9-甲基-3-硝基-9h-咔唑 | 61166-05-0

• 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: 9-甲基-3-硝基-9h-咔唑
• 英文名称: 9-methyl-3-nitro-9H-carbazole
• 英文别名: 3-nitro-N-methyl carbazole；3-nitro-9-methylcarbazole；9-methyl-3-nitrocarbazole；9-methyl-3-nitro-carbazole；9-Methyl-3-nitro-carbazol；3-Nitro-9-methyl-carbazol
• CAS: 61166-05-0
• 化学式: C₁₃H₁₀N₂O₂
• mdl: MFCD00218829
• 分子量: 226.235
• InChiKey: LUWUTJWWCMXMSA-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 溶解度：
  <0.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Name:	9-Methyl-3-nitro-9h-carbazole 97% Material Safety Data Sheet
Synonym:
CAS:	61166-05-0

Section 1 - Chemical Product MSDS Name:9-Methyl-3-nitro-9h-carbazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
61166-05-0	9-Methyl-3-nitro-9H-carbazole	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 68

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Possible risk of irreversible effects.
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:
Possible risk of irreversible effects.

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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.
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.

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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.

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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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 61166-05-0: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 172 - 173.5 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: C13H10N2O2
Molecular Weight: 226

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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.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 61166-05-0: FE6270000 LD50/LC50:
Not available.
Carcinogenicity:
9-Methyl-3-nitro-9H-carbazole - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 68 Possible risk of irreversible effects.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
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# 61166-05-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 61166-05-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 61166-05-0 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：

  9-甲基-3-硝基-9h-咔唑 在 吡啶 、 盐酸 、 乙醇 、 tin(ll) chloride 作用下， 生成 9-methyl-3-carbethoxyamino carbazole
  参考文献：
  名称：

  Synthesis and Ultraviolet Absorption Spectra Studies of 2,3- and 3,4-Disubstituted Carbazoles¹

  摘要：

  DOI：

  10.1021/ja01632a009
• 作为产物：
  描述：

  3-硝基-9-硝基咔唑 在 sodium hydroxide 作用下， 生成 9-甲基-3-硝基-9h-咔唑
  参考文献：
  名称：

  Stevens; Tucker, Journal of the Chemical Society, 1923, vol. 123, p. 2147

  摘要：

  DOI：

文献信息

• Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Brønsted Acidic NO₂⁺ Generation
  作者：Kevin A. Juárez-Ornelas、J. Oscar C. Jiménez-Halla、Terumasa Kato、César R. Solorio-Alvarado、Keiji Maruoka

  DOI：10.1021/acs.orglett.8b04141

  日期：2019.3.1

  The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Brønsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT)

  使用碘基苯作为基于碘（III）和硝酸铝作为硝基基团来源的有机催化剂，开发了用于苯酚亲电硝化的第一个催化程序。该原子经济方案发生在温和的，非布朗斯台德酸性和开放式烧瓶反应条件下，具有宽泛的官能团耐受性，包括多个杂环。（SMD：MeCN）Mo8-HX /（LANLo8 + f，6-311 + G *）水平的密度泛函理论（DFT）计算表明反应通过阳离子途径进行，该途径有效地产生了NO 2 +离子，从而是中性条件下的硝化物种。
• 3-Aminocarbazole Compounds, Pharmaceutical Composition Containing the Same and Method for the Preparation Thereof
  申请人：Alisi Maria Alessandra

  公开号：US20080207727A1

  公开（公告）日：2008-08-28

  A compound of formula (I), in which R1, R2, R3, R4, R5, R6, X and Y have the meanings indicated in the description, and the pharmaceutically acceptable salts thereof. A pharmaceutical composition containing a compound of formula (I) or a pharmaceutically acceptable salt thereof. A method for preparing the abovementioned compound of formula (I) and the pharmaceutically acceptable salts thereof.

  公式（I）的化合物，其中R1、R2、R3、R4、R5、R6、X和Y具有描述中指示的含义，以及其药学上可接受的盐。含有公式（I）的化合物或其药学上可接受的盐的药物组合物。制备上述公式（I）化合物及其药学上可接受的盐的方法。
• Synthesis of Novel 3-<i>N</i> -substituted Carbazole Derivatives and Evaluation of their Abilities to Inhibit Platelet Aggregation
  作者：Jiseon Kim、Sang-Hyuk Jung、Eunju Yun、Soo-Hyun Cho、O Yuseok、Ji-Eun Kim、Young-Ho Kim、Chang-Seon Myung、Gyu-Yong Song

  DOI：10.1002/bkcs.11462

  日期：2018.6

  activities, including anticancer, antiviral, anti‐inflammatory, and antimicrobial activities; some compounds containing the moiety also inhibit platelet aggregation. In the present study, we synthesized a series of 3‐N‐substituted carbazole derivatives and evaluated their abilities to inhibit in vitro platelet aggregation induced by collagen (5 μg/mL). Of the synthesized compounds, compound 5q (JSCa15), with

  咔唑部分具有多种生物学活性，包括抗癌，抗病毒，抗炎和抗微生物活性。一些含有该部分的化合物也抑制血小板凝集。在本研究中，我们合成了一系列3 N取代的咔唑衍生物，并评估了它们抑制胶原蛋白（5μg/ mL）诱导的体外血小板聚集的能力。在合成的化合物中，在咔唑骨架内具有脲键的化合物5q（JSCa15）表现出最强的抑制活性（30μM时为98.25％）。有趣的是，化合物5q的硝基还原为胺后，其活性大大降低（化合物5r，在30μM时为5.18％）。同样，用氨基甲酸酯部分代替化合物5q的脲部分导致活性的显着损失（化合物8a，在30μM时5.91％）。这些结果表明，3 N取代的咔唑衍生物的尿素部分和硝基可能在抑制胶原蛋白诱导的体外血小板凝集中起关键作用。
• Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration
  作者：Masahito Murai、Naoki Nishinaka、Mizuki Kimura、Kazuhiko Takai

  DOI：10.1021/acs.joc.9b00598

  日期：2019.5.3

  Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C–Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C–H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under

  尽管使用9硅芴作为功能材料和结构单元，但对其骨架进行有效功能化的方法却很少，这可能是由于存在易于裂解的C-Si键所致。尽管很难控制铱催化的C–H键直接硼化的区域选择性，但我们发现2-甲氧基-9-硅芴在温和条件下的溴化和硝化主要发生在富电子位置。具有甲氧基和溴基的所得产物可用作合成不对称取代的含9-硅芴的π-共轭分子的结构单元。
• METHOD FOR PRODUCING AMINOCARBAZOLES
  申请人：——

  公开号：US20010049448A1

  公开（公告）日：2001-12-06

  Disclosed is a method for producing an aminocarbazole by catalytically reducing a nitrocarbazole, wherein as a catalyst is used an active nickel-based catalyst prepared by contacting a nickel-based catalyst with an alkali and an iron compound under a hydrogen gas or inert gas atmosphere in an inert solvent, and according to the method of the present inventions decrease in reaction speed, decrease in yield of a product or the like depending upon the lot of the starting nitrocarbazoles can be prevented, and aminocarbazoles can be produced in a good yield constantly.

  公开了一种通过催化还原硝基咔唑来生产氨基咔唑的方法，其中所使用的催化剂为通过将镍基催化剂与碱和铁化合物接触，在惰性溶剂中在氢气或惰性气氛下制备的活性镍基催化剂。根据本发明的方法，可以预防由于起始硝基咔唑的批次而导致的反应速度减慢、产物收率减少等问题，并且可以持续地以良好的产率生产氨基咔唑。

表征谱图