2-硝基苯磺酰肼 | 6655-77-2

• 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: 2-硝基苯磺酰肼
• 英文名称: 3-nitrophenylsulfonohydrazide
• 英文别名: 3-nitrobenzenesulfonohydrazide；3-nitrobenzenesulfonyl hydrazide；3-Nitro-benzolsulfonsaeure-hydrazid
• CAS: 6655-77-2
• 化学式: C₆H₇N₃O₄S
• mdl: MFCD01859908
• 分子量: 217.205
• InChiKey: IHLRXXTYALIWND-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  421.8±47.0 °C(Predicted)
• 密度：
  1.562±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Nitrobenzenesulfonohydrazide
Synonyms: 3-Nitrobenzenesulfonylhydrazide

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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-Nitrobenzenesulfonohydrazide
CAS number: 6655-77-2

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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: C6H7N3O4S
Molecular weight: 217.2

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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, sulfur 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

反应信息

• 作为反应物：
  描述：

  2-硝基苯磺酰肼 在 磷化氢 、 水 、 碘 作用下， 生成 3,3'-二硝基二苯二硫醚
  参考文献：
  名称：

  Kawahara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 963

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基苯磺酰氯 在 hydrazine hydrate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到2-硝基苯磺酰肼
  参考文献：
  名称：

  磺酰腙和酰基腙取代的 8-Ethoxy-3-nitro-2H-chromenes 的合成作为有效的抗增殖和凋亡诱导剂

  摘要：

  3-硝基-2H-色烯最近被鉴定为一类新型的强效抗肿瘤剂。鉴于磺酰腙和酰腙显示出的良好效果，我们设计合成了一系列磺酰腙和酰腙取代的8-乙氧基-3-硝基-2H-色烯衍生物，并评估了它们对A549、KG-的细胞生长抑制活性。 1、A2780 和 K562 细胞。所有测试的化合物对 KG-1 细胞都表现出比 BENC-511 更强的抗增殖活性。这些化合物对 A2780 细胞显示出纳摩尔范围内的 IC50 值。化合物 7d 对 K562 细胞显示出显着的细胞毒性，IC50 为 0.11 µM，与 BENC-511 相当。化合物 7d 以高浓度将 K562 细胞阻滞在 G1 期并诱导 K562 细胞凋亡。此外，7d 增加裂解的 caspase-3 的水平，降低 bcl-2 的表达并诱导 K562 细胞中聚（ADP-核糖）聚合酶的裂解。因此，本研究提供了一系列新型化合物作为具有凋亡死亡能力的有效抗肿瘤剂的开发。

  DOI：

  10.1002/ardp.201400082
• 作为试剂：
  描述：

  1-溴-3,5-二氟苯 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 正丁基锂 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 Adam’s catalyst 、 二氧化碳 、 2-硝基苯磺酰肼 、 氢气 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 、 二异丙胺 、 苯甲醇钠 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 142.42h， 生成 ((2S,3S)-2-(6-(benzyloxy)pyridin-2-yl)-5-chloro-6-fluoro-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzofuran-2-yl)methanol
  参考文献：
  名称：

  [EN] BIARYL DERIVATIVES AS YAP/TAZ-TEAD PROTEIN-PROTEIN INTERACTION INHIBITORS
  [FR] DÉRIVÉS BIARYLE EN TANT QU'INHIBITEURS D'INTERACTION PROTÉINE-PROTÉINE YAP/TAZ-TEAD

  摘要：

  本发明提供了化合物(I)或其药学上可接受的盐；(I)制造所述化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合物和包括所述化合物的药物组合。

  公开号：

  WO2021186324A1

文献信息

• Electrochemical sulfonylation of thiols with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of thiosulfonates
  作者：Zu-Yu Mo、Toreshettahally R. Swaroop、Wei Tong、Yu-Zhen Zhang、Hai-Tao Tang、Ying-Ming Pan、Hong-Bin Sun、Zhen-Feng Chen

  DOI：10.1039/c8gc02143k

  日期：——

  We have developed a new metal- and oxidant-free method for the synthesis of anticancer thiosulfonates via sulfonylation of thiols.

  我们已经开发出一种新的无金属和氧化剂的方法，通过对硫醇进行磺化合成抗癌硫代磺酸酯。
• Sulphonhydrazides and related compounds. Part VI. Some halogeno- and nitro-benzenesulphonhydrazides
  作者：R. J. W. Cremlyn

  DOI：10.1039/j39660001229

  日期：——

  4-Chloro-3-nitro-, 4-hydrazino-3-nitro-, o- and m-nitro-, p-bromo-, 2,4-, 2,5-, and 3,4-dichloro-, also 2,3,4- 2,4,5-, and 2,4,6-trichloro-benzenesulphonhydrazides have been prepared and converted into a number of derivatives (e.g., hydrazones, azides) required as potential pest-control agents. The relative stability of the various sulphonyl hydrazides is briefly discussed.

  4-氯-3-硝基- ，4-肼基-3-硝基，ö -和米硝基- ，p溴代，2,4-，2,5-，和3,4-二氯，也已经制备了2,3,4- 2,4,5-和2,4,6-三氯苯磺酰肼，并将其转化为许多潜在的害虫防治剂所需的衍生物（例如，hydr，叠氮化物）。简要讨论了各种磺酰肼的相对稳定性。
• Base-mediated tandem sulfonylation and oximation of alkenes in water
  作者：Bin Wang、Lin Tang、Liyan Liu、Yanan Li、Yu Yang、Zhiyong Wang

  DOI：10.1039/c7gc03051g

  日期：——

  A base-mediated bifunctionalization of alkenes for the synthesis of α-sulfonylethanone oximes was developed in water under metal-free conditions. This reaction features a wide substrate scope and facile starting materials to afford the desired products in high yields.

  烯烃的碱介导的双官能团化反应在无金属条件下在水中进行，用于合成α-磺酰乙酮肟。该反应具有广泛的底物范围和易得的起始物质，可以高产率地得到所需的产物。
• Desulfinative and denitrogenative palladium-catalyzed cross-coupling of arylsulfonyl hydrazides with aryl diazonium salts
  作者：Yonghui Shang

  DOI：10.1002/aoc.4484

  日期：2018.11

  Palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides with aryl diazonium salts to provide biaryl products under relatively mild conditions is established. This reaction proceeded smoothly with tetrabutylammonium iodide and gave the corresponding products with CC bonds formed using PdCl2/bis (dicyclohexylphosphino) methane catalyst under air. This method also allowed easy access to significant

  建立了在相对温和的条件下钯催化的芳基磺酰肼与芳基重氮盐的交叉偶联，以提供联芳基产物。该反应用四丁基碘化铵平稳地进行，并得到在空气中用PdCl 2 /双（二环己基膦基）甲烷催化剂形成的具有CC键的相应产物。该方法还允许容易地获得重要的功能性联芳基，以用于药物和有机化学的潜在应用。
• New arylsulfonohydrazide inhibitors of enzymes MurC and MurD
  申请人：UNIVERZA V LJUBLJANI, FAKULTETA ZA FARMACIJO

  公开号：EP1845083A3

  公开（公告）日：2009-12-30

  This invention belongs to the field of pharmaceutical chemistry and relates to new arylsulfonohydrazides as inhibitors of UDP-N-acetylmuramyl:L-alanine ligaze (MurC) and UDP-N-acetylmuramyl-L-alanine:D-glutamate ligaze (MurD), to procedures for their preparation and pharmaceutical preparations containing the same. The enzymes MurC and MurD are the key enzymes involved in the synthesis of bacterial peptidoglycan, so arylsulfonohydrazide inhibitors possess antibacterial activity. Compounds of general formula I and the pharmaceutically acceptable salts are described. The appropriate substituents are clearly presented in the body of the text and in claims.

  这项发明属于药物化学领域，涉及新的芳基磺酰肼作为UDP-N-乙酰基葡萄糖胺基莫拉酰基:L-丙氨酸连接酶（MurC）和UDP-N-乙酰基葡萄糖胺基-L-丙氨酸:D-谷氨酸连接酶（MurD）的抑制剂，以及它们的制备方法和含有相同物质的药物制剂。酶MurC和MurD是参与细菌肽聚糖合成的关键酶，因此芳基磺酰肼抑制剂具有抗菌活性。描述了一般式I的化合物及其药用盐。适当的取代基在文本主体和权利要求中清晰呈现。