5-硝基吲哚-3-甲醛 | 6625-96-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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-硝基吲哚-3-甲醛
• 中文别名: 5-硝基-1H-吲哚-3-甲醛
• 英文名称: 5-nitro-1H-indole-3-carbaldehyde
• 英文别名: 5-nitroindole-3-carbaldehyde；5-nitroindole-3-carboxaldehyde；5-Nitroindol-3-aldehyd；3-formyl-5-nitroindole；5-nitro-1H-indole-3-carboxaldehyde；5-nitro-3-carboxaldehydeindole；5-Nitroindol-3-carbaldehyd；5-nitro-3-formylindol
• CAS: 6625-96-3
• 化学式: C₉H₆N₂O₃
• mdl: MFCD01313781
• 分子量: 190.158
• InChiKey: PHKYMSLVWLYDKP-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C
• 沸点：
  441.5±25.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Name:	5-Nitro-1h-indole-3-carbaldehyde, 97% Material Safety Data Sheet
Synonym:
CAS:	6625-96-3

Section 1 - Chemical Product MSDS Name: 5-Nitro-1h-indole-3-carbaldehyde, 97% Material Safety Data Sheet
Synonym:

---

SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6625-96-3	5-Nitro-1H-indole-3-carbaldehyde	97%	unlisted

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

---

SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Not available. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

---

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.

---

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.

---

SECTION 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container. Store under an inert atmosphere.

---

SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 6625-96-3: 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.

---

SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 290 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: C9H6N2O3
Molecular Weight: 190

---

SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

---

SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 6625-96-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Nitro-1H-indole-3-carbaldehyde - Not listed by ACGIH, IARC, or NTP.

---

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 No information available. IMO No information available. RID/ADR No information available.

---

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# 6625-96-3: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 6625-96-3 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 6625-96-3 is not listed on the TSCA inventory. It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 6/10/2003 Revision #0 Date: Original. 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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

5-硝基吲哚-3-甲醛可用作医药合成中间体。该化合物可通过将5-硝基-1H-吲哚作为反应原料来制备，并用于制备新型的3,5-二取代1H-吲哚衍生物，对胰腺癌细胞株BxPC-3具有较好的抑制活性。

制备

在0℃下，逐步滴加POCl₃(9.2ml，98.5mmol)至DMF(9.5ml，123.1mmol)中，搅拌0.5小时后，加入5-硝基-1H-吲哚(2.0g，12.3mmol)，然后在室温下反应1.5小时。随后将反应液倒入大量冰水中，并用6N NaOH调节pH至7，再用乙酸乙酯萃取三次，浓缩后得到2.34g灰色固体5-硝基吲哚-3-甲醛，产率为98%，纯度为95.2%。

反应信息

• 作为反应物：
  描述：

  5-硝基吲哚-3-甲醛 在 sodium tetrahydroborate 、 Montmorillonite 、 sodium hydride 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 4.17h， 生成 3-戊烯-2-酮,3,4-二氟-,(3Z)-(9CI)
  参考文献：
  名称：

  质子交换蒙脱石介导的乙酸异苄酯反应：在扎鲁司特的合成中的应用

  摘要：

  具有出色表面特性的质子交换蒙脱石（H-mont）可以在中孔中提供丰富的酸性位点，并且可以作为一种高效的非均相催化剂，用于通过（杂）芳烃的Friedel-Crafts烷基化合成含杂环的二芳基甲烷杂乙酸乙酸酯在温和的反应条件下不需要任何添加剂或惰性气氛。使用该策略，以高收率完成了含吲哚的二芳基甲烷13的克级合成，从而制备了Zafirlukast。此外，H-mont可用于乙酸杂苄酯5p与多种醇和1,3-二羰基化合物的亲核取代反应。

  DOI：

  10.1016/j.tetlet.2020.152123
• 作为产物：
  描述：

  5-硝基芦竹碱 在 碘 、 sodium carbonate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以79%的产率得到5-硝基吲哚-3-甲醛
  参考文献：
  名称：

  分子碘介导的芳基和杂芳基（二甲基氨基）甲基的C–N键氧化裂解为醛

  摘要：

  芳基和杂芳基（二甲基氨基）甲基的C–N键的氧化裂解可通过在环境条件下，弱碱存在下使用分子碘作为弱氧化剂来实现。游离NH和含有各种取代基的取代的吲哚的C 3甲酰化的重要反应是由相应的曼尼希碱完成的。该方法还可以扩展为芳基和其他杂芳基醛和酮的合成。此外，该方法的实用性已成功以克为单位进行了证明。

  DOI：

  10.1039/d0nj05832g

文献信息

• CuI-catalyzed highly regioselective C H functionalization of indoles using indole-3-tosylhydrazones as carbene precursor: An efficient synthesis of 3,3-bis(indolyl)methane derivatives
  作者：Priya Kamboj、Sunil Dutt、Sourav Chakroborty、Vikas Tyagi

  DOI：10.1016/j.tetlet.2019.151162

  日期：2019.10

  Herein, we have developed a novel approach for synthesizing symmetrical and unsymmetrical 3,3-bis(indolyl)methane derivatives via CuI-catalyzed CH functionalization of indole using indole-3-tosylhydrazones as carbene precursor. This procedure works well with different substitutions such as NO2, Br, CH3 and OMe on indole or indole-3-tosylhydrazones and features high regioselectivity for C-3 functionalization

  本文中，我们开发了一种新颖的方法，该方法通过使用吲哚-3-甲苯磺酰azo作为卡宾前体通过CuI催化的吲哚的C H官能化合成对称和不对称的3,3-双（吲哚基）甲烷衍生物。该方法与吲哚或吲哚-3-甲苯磺酰hydr上的NO 2，Br，CH 3和OMe的不同取代效果很好，并且对C-1和N-1位置的C-3功能化具有很高的区域选择性。此外，我们还从吲哚-3-羧醛开始以一锅法揭示了该方案的可行性。
• Substitution Effect on Near Infrared Absorbance Based Selective Fluoride Sensing of Indole Functionalized Thiourea Molecules
  作者：Bijit Chowdhury、Sanghamitra Sinha、Pradyut Ghosh

  DOI：10.1002/ejoc.201801534

  日期：2019.2.7

  Selective sensing of fluoride within a broad NIR window (825 nm to 1160 nm) by prompt visible color changes by six new symmetrically substituted, thiourea based, indole conjugated sensors is demonstrated. Different substituents lead to specific coloration and absorption spectral shifts in the presence of fluoride. This structure‐property correlation could be helpful to design a series of new NIR based

  通过六个新的对称取代的，基于硫脲的吲哚共轭传感器，通过迅速可见的颜色变化，证明了在较宽的NIR窗口（825 nm至1160 nm）内对氟的选择性感测。在氟化物存在下，不同的取代基会导致特定的着色和吸收光谱偏移。这种结构属性的关联可能有助于设计一系列具有特定颜色变化的基于NIR的新型传感器。
• 含N-嘧啶吲哚结构的二胺单体及其制备方法
  申请人：江汉大学

  公开号：CN107445944B

  公开（公告）日：2018-07-10

  本发明公开了一种含N‑嘧啶吲哚结构的二胺单体及其制备方法，该制备方法具体为将化合物A、硝基苯硼酸类化合物、三氟乙酸银、催化剂[RhCp*Cl2]2在甲醇中反应，得到硝基化合物B；N2保护下，将硝基化合物B溶于二甲基亚砜中，在活性铁粉和乙酸条件下，回流进行反应将硝基还原为氨基，得到具有含N‑嘧啶吲哚结构的二胺单体C。本发明含N‑嘧啶吲哚结构的二胺单体的制备方法简单，反应过程易控，且收率较高，可作为合成聚酰亚胺的一种二胺单体，在耐高温及柔性显示基板等特殊领域具有潜在的应用价值。
• Indole derivatives for use as chemical uncoupler
  申请人：Christiansen Brown Lise

  公开号：US20070010559A1

  公开（公告）日：2007-01-11

  Novel 3-vinylsulfonyl indole derivatives are chemical uncouplers useful e.g. for treatment of obesity.

  3-乙烯磺酰吲哚衍生物是一种化学解偶联剂，例如可用于治疗肥胖。
• [EN] 5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS DE 5-SULFAMOYL-2-HYDROXYBENZAMIDE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017153952A1

  公开（公告）日：2017-09-14

  The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代水杨酰胺衍生物。具体而言，本发明涉及根据公式(I)的化合物：其中R、R1和R2如本文所述，或其药用可接受的盐。本发明的化合物是CD73的抑制剂，可用于治疗癌症、前癌症综合症以及与CD73抑制相关的疾病，例如艾滋病、治疗HIV、自身免疫疾病、感染、动脉粥样硬化和缺血再灌注损伤。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制CD73活性和治疗与之相关的疾病的方法。

表征谱图