2-硝基-N-苯基苯磺酰胺 | 5454-97-7

• 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-N-苯基苯磺酰胺
• 英文名称: 2-nitro-N-phenylbenzenesulfonamide
• 英文别名: N-phenyl-2-nitrobenzenesulfonamide
• CAS: 5454-97-7
• 化学式: C₁₂H₁₀N₂O₄S
• 分子量: 278.288
• InChiKey: MLPVALKIJBKOGG-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  462.0±47.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Nitro-N-phenylbenzenesulfonamide
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: 2-Nitro-N-phenylbenzenesulfonamide
CAS number: 5454-97-7

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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: C12H10N2O4S
Molecular weight: 278.3

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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-N-苯基苯磺酰胺 在 盐酸 、 氢氧化钾 、 tin(ll) chloride 作用下， 生成 2-氨基-N-甲基-N-苯基苯磺酰胺
  参考文献：
  名称：

  Ullmann; Gross, Chemische Berichte, 1910, vol. 43, p. 2700

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯磺酰氯 、 苯胺 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以88%的产率得到2-硝基-N-苯基苯磺酰胺
  参考文献：
  名称：

  二苯并[1,2,5]硫氮卓类是非竞争性GABAA受体拮抗剂

  摘要：

  描述了一种获得二苯并 [c,f][1,2,5] 噻二氮 (DBTDs) 的新方法及其对豚鼠肌间神经元 GABAA 受体的影响。DBTD 衍生物的合成始于两种商业芳香族化合物。两个连续反应后得到一个叠氮化物基团，中心环通过氮烯闭合，得到三环磺酰胺（DBTDs）。全细胞记录显示，DBTDs 的应用不影响保持电流，但抑制了由 GABAA 受体介导的 GABA (IGABA) 诱导的电流。这些 DBTDs 效应在应用后 3 分钟达到最大值，并且是：（i）可逆，（ii）浓度依赖性（效力等级为 2c = 2d > 2b），（iii）由非竞争性拮抗作用介导， (iv) 仅在细胞外应用时观察到。当两种物质同时使用时，苦味毒素（结合在通道口中）和 DBTDs 的效果没有改变。我们的结果表明，DBTD 作用于 GABAA 通道的细胞外结构域，但不依赖于苦味毒素、苯二氮卓和 GABA 结合位点。这里使用的 DBTD

  DOI：

  10.3390/molecules18010894

文献信息

• Pro-neurogenic compounds
  申请人：Board of Regents of the University of Texas System

  公开号：US09095571B2

  公开（公告）日：2015-08-04

  This invention relates generally to stimulating neurogenesis (e.g., post-natal neurogenesis, e.g., post-natal hippocampal neurogenesis) and protecting from neuron cell death.

  这项发明通常涉及刺激神经发生（例如，后生神经发生，例如，后生海马神经发生）并保护免受神经细胞死亡的影响。
• Facile Access to Bicyclic Sultams with Methyl 1-Sulfonylcyclopropane-1-carboxylate Moieties
  作者：Valentin A. Rassadin、Aleksandr A. Tomashevskiy、Viktor V. Sokolov、Arne Ringe、Jörg Magull、Armin de Meijere

  DOI：10.1002/ejoc.200900113

  日期：2009.6

  4-dibromobutyl)(methoxycarbonyl)methanesulfanilides upon treatment with potassium carbonate in DMF furnish methyl 3-aryl-2,2-dioxo-2-thia-3-azabicyclo[n.1.0]alkane-1-carboxylates in yields ranging from 54 to 84 % (10 examples). The starting materials were obtained by sulfonylation of N-alkenylanilines with methyl (chlorosulfonyl)acetate and subsequent bromination. For the N-alkenylanilines (10 examples, 60–77 %

  N-(2,3-二溴丙基)-和 N-(3,4-二溴丁基)(甲氧基羰基)甲磺酰苯胺在 DMF 中用碳酸钾处理后得到甲基 3-芳基-2,2-二氧-2-硫杂-3-氮杂双环[n.1.0] 烷烃-1-羧酸盐的产率范围为 54% 至 84%（10 个实例）。通过用(氯磺酰基)乙酸甲酯磺酰化N-链烯基苯胺并随后溴化来获得起始材料。对于 N-烯基苯胺（10 个实例，60-77% 的产率），已经开发出一种采用 2-硝基苯磺酰基取代基作为保护基团和活化基团的高效新合成方法。通过用硝酸铈 (IV) 铵处理，可以很容易地从 sultam 氮原子上去除 4-甲氧基苯基 (PMP) 基团。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• One-pot synthesis of <i>N</i>-substituted benzannulated triazoles <i>via</i> stable arene diazonium salts
  作者：Rochelle McGrory、Réka J. Faggyas、Andrew Sutherland

  DOI：10.1039/d1ob00968k

  日期：——

  A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamides via stable diazonium salts, prepared using a polymer-supported nitrite reagent and p-tosic acid. The transformation was compatible with a wide range

  开发了一种温和有效的一锅法合成 1,2,3-benzotriazin-4(3 H )-ones 和 benzothiatriazine-1,1( 2H )-dioxide 类似物。该方法涉及通过使用聚合物负载的亚硝酸盐试剂和对甲苯磺酸制备的稳定的重氮盐对 2-氨基苯甲酰胺和 2-氨基苯磺酰胺进行重氮化和随后的环化。该转化与多种芳基官能团和酰胺/磺酰胺取代基相容，可用于合成药学上重要的靶标。通过制备含有 1,2,3-benzotriazin-4(3 H )-one的 α-氨基酸，进一步证明了一锅重氮环化过程的合成效用。
• Development of Helical Aromatic Amide Foldamers with a Diphenylacetylene Backbone
  作者：Ko Urushibara、Tatsunori Yamada、Akihiro Yokoyama、Hirotoshi Mori、Hyuma Masu、Isao Azumaya、Hiroyuki Kagechika、Tsutomu Yokozawa、Aya Tanatani

  DOI：10.1021/acs.joc.9b02758

  日期：2020.2.21

  groups takes a left-handed helical conformation, while the polyamide β-DPA with (S)-β-methyl-substituted TEG groups takes a right-handed helical conformation. The difference in the screw sense of α-DPA and β-DPA would be caused by the steric interaction between the main chain and the side chain, as observed in poly(p-benzamide) possessing (S)-β-methyl-substituted TEG side chains (β-PA) because the large

  我们设计并合成了带有二苯乙炔主链，α-DPA和β-DPA，分别带有（S）-α-和（S）-β-甲基取代的三乙二醇（TEG）侧链的芳族聚酰胺，并检查了它们的构象。解。两种聚合物均显示出强的，与溶剂极性有关的圆二色性光谱，这表明它们在低极性溶剂中呈螺旋构象。光谱是镜像的，取决于侧链的手性位置。因此，具有（S）-α-甲基取代的TEG基团的聚酰胺α-DPA具有左旋螺旋构象，而具有（S）-β-甲基取代的TEG基团的聚酰胺β-DPA具有右旋螺旋构象。螺旋构象。α-DPA和β-DPA的螺丝感不同是由主链和侧链之间的空间相互作用引起的，如在具有（S）-β-甲基取代的TEG侧链（β-PA）的聚对苯甲酰胺中所观察到的，这是因为DPA螺旋结构的大空腔会干扰溶剂化引起的螺旋折叠。对带有β-甲基取代的TEG基团的寡酰胺6-12进行了详细的构象分析。理论计算表明，具有β-甲基取代的TEG基团的低酰胺以螺旋构象存在，其空腔的直径为7。低聚物的1
• Ortho Effect in Dissociation of Substituted N-Phenylbenzenesulfonamides
  作者：Jiří Nádvorník、Miroslav Ludwig

  DOI：10.1135/cccc20011380

  日期：——

  Twenty-five 2,2'-disubstituted N-phenylbenzenesulfonamides (2-X-C₆H₄SO₂NHC₆H₄-Y-2') were synthesised and their purity checked by elemental analysis. This set of model substrates involved all possible combinations of methoxy, methyl, hydrogen, chloro, and nitro substituents. The dissociation constants of the sulfonamides were determined by potentiometric titration in methanol, pyridine, dimethyl sulfoxide, N,N-dimethylformamide, acetone, and acetonitrile. The dissociation constants pK_HA obtained were correlated with various sets of substituent constants describing electronic and steric effects of the substituents, and the statistically treated data were used to discuss the contribution of the substituent effects in the dissociation and the difference between the effects transmitted from the two rings. A linear regression model explaining 99% of the variability of experimental data in all the solvents has been found and discussed. Moreover, the experimental data were also interpreted by the methods using latent variables, the principal component analysis (PCA) and conjugated deviation analysis (CDA), and two latent variables were shown to be statistically significant in the description of dissociation. The first obviously describes common action of electronic and steric effects of substituents; the other probably concerns a combined effect of substituent and solvent on the position of acid-base equilibrium.

  二十五种2,2'-二取代N-苯基苯磺酰胺（2-X-C6H4SO2NHC6H4-Y-2'）被合成，并通过元素分析检查其纯度。这组模型底物涉及甲氧基、甲基、氢、氯和硝基取代基的所有可能组合。苯磺酰胺的解离常数通过在甲醇、吡啶、二甲基亚砜、N,N-二甲基甲酰胺、丙酮和乙腈中的电位滴定确定。所得到的解离常数pKHA与描述取代基电子和立体效应的各种取代基常数相关联，统计处理的数据用于讨论取代基效应在解离中的贡献以及从两个环传递的效应之间的差异。已找到并讨论了一个线性回归模型，解释了在所有溶剂中实验数据变异性的99%。此外，实验数据还通过使用潜在变量的方法进行解释，主成分分析（PCA）和共轭偏差分析（CDA），并且显示两个潜在变量在描述解离中具有统计显著性。第一个明显描述了取代基的电子和立体效应的共同作用；另一个可能涉及取代基和溶剂对酸碱平衡位置的联合影响。