1-苯基靛红 | 723-89-7

• 物质功能分类: 分析化学 - 分析试剂 - 常用分析试剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-苯基靛红
• 中文别名: 1-苯基-1H-吲哚-2,3-二酮；1-苯基吲哚-2,3-二酮；1-苯基靛红,98；1-苯基-2,3-吲哚二酮；1-苯基靛红,98%
• 英文名称: 1-phenyl-indole-2,3-dione
• 英文别名: 1-phenylindoline-2,3-dione；N-phenylisatin；1-phenylisatin；1-phenylindole-2,3-dione
• CAS: 723-89-7
• 化学式: C₁₄H₉NO₂
• mdl: MFCD00082681
• 分子量: 223.231
• InChiKey: UWCPWBIMRYXUOU-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C (lit.)
• 沸点：
  388.8±25.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  419nm(EtOH)(lit.)
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与氧化物直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  T
• 安全说明：
  S27,S28,S36/37/39,S45
• 危险类别码：
  R23/24/25
• WGK Germany：
  3
• 海关编码：
  2933990090
• RTECS号：
  NL7984000
• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302
• 储存条件：
  请将容器密封后，存放在干燥、阴凉的地方。

SDS

Name:	1- Phenylisatin Material Safety Data Sheet
Synonym:	1H-Indole-2,3-Dione, 1-Phenyl-; 1-Phenyl-1H-Indole-2,3-Dione; 1-Phenyl-Indole-2,3-Dione
CAS:	723-89-7

Section 1 - Chemical Product MSDS Name:1- Phenylisatin Material Safety Data Sheet
Synonym:1H-Indole-2,3-Dione, 1-Phenyl-; 1-Phenyl-1H-Indole-2,3-Dione; 1-Phenyl-Indole-2,3-Dione

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
723-89-7	1-Phenylisatin	ca 100	unlisted

Hazard Symbols: T
Risk Phrases: 23/24/25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. 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: 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. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 723-89-7: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 139 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H9NO2
Molecular Weight: 223.23

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 723-89-7: NL7984000 LD50/LC50:
Not available.
Carcinogenicity:
1-Phenylisatin - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 28 After contact with skin, wash immediately
with...
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 37 Wear suitable gloves.
S 38 In case of insufficient ventilation, wear
suitable respiratory equipment.
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# 723-89-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 723-89-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 723-89-7 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：

  1-苯基靛红 在 sodium hydroxide 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 溶剂黄146 、 异丙醇 为溶剂， 反应 2.0h， 生成 利诺吡啶
  参考文献：
  名称：

  A Large Scale Preparation of the Cognitive Enhancer Linopirdine

  摘要：

  Linopirdine is a pharmacologically potent drug which stimulates central nervous system neurotransmitter release. A facile process used to synthesize linopirdine on a commercial manufacturing scale consisting of seven chemical steps with only a single isolated intermediate is described.

  DOI：

  10.1080/00397919308011258
• 作为产物：
  描述：

  3-(N,N-diphenylamino)-3-oxopropanenitrile 在 硫酸 作用下， 生成 1-苯基靛红
  参考文献：
  名称：

  DE515542

  摘要：

  公开号：
• 作为试剂：
  描述：

  靛红 、 Triphenyl bismuth diacetate 在 铜 氮 、 1-苯基靛红 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以The desired product, N-phenyl isatin (42.1 mg) was obtained的产率得到1-苯基靛红
  参考文献：
  名称：

  N-arylation of isatins

  摘要：

  本发明揭示了一种使用有机铋试剂进行异色酮的N-芳基化的方法。

  公开号：

  US05151518A1

文献信息

• A <i>para</i> -C-H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents
  作者：Chao Tian、Xu Yao、Weizhe Ji、Qian Wang、Guanghui An、Guangming Li

  DOI：10.1002/ejoc.201801058

  日期：2018.11.25

  A general para‐selective C‐H functionalization was achieved via a steric control strategy. Para‐iodo, bromo, chloro, nitro, and trifluormethyl aniline derivatives were prepared via in situ generated, bulky hypervalent iodinium reagents in as little as 10 min. Products can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work‐up

  通过空间控制策略可实现一般的对选择性C-H功能化。对碘，溴，氯，硝基和三氟甲基苯胺衍生物可在短短10分钟内通过原位生成的大体积高价碘试剂制备。无需柱色谱或重结晶即可纯化产品，从而大大减少了浪费并简化了后处理过程。
• Scaffold-Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin-3,2′-oxindoles] with Structural Diversity through Catalytic Isatin-Derived 1,3-Dipolar Cycloadditions
  作者：Feng Shi、Zhong-Lin Tao、Shi-Wei Luo、Shu-Jiang Tu、Liu-Zhu Gong

  DOI：10.1002/chem.201200358

  日期：2012.5.29

  Catalytic asymmetric construction of the biologically important spiro[pyrrolidin‐3,2′‐oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee) has been established by using an organocatalytic 1,3‐dipolar cycloaddition of isatin‐based azomethine ylides. This protocol represents the first example of catalytic asymmetric 1,3‐dipolar

  通过使用有机催化1,3，已经建立了具有重要立体选择性（具有高达99：1 dr，98％ee的连续性）的具有重要季螺立体构象中心的重要生物学螺旋[pyrrolidin-3,2'-oxindole]支架的催化不对称结构。 基于靛红的甲亚胺烷基化物的偶极环加成。该方案代表了催化不对称1,3-偶极环加成反应的第一个例子，涉及不对称环酮就地生成的甲亚胺基化物。另外，对反应的过渡态进行了理论计算以了解立体化学。使用这些螺[吡咯烷酮-3,2'-羟吲哚]的初步生物测定显示，几种化合物对SW116细胞显示中等程度的细胞毒性。
• 一种含吡唑啉酮取代-3-羟基氧化吲哚衍生物 及制备方法
  申请人：赣南师范大学

  公开号：CN110256407B

  公开（公告）日：2020-08-25

  本发明提供了一种含吡唑啉酮取代‑3‑羟基氧化吲哚衍生物及制备方法，属于有机合成技术领域。本发明提供的含吡唑啉酮取代‑3‑羟基氧化吲哚衍生物，具有式I所示结构，式I中，R1包括氢、甲基、乙基、烯丙基、苯基或苄基；或者5位的氢替换为硝基、卤素、甲基、甲氧基或三氟甲氧基；或者，7位的氢替换为卤素；或者，4位和7位的氢替换为卤素。本发明提供的含吡唑啉酮取代‑3‑羟基氧化吲哚衍生物具有潜在的生物活性和药物活性，还可以与亲核试剂在酸催化的作用下发生亲核取代反应；本发明提供的含吡唑啉酮取代‑3‑羟基氧化吲哚衍生物的制备方法收率高，且操作简单。
• Polymer-Supported Copper Complex for C−N and C−O Cross-Coupling Reactions with Aryl Boronic Acids
  作者：Gary C. H. Chiang、Thomas Olsson

  DOI：10.1021/ol048943e

  日期：2004.9.1

  [reaction: see text] Immobilization of copper onto modified Wang resin provided a polymer-supported copper catalyst, which is effective in cross-coupling reactions between N- or O-containing substrates and arylboronic acids. The copper catalyst is air stable and can be recycled with minimal loss of activity.

  [反应：见正文]将铜固定在改性的Wang树脂上提供了一种聚合物负载的铜催化剂，该催化剂对含N或O的底物与芳基硼酸之间的交叉偶联反应有效。铜催化剂是空气稳定的，可以在活性损失最小的情况下进行回收。
• Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy
  作者：Craig S. Buxton、David C. Blakemore、John F. Bower

  DOI：10.1002/anie.201707531

  日期：2017.10.23

  next cycle where it serves as the reductant for C-C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C-C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.

  丙烯酸苄酯与活化的酮和亚胺在镍催化下偶联，分别生成γ-丁内酯和内酰胺。内酯化/内酰胺化过程中释放的苯甲醇副产物被传递到下一个循环，在其中充当 CC 键形成的还原剂。该策略代表了一种概念上独特的转移氢化CC键形成方法，从而提供了还原性杂环化的例子，其中氢嵌入醇离去基团中促进周转。

表征谱图