2,3,4-三甲氧基苯甲腈 | 43020-38-8

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 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: 2,3,4-三甲氧基苯甲腈
• 中文别名: 2,3,4-三甲氧基苄氰
• 英文名称: 2,3,4-trimethoxybenzonitrile
• CAS: 43020-38-8
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD00001785
• 分子量: 193.202
• InChiKey: YCSGHMDKBZNXJC-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C(lit.)
• 沸点：
  329.41°C (rough estimate)
• 密度：
  1.2307 (rough estimate)
• 溶解度：
  溶于甲醇
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xn,T
• 安全说明：
  S26,S37/39
• 危险类别码：
  R23/24/25,R20/21/22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  3276
• 储存条件：
  密封、阴凉、干燥保存

SDS

Name:	2 3 4-Trimethoxybenzonitrile 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	43020-38-8

Section 1 - Chemical Product MSDS Name:2 3 4-Trimethoxybenzonitrile 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
43020-38-8	2,3,4-Trimethoxybenzonitrile	97	256-049-5

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. May cause cardiac disturbances. The toxicological properties of this substance have not been fully investigated. May cause central nervous system depression.
Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May cause cardiac abnormalities. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. Chronic exposure to cyanide solutions may lead to the development of a "cyanide" rash, characterized by itching, and by macular, papular, and vesicular eruptions, and may be accompanied by secondary infections. Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes.

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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:
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 breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
May be partially metabolized to cyanide in the body.
Antidote: Always have a cyanide antidote kit on hand when working with cyanide compounds. Get medical advice to use.

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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. Containers may explode in the heat of a fire. Non-combustible, substance itself does not burn but may decompose upon heating to produce irritating, corrosive and/or toxic fumes. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Substance is noncombustible; use agent most appropriate to extinguish surrounding fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. 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# 43020-38-8: 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: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 56.00 - 57.00 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: C10H11NO3
Molecular Weight: 193.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, cyanide fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 43020-38-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3,4-Trimethoxybenzonitrile - 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: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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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 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 43020-38-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 43020-38-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 43020-38-8 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：

  2,3,4-三甲氧基苯甲腈 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-金刚烷甲酸 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 butyl 2-(3-ethoxy-4,5,6-trimethoxy-1H-isoindol-1-yl)acetate
  参考文献：
  名称：

  Ruthenium(II)-Catalyzed Redox-Neutral Oxidative Cyclization of Benzimidates with Alkenes with Hydrogen Evolution

  摘要：

  1H-Isoindoles and 2H-isoindoles are synthesized via a ruthenium-catalyzed oxidant-free cyclization of benzimidates with alkenes at room temperature with the liberation of H-2. Later, 1H-isoindoles were converted into nitrogen containing heterocycles. The proposed reaction mechanism was strongly supported by experimental evidence and DFT calculations.

  DOI：

  10.1021/acs.orglett.7b03405
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 Mexican Bentonite 、 盐酸羟胺 作用下， 反应 0.25h， 以86%的产率得到2,3,4-三甲氧基苯甲腈
  参考文献：
  名称：

  在没有溶剂的情况下，使用墨西哥膨润土和微波或红外辐射从醛中直接合成芳香腈

  摘要：

  摘要 一种高效、简单的方法，用于通过红外或微波辐射，用盐酸羟胺和墨西哥膨润土将芳香醛直接转化为相应的腈。

  DOI：

  10.1080/00397919208021348

文献信息

• Copper- and Silver-Mediated Cyanation of Aryl Iodides Using DDQ as Cyanide Source
  作者：Kui Zheng、Peng Yu、Shuyou Chen、Fen Chen、Jiang Cheng

  DOI：10.1002/cjoc.201201140

  日期：2013.4

  A new copper and silver‐mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved, providing nitriles with good yields. This new approach represents a safe method leading to aryl nitriles.

  用DDQ作为氰化物源，实现了新的铜和银介导的芳基碘化物的氰化，为腈提供了良好的收率。这种新方法代表了一种可产生芳基腈的安全方法。
• Iron and Phenol Co-Catalysis for Rapid Synthesis of Nitriles under Mild Conditions
  作者：Hong Meng、Sen Gao、Meiming Luo、Xiaoming Zeng

  DOI：10.1002/ejoc.201900831

  日期：2019.7.31

  Using inexpensive and environmentally benign FeCl3 and 2,6‐di‐tert‐butyl‐4‐methylphenol as cooperative catalyst, benzoyl aldehyde oximes converted into nitriles in excellent yields within minutes under mild reaction conditions.

  使用廉价且对环境无害的FeCl 3和2,6-二叔丁基-4-甲基苯酚作为协同催化剂，在温和的反应条件下，苯甲酰醛肟在短短几分钟内即可以优异的收率转化为腈。
• Stable and reusable nanoscale Fe₂O₃-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
  作者：Kathiravan Murugesan、Thirusangumurugan Senthamarai、Manzar Sohail、Muhammad Sharif、Narayana V. Kalevaru、Rajenahally V. Jagadeesh

  DOI：10.1039/c7gc02627g

  日期：——

  nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process

  在腈纶或酰胺基团形式的功能化分子中可持续引入氮基是至关重要的，因为在许多生命科学分子，天然产物和材料中都发现了含氮基序。因此，非常需要使用具有成本效益的催化剂和绿色试剂从容易获得的起始原料合成腈和酰胺的方法。就这一点而言，本文报道了在1 bar O 2的存在下，由醛和氨水进行的纳米级氧化铁催化的腈和伯酰胺的环境友好合成。或空气。在温和的反应条件下，该铁催化的需氧氧化过程继续进行，以合成功能化且结构多样的芳族，脂族和杂环腈。另外，应用该铁基方案，还已经在水介质中制备了伯酰胺。
• Direct Carbon Isotope Exchange of Pharmaceuticals via Reversible Decyanation
  作者：Minghao Feng、Joao De Oliveira、Antoine Sallustrau、Gianluca Destro、Pierre Thuéry、Sebastien Roy、Thibault Cantat、Charles S. Elmore、Jorg Blankenstein、Frédéric Taran、Davide Audisio

  DOI：10.1021/jacs.1c01923

  日期：2021.4.21

  described. By utilizing the radiolabeled precursor Zn([14C]CN)2, this protocol allows the insertion of the desired carbon tag without the need for structural modifications, in a single step. By reducing synthetic costs and limiting the generation of radioactive waste, this procedure will facilitate the labeling of nitrile containing drugs and accelerate 14C-based ADME studies supporting drug development

  碳 14 的加入可以追踪有机分子并提供有关其命运的重要知识。这些信息对于药物开发、作物科学和人类食品安全评估至关重要。在此，描述了一种能够在芳腈上进行碳同位素交换的过渡金属催化过程。通过利用放射性标记的前体 Zn([ 14 C]CN) 2，该协议允许在一个步骤中插入所需的碳标签，而无需进行结构修改。通过降低合成成本和限制放射性废物的产生，该程序将促进含腈药物的标记，并加速支持药物开发的基于14 C 的 ADME 研究。
• Metal-Free One-Pot Conversion of Electron-Rich Aromatics into Aromatic Nitriles
  作者：Hideo Togo、Sousuke Ushijima

  DOI：10.1055/s-0029-1219575

  日期：2010.4

  Various electron-rich aromatics could be smoothly converted into the corresponding aromatic nitriles in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with molecular iodine in aqueous ammonia. The present reaction is a novel metal-free one-pot method for the preparation of aromatic nitriles from electron-rich aromatics.

  通过使用POCl3和DMF处理电子富集芳香化合物，然后在水合氨中用分子碘处理，可以将多种电子富集的芳香化合物顺利转化为相应的中等到良好的产率的芳香腈。该反应是一种新颖的无金属单锅法，用于从电子富集的芳香化合物制备芳香腈。

表征谱图