1,2,3-苯并三唑-5-羧酸甲酯 | 113053-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 1,2,3-苯并三唑-5-羧酸甲酯
• 中文别名: 1,2,3-苯并噻唑-5-羧酸甲酯
• 英文名称: methyl 1H-benzo[d][1,2,3]triazole-5-carboxylate
• 英文别名: methyl benzotriazole-5-carboxylate；methyl 1H-1,2,3-benzotriazole-5-carboxylate；methyl 2H-benzotriazole-5-carboxylate
• CAS: 113053-50-2
• 化学式: C₈H₇N₃O₂
• mdl: MFCD00174276
• 分子量: 177.162
• InChiKey: ZMMBQCILDZFYKX-UHFFFAOYSA-N

物化性质

• 熔点：
  177-179°C
• 沸点：
  413.6±18.0 °C(Predicted)
• 密度：
  1.403
• 稳定性/保质期：
  常温常压下稳定，避免与还原剂、强碱、酸性物质及氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 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：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933990090
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中，并远离氧化剂、还原剂、酸和碱。

SDS

Name:	Methyl 1 2 3-Benzotriazole-5-Carboxylate Material Safety Data Sheet
Synonym:	None Known
CAS:	113053-50-2

Section 1 - Chemical Product MSDS Name:Methyl 1 2 3-Benzotriazole-5-Carboxylate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
113053-50-2	Methyl 1,2,3-Benzotriazole-5-Carboxyla	ca. 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
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# 113053-50-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: 177 - 179 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: C8H7N3O2
Molecular Weight: 177.06

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 113053-50-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 1,2,3-Benzotriazole-5-Carboxylate - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 113053-50-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 113053-50-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 113053-50-2 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：

  1,2,3-苯并三唑-5-羧酸甲酯 在 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 8.0h， 生成 1H-苯并[d][1,2,3]噻唑-5-甲醛
  参考文献：
  名称：

  Synthesis and Practical Use of 1H‐1,2,3‐Benzotriazole‐5‐carboxaldehyde for Reductive Amination

  摘要：

  A reliable synthetic procedure to obtain multigram quantities of 1H-1,2,3-benzotriazole-5-carboxaldehyde has been developed. This material can be used in reductive amination reactions with primary and secondary amines to provide good to excellent yields of the desired products without protection of the starting material.

  DOI：

  10.1080/00397910500214151
• 作为产物：
  描述：

  3,4-二氨基苯甲酸甲酯 在 三氧化二氮 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 0.17h， 以97%的产率得到1,2,3-苯并三唑-5-羧酸甲酯
  参考文献：
  名称：

  用于生成无水三氧化二氮的按需流动平台及其在 N-亚硝化反应中的进一步应用

  摘要：

  报道了一种多功能连续流动平台，用于生成浓度精确且可调的浓缩三氧化二氮 (N 2 O 3 ) 溶液。它解锁了 N 2 O 3在流动和间歇亚硝化合成杂环化合物中的用途。

  DOI：

  10.1002/anie.202210146

文献信息

• Zinc‐Catalysed N‐Iodosuccinimide‐Enabled Selective N2‐Olefination of Benzotriazoles with Alkenes
  作者：Lili Zhu、Lifang Tian、Hui Zhang、Lina Xiao、Wen Luo、Bin Cai、Haifeng Wang、Chunjie Wang、Guanglu Liu、Chaoyu Pei、Yahui Wang

  DOI：10.1002/adsc.201801303

  日期：——

  Herein, we describe a zinc‐catalysed N2‐selective olefination of benzotriazoles with unactivated alkenes and styrenes. The transformation is achieved by a N‐iodosuccinimide (NIS)‐mediated two‐step, one‐pot approach, proceeding through sequential regioselective β‐iodoalkylation of benzotriazoles with alkenes and a subsequent base‐promoted 1,2‐elimination. The N2‐selective β‐iodoalkylation of benzotriazoles

  在本文中，我们描述了苯并三唑与未活化的烯烃和苯乙烯的锌催化N 2选择性烯化反应。该转化是通过N碘代琥珀酰亚胺（NIS）介导的两步一锅法完成的，该方法通过依次进行苯并三唑与烯烃的区域选择性β碘烷基化和随后的碱促进的1,2消除。苯并三唑的N 2选择性β碘烷基化具有高度立体定向性，可在非常简单温和的条件下发挥作用，表现出出色的官能团耐受性。N 2的高选择性归因于N之间的分子间氢键碘代琥珀酰亚胺和苯并三唑的1位上的NH氢键供体。这种可扩展的过程，作为结构多样的N 2烯烃化苯并三唑的模块化组装的有效方法，将极大地促进苯并三唑的N 2功能化的化学反应。
• Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2‐Aryldiamines
  作者：Réka J. Faggyas、Nikki L. Sloan、Ned Buijs、Andrew Sutherland

  DOI：10.1002/ejoc.201900463

  日期：2019.9

  mild conditions, using a polymer‐supported nitrite reagent and p‐tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N‐alkyl, ‐aryl, and ‐acyl ortho‐aminoanilines leading to the synthesis of N1‐substituted benzotriazoles. The synthetic utility of this one‐pot heterocyclization process was exemplified with the preparation of a

  已经开发了一种操作简单的方法，通过使用聚合物负载的亚硝酸盐试剂和对甲苯磺酸在温和条件下通过重氮化和分子内环化多种 1,2-芳基二胺来制备 N-未取代的苯并三唑。通过有效活化和环化 N-烷基、-芳基和-酰基邻-氨基苯胺，合成 N1 取代的苯并三唑，进一步证明了该方法的官能团耐受性。这种单锅杂环化过程的合成效用可以通过制备许多具有生物学和医学意义的苯并三唑支架来举例说明，包括一种 α-氨基酸类似物。
• Electro-oxidative C(sp3)–H Amination of Azoles via Intermolecular Oxidative C(sp3)–H/N–H Cross-Coupling
  作者：Jiwei Wu、Yi Zhou、Yuchen Zhou、Chien-Wei Chiang、Aiwen Lei

  DOI：10.1021/acscatal.7b03551

  日期：2017.12.1

  electrooxidative C(sp3)–H amination via intermolecular oxidative C(sp3)–H/N–H cross-coupling has been developed under metal- and oxidant-free conditions. The C(sp3)–H bonds adjacent to oxygen, nitrogen, and sulfur atoms could all react smoothly with various amines to give the corresponding products with moderate to good yields (30–93%). In addition, the C(sp3)–H bonds of benzylic and allylic are also tolerated

  已经开发了一种在无金属和无氧化剂条件下通过分子间氧化C（sp3）-H / N-H交叉偶联进行电氧化C（sp3）-H胺化的方法。与氧，氮和硫原子相邻的C（sp3）–H键均可以与各种胺顺利反应，从而以中等至良好的收率（30–93％）得到相应的产物。此外，该反应中还可以耐受苄基和烯丙基的C（sp3）–H键。初步的机理研究表明，四氢呋喃的C–H裂解可能不参与速率测定步骤。
• Tetrazolyl substituted benzonitriles and anti-tumor use thereof
  申请人：Ciba-Geigy Corporation

  公开号：US05073574A1

  公开（公告）日：1991-12-17

  Compounds of formula I, ##STR1## wherein Tetr, R, R.sub.0, R.sub.1 and R.sub.2 are as defined in the description, have valuable pharmaceutical properties and are especially effective against tumors. They are prepared in a manner known per se.

  公式I的化合物，其中Tetr、R、R.sub.0、R.sub.1和R.sub.2按描述定义，具有宝贵的药物性质，特别是对肿瘤具有显著的疗效。它们以已知的方式制备。
• [DE] NEUE BICYCLISCHE INHIBITOREN DER HORMON SENSITIVEN LIPASE<br/>[EN] NOVEL BICYCLIC INHIBITORS OF HORMONE SENSITIVE LIPASE<br/>[FR] INHIBITEURS BICYCLIQUES DE LA LIPASE HORMONO-SENSIBLE
  申请人：AVENTIS PHARMA GMBH

  公开号：WO2004035550A1

  公开（公告）日：2004-04-29

  Es werden Benzotriazole der allgemeinen Formel (I) beschrieben, worin R1 bis R8 die genannten Bedeutungen haben sowie Verfahren zu deren Herstellung. Die Verbindungen zeigen eine hemmende Wirkung an der hormon sensitiven Lipase.

  通用公式（I）描述了苯并三唑，其中R1至R8具有所述的含义，以及其制备方法。这些化合物显示对激素敏感脂肪酶的抑制作用。