对硝基苯硫醚 | 1223-31-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 对硝基苯硫醚
• 中文别名: 二(对硝基苯)硫醚；双(4-硝基苯基)硫醚；双(4-硝基苯)硫
• 英文名称: bis(4-nitrophenyl)sulfide
• 英文别名: 4,4'-dinitrodiphenyl sulfide；bis(4-nitrophenyl)sulfane；di(4-nitrophenyl) sulfide；p-nitrophenyl sulfide；1-nitro-4-(4-nitrophenyl)sulfanylbenzene
• CAS: 1223-31-0
• 化学式: C₁₂H₈N₂O₄S
• mdl: MFCD00039745
• 分子量: 276.273
• InChiKey: ZZTJMQPRKBNGNX-UHFFFAOYSA-N

物化性质

• 熔点：
  160°C
• 沸点：
  487.4±30.0 °C(Predicted)
• 密度：
  1.4634 (rough estimate)
• 溶解度：
  溶于丙酮
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，没有已知危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险类别码：
  R23/24/25
• 危险品运输编号：
  2811
• RTECS号：
  WQ2150000
• 海关编码：
  2930909090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉干燥处。同时，确保工作环境具备良好的通风或排气设施。

SDS

Bis(4-nitrophenyl) Sulfide Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Bis(4-nitrophenyl) Sulfide

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Harmful if swallowed
Precautionary statements:
[Prevention] Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
[Response]
Rinse mouth.
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Bis(4-nitrophenyl) Sulfide
Percent: >99.0%(GC)
CAS Number: 1223-31-0
Synonyms: 4,4'-Dinitrodiphenyl Sulfide , Di(4-nitrophenyl) Sulfide
Chemical Formula: C12H8N2O4S

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Bis(4-nitrophenyl) Sulfide

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Section 4. FIRST AID MEASURES
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: Pale yellow - Reddish yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:160°C
Bis(4-nitrophenyl) Sulfide

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Acetone

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: orl-rat LD50:1490 mg/kg
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available
RTECS Number: WQ2150000

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
Bis(4-nitrophenyl) Sulfide

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
橙色片状结晶，熔点为156-157℃。该物质溶于冰乙酸，而不溶于水。

用途
作为有机合成中间体使用。

生产方法
将157.5克对硝基氯苯、160克黄原酸钾和450毫升95%乙醇加热回流48小时。过滤后，用热乙醇和热水洗涤，最终得到约105-113克二（对硝基苯）硫醚。

类别
有毒物质

毒性分级
中毒级别

急性毒性
口服：大鼠LD₅₀为1490毫克/公斤

可燃性危险特性
受热时会排放有毒的氮氧化物和硫氧化物

储运特性
需在通风、干燥和防晒条件下储存与运输

灭火剂
使用沙土、水、泡沫或二氧化碳进行灭火

反应信息

• 作为反应物：
  描述：

  对硝基苯硫醚 在 硼烷铵络合物 、 nickel(II) chloride hexahydrate 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙醇 为溶剂， 以88 %的产率得到4,4-二氨基二苯硫醚
  参考文献：
  名称：

  均相镍催化氨-硼烷功能化硝基芳烃化学选择性转移氢化

  摘要：

  以NH 3 BH 3为氢源，成功建立了均相Ni催化硝基芳烃高选择性转移加氢反应。选择性还原多种官能团，以良好到高产率提供相应的苯胺。此外，可以制备否则难以获得的药物活性化合物。

  DOI：

  10.1039/d3cc05173k
• 作为产物：
  描述：

  4-硝基苯基乙酸酯 在 copper(l) iodide 、 sulfur 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以90%的产率得到对硝基苯硫醚
  参考文献：
  名称：

  以S8为硫源时，通过C–O键的裂解，形成铜催化的C–S键的形成

  摘要：

  摘要 提出了一种有用且适用的通过C–O键活化一锅无味合成不对称和对称二芳基硫化物的方法。首先，报道了一种新的有效方法，用于合成不对称硫化物，该方法使用酚酯（如乙酸酯，甲苯磺酸酯和三氟甲磺酸酯）的交叉偶联反应，并以芳基硼酸或三苯基氯化锡为偶联伙伴。取决于反应，发现S 8 / KF或S 8 / NaO t -Bu体系在铜盐存在下和在聚乙二醇中作为绿色溶剂是硫的有效来源。然后，以S 8为硫源和NaO t由酚类化合物合成对称的二芳基硫醚描述了在N 2下在120°C的无水DMF中的-Bu 。通过这些方案，与不直接将硫醇和芳基卤化物用于制备硫化物的现有方案相比，各种不对称和对称硫化物的合成变得更加容易。 提出了一种有用且适用的通过C–O键活化一锅无味合成不对称和对称二芳基硫化物的方法。首先，报道了一种新的有效方法，用于合成不对称硫化物，该方法使用酚酯（如乙酸酯，甲苯磺酸酯和三氟甲磺酸酯）的交叉偶联反应

  DOI：

  10.1055/s-0036-1588508

文献信息

• Fe3O4-AMPD-Pd: A novel and efficient magnetic nanocatalyst for synthesis of sulfides and oxidation reactions
  作者：Taiebeh Tamoradi、Nazanin Moeini、Mohammad Ghadermazi、Arash Ghorbani-Choghamarani

  DOI：10.1016/j.poly.2018.07.002

  日期：2018.10

  Abstract A novel magnetic nanoparticle was synthesized with effective catalytic properties and recyclable ability. This heterogeneous nanocatalyst was identified using Fourier transform infrared, scanning electron microscopies, X‐ray diffraction, vibrating sample magnetometer, inductively coupled plasma atomic emission spectroscopy and thermogravimetric analysis methods. The nanocatalyst was used for

  摘要合成了具有有效催化性能和可回收能力的新型磁性纳米粒子。使用傅立叶变换红外光谱仪，扫描电子显微镜，X射线衍射，振动样品磁力计，电感耦合等离子体原子发射光谱法和热重分析方法鉴定了这种非均相纳米催化剂。纳米催化剂用于在100°C下以DMSO为溶剂的KOH，S8作为硫源存在下，一硫化碳的一锅CS偶联合成。另外，测试了在催化剂存在下硫化物氧化为亚砜以及硫醇氧化为二硫化物的过程。该催化剂具有独特的性质，例如从反应中磁性分离的能力，高重复性以及高的热稳定性和化学稳定性。
• Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C–S cross-coupling reactions
  作者：Nasrin Yarmohammadi、Mohammad Ghadermazi、Roya Mozafari

  DOI：10.1039/d1ra01029h

  日期：——

  copper(II) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfides via the reaction of aryl halides with thiourea as the sulfur source

  在这项工作中，将铜（ II ）固定在1,8-二氨基萘（DAN）包覆的磁性纳米粒子表面上，为硫化物氧化成亚砜以及使用氢气将硫醇氧化偶联成二硫化物提供了高活性催化剂。过氧化物（H 2 O 2 ）。该催化剂还可用于芳基卤化物与硫脲作为硫源在NaOH存在下反应一锅合成对称硫化物，取代了以往的强碱性和苛刻的反应条件。在最佳条件下，亚砜、对称硫化物和二硫化物的合成收率分别约为99%、95%和96%，且选择性最高。本发明的非均相铜基催化剂具有催化剂易于回收、产物易于分离、催化剂分离过程中产物浪费少等优点。这种多相纳米催化剂通过 FESEM、FT-IR、VSM、XRD、EDX、ICP 和 TGA 进行了表征。此外，回收的催化剂可以重复使用多次，并且经济有效。
• [EN] METHODS FOR PRODUCING ARYLSULFUR PENTAFLUORIDES<br/>[FR] PROCÉDÉS DE PRODUCTION DE PENTAFLUORURES DE SOUFRE ARYLÉS
  申请人：IM & T RES INC

  公开号：WO2010014665A1

  公开（公告）日：2010-02-04

  Novel methods for preparing arylsulfur pentafluorides are disclosed. Arylsulfur halotetrafluoride is reacted with a fluoride source under hydrous conditions to form an arylsulfur pentafluoride. The purification method is also disclosed.

  揭示了制备芳基硫五氟化物的新方法。芳基硫卤四氟化物在湿润条件下与氟化物源反应，形成芳基硫五氟化物。还公开了纯化方法。
• A Highly Efficient Method for the Copper-Catalyzed Selective Synthesis of Diaryl Chalcogenides from Easily Available Chalcogen Sources
  作者：Yaming Li、Caiping Nie、Huifeng Wang、Xiaoying Li、Francis Verpoort、Chunying Duan

  DOI：10.1002/ejoc.201101121

  日期：2011.12

  copper-catalyzed C–S or C–Se bond formation between aryl iodides and easily available chalcogen sources leading to diaryl chalcogenides is reported. A variety of symmetrical diaryl sulfides and diaryl selenides were synthesized in good to excellent yields. Unsymmetrical diaryl sulfides were also obtained in moderate yields from two different aryl iodides by a one-pot tandem process. This strategy was

  报告了在芳基碘化物和容易获得的硫属元素源之间形成铜催化的 C-S 或 C-Se 键的有效方案，导致二芳基硫属元素化物。各种对称的二芳基硫化物和二芳基硒化物以良好到极好的产率合成。不对称二芳基硫化物也可以通过一锅串联工艺从两种不同的芳基碘化物中以中等产率获得。该策略进一步成功地用于合成 2-苯基苯并 [b] 噻吩和 [1] 苯并噻吩并 [3,2-b] 苯并噻吩。
• Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C–S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study
  作者：Hsing-Ying Chen、Wei-Te Peng、Ying-Hsien Lee、Yu-Lun Chang、Yen-Jen Chen、Yi-Chun Lai、Nai-Yuan Jheng、Hsuan-Ying Chen

  DOI：10.1021/om400784w

  日期：2013.10.14

  Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be

  先前的研究报道，当前体包括硫粉和使用CuI作为催化剂的芳基卤化物时，S-芳基化反应将生成二芳基二硫化物。但是，我们的研究表明，在上述S-芳基化过程中使用不同的碱会导致联产二芳基硫烷和二芳基二硫烷。另外，我们证明了可以通过选择碱的碱度来控制两种产物的比例。1个1 H NMR谱表明，二芳基二硫醚是第一产物，通过CuI催化与芳基卤化物反应生成二芳基硫烷成为试剂。使用各种不同的碱，对各种芳基卤化物进行了测试，以提高二芳基硫烷和二芳基二硫烷之间的选择性，从而得出以下原理。弱碱，例如金属碳酸盐或乙酸盐，只会产生二芳基二硫醚；强碱（例如金属氢氧化物）会同时生成二芳基二硫烷和二芳基硫烷。根据DFT计算，氢氧根离子被碘离子交换并与铜键合，从而更强烈地影响铜电子以还原二芳基二硫化物。

表征谱图