二苯硒醚 | 1132-39-4

• 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: 二苯硒醚
• 中文别名: 二苯基硒醚；二苯硒；二苯基锡醚
• 英文名称: diphenylselenide
• 英文别名: diphenylselane；diphenyl diselenide；diphenylselenoether；Diphenyl selenide；phenylselanylbenzene
• CAS: 1132-39-4
• 化学式: C₁₂H₁₀Se
• 分子量: 233.171
• InChiKey: ORQWTLCYLDRDHK-UHFFFAOYSA-N

物化性质

• 熔点：
  3°C
• 沸点：
  115-117 °C(lit.)
• 密度：
  1.338 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 暴露限值：
  ACGIH: TWA 0.2 mg/m3NIOSH: IDLH 1 mg/m3; TWA 0.2 mg/m3
• 稳定性/保质期：
  如果按照规格正确使用和存储，则不会发生分解，也没有已知的危险反应。请避免接触氧化剂、空气以及水或潮湿环境。

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  13
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  T,N
• 安全说明：
  S20/21,S28,S45,S60,S61
• 危险类别码：
  R23/25,R33,R50/53
• WGK Germany：
  3
• 海关编码：
  2931900090
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3082 9/PG 3
• 储存条件：
  请将贮藏器保持密封，并将其存放在阴凉、干燥处。确保工作间有良好的通风或排气设施。

SDS

Name:	Diphenylselenide 95% Material Safety Data Sheet
Synonym:	Diphenyl selenium; Phenylselenide; 1,1'-Selenobisbenzene; Benzene, 1,1'-selenobis- (9 CI); Biphenyl selenide; Biphenyl selenium; Difenylselenium; Phenyl selenid
CAS:	1132-39-4

Section 1 - Chemical Product MSDS Name:Diphenylselenide 95% Material Safety Data Sheet
Synonym:Diphenyl selenium; Phenylselenide; 1,1'-Selenobisbenzene; Benzene, 1,1'-selenobis- (9 CI); Biphenyl selenide; Biphenyl selenium; Difenylselenium; Phenyl selenid

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1132-39-4	Diphenylselenide	95	214-474-3

Hazard Symbols: T
Risk Phrases: 23/25 33

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation and if swallowed. Danger of cumulative effects.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Vapors cause eye irritation.
Skin:
May cause skin irritation. May be absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May cause liver and kidney damage. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Harmful if inhaled. The toxicological properties of this substance have not been fully investigated. May cause dyspnea (difficult or labored breathing). Vapors cause irritation of the respiratory system.
Chronic:
Prolonged or repeated skin contact may cause dermatitis. Chronic selenium poisoning is characterized by loss of hair and nails, skin lesions, and abnormalities of the nervous system.

---

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.
Skin:
Get medical aid. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Wash clothing before reuse.
Ingestion:
Call a poison control center. If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

---

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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Use only in a chemical fume hood. Wash clothing before reuse.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use only under a chemical fume hood.
Exposure Limits CAS# 1132-39-4: United Kingdom, WEL - TWA: (listed as selenium compounds): 0.1 mg TWA (except hydrogen selenide, as Se) United Kingdom, WEL - STEL: (listed as selenium compounds): 0.3 m STEL (except hydrogen selenide, as Se) United States OSHA: 0.2 mg/m3 TWA (as Se) (listed under Selenium compounds).
Belgium - TWA: (listed as selenium compounds): 0.2 mg/m3 VLE (as Japan: (listed as selenium compounds): 0.1 mg/m3 OEL (except SeH2 SeF6, as Se) Malaysia: (listed as selenium compounds): 0.2 mg/m3 TWA (as Se) Netherlands: (listed as selenium compounds): 0.1 mg/m3 MAC (as Se Spain: (listed as selenium compounds): 0.1 mg/m3 VLA-ED (except hydrogen selenide, as Se) Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 115 - 117 deg C @ 1.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 230 deg F (> 110.00 deg C)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.3380g/cm3
Molecular Formula: C12H10Se
Molecular Weight: 233.17

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, selenium/selenium oxides.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1132-39-4: SX1825000 LD50/LC50:
CAS# 1132-39-4: Oral, rat: LD50 = 360 mg/kg.
Carcinogenicity:
Diphenylselenide - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

---

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# 1132-39-4: No information available.
Canada
CAS# 1132-39-4 is listed on Canada's NDSL List.
CAS# 1132-39-4 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1132-39-4 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二苯硒醚 在 aluminum oxide 、 sodium hypochlorite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.12h， 以89%的产率得到二苯基硒亚砜
  参考文献：
  名称：

  通过微波照射，次氯酸钠水溶液介导的硫属化物化学选择性氧化为一氧化碳和二氧化物

  摘要：

  已使用水相开发了无溶剂、快速和高度选择性地将硫化物、硒化物和碲化物（硫属化物）氧化为相应的一氧化物（亚砜、硒氧化物和碲氧化物）或相应的二氧化物（砜、硒酮和碲酮）通过微波暴露在固体载体上的次氯酸钠。在大多数情况下已达到化学选择性和定量产率。

  DOI：

  10.1139/v10-060
• 作为产物：
  描述：

  氧氯化硒 在 苯基溴化镁 作用下， 以 not given 为溶剂， 生成 二苯硒醚
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Se: MVol.B, 64, page 142 - 143

  摘要：

  DOI：
• 作为试剂：
  描述：

  4-(2,2-difluorovinyl)-1,1'-biphenyl 、 1-对甲苯硫基-吡咯啉-2,5-二酮 、 异丁酸 在 三氟甲磺酸三甲基硅酯 、 二苯硒醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到1-([1,1'-biphenyl]-4-yl)-2,2-difluoro-2-(p-tolylthio)ethyl isobutyrate
  参考文献：
  名称：

  硫属元素化物催化的宝石-二氟烯烃分子间亲电硫-和卤代官能化：不同的二氟烷基硫化物和卤化物的构建。

  摘要：

  硫代和卤代二氟甲基化的化合物在药物化学和有机合成中是一类重要的化合物。在本文中，我们报道了通过硫族化物催化的宝石-二氟烯烃的分子间亲电硫代和卤代官能团构建这些化合物的简便方法。用亲电子的硫/卤素试剂和各种O-或N-亲核试剂对宝石-二氟烯烃进行简单处理，即可得到各种多功能的硫代和卤代二氟甲基化化合物。该反应具有相对较宽的底物范围，良好的官能团耐受性和温和的反应条件。

  DOI：

  10.1021/acs.orglett.0c02784

文献信息

• Co-ordination chemistry of higher oxidation states. Part 23. Synthesis and properties of tetrahalogenoiridium(IV) complexes, [IrL2X4][X = Cl or Br; L = pyridine, PR3, AsR3, SbR3, SR2, or SeR2]. Crystal and molecular structure of trans-[Ir(AsEt3)2Br4]
  作者：Robert A. Cipriano、William Levason、Derek Pletcher、Nigel A. Powell、Michael Webster

  DOI：10.1039/dt9870001901

  日期：——

  them from chemical syntheses. Cyclic voltammograms for [RhL2Cl4]–(L = PEt3, SMe2, SeMe2, or py) show that oxidation occurs at more positive potentials, but the rhodium(IV) complexes are unstable. Neutral iridium(III) complexes [IrL3X3] are not oxidised by X2 or HNO3, and possible reasons for this and the crucial role of the [IrL2X4]– intermediates in the preparation of [IrL2X4] are discussed.

  铱（III）阴离子的反式- [IRL 2氯4 ] - [L =吡啶（PY），PET 3，PET 2 PH，PEtPh 2，ASET 3，ASME 2 PH，SMe的2，或SEME 2 ]已制备并用氯氧化为紫色铱（IV）反式-[IrL 2 Cl 4 ]。深绿色反式-[IrL 2 Br 4 ]（L = py ，PEt 3，PMe 2 Ph，AsEt 3，AsMe 2从反式-[IrL 2 Br 4 ] -和Br 2或HNO 3相似地获得Ph或SMe 2）。[IrL 2 Cl 4 ]（L = PPh 3 AsPh 3或SbPh 3）直接由IrCl 3 · n H 2 O + 2L制备，然后氯化生成的中间体[（IrL 2 Cl 3）n ]；顺式-[IrL 2 Cl 4 ]（L = py或SbMe 3）和还描述了反式-[IrL 2 X 4 ] –（L = TeMe 2，X = Cl； L = SeMe
• The Chan-Lam Reaction of Chalcogen Elements Leading to Aryl Chalcogenides
  作者：Jin-Tao Yu、Huan Guo、Yuanqiuqiang Yi、Haiyang Fei、Yan Jiang

  DOI：10.1002/adsc.201300853

  日期：2014.3.10

  is established, which provides diaryl disulfides or diaryl monoselenides in moderate to good yields with excellent selectivities, respectively. Moreover, after sequential reduction and coupling with aryl/alkyl iodides in one pot, unsymmetrical monosulfides were obtained in good yields.

  建立了用元素硫或硒进行铜催化的芳基硼酸硫属化合物，分别以中等至良好的收率提供了二芳基二硫化物或二芳基单硒化物，并具有优异的选择性。此外，在一罐中顺序还原并与芳基/烷基碘偶联后，以良好的收率获得了不对称的单硫化物。
• 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。
• Copper nano-catalyst: sustainable phenyl-selenylation of aryl iodides and vinyl bromides in water under ligand free conditions
  作者：Amit Saha、Debasree Saha、Brindaban C. Ranu

  DOI：10.1039/b819137a

  日期：——

  A simple and efficient procedure for the synthesis of aryl- and vinyl-selenides has been developed by a copper nanoparticle catalysed reaction of aryl iodide/vinyl bromide with diphenyl diselenide in the presence of zinc in water. (E)-Vinyl bromides produce (E)-vinyl selenides stereoselectively, whereas (Z)-vinyl bromides provide mixtures of (E) and (Z) isomers. The catalyst was recycled.

  通过铜纳米粒子催化的反应，在水中的锌存在下，已开发出一种合成芳基和乙烯基硒化物的简单高效过程。这一过程利用芳基碘化物/乙烯基溴化物与二苯基二硒化物的反应。(E)-乙烯基溴化物有选择性地生成(E)-乙烯基硒化物，而(Z)-乙烯基溴化物则生成(E)和(Z)异构体的混合物。催化剂可以回收利用。
• A Simple Copper Salt-Catalyzed Synthesis of Unsymmetrical Diaryl Selenides and Tellurides from Arylboronic Acids with Diphenyl Diselenide and Ditelluride
  作者：Lei Wang、Min Wang、Fuping Huang

  DOI：10.1055/s-2005-871936

  日期：——

  In the presence of a catalytic amount of simple copper salt, the reaction of arylboronic acids with diphenyl diselenide and ditelluride was accomplished without any additive to afford the corresponding unsymmetrical diarylselenides and tellurides in good yields.

  在催化量的简单铜盐存在下，芳基硼酸与二苯基二硒化物和二碲化物的反应在没有任何添加剂的情况下完成，以良好的产率得到相应的不对称二芳基硒化物和碲化物。

表征谱图