苯亚硒酸酐 | 17697-12-0

• 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: 苯亚硒酸酐
• 英文名称: benzeneseleninic anhydride
• 英文别名: phenylseleninyl benzeneseleninate
• CAS: 17697-12-0
• 化学式: C₁₂H₁₀O₃Se₂
• 分子量: 360.13
• InChiKey: FHPZOWOEILXXBD-UHFFFAOYSA-N

物化性质

• 熔点：
  165-170 °C (lit.)
• 沸点：
  184.2±23.0 °C(Predicted)
• 稳定性/保质期：
  - 常温常压下稳定。 - 避免与水分、潮湿和氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  17
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 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：
  R50/53,R23/25,R33
• WGK Germany：
  3
• 海关编码：
  2916399090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3283 6.1/PG 2
• 危险性防范说明：
  P261,P273,P301+P310+P330,P304+P340+P312,P403+P233,P501
• 危险性描述：
  H301+H331,H373,H410
• 储存条件：
  常温下应密闭、避光、通风和干燥的环境中，并在惰性气体保护下保存。

SDS

Name:	Benzeneseleninic anhydride, 98% Material Safety Data Sheet
Synonym:	None
CAS:	17697-12-0

Section 1 - Chemical Product MSDS Name: Benzeneseleninic anhydride, 98% Material Safety Data Sheet
Synonym: None

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17697-12-0	BENZENESELENINIC ANHYDRIDE	98	241-701-3

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.The toxicological properties of this material have not been fully investigated.Moisture sensitive. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
No information regarding skin irritation and other potential effects was found.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Flush skin with plenty of soap and water.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

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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. Avoid generating dusty conditions.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Avoid contact with skin and eyes. Avoid ingestion and inhalation. 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# 17697-12-0: 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:
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: almost white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 170 - 173 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: C12H10O3Se2
Molecular Weight: 360.13

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Bases - oxidizing agents - metals.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, selenium/selenium oxides.
Hazardous Polymerization: Has not been reported.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 17697-12-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
BENZENESELENINIC ANHYDRIDE - 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: II IMO
Shipping Name: SELENIUM COMPOUND, N.O.S.
Hazard Class: 6.1
UN Number: 3283
Packing Group: II RID/ADR
Shipping Name: SELENIUM COMPOUND, N.O.S.
Hazard Class: 6.1
UN Number: 3283
Packing group: II

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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# 17697-12-0: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 17697-12-0 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 17697-12-0 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：固体。

用途：它是一种温和的氧化剂。

反应信息

• 作为反应物：
  描述：

  苯亚硒酸酐 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 3.33h， 以95%的产率得到phenylselenium trichloride
  参考文献：
  名称：

  A new polymorph of phenylselenium trichloride

  摘要：

  本文公开了苯基三氯化硒的第二种多晶型，即 PhSeCl3 或 C6H5Cl3Se，它由不对称的氯键非共价二聚单元而非聚合物链组成。这些二聚体通过非共价的 Se...Cl 键相互作用与相邻的二聚体弱结合。每个二聚体中的苯基环以同步方式定向。密度泛函理论（DFT）计算显示，推定的反异构体与实验观察到的形式相差 5 kJ mol-1。该结构代表了首次发现的有机硒三卤化物的额外多态性。

  DOI：

  10.1107/s2053229619013019
• 作为产物：
  描述：

  苯亚硒酸 生成 苯亚硒酸酐
  参考文献：
  名称：

  Doughty, American Chemical Journal, 1909, vol. 41, p. 329

  摘要：

  DOI：
• 作为试剂：
  描述：

  5-苯基-4,5-二氢-1H-吡唑 在 苯亚硒酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到反式肉桂醛
  参考文献：
  名称：

  2-吡唑啉的氧化性开环。适用于1,3-6h-噻嗪的内酰胺化和甲酰化。

  摘要：

  苯亚硒酸酐允许2-吡唑啉氧化成α，β-不饱和羰基化合物。因此，在从1，3-6H-噻嗪合成7-氨基4-甲酰基头孢烯中，吡唑啉环可用作掩蔽，立体定向和潜在的甲酰基。

  DOI：

  10.1016/s0040-4039(00)82317-5

文献信息

• Studies on the reaction of primary and secondary amines with phenylseleninic anhydride and with phenylseleninic acid
  作者：Derek H.R. Barton、Xavier Lusinchi、Pierre Milliet

  DOI：10.1016/s0040-4020(01)96711-0

  日期：1985.1

  The dehydrogenation under mild conditions of indolines with phenylseleninic anhydride or acid affords good yields of indoles or of 3-phenylselenenyl indoles. Tetrahydroquinoline and -isoquinoline show comparable behaviour. The dehydrogenation of primary amines gives more complicated mixtures from which nitriles and bis-2-phenylselenenylaldehydes can be isolated.

  在温和的条件下用二苯硒酸酐或苯二酸在二氢吲哚条件下脱氢，可得到良好的吲哚或3-苯基硒烯基吲哚收率。四氢喹啉和-异喹啉表现出可比的行为。伯胺的脱氢得到更复杂的混合物，从中可以分离出腈和双-2-苯基硒烯醛。
• Oxidation of Olefins with Benzeneseleninic Anhydride in the Presence of TMSOTf
  作者：Izabella Jastrzębska、Maja Morawiak、Joanna E. Rode、Barbara Seroka、Leszek Siergiejczyk、Jacek W. Morzycki

  DOI：10.1021/acs.joc.5b00410

  日期：2015.6.19

  been shown that different products are formed with this species depending on the specific structure of olefin. The 1,1-disubstituted olefins afforded mostly α,β-unsaturated carbonyl compounds. The sterically encumbered tri- or tetrasubstituted olefins yielded 1,2- or 1,4-dihydroxylated products, presumably via four-membered cyclic intermediates.

  研究了一种新的烯烃氧化体系，该体系由苯硒酸酐和三甲基甲硅烷基三氟甲磺酸酯组成。推测在这些条件下形成了高反应性的苯硒烯基阳离子。已经表明，取决于烯烃的具体结构，与该物质形成不同的产物。1，1-二取代的烯烃主要提供α，β-不饱和羰基化合物。在空间上受阻的三或四取代的烯烃产生了1,2-或1,4-二羟基化的产物，大概是通过四元环状中间体。
• Studies on the Chemistry of 2-[3-(2-Nitrophenyl)-2-oxopropyl]benzaldehydes: Novel Syntheses of 5H-Benzo[b]carbazole-6,11-diones and Indolo[1,2-b]isoquinoline-6,11-diones
  作者：Marcos Fernández

  DOI：10.1055/s-0029-1216919

  日期：2009.9

  Syntheses of 5H-benzo[b]carbazole-6,11-diones and indolo[1,2-b]isoquinoline-6,11-diones are described. Both compounds are synthesized from 2-[3-(2-nitrophenyl)-2-oxopropyl]benzaldehydes, which were obtained from commercially available indan-1-ones in six steps.

  描述了5H-苯并[b]咔唑-6,11-二酮和吲哚[1,2-b]异喹啉-6,11-二酮的合成方法。这两种化合物均由2-[3-(2-硝基苯基)-2-氧代丙基]苯甲醛合成，后者是通过商业上可获得的茚-1-酮经过六步反应得到的。
• Chemoselective α,β‐Dehydrogenation of Saturated Amides
  作者：Christopher J. Teskey、Pauline Adler、Carlos R. Gonçalves、Nuno Maulide

  DOI：10.1002/anie.201808794

  日期：2019.1.8

  We report a method for the selective α,β‐dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium‐mediated dehydrogenation. The α,β‐unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations.

  我们报告了一种在温和条件下在其他羰基存在下选择性 α,β-脱氢酰胺的方法。我们的策略依赖于亲电激活与原位选择性硒介导的脱氢作用相结合。α,β-不饱和产物以中等至优异的收率获得，并且它们的合成多功能性通过一系列转化得到证明。机理实验表明亲电子 Se IV物质的形成。
• Fully Stereocontrolled Total Syntheses of the Prostacyclin Analogues 16<i>S</i>-Iloprost and 16<i>S</i>-3-Oxa-Iloprost by a Common Route, Using Alkenylcopper-Azoalkene Conjugate Addition, Asymmetric Olefination, and Allylic Alkylation
  作者：Guido J. Kramp、Mikhail Kim、Hans-Joachim Gais、Cornelia Vermeeren

  DOI：10.1021/ja0558037

  日期：2005.12.1

  stereocontrolled total syntheses of 16S-iloprost (16S-2), the most active component of the drugs Ilomedin and Ventavis, and of 16S-3-oxa-iloprost (16S-3), a close analogue of 16S-2 having the potential for a high oral activity, by a new and common route. The key steps of this route are (1) the establishment of the complete C13-C20 omega side chain of the target molecules through a stereoselective conjugate addition

  在本文中，我们描述了 16S-伊洛前列素 (16S-2)（药物 Ilomedin 和 Ventavis 中最活跃的成分）和 16S-3-氧杂-伊洛前列素（16S-3）（16S 的近似类似物）的完全立体控制的全合成-2 具有通过新的和通用的途径进行高口腔活性的潜力。该路线的关键步骤是（1）通过将烯基铜衍生物9立体选择性共轭加成到双环C6-C12偶氮烯烃10并形成腙8，建立目标分子的完整C13-C20ω侧链，（ 2) 酮 7 与手性磷酸磷酸酯 39 的非对映选择性烯化，以及 (3) 烯丙基乙酸酯 43 与铜酸盐 42 的区域和立体选择性烷基化。这些措施允许 16S-2 的 5E,15S,16S-立体选择性合成和 16S-3，以前没有实现的目标。如前所述，通过使用对映选择性去质子化作为关键步骤，从非手性双环 C6-C12 酮 11 获得偶氮烯烃 10。欧米茄侧链结构单元 9 的 C16 处的构型