双(2-硝基苯)二硒 | 35350-43-7

• 物质功能分类: 化学试剂 - 有机试剂 - 硒化合物
• 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: 双(2-硝基苯)二硒
• 英文名称: bis(o-nitrophenyl) diselenide
• 英文别名: Bis(2-nitrophenyl) diselenide；1-nitro-2-[(2-nitrophenyl)diselanyl]benzene
• CAS: 35350-43-7
• 化学式: C₁₂H₈N₂O₄Se₂
• 分子量: 402.127
• InChiKey: QUTPYNJBIHTIGA-UHFFFAOYSA-N

物化性质

• 熔点：
  212-213 °C
• 沸点：
  533.0±60.0 °C(Predicted)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  20
• 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：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  T,N-T,N
• 安全说明：
  S20/21,S28A,S45,S60,S61
• 危险类别码：
  R23/25,R50/53,R33
• 海关编码：
  2904209090
• 储存条件：
  存放于0-6℃阴凉干燥处

SDS

Name:	Bis(2-nitrophenyl)diselenide 97% Material Safety Data Sheet
Synonym:
CAS:	35350-43-7

Section 1 - Chemical Product MSDS Name:Bis(2-nitrophenyl)diselenide 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
35350-43-7	Bis(2-nitrophenyl)diselenide	97%	252-522-5

Hazard Symbols: T
Risk Phrases: 23/25 33

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation and if swallowed. Danger of cumulative effects.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Poison by ingestion. The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated. Toxic if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 35350-43-7: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow to brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 212 - 213 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 402.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 35350-43-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Bis(2-nitrophenyl)diselenide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: SELENIUM COMPOUND, N.O.S.
Hazard Class: 6.1
UN Number: 3283
Packing Group: III
IMO
Shipping Name: SELENIUM COMPOUND, N.O.S.
Hazard Class: 6.1
UN Number: 3283
Packing Group: III
RID/ADR
Shipping Name: SELENIUM COMPOUND, N.O.S.
Hazard Class: 6.1
UN Number: 3283
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/25 Toxic by inhalation and if swallowed.
R 33 Danger of cumulative effects.
Safety Phrases:
S 20/21 When using do not eat, drink or smoke.
S 28A After contact with skin, wash immediately with
plenty of water.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 35350-43-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 35350-43-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 35350-43-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  双(2-硝基苯)二硒 在 溴 作用下， 以 四氯化碳 、 乙腈 为溶剂， 生成 2-nitro-benzeneselenenyl bromide
  参考文献：
  名称：

  烯醇化物与乙烯基硒氧化物和乙烯基硒酮的反应。环丙基羰基化合物的一步合成

  摘要：

  在与烯醇阴离子的反应中，芳基乙烯基硒氧化物和硒酮的有机硒部分表现出两个重要作用，例如，激活 C=C 键以进行共轭加成反应和作为优良的离去基团的行为。由于这些特征，酮烯醇化物与对氯苯基乙烯基氧化硒反应，通过最初的共轭加成和取代过程提供相应的环丙基酮。另一方面，使用乙烯基硒酮通常会对活性亚甲基化合物的阴离子物质产生更好的结果。带有羟基、酮和酯基团的乙烯基硒酮也同样适用于这种类型的转化。

  DOI：

  10.1246/bcsj.57.2897
• 作为产物：
  描述：

  2-nitro-benzeneselenenyl bromide 在 甲醇 、 氯仿 作用下， 生成 双(2-硝基苯)二硒
  参考文献：
  名称：

  Behaghel; Seibert, Chemische Berichte, 1933, vol. 66, p. 708,716

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-萘酚 在 双(2-硝基苯)二硒 、 双氧水 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 以100%的产率得到2-[(E)-2-羧基乙烯]苯甲酸
  参考文献：
  名称：

  通过催化多米诺氧化萘酚和氢萘醌的氧官能化反式-2-羧基肉桂酸

  摘要：

  摘要 研究了萘的催化氧化。过氧化氢（30% 水溶液）用作氧源，2,2'-二硝基-4,​​4'-二三氟甲基二苯基二硒化物是氧转移催化剂。未取代的萘酚以几乎定量的产率生产反式-2-羧基肉桂酸。在共轭环上带有取代基的两种萘酚都以良好到极好的产率提供相应的反式-2-羧基肉桂酸。被羧基和羧甲基基团取代的 1,7- 和 2,6- 氢萘醌以令人满意的至极好的产率生产羟基肉桂酸。提出了催化多米诺反应机制。图形概要

  DOI：

  10.1080/00397911.2011.561945

文献信息

• Selenols are resistant to irreversible modification by HNO
  作者：Christopher L. Bianco、Cathy D. Moore、Jon M. Fukuto、John P. Toscano

  DOI：10.1016/j.freeradbiomed.2016.07.008

  日期：2016.10

  to be additional potential targets of HNO. Indeed, as determined in the current work, selenols are targeted by HNO. Such reactions appear to result only in formation of diselenide products, which can be easily reverted back to the free selenol. This characteristic is distinct from the reaction of HNO with thiols/thiolproteins. These findings suggest that, unlike thiolproteins, selenoproteins are resistant

  一氧化氮（NO）作为哺乳动物细胞内源性产生的信号传导物种的发现，引起了对氮氧化物化学生物学研究的巨大兴趣。其中，硝酰氧基（氮杂酮，HNO）作为心血管疾病的治疗剂具有潜在的作用。HNO的已知靶标包括血红素/血红素蛋白和含硫醇/含硫醇的蛋白。最近，由于它们在氧化还原信号传导和细胞防御中的作用，硒醇和硒蛋白也被认为是HNO的其他潜在靶标。确实，如当前工作所确定，硒醇是HNO的目标。这样的反应似乎仅导致二硒化物产物的形成，其可以容易地还原成游离硒醇。该特征不同于HNO与硫醇/硫醇蛋白的反应。
• Aldehyde Capture Ligation for Synthesis of Native Peptide Bonds
  作者：Monika Raj、Huabin Wu、Sarah L. Blosser、Marc A. Vittoria、Paramjit S. Arora

  DOI：10.1021/jacs.5b03538

  日期：2015.6.3

  reactions for amide bond formation have transformed the ability to access synthetic proteins and other bioconjugates through ligation of fragments. In these ligations, amide bond formation is accelerated by transient enforcement of an intramolecular reaction between the carboxyl and the amine termini of two fragments. Building on this principle, we introduce an aldehyde capture ligation that parlays

  酰胺键形成的化学选择性反应改变了通过片段连接获得合成蛋白质和其他生物偶联物的能力。在这些连接中，两个片段的羧基和胺末端之间的分子内反应的瞬时增强加速了酰胺键的形成。基于这一原则，我们引入了一种醛捕获连接，它利用醛和胺的高化学选择性反应性来加强现有技术难以连接的氨基酸残基和肽之间的酰胺键形成。
• Preparative and Mechanistic Studies toward the Rational Development of Catalytic, Enantioselective Selenoetherification Reactions
  作者：Scott E. Denmark、Dipannita Kalyani、William R. Collins

  DOI：10.1021/ja106837b

  日期：2010.11.10

  attached to the selenium atom significantly attenuates the racemization of seleniranium ions. A variety of achiral Lewis bases catalyze the intramolecular selenoetherification of alkenes using N-(2-nitrophenylselenenyl)succinimide as the electrophile along with a Brønsted acid. Preliminary mechanistic studies suggest the intermediacy of ionic Lewis base-selenium(II) adducts. Most importantly, a broad

  描述了对路易斯碱催化的、不对称的、烯烃分子内硒醚化的系统研究。该工艺开发的一个关键挑战是识别和抑制可用于芳基硒离子中间体的外消旋途径。该报告详细介绍了芳基硒基的空间和电子调节对对映体富集硒离子构型稳定性影响的全面研究。这些研究表明，连接到硒原子上的 2-硝基苯基显着减弱了硒离子的外消旋作用。各种非手性路易斯碱使用 N-(2-硝基苯基硒基)琥珀酰亚胺作为亲电子试剂与布朗斯台德酸一起催化烯烃的分子内硒醚化。初步机理研究表明离子路易斯碱-硒(II) 加合物的中介作用。最重要的是，对手性路易斯碱的广泛研究表明，1,1'-联萘-2,2'-二胺 (BINAM) 衍生的硫代磷酰胺在 N-(2-硝基苯基硒基)琥珀酰亚胺存在下催化不饱和醇的环化，并且甲磺酸。以良好的化学产率和中等至良好的对映选择性生产了多种环状硒醚，这构成了未活化烯烃的第一个催化、对映选择性硒基官能化。
• Synthesis of disulfides and diselenides by copper-catalyzed coupling reactions in water
  作者：Zhengkai Li、Fang Ke、Hang Deng、Hualong Xu、Haifeng Xiang、Xiangge Zhou

  DOI：10.1039/c3ob40464a

  日期：——

  A simple and efficient protocol for copper-catalyzed coupling reactions between aryl halides and elemental sulfur or selenium has been developed. A variety of disulfides and diselenides can be obtained in moderate to excellent yields up to 96%.

  开发了一种简单高效的铜催化偶联反应方案，用于实现芳基卤化物与硫或硒元素之间的反应。多种二硫化物和二硒化物可以在中等至优异的产率下获得，最高可达96%。
• Lithium diselenide in aprotic medium - a convenient reagent for synthesis of organic diselenides
  作者：Ludwik Syper、Jacek Mlochowski

  DOI：10.1016/s0040-4020(01)89801-x

  日期：1988.1

  The reduction of selenium with lithium in THF in the presence of diphenylacetylene as a catalyst afforded lithium diselenide, which reacted with electrophiles giving alkyl or aryl diselenides 1 - 3 and selenides 4, as by-products. The useful method for preparation of diselenides based on this reaction was elaborated.

  在二苯乙炔作为催化剂的存在下，用锂在THF中还原硒，得到二硒化锂，其与亲电试剂反应生成副产物烷基或芳基二硒化物1-3和硒化物4。阐述了基于该反应制备二硒化物的有用方法。

表征谱图