2,6-二甲氧基苯甲腈 | 16932-49-3

• 物质功能分类: 有机原料
• 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: 2,6-二甲氧基苯甲腈
• 中文别名: 2,6-二甲氧基苯腈；2.6-二甲氧基苯腈
• 英文名称: 2,6-dimethoxybenzonitrile
• 英文别名: 2,6-bismethoxybenzonitrile
• CAS: 16932-49-3
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: XHAHKSSLDJIEDH-UHFFFAOYSA-N

物化性质

• 熔点：
  119-123 °C
• 沸点：
  310 °C
• 密度：
  1.2021 (rough estimate)
• 稳定性/保质期：
  密闭于阴凉干燥环境中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S36/37
• 海关编码：
  2926909090
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于阴凉干燥处

SDS

Name:	2 6-Dimethoxybenzonitrile 97% Material Safety Data Sheet
Synonym:	None known
CAS:	16932-49-3

Section 1 - Chemical Product MSDS Name:2 6-Dimethoxybenzonitrile 97% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16932-49-3	2,6-Dimethoxybenzonitrile	97	241-000-2

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful 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. Harmful if absorbed through the skin. May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. Most nitrile compounds are well absorbed through intact skin, and may cause delayed onset of symptoms following exposure by this route.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
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 be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration. Inhalation may result in symptoms similar to cyanide poisoning which include tachypnea, hyperpnea (abnormally rapid or deep breathing), and dyspnea (labored breathing) followed rapidly by respiratory depression. Pulmonary edema may occur.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. 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: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Combustion by-products include oxides of nitrogen and hydrogen cyanide.
Extinguishing Media:
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. 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# 16932-49-3: 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: Crystalline powder
Color: light beige
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 310 deg C @ 760 mm Hg
Freezing/Melting Point: 119 - 123 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: C9H9NO2
Molecular Weight: 163.18

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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:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, cyanides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16932-49-3: DI4355400 LD50/LC50:
Not available.
Carcinogenicity:
2,6-Dimethoxybenzonitrile - 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
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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 16932-49-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16932-49-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16932-49-3 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

制备方法与用途

化学性质：

• 白色针状结晶体，熔点为119-123℃，沸点为310℃，不溶于水。

用途： 主要用于有机合成中间体。

生产方法： 将2-甲氧基-6-硝基苯甲腈与氢氧化钾和醇溶液一起回流2小时。然后蒸馏浓缩后倾入冰水中，过滤得到棕色固体，用冷水洗涤并干燥，得到粗品。粗品经过重结晶、活性炭脱色处理即为成品，收率约为70%。

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基苯甲腈 在 kieselguhr-catalyst 、 nickel-copper 作用下， 生成 间苯二甲醚
  参考文献：
  名称：

  Catalytic Hydrogenation of Aromatic Nitrites

  摘要：

  DOI：

  10.1246/bcsj.32.861
• 作为产物：
  描述：

  (2,6-二甲氧基苯基)甲醇 在 氨 、 氧气 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以88%的产率得到2,6-二甲氧基苯甲腈
  参考文献：
  名称：

  磁性可回收的氢氧化镧作为伯醇有氧氧化转化为腈的有效催化剂

  摘要：

  在这里，我们报告了一种新颖的可磁性回收的氢氧化镧纳米颗粒，用于直接从相应的醇中以氨为氮源氧化合成腈。研究了La（OH）3 / Fe 3 O 4磁性纳米粒子的制备和表征方法，并探讨了该方法的范围和一般性，适用于一系列具有给电子和吸电子基团的结构多样的伯醇。当在O 2气氛下在回流条件下使用相对于苄醇为5摩尔％的La时，观察到最佳结果。La（OH）3 / Fe 3 O 4 可以使用外部磁体轻松地将磁性纳米颗粒从反应混合物中分离出来，并重复使用至少5次，而不会显着降低活性。

  DOI：

  10.1002/aoc.4253

文献信息

• Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions
  作者：Ko Uchida、Hideo Togo

  DOI：10.1016/j.tet.2019.130550

  日期：2019.9

  by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions. © 2019 Elsevier Science

  通过先用正丁基锂然后再用新戊腈处理芳基溴化物，然后在无过渡金属的条件下用分子碘在70°C的温度下处理（不使用金属氰化物），可以以高收率获得各种芳族腈。本反应通过在加热条件下由亚胺和N-碘亚胺的反应形成的以亚氨基氮为中心的自由基的β-消除进行。分级为4 +©2019 Elsevier Science。版权所有。
• A Metal‐Free Direct Arene C−H Amination
  作者：Tao Wang、Marvin Hoffmann、Andreas Dreuw、Edina Hasagić、Chao Hu、Philipp M. Stein、Sina Witzel、Hongwei Shi、Yangyang Yang、Matthias Rudolph、Fabian Stuck、Frank Rominger、Marion Kerscher、Peter Comba、A. Stephen K. Hashmi

  DOI：10.1002/adsc.202100236

  日期：2021.6.8

  The synthesis of aryl amines via the formation of a C−N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C−H amination using hydroxylamine derivatives under benign

  通过形成 CN 键合成芳胺是制备功能材料、活性药物成分和生物活性产品的重要工具。通常，这种化学连接只能通过过渡金属催化的反应、光化学或电化学来实现。在这里，我们报告了在良性条件下使用羟胺衍生物进行的无金属芳烃 C-H 胺化。即使在存在各种官能团的情况下，胺化试剂 TsONHR 和芳烃底物之间的电荷转移相互作用也能实现芳烃的化学选择性胺化。氧气对于有效转化至关重要，其对电子转移步骤的加速作用已通过实验证明。此外，
• Catalytic oxidative conversion of alcohols, aldehydes and amines into nitriles using KI/I2–TBHP system
  作者：K. Rajender Reddy、C. Uma Maheswari、M. Venkateshwar、S. Prashanthi、M. Lakshmi Kantam

  DOI：10.1016/j.tetlet.2009.02.057

  日期：2009.5

  The oxidative conversion of alcohols, aldehydes and amines to give corresponding nitriles in excellent yields was easily achieved by the catalytic amount of KI or I2 in combination with TBHP as an external oxidant. This non-transition metal catalyst is cost effective and provides easy work-up and separation of the product.

  通过催化量的KI或I 2结合TBHP作为外部氧化剂，可以轻松实现醇，醛和胺的氧化转化，从而以优异的收率得到相应的腈。这种非过渡金属催化剂具有成本效益，并易于处理和分离产物。
• Tandem Retro-Michael Addition-Claisen Rearrangement-Intramolecular Cyclization: One-Pot Synthesis of Densely Functionalized Ethyl Dihydropyrimidine-4-carboxylates from Simple Building Blocks
  作者：B. Naidu

  DOI：10.1055/s-2008-1032088

  日期：——

  Pyrolysis of suitably functionalized oxadiazoline diesters in refluxing xylenes provided ethyl 1,2-disubstituted 5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylates in moderate to good yields. Under thermal conditions, the oxadiazoline esters undergo a sequence of complex molecular reorganizations, namely retro-Michael addition, Claisen rearrangement, and cyclization, to produce the desired pyrimidinones.

  在回流的二甲苯中，通过适宜功能化的1,3,4-噁二唑啉二酯的热解，以中等至良好的产率合成了乙基1,2-二取代的5-羟基-6-氧代-1,6-二氢嘧啶-4-羧酸酯。在热条件下，噁二唑啉酯经历一系列复杂的分子重排过程，包括逆迈克尔加成、克莱森重排和环化，从而生成所需的嘧啶酮。
• Cu₂O-Mediated Room Temperature Cyanation of Aryl Boronic Acids/Esters and TMSCN
  作者：Yong Ye、Yanhua Wang、Pengtang Liu、Fushe Han

  DOI：10.1002/cjoc.201200711

  日期：2013.1

  A method for the efficient and reliable synthesis of aryl nitriles via the Cu2O‐catalyed cross‐coupling of aryl boronic acids or esters and TMSCN is presented. A broad range of substrates decorated by electron‐rich and deficient, sterically very congested, and labile functionalities were tolerated. Moreover, the reaction can proceed under mild conditions at room temperature. These advantages paired

  提出了一种通过Cu 2 O催化的芳基硼酸或酯与TMSCN的交叉偶联有效而可靠地合成芳基腈的方法。可以容忍各种各样的基板，这些基板被富电子和不足的电子装饰，空间上非常拥挤，并且功能不稳定。此外，该反应可以在室温下在温和条件下进行。这些优点与廉价，易得且不含卤素的Cu 2 O用作催化剂相结合，使该方案成为芳基氰化反应的诱人选择。

表征谱图