3,4,5-三甲氧基苯甲酰肼 | 3291-03-0

• 物质功能分类: 有机原料 - 肼或胲的有机衍生物
• 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: 3,4,5-三甲氧基苯甲酰肼
• 中文别名: 3,4,5-三甲氧基苯酰肼
• 英文名称: 3,4,5-trimethoxybenzohydrazide
• 英文别名: 3,4,5-trimethoxy-benzoic acid hydrazide；3,4,5-trimethoxybenzoylhydrazine；3,4,5-trimethoxybenzhydrazide；3,4,5-trimethoxyphenyl hydrazide；3,4,5-Trimethoxy-benzoesaeure-hydrazid
• CAS: 3291-03-0
• 化学式: C₁₀H₁₄N₂O₄
• mdl: MFCD00014758
• 分子量: 226.232
• InChiKey: KQXHMNUXNHQSOW-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160°C
• 密度：
  1.197
• 稳定性/保质期：
  在常温常压下，该物质保持稳定。参见发泡剂ＴＳＨ（对甲苯磺酰肼）。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.8
• 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
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下避光保存，并置于通风干燥处密封保存。内衬塑料袋，外用铁桶或木桶包装，宜存放在阴凉、通风的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,4,5-Trimethoxybenzhydrazide
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3,4,5-Trimethoxybenzhydrazide
CAS number: 3291-03-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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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.
Store in closed vessels.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H14N2O4
Molecular weight: 226.2

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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

化学性质：结晶态。熔点为159-161℃。

用途：作为甲氧苄氨嘧啶的中间体。

生产方法：通过在碱性条件下用硫酸二甲酯对没食子酸进行甲基化，生成3,4,5-三甲氧基苯甲酸甲酯，后者再与水合肼反应得到目标产物。

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯甲酰肼 在 ammonium hydroxide 、 汞 、 potassium hexacyanoferrate(III) 、 锌 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 4.75h， 生成 3,4,5-三甲氧基甲苯
  参考文献：
  名称：

  SYNTHESIS OF 2,3-DIMETHOXY-5-METHYL-1,4-BENZOQUINONE: A KEY FRAGMENT IN COENZYME-Q SERIES^*

  摘要：

  Preparation of the title compound by a reaction sequence starting from gallic acid present in mango kernel is described.

  DOI：

  10.1081/scc-100103252
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰氯 在 sodium 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 3,4,5-三甲氧基苯甲酰肼
  参考文献：
  名称：

  Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase

  摘要：

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.

  DOI：

  10.1021/jm060742o

文献信息

• ACYL-HYDRAZONE AND OXADIAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND USES THEREOF
  申请人：Universidade Federal de Santa Catarina

  公开号：US20150191445A1

  公开（公告）日：2015-07-09

  The present invention relates to acyl-hydrazone compounds, in particular 3,4,5-trimethoxyphenyl-hydrazide derivatives, as well as the oxadiazole analogs thereof and other similar compounds, and to the pharmaceutical use of the same for the treatment of various diseases associated with cell proliferation, such as leukemias, including acute lymphoblastic leukemia (ALL), tumours and inflammation. Acyl-hydrazones have been obtained having activity similar to that of the compound used as a standard in experiments (colchicine). The greater selectivity of the compounds according to the invention is an important feature, associated with fewer side effects than the pharmaceuticals used at present in clinical treatments. The synthetised acyl-hydrazones, more particularly the compounds 02 and 07, exhibited important antileukemic activity, which suggests 02 and 07 as candidates to pharmaceutical prototypes, or to pharmaceuticals for the treatment of leukemias, in particular acute lymphoblastic leukemia (ALL), tumours and other proliferative diseases, such as inflammation. The action mechanism of the most active compounds was determined by using DNA microarrays and subsequent tests indicated by the chip, besides selectivity studies in healthy human lymphocytes.

  本发明涉及酰基腙化合物，特别是3,4,5-三甲氧基苯基腙衍生物，以及其噁二唑类似物和其他类似化合物，以及它们在治疗与细胞增殖相关的各种疾病，如白血病（包括急性淋巴细胞白血病（ALL））、肿瘤和炎症方面的药用。已获得具有与实验中使用的化合物（秋水仙碱）相似活性的酰基腙。根据本发明的化合物具有更大的选择性，与目前在临床治疗中使用的药物相比，副作用更少是一个重要特征。合成的酰基腙，尤其是化合物02和07，表现出重要的抗白血病活性，这表明02和07可能成为药物原型的候选，或用于治疗白血病，特别是急性淋巴细胞白血病（ALL）、肿瘤和其他增殖性疾病，如炎症的药物。最活性化合物的作用机制是通过使用DNA微阵列确定的，并且通过芯片指示的后续测试，以及对健康人类淋巴细胞的选择性研究。
• Synthesis and Biological Activity of Novel (E)-N’-(Substituted)-3,4,5-Trimethoxybenzohydrazide Analogs
  作者：Namala Rambabu、Bhavani Ram、Pramod Kumar Dubey、Bhavani Vasudha、Bhavani Balram

  DOI：10.13005/ojc/330126

  日期：2017.2.28

  Aspergillus niger and Candida albicans (Fungal strains). The results revealed that most of the hydrazone derivatives exhibited significant antibacterial activity. Furthermore, the synthesized hydrazone derivatives were found to exhibit significant antidiabetic activity when compared to insulin.

  通过3，4，5-三甲氧基苯并酰肼3与各种芳族和杂芳族醛a1的缩合描述了酰肼-hydr类似物4a-4l。利用各种光谱技术，即（1 H NMR，13 C NMR，IR和MS）来确定合成的化合物的结构。对这些化合物进行了针对金黄色葡萄球菌，酿脓链球菌，大肠杆菌，铜绿假单胞菌，黑曲霉和白色念珠菌（真菌菌株）的抗菌，抗真菌筛选。结果表明，大多数derivatives衍生物表现出显着的抗菌活性。此外，发现与胰岛素相比，合成的derivatives衍生物显示出显着的抗糖尿病活性。
• Inhibitors of histone deacetylase
  申请人：——

  公开号：US20020177594A1

  公开（公告）日：2002-11-28

  Compounds having the formula 1 or therapeutically acceptable salts thereof, are histone deacetylase (HDAC) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed.

  具有以下化学式的化合物或其治疗上可接受的盐是组蛋白去乙酰化酶（HDAC）抑制剂。本文揭示了该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法。
• Studies in the triazine series including a new synthesis of 1:2:4-triazines
  作者：P.V. Laakso、R. Robinson、H.P. Vandrewala

  DOI：10.1016/0040-4020(57)85014-5

  日期：1957.1

  mono-aroylhydrazones of benzil are cyclised by ammonium acetate in hot acetic acid to tri-substituted-1:2:4-triazines. The yield is favourable and it is not necessary, or even advantageous, to isolate the presumed intermediates. The new synthesis has been applied to a sufficient range of examples to establish its status as a general method. In the case of phenanthraquinone the reaction took a more complex course and

  通过乙酸铵在热乙酸中将苯甲酰的单芳酰基hydr环化为三取代的1：2：4-三嗪。产率是有利的，分离假定的中间体不是必需的，甚至是不利的。新的合成方法已应用于足够多的实例中，以确立其作为一般方法的地位。在菲醌的情况下，反应过程更为复杂，可能涉及两个二酮分子。
• Synthesis and biological evaluation of novel disulfides incorporating 1,3,4-thiadiazole scaffold as promising antitumor agents
  作者：Sha Li、Hai-Xin Wang、Hai-Ying Liu、Fen Jing、Xiao-Yun Fu、Cai-Wen Li、Yan-Ping Shi、Bao-Quan Chen

  DOI：10.1007/s00044-019-02389-3

  日期：2019.9

  and A549 lines. Bioassay indicated that some compounds showed stronger antitumor effects than reference drugs PX-12 and 5-fluorouracil. Among these screened compounds, compound 7h showed excellent biological activities in inhibiting SMMC-7721 cell proliferation with IC50 at 1.93 ± 0.08 μM. Compounds 7k and 7i manifested highly effective growth inhibitory activity versus MCF-7 cells, with IC50 at 3.04 ± 0

  在本研究中，制备了十四个含二硫基的2,5-二取代的1,3,4-噻二唑衍生物。通过IR，NMR，MS和元素分析鉴定了所得化合物7a – 7n。使用针对SMMC-7721，MCF-7和A549品系的标准CCK-8分析法研究了它们的体外抗增殖特性。生物测定表明，某些化合物显示出比参考药物PX-12和5-氟尿嘧啶更强的抗肿瘤作用。在这些筛选出的化合物中，化合物7h以1.93±0.08μM的IC 50抑制SMMC-7721细胞增殖具有优异的生物学活性。化合物7k和7i与MCF-7细胞相比，具有明显的高效生长抑制活性，IC 50分别为3.04±0.09和3.54±0.17μM。对于A549细胞，发现化合物7m具有最高的抗肿瘤效力，IC 50为3.67±0.13μM。

表征谱图