N,N'-二(4-硝基苯基)-磺酰胺 | 19757-13-2

• 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: N,N'-二(4-硝基苯基)-磺酰胺
• 英文名称: N,N′-di-(pnitrophenyl)sulfamide
• 英文别名: N,N’-bis(4-nitrophenyl)sulfamide；p,p'-Dinitro-N,N'-sulfonyldianilin；4.4'-Dinitro-sulfanilid；N.N'-Bis-<4-nitro-phenyl>-sulfamid；Sulfamide, N,N'-bis(4-nitrophenyl)-；4-nitro-N-[(4-nitrophenyl)sulfamoyl]aniline
• CAS: 19757-13-2
• 化学式: C₁₂H₁₀N₄O₆S
• 分子量: 338.301
• InChiKey: AHQKAJFDGDOBMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  8

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name N,N'-BIS(4-NITROPHENYL)SULFAMIDE

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
N,N'-BIS(4-NITROPHENYL)SULFAMIDE None None None

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If not breathing give
artificial respiration. If breathing is difficult, give oxygen.
AFTER SKIN CONTACT
In case of contact, immediately wash skin with soap and copious
amounts of water.
AFTER EYE CONTACT
In case of contact, immediately flush eyes with copious amounts
of water for at least 15 minutes.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
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SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear self-contained breathing apparatus, rubber boots, and heavy
rubber gloves.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Avoid contact and inhalation. Do
not get in eyes, on skin, on clothing.
STORAGE
Conditions of Storage: Keep tightly closed. Store in a cool dry
place.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Safety shower and eye bath. Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling. Wash contaminated clothing before
reuse.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Respiratory protection is not required. Where
protection from nuisance levels of dusts are desired, use type N95
(US) or type P1 (EN 143) dust masks.
Hand Protection: Rubber gloves.
Eye Protection: Chemical safety goggles.

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9 - Physical and Chemical Properties

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Appearance Physical State: Solid
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
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Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Stable: Stable.
Materials to Avoid: Strong oxidizing agents, Strong bases, Strong
acids.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Nitrogen oxides, Sulfur oxides.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur

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11 - Toxicological Information

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SIGNS AND SYMPTOMS OF EXPOSURE
To the best of our knowledge, the chemical, physical, and
toxicological properties have not been thoroughly investigated.
ROUTE OF EXPOSURE
Inhalation: Material is irritating to mucous membranes and upper
respiratory tract.
Multiple Routes: Causes eye and skin irritation. May be harmful
by inhalation, ingestion, or skin absorption.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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15 - Regulatory Information

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Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
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Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N,N'-二(4-硝基苯基)-磺酰胺 在 sodium hydroxide 、 sodium hypochlorite 作用下， 生成 二(4-硝基苯基)二氮烯
  参考文献：
  名称：

  Ohme,R.; Preuschhof,H., Justus Liebigs Annalen der Chemie, 1968, vol. 713, p. 74 - 86

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯胺 在 吡啶 、 磺酰氯 作用下， 生成 N,N'-二(4-硝基苯基)-磺酰胺
  参考文献：
  名称：

  使用各种标准研究N，N'-二芳基磺酰胺的酸催化水解及其反应机理

  摘要：

  在无机酸水溶液中研究了一系列对位取代的N，N'-二芳基磺酰胺的酸催化水解机理。速率分布，反应活化参数，强酸的催化顺序，溶剂同位素效应以及通过过量酸度法对动力学数据的分析表明，机理从A2变为A1。当水解在低酸度区域以A2机理进行时，在高酸浓度下发生A1机理。版权所有©2013 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.3242

文献信息

• Electrochemical synthesis of sulfamides
  作者：Stephan P. Blum、Lukas Schäffer、Dieter Schollmeyer、Siegfried R. Waldvogel

  DOI：10.1039/d1cc01428e

  日期：——

  Herein we demonstrate the first electrochemical synthesis protocol of symmetrical sulfamides directly from anilines and SO2 mediated by iodide. Sulfamides are an emerging functional group in drug design. Highlights are the direct use of SO2 from a stock solution and no necessity of any supporting electrolyte. Overall, the reaction has been demonstrated for 15 examples with yields up to 93%.

  在这里，我们证明了直接从苯胺和碘化物介导的SO 2直接合成对称磺酰胺的第一个电化学合成方案。磺酰胺是药物设计中一个新兴的官能团。重点是直接从储备溶液中使用SO 2，无需任何辅助电解质。总体而言，已针对15个实例证明了该反应，产率高达93％。
• Sulfamides and sulfamide polymers directly from sulfur dioxide
  作者：Alexander V. Leontiev、H. V. Rasika Dias、Dmitry M. Rudkevich

  DOI：10.1039/b605063h

  日期：——

  SO2 gas is effectively used for the preparation of N,N′-diarylsulfamides and shape-persistent sulfamide polymers, which utilize a network of intermolecular N–H⋯OS hydrogen bonds to self-assemble into soft porous materials.

  二氧化硫气体有效用于制备N,N′-二芳基磺酰胺和结构持久的磺酰胺聚合物，这些聚合物利用分子间N–H⋯OS氢键网络自组装成柔软的多孔材料。
• Basicity of nitrogen–sulphur(<scp>VI</scp>) compounds. Part 5. Ionization of trisubstituted sulphamides
  作者：Séan D. McDermott、Padraig O. Burke、William J. Spillane

  DOI：10.1039/p29840000499

  日期：——

  The ionization equilibria in base of 27 trisubstituted sulphamides, mainly represented by the following series: X-C6H4NHSO2NR2R1, where NR2R1= piperidyl, morpholinyl, and NPrn2, and RHNSO2NR2R1, where R, R1, and R2 are cyclo-C6H11, Ac, and X-C6H4 and X-C6H4, Ac, and X-C6H4, have been studied in 60% v/v ethanol–water using the potentiometric method. In a few cases pKa values have been determined by

  27种三取代硫酰胺的碱中的电离平衡，主要由以下序列表示：XC 6 H 4 NHSO 2 NR 2 R 1，其中NR 2 R 1 =哌啶基，吗啉基和NPr n 2，以及RHNSO 2 NR 2 R 1，其中R，R 1和R 2是环C 6 H 11，Ac和XC 6 H 4以及XC 6 H 4，Ac和XC 6 H 4，已使用电位法在60％v / v乙醇-水中进行了研究。在少数情况下，已经通过uv方法确定了p K a值。取代基的效应在哈米特地块被关联和值通常是CA。2.6（关于磺酰苯胺离子化中的芳基连接的内源）。乙酰基的酸增强作用和甲基的酸弱化作用在一些系列中可见。
• Competition between carbon, nitrogen, and oxygen nucleophilic centres for sulphur(<scp>VI</scp>) attack in NN′-disubstituted sulphamides
  作者：F. L. Scott、J. A. Barry、W. J. Spillane

  DOI：10.1039/p19720002666

  日期：——

  the hexavalent sulphur atom, hinders all these processes, whereas electron withdrawal facilitates them. Because of this consistency we regard the key process around which this present work was constructed (the trans-sulphamoylation reaction) as being best interpreted in terms of direct nucleophilic attack at sulphur (VI) in the protonated sulphamide, most probably by the para-aryl carbon site in the aromatic

  有五种反应，即（i）取代的氨基磺酰胺水解为氨基磺酸，（ii）取代的氨基磺酸水解为芳基硫酸盐，（iii）氨基磺酸的反磺化反应，（iv）反式取代sulphamides的-sulphamoylation反应，和（v）所述的胺交换过程NN '二取代sulphamides所有似乎表明某些共同关键特性。给反应位点的六价硫原子给电子，阻碍了所有这些过程，而电子撤离则促进了这些过程。由于这种一致性，我们认为构建本发明的关键过程（反式-磺酰化反应）可以用对硫的直接亲核攻击得到最好的解释（VI）在质子化的磺酰胺中，最有可能是在芳族亲核底物中的对-芳基碳位点。
• Vicinal Diamination of Arenes with Domino Aryne Precursors
  作者：Lu Li、Dachuan Qiu、Jiarong Shi、Yang Li

  DOI：10.1021/acs.orglett.6b01747

  日期：2016.8.5

  Vicinal diamination of domino aryne precursors was achieved with sulfamides. The reaction proceeds through a two-aryne pathway, accepting two N-nucleophiles at the 1,2-positions of an arene ring. Symmetrical and unsymmetrical diaminobenzenes were readily obtained.