5,7-二甲基靛红 | 39603-24-2

• 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: 5,7-二甲基靛红
• 中文别名: 5,7-二甲基-1H-吲哚-2,3-二酮；5,7-二甲基伊斯汀
• 英文名称: 5,7-dimethylisatin
• 英文别名: 5,7-dimethylindoline-2,3-dione；isatin；5,7-dimethyl-1H-indole-2,3-dione
• CAS: 39603-24-2
• 化学式: C₁₀H₉NO₂
• mdl: MFCD00047219
• 分子量: 175.187
• InChiKey: HFZSCCJTJGWTDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C
• 沸点：
  306.47°C (rough estimate)
• 密度：
  1.250
• 稳定性/保质期：
  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S22,S24/25
• 海关编码：
  2933990090
• 危险品标志：
  Xi
• RTECS号：
  NL7930000
• 危险性防范说明：
  P273,P305+P351+P338
• 危险性描述：
  H302,H319,H412
• 储存条件：
  请将密封、阴凉、干燥的环境作为保存条件。

SDS

Name:	5 7-Dimethylisatin 95% Material Safety Data Sheet
Synonym:	5,7-Dimethyl-2,3-Indolinedion
CAS:	39603-24-2

Section 1 - Chemical Product MSDS Name:5 7-Dimethylisatin 95% Material Safety Data Sheet
Synonym:5,7-Dimethyl-2,3-Indolinedion

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
39603-24-2	5,7-Dimethylisatin	95	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
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.

---

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:
Never give anything by mouth to an unconscious person. 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:

---

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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

---

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.

---

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.

---

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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 39603-24-2: 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 minimize contact with skin.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: red - rust
Odor: characteristic odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 245 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: Insoluble.
Specific Gravity/Density:
Molecular Formula: C10H9NO2
Molecular Weight: 175.19

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable. 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:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 39603-24-2: NL7930000 LD50/LC50:
Not available.
Carcinogenicity:
5,7-Dimethylisatin - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 39603-24-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 39603-24-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 39603-24-2 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5,7-二甲基靛红 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-苄基-5,7-二甲基吲哚烷-2,3-二酮
  参考文献：
  名称：

  镍（II）催化的羟吲哚衍生物的不对称炔丙基[2,3] Wittig重排：手性放大作用

  摘要：

  通过在温和的反应条件下使用手性N，N'-二氧化物/ Ni II络合物作为催化剂，可以实现羟吲哚衍生物的高对映选择性[2,3] Wittig重排。观察到很强的手性扩增效果，并且通过使用仅含15％ee的配体，可以高收率和对映选择性（高达92％ee）接近带有烯丙基的手性3-羟基3-取代的羟吲哚。根据实验研究和对映体纯和外消旋催化剂的X射线晶体结构，给出了合理的解释。此外，通过[2,3] Wittig重排实现了外消旋羟吲哚衍生物的第一催化动力学拆分，具有很高的效率和立体选择性。

  DOI：

  10.1002/anie.201804080
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 5,7-二甲基靛红
  参考文献：
  名称：

  钯（0）催化的单和双异腈插入：苯并呋喃，吲哚和Isatins的简便合成

  摘要：

  由异腈插入和α-CSP的钯（0） -催化级联过程3  ħ交叉耦合可以为苯并呋喃和吲哚的合成来实现。通过Pd催化的级联反应（结合双异腈插入，胺化和水解作用），也可以实现Isatin的构建。这项工作的关键特征包括多种杂环合成，无膦配体的反应条件，一锅法，简单且可商购的起始原料，广泛的官能团相容性以及中等至良好的反应产率。

  DOI：

  10.1002/chem.201405933

文献信息

• Synthesis and Biological Evaluation of Quinoline Salicylic Acids As P-Selectin Antagonists
  作者：Neelu Kaila、Kristin Janz、Silvano DeBernardo、Patricia W. Bedard、Raymond T. Camphausen、Steve Tam、Desirée H. H. Tsao、James C. Keith、Cheryl Nickerson-Nutter、Adam Shilling、Ruth Young-Sciame、Qin Wang

  DOI：10.1021/jm0602256

  日期：2007.1.1

  junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis

  白细胞炎症和组织损伤部位的募集涉及白细胞沿内皮壁滚动，然后白细胞牢固粘附，最后白细胞跨细胞连接转运到下面的组织中。初始滚动步骤由包含活性部分的白细胞糖蛋白（如唾液酸化的Lewisx（sLex））与在内皮细胞上表达的P-选择蛋白的相互作用介导。因此，借助于小分子P-选择蛋白拮抗剂抑制这种相互作用是治疗炎性疾病如关节炎的有吸引力的策略。惠氏化学文库的高通量筛选确定了喹啉水杨酸类化合物（1）作为P-选择素的拮抗剂，其体外和基于细胞的测定方法的功效远远优于sLex。通过迭代药物化学，我们鉴定出具有改善的P-选择素活性，减少的二氢Orate脱氢酶抑制作用和可接受的CYP谱的类似物。铅化合物36在类风湿关节炎的大鼠AIA模型中有效。
• Thermal Decomposition Modes for Four-Coordinate Ruthenium Phosphonium Alkylidene Olefin Metathesis Catalysts
  作者：Erin M. Leitao、Stuart R. Dubberley、Warren E. Piers、Qiao Wu、Robert McDonald

  DOI：10.1002/chem.200801584

  日期：——

  The four-coordinate ruthenium phosphonium alkylidenes 1-Cy and 1-iPr, differing in the substituent on the phosphorus center, were observed to decompose thermally in the presence of 1,1-dichloroethylene to produce [H(3)CPR(3)][Cl]. The major ruthenium-containing product was a trichloro-bridged ruthenium dimer that incorporates the elements of the 1,1-dichloroethylene as a dichlorocarbene ligand and

  观察到在磷中心的取代基不同的四配位钌phospho烷基亚烷基1-Cy和1-iPr在1,1-二氯乙烯的存在下热分解产生[H（3）CPR（3）] [Cl]。含钌的主要产物是三氯桥联的钌二聚体，该单体在二氯卡宾配体中掺入了1,1-二氯乙烯和在支持的NHC配体上有苯乙烯基乙烯基。光谱，动力学和氘标记实验探究了该过程的机制，该过程涉及NHC异丁基邻甲基的限速CH活化。这些研究为活性Grubbs型烯烃复分解催化剂的内在分解过程提供了见识，为新的催化剂设计方向指明了道路。
• Multicomponent Reaction to Construct Spirocyclic Oxindoles with a Michael (Triple Michael)/Cyclization Cascade Sequence as the Key Step
  作者：Jian Li、Ning Wang、Chunju Li、Xueshun Jia

  DOI：10.1002/chem.201104071

  日期：2012.7.27

  new strategy to access highly unusual tricyclic oxindoles. From a synthetic point of view, this protocol is very interesting considering the high level of complexity reached in one step. The mechanism is thought to proceed by a triple Michael/cyclization process by using allenoate as a three carbon atom component (3 C). Furthermore, multicomponent reaction with γ‐substituted allenoate also results in

  公开了具有容易获得的异氰酸酯，脲基酸酯和异亚丙基丙二腈的多组分环加成物。该反应不需要任何催化剂的帮助，使得能够以优异的区域选择性有效地合成螺环恶吲哚。还充分探讨了与2,3-丁二烯酸乙酯和各种结构不同的α-和γ-取代的烯醇酸酯的反应。值得注意的是，我们已经表明，通常的三组分过程可以在存在水的情况下进一步发展为史无前例的四组分环加成反应，这提供了一种新的策略来获得高度不寻常的三环羟吲哚。从综合的角度来看，考虑到一步就可以达到很高的复杂性，该协议非常有趣。该机理被认为是通过使用烯丙酸酯作为三个碳原子组分（3 C）通过三重迈克尔/环化过程进行的。此外，与γ-取代的脲基甲酸酯的多组分反应也导致非常有趣的转化。在这种情况下，总是观察到异亚丙基丙二腈的“CC”双键和脲基酸酯的“CC”双键之一的不寻常断裂。
• Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro [indole-thiazolidinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3,2′-thiazolidine]-3′(1,2,4-triazol-3-yl)-2,4′(1H)-dione
  作者：Anshu Dandia、Ruby Singh、Sarita Khaturia、Claude Mérienne、Georges Morgant、André Loupy

  DOI：10.1016/j.bmc.2005.11.025

  日期：2006.4

  A microwave-assisted three-component, regioselective one-pot cyclocondensation method has been developed for the synthesis of a series of novel spiro[indole-thiazolidinones] (6a-l) using an environmentally benign procedure at atmospheric pressure in open vessel. This rapid method produces pure products in high yields within few minutes in comparison to a conventional two-step procedure. The crystal

  已开发了一种微波辅助的三组分区域选择性单锅环缩合方法，该方法用于在开放容器中在大气压力下使用环境友好的方法合成一系列新型螺[吲哚-噻唑烷酮]（6a-1）。与常规的两步法相比，这种快速的方法可在几分钟内以高收率生产纯净的产品。一种代表性化合物的晶体结构已经通过X射线衍射确定。已对合成的化合物进行了“体外”筛选，以检测其对茄根枯病菌，尖孢镰刀菌和辣椒辣椒的抗真菌活性。所有化合物均显示出对这些病原体的良好活性。
• Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity
  作者：Anshu Dandia、Ruby Singh、Jyoti Joshi、Shuchi Maheshwari、Pragya Soni

  DOI：10.1039/c3ra43745k

  日期：——

  A novel and catalyst-free aqueous mediated multicomponent domino reaction (MCR) capable of affording medicinally important spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] under sonication in excellent yield and in shorter time is reported. This new protocol provides a new seven-membered ring system selectively instead of the expected five-membered ring system or other possible isomers. The structure and relative stereochemistry of spiro products was established by single crystal X-ray analysis of a representative compound and spectroscopic techniques. In comparison to conventional synthesis, the advantages of this method are that it is catalyst-free, has an easy workup and uses water as the solvent which is considered to be relatively environmentally benign, and this work offers a new way to create molecular complexity with maximum simplicity. The representative compounds were screened for their ability to inhibit the enzyme α-amylase.

  报道了一种新颖的无催化剂的水相介导的多组分多米诺反应（MCR），该反应在超声波作用下能够以优异的产率和更短的时间合成具有药物重要性的螺[吲哚-3,4'-吡唑并[3,4-e][1,4]噻嗪]。这种新方案选择性地提供了新的七元环系统，而非预期的五元环系统或其他可能的异构体。通过代表性化合物的单晶X射线分析和光谱技术确定了螺产物结构及其相对立体化学。与传统合成相比，该方法的优点在于无需催化剂，操作简便，使用水作为溶剂，相对环境友好，并且为创造分子复杂性提供了最大限度简化的途径。对代表性化合物进行了α-淀粉酶抑制能力的筛选。