

Section 1 - Chemical Product MSDS Name:1-Benzyl-5-methyl-1H-[1 2 3-]triazole-4-carboxylic acid Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
54698-60-1	1-Benzyl-5-methyl-1H-[1,2,3-]triazole-	97+%	unlisted

Hazard Symbols: F
Risk Phrases: 11 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Harmful by inhalation, in contact with skin and if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
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:

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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. Exposure to heat may promote violent decomposition.
Flammable solid.
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:
Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Keep away from sources of ignition. Store in a cool, dry place.
Store in a tightly closed container. Flammables-area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 54698-60-1: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 169 - 170 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: C11H11N3O2
Molecular Weight: 217.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
High temperatures, incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 54698-60-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Benzyl-5-methyl-1H-[1,2,3-]triazole-4-carboxylic acid - 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: FLAMMABLE SOLID, TOXIC, ORGANIC, N.O.S.*
Hazard Class: 4.1 (6.1)
UN Number: 2926
Packing Group: III
IMO
Shipping Name: FLAMMABLE SOLID, TOXIC, ORGANIC, N.O.S.
Hazard Class: 4.1 (6.1)
UN Number: 2926
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE SOLID, TOXIC, ORGANIC, N.O.S.
Hazard Class: 4.1 (6.1)
UN Number: 2926
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F
Risk Phrases:
R 11 Highly flammable.
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 22 Do not breathe dust.
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.
WGK (Water Danger/Protection)
CAS# 54698-60-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 54698-60-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 54698-60-1 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：

  1-苄基-5-甲基-1H-[1,2,3]三唑-4-甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 27.0h， 生成 1-benzyl-5-methyl-4-(N-methyl)carboxamido-1H-1,2,3-triazole
  参考文献：
  名称：

  N6-环烷基-2-苯基-3-deaza-8-azaadenines：一类新的A1腺苷受体配体。与相应的腺嘌呤和8-氮杂腺嘌呤的比较。

  摘要：

  几种9-苄基-N6-环烷基-2-苯基ade啶，9-苄基-N6-环烷基-2-苯基-8-氮杂腺嘌呤和4-环烷基氨基-1-苄基-6-苯基-1H-1,2,3-三唑制备[4，5-c]吡啶并测定为A1腺苷受体配体。1H-1,2,3-三唑并[4,5-c]吡啶是从N，N-二乙基-1-苄基-4-羧基酰胺基-5-甲基-1H-1,2,3-三唑开始得到的苯甲腈存在下，在无水四氢呋喃中进行锂化反应。通常的处理提供了分离的1-苄基-6-苯基-1H-1,2,3-三唑并[4,5-c]吡啶-4-酮，其用三氯氧磷和环烷基胺处理。一些化合物表现出高亲和力和选择性，Ki值的趋势对应于9-苄基-N6-环烷基-2-苯基ade啶和9-苄基-N6-环烷基-2-苯基-8-氮杂腺嘌呤的系列，因此它们可以是被认为是生物等排体。

  DOI：

  10.1016/j.ejmech.2003.09.003
• 作为产物：
  描述：

  1-benzyl-5-methyl-1H-1,2,3-triazol-4-carbonyl chloride 在 盐酸 、 二氯(N,N,N',N'-四甲基乙二胺)锌(II) 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 19.16h， 生成 1-苄基-5-甲基-1H-[1,2,3]三唑-4-甲酸
  参考文献：
  名称：

  铁催化三取代的三唑活化的苄基和芳基胺的C–H活化

  摘要：

  三取代三唑的设计为邻近诱导铁催化苄基和芳基胺的C–H活化提供了广阔的舞台。因此，通过无外消旋的铁催化，可重复使用的三唑被无痕去除，CH烷基化和CH芳基化被证明对高水平的化学和位置选择性是可行的。

  DOI：

  10.1021/acs.orglett.7b01672

文献信息

• Boronic Acid Catalysis for Mild and Selective [3+2] Dipolar Cycloadditions to Unsaturated Carboxylic Acids
  作者：Hongchao Zheng、Robert McDonald、Dennis G. Hall

  DOI：10.1002/chem.200903484

  日期：2010.5.10

  activation of unsaturated carboxylic acids is applied in several classic dipolar [3+2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can

  在本文中，用于不饱和羧酸活化的硼酸催化（BAC）的概念被应用在几种经典的偶极[3 + 2]环加成中，涉及叠氮化物，腈氧化物和硝酮作为伙伴。这些环加成物可用于生产药学上感兴趣的小的杂环产物，例如三唑，异恶唑和异恶唑烷。这些环加合物是直接形成的，并且包括可以用于进一步转化的游离羧酸官能度，从而避免了事先的掩蔽或官能化。在所有情况下，BAC都能在较温和的条件下提供更快的反应，并大大提高了产品收率和区域选择性。在某些情况下，例如叠氮化物与2-链烷酸反应生成三唑，邻位催化使用热活化时，硝基苯硼酸可避免不良的产物脱羧反应。通过使用NMR光谱研究，表明硼酸催化剂可以通过不饱和羧酸中的LUMO降低作用来提供活化作用，这很可能是通过单酰化的半硼酸酯中间体造成的。
• [EN] SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS SPIROLACTAMES D'UN RÉCEPTEUR NMDA ET LEURS UTILISATIONS
  申请人：NAUREX INC

  公开号：WO2014120783A1

  公开（公告）日：2014-08-07

  Disclosed are compounds having enhanced potency in the modulation of NMD A receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  揭示了在调节NMDA受体活性方面具有增强效力的化合物。这些化合物可用于治疗抑郁症和相关疾病。此外，还披露了口服制剂和其他药用可接受的化合物给药形式，包括静脉注射制剂。
• Facile Conversion of Molecularly Complex (Hetero)aryl Carboxylic Acids into Alkynes for Accelerated SAR Exploration
  作者：Ferdinand H. Lutter、Matthieu Jouffroy

  DOI：10.1002/chem.202102130

  日期：2021.10.25

  molecularly complex (hetero)aryl carboxylic acids into the bioisostere world: A functional-group-tolerant and operationally simple decarbonylative alkynylation is reported that allows the synthesis of aryl alkynes from highly functionalized aryl and heteroaryl carboxylic acids. The reaction shows an unmatched substrate scope mainly thanks to its remarkably mild reaction conditions using a homogenous Pd/Cu

  将分子复杂的（杂）芳基羧酸带入生物电子等排世界：据报道，一种具有官能团耐受性且操作简单的脱羰炔基化反应允许从高度官能化的芳基和杂芳基羧酸合成芳基炔烃。该反应显示出无与伦比的底物范围，这主要归功于其使用均质 Pd/Cu 双金属系统的非常温和的反应条件。商业药物吗氯贝胺的三唑类似物的制备展示了该协议的效用。
• Design, Synthesis, and Fungicidal Activities of Novel 5-Methyl-1H-1,2,3- trizole-4-carboxyl Amide Analogues
  作者：Zhen-Jun Wang、Hui-Hui Yang、Lei Tian、Wei-Guang Zhao

  DOI：10.2174/1573406412666151112125006

  日期：2016.3.31

  that some of designed N-phenethyl-1,2,3-trizole-4-carboxyl amide analogues exhibited good fungicidal activities toward Sclerotinia sclerotiorum and Botrytis cinerea, while some of Nbenzyl- 1,2,3-trizole-4-carboxyl amide analogues exhibited good fungicidal activities toward Phytophthora capsici and Cercospora arachidicola. EC50 value of compound 5d against Cercospora arachidicola (6.6 µg/mL) was lower

  琥珀酸脱氢酶抑制剂（SDHIs）是具有酰胺键的杀菌剂，广泛用于控制由植​​物致病真菌引起的植物病害。由于新SDHI的广泛活动，它们引起了研究界的广泛关注。设计并合成了具有生物活性的1,2,3-三唑部分的一系列结构新颖的SDHI。生物活性筛选表明，某些设计的N-苯乙基-1,2,3-三唑-4-羧基酰胺类似物对菌核盘菌和灰葡萄孢表现出良好的杀真菌活性，而一些N苄基1,2,3-三唑-4-羧基酰胺类似物对辣椒疫霉和花生毛孢菌表现出良好的杀真菌活性。EC 50 化合物5d对阿拉伯头孢菌（Cercospora arachidicola）（6.6 µg / mL）的测定值低于百菌清（12.3 µg / mL）。
• Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues
  作者：Zhen-Jun Wang、Yang Gao、Yan-Ling Hou、Cheng Zhang、Shu-Jing Yu、Qiang Bian、Zheng-Ming Li、Wei-Guang Zhao

  DOI：10.1016/j.ejmech.2014.08.029

  日期：2014.10

  3-trizole-4-carboxyl amide (ester) analogues exhibit good fungicidal activities, especially towards Sclerotinia sclerotiorum, and a structure–activity relationship study confirmed that the replacement of the amide group with an ester group had little effect on fungicidal activity, which could be provideous in terms of issues and metabolism. 1,6-Dimethyl phenyl was confirmed as the most efficient substituent of the

  琥珀酸脱氢酶抑制剂（SDHIs）是有效的杀真菌剂，被广泛用于控制由植​​物病原性真菌引起的植物病害，尽管它们的有效性由于在多种不同真菌中产生的抗性而受到损害。SDHIs最常见的结构特征之一是它们的酰胺键。向SDHIs引入更大的结构多样性是延迟抗药性发作的有前途的策略。已经设计和合成了一系列含有生物活性1,2,3-三唑部分的新型SDHI，并评估了其杀真菌和杀虫活性。这些分析的结果表明，大多数新合成的1,2,3-三唑-4-羧基酰胺（酯）类似物表现出良好的杀真菌活性，尤其是对核盘菌和结构-活性关系研究证实，用酯基取代酰胺基对杀真菌活性影响很小，这在问题和新陈代谢方面可能是有用的。1,6-二甲基苯基被确认为当前研究中最有效的取代基，当它同时被置于酰胺和酯化合物上时。有趣的是，一些新合成的化合物显示出对淡色库蚊的良好杀虫活性。目前的研究结果表明，这些1,2,3-三唑-4-羧基酰胺和酯类似物代表一种新型SDHI，可用于开发新型农药。