1H-吡咯-2-羧肼 | 50269-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1H-吡咯-2-羧肼
• 中文别名: 2-吡咯甲酰肼；1H-吡咯-2-甲酰肼
• 英文名称: 1H-pyrrole-2-carbohydrazide
• 英文别名: 1H-pyrrole-2-carboxylic acid hydrazide；pyrrole-2-carboxylic acid hydrazide
• CAS: 50269-95-9
• 化学式: C₅H₇N₃O
• mdl: MFCD00141885
• 分子量: 125.13
• InChiKey: FQIAWPZQJCAPSW-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C
• 密度：
  1.313

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2933990090

SDS

Name:	1H-Pyrrole-2-carbohydrazide 97% Material Safety Data Sheet
Synonym:
CAS:	50269-95-9

Section 1 - Chemical Product MSDS Name:1H-Pyrrole-2-carbohydrazide 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
50269-95-9	1H-Pyrrole-2-carbohydrazide	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 50269-95-9: 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: 231 - 238 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: C5H7N3O
Molecular Weight: 125.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong 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# 50269-95-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1H-Pyrrole-2-carbohydrazide - 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: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 50269-95-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 50269-95-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 50269-95-9 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：

  1H-吡咯-2-羧肼 在 氢氧化钾 、 三氯氧磷 作用下， 反应 4.5h， 生成 dihydro-2,3 carbethoxy-4 oxo-2 (pyrrolyl-2)-5 oxadiazole-1,3,4
  参考文献：
  名称：

  吡咯并[1,2 - d ]三嗪-1,2,4。I.德雷维斯（Dérivés）

  摘要：

  酰肼合成吡咯烷氧基吡咯羰基2和吡咯羰基合成吡咯羰基2。吡咯基-2恶二唑和噻二唑类可从酰化吡咯烷氧基化氯和硫代磷酸二环酯获得。吡咯并[1,2- d ]三嗪-1,2,4的环己基转移反应或重新安排。

  DOI：

  10.1002/jhet.5570170401
• 作为产物：
  描述：

  吡咯-2-羧酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 1H-吡咯-2-羧肼
  参考文献：
  名称：

  4-烷基-1,2,4-三唑-3-硫酮类似物作为金属-β-内酰胺酶抑制剂

  摘要：

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如

  DOI：

  10.1016/j.bioorg.2021.105024

文献信息

• Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides
  作者：Xiaomei Ding、Manna Huang、Zhou Yi、Dongchen Du、Xinhai Zhu、Yiqian Wan

  DOI：10.1021/acs.joc.7b00290

  日期：2017.5.19

  general and effective CuI/N′,N′-diaryl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the amination of aryl iodides and bromides at room temperature with good chemoselectivity between −OH and −NH2 groups. Only 5 mol % of CuI and ligands was needed in this protocol to effect the amination of various aryl bromides and aryl iodides with a wide range of aliphatic and aryl amines (1.3 equiv)

  开发了一种通用有效的CuI / N'，N'-二芳基-1 H-吡咯-2-碳酰肼催化剂体系，用于在室温下胺基碘和溴化物的胺化反应，并在-OH和-NH 2基团之间实现了良好的化学选择性。在该方案中，仅需要5 mol％的CuI和配体即可实现各种芳族溴化物和芳基碘化物与各种脂族和芳基胺（1.3当量）的胺化。
• Reinvestigation of the structure-activity relationships of isoniazid
  作者：Pooja Hegde、Helena I.M. Boshoff、Yudi Rusman、Wassihun Wedajo Aragaw、Christine E. Salomon、Thomas Dick、Courtney C. Aldrich

  DOI：10.1016/j.tube.2021.102100

  日期：2021.7

  Isoniazid (INH) remains a cornerstone for treatment of drug susceptible tuberculosis (TB), yet the quantitative structure-activity relationships for INH are not well documented in the literature. In this paper, we have evaluated a systematic series of INH analogs against contemporary Mycobacterium tuberculosis strains from different lineages and a few non-tuberculous mycobacteria (NTM). Deletion of

  异烟肼 (INH) 仍然是治疗药物敏感结核病 (TB) 的基石，但文献中尚未详细记录 INH 的定量构效关系。在本文中，我们评估了一系列 INH 类似物对来自不同谱系的当代结核分枝杆菌菌株和一些非结核分枝杆菌 (NTM) 的系统性影响。吡啶基氮原子的缺失、吡啶氮异构化到其他位置、用等排杂环取代吡啶环以及修饰INH的酰肼部分会消除抗结核活性。类似地，吡啶环在3位上的取代是不能容忍的，而在2位上的取代允许用2-甲基-INH 9进行，其抗分枝杆菌活性与INH相当。为了评估这一系列 INH 类似物针对分枝杆菌的比活性，我们对一组革兰氏阳性和革兰氏阴性细菌以及一些真菌进行了测定。正如预期的那样，INH 及其类似物显示出较窄的活性谱，并且对所评估的所有非分枝杆菌菌株均无活性，但4 菌株除外，该菌株对新型隐球菌具有适度的抑制活性。我们的研究结果提供了对 INH 结构-活性关系的最新分析，我们希望这能为社区提供有用的资源。
• Synthesis and crystal structure of phosphonic acid and bisphosphoramidate derivatives: QSAR studies of their anti-fungal potential on Macrophomina Phaseolina (Tassi) Goid
  作者：Khodayar Gholivand、Mohsen Abbod、Ali Asghar Ebrahimi Valmoozi、Omolbanin Barzegar、Hadis Nasrollah Tabar、Rouhollah Yaghoubi、Mahdieh Hosseini、Naser Safaie、Maryam Rahimzadeh Dashtaki、Michal Dusek、Ahmad Mani-Varnosfaderani

  DOI：10.1007/s13738-020-02133-4

  日期：2021.7

  series of phosphonic acid and bisphosphoramidate derivatives were synthesized and characterized. The bioactivities against the fungal pathogen Macrophomina phaseolina and human acetylcholinesterase AChE enzyme were studied using QSAR based on multiple linear regression. L17, with (p-Cl–C6H4–NH) (p-Cl–C6H4)C(H)P(O)(OC2H5)2 skeleton, demonstrated a great mortality on the M. phaseolina mycelial growth by

  合成并表征了一系列膦酸和双磷酸氨基酯衍生物。基于多重线性回归的QSAR研究了针对真菌病原体菜豆巨噬菌和人乙酰胆碱酯酶AChE酶的生物活性。具有（p -Cl–C 6 H 4 -NH）（p -Cl–C 6 H 4）C（H）P（O）（OC 2 H 5）2骨架的L17在M上显示出很高的死亡率。菜豆在150 mg / L时，菌丝体生长受到83％的抑制；另一种测试的衍生物对真菌表现出中等至弱的抗真菌活性。基于GA-MLR方法的QSAR模型揭示了3D描述符（De，Mor18e，H8m和Mor30p）对抗真菌活性的重要性。它显示出良好的预测所研究分子杀真菌活性的能力。具有（m -CH 3 -NC 5 H 4 -NH）（m -CH 3 -C 6 H 4）C（H）P（O）（OCH 3）2骨架的另一种衍生物L5显示出最有效的抗- AChE活动。电子参数ΔE L-H和E LUMO，对人类AChE的贡献最大。作者认
• Synthesis and biological activities of novel pyrrolo[1,2-d][1,2,4]triazin-1(2H)-one derivatives
  作者：Jesurajan Jebamani、Shubha Pranesh、Jayadev Shivalingappa、Manjunatha Narayanarao、Mussuvir Pasha

  DOI：10.1080/00397911.2020.1859117

  日期：——

  which a novel 6-(4-aminophenyl)pyrrolo[1,2-d][1,2,4]triazin-1(2H)-one derivatives were synthesized and tested for their antimicrobial and antifungal activities. Among all synthesized compounds, compound 7a showed remarkable antimicrobial activity with overall target micro-organisms and compounds 7g and 7l displayed significant inhibitory activity against Escherichia coli (Ec) and Scedosporium (Sc) respectively

  摘要 合成了一系列新的6-（4-氨基苯基）吡咯并[1,2-d] [1,2,4]三嗪-1（2H）-one衍生物的化合物，并测试了它们的抗微生物和抗真菌活性。在所有合成的化合物中，化合物7a对总体目标微生物均表现出显着的抗菌活性，化合物7g和7l分别对大肠杆菌（Ec）和景天孢子（Sc）表现出显着的抑制活性。
• Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides
  作者：Agata Siwek、Monika Wujec、Maria Dobosz、Irena Wawrzycka-Gorczyca

  DOI：10.1002/hc.20643

  日期：——

  , a study on the influence of azole moiety on the capability for intramolecular cyclization and its direction was carried out. It was found that for 4-aryl/alkyl-thiosemicabazides with triazole, imidazole, or pyrrole moiety at N-1 nitrogen atom possible products were only s-triazoles, both in alkaline and acidic medium. Successful dehydrocyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides leading

  对四个系列的1-唑啉-4-芳基/烷基-氨基硫脲进行了唑基对分子内环化能力的影响及其方向的研究。发现对于在 N-1 个氮原子上具有三唑、咪唑或吡咯部分的 4-芳基/烷基-氨基硫脲，在碱性和酸性介质中，可能的产物仅为 s-三唑。仅针对一系列 1-(4-甲基-1,2,3-噻二唑-5-基-羰基)-4- 1-唑基-4-芳基/烷基-氨基硫脲成功脱氢环化生成噻二唑芳基/烷基氨基硫脲。可以推测，1-唑啉-4-芳基/烷基-氨基硫脲的氧原子pKa值的测定可能是预测脱氢环化形成噻二唑的可能性的非常有价值的参数。© 2010 威利期刊公司。杂原子化学 21:521–532, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20643