间甲氧基苯丙酮 | 37951-49-8

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 间甲氧基苯丙酮
• 中文别名: 3-甲氧基苯丙酮；3'-甲氧基苯丙酮；3甲氧基丙苯酮
• 英文名称: 1-(3-methoxyphenyl)propan-1-one
• 英文别名: 3'-methoxypropiophenone；3’-methoxypropiophenone；m-methoxy propiophenone；3-Methoxypropiophenon；m-Methoxypropiophenon
• CAS: 37951-49-8
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD08458823
• 分子量: 164.204
• InChiKey: LPDJHUUWTGXTCU-UHFFFAOYSA-N

物化性质

• 沸点：
  259℃
• 密度：
  1.0812

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914509090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2~8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3’-Methoxypropiophenone
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3’-Methoxypropiophenone
CAS number: 37951-49-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H12O2
Molecular weight: 164.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

在容器中加入40-50份（按重量计）镁屑、100-160份四氢呋喃和300-400份甲苯，先滴加少量溴乙烷引发反应，随后缓慢滴加剩余的溴乙烷，整个过程保温1.5-2.5小时。接着加入150-170份间甲氧基苯甲腈，并继续保温5-7小时。

在另一容器中加入600-800份水，将上述反应液缓慢倒入水中进行酸化处理，静置后分层、萃取并用水洗清。最后通过蒸馏即可得到间甲氧基苯丙酮成品。

反应信息

• 作为反应物：
  描述：

  间甲氧基苯丙酮 在 水 、 四氯化锡 、 碳酸氢钠 、 sulfur 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.33h， 生成 2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS

  摘要：

  本发明涉及新型NADPH氧化酶II抑制剂及其在治疗由NADPH氧化酶II酶介导的疾病中的应用。

  公开号：

  WO2011075559A1
• 作为产物：
  描述：

  3-甲氧基苯甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 间甲氧基苯丙酮
  参考文献：
  名称：

  Phosphodiesterase inhibitors. Part 5: Hybrid PDE3/4 inhibitors as dual bronchorelaxant/anti-inflammatory agents for inhaled administration

  摘要：

  (-)-6-(7-甲氧基-2-(三氟甲基)吡唑[1,5-a]嘧啶-4-基)-5-甲基-4,5-二氢嘧啶啶-3(2H)-酮 (KCA-1490)表现出中等的双重PDE3/4抑制活性，并有望作为一种联合支气管扩张/抗炎剂。嘧啶酮环的N-烷基化显着增强了对PDE4的效力，但抑制了PDE3的抑制作用。在N-烷基上添加一个6-芳基-4,5-二氢嘧啶啶-3(2H)-酮延伸有利于提高PDE4抑制活性并恢复对PDE3的强抑制作用。复合核心和延伸中的两个二氢嘧啶-酮环可以被无手性4,4-二甲基吡咯酮基团取代，而核心吡唑嘧啶被等效力的双环杂芳香族化合物取代。这些修饰的结合提供了强效的双重PDE3/4抑制剂，它抑制组织胺诱导的支气管收缩在体内和通过气管内给药表现出有希望的抗炎活性。版权属于(C) 2012 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.bmcl.2012.08.121
• 作为试剂：
  描述：

  间甲氧基苯丙酮 、 [1-(dimethylcarbamoyl)ethyl] phosphonic acid bis-(2,2,2-trifluoroethyl) ester 在 间甲氧基苯丙酮 作用下， 以75的产率得到(2Z)-3-(3-methoxyphenyl)-N,N,2-trimethylpent-2-enamide
  参考文献：
  名称：

  [EN] INTERMEDIATE COMPOUNDS AND PROCESSES FOR THE PREPARATION OF TAPENTADOL AND RELATED COMPOUNDS
  [FR] COMPOSÉS INTERMÉDIAIRES ET PROCÉDÉS POUR LA PRÉPARATION DE TAPENTADOL ET DE COMPOSÉS APPARENTÉS

  摘要：

  本发明公开了制备3-[(1R,2R)-3-(二甲氨基)-1-乙基-2-甲基丙基]苯酚（Tapentadol）、其盐及相关化合物的过程，包括其立体异构体及其药学上可接受的盐，并公开了用于此类过程的某些中间体。

  公开号：

  WO2011080736A1

文献信息

• [EN] CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE LA CÉRAMIDE GALACTOSYLTRANSFÉRASE POUR LE TRAITEMENT DE MALADIES
  申请人：BIOMARIN PHARM INC

  公开号：WO2017214505A1

  公开（公告）日：2017-12-14

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物、以及使用这种化合物治疗或预防与酶神经鞘糖脂转移酶（CGT）相关的疾病或紊乱的方法，例如溶酶体贮积症。溶酶体贮积症的例子包括 Krabbe 病和白质变性白血病。
• Efficient and scalable synthesis of ketones via nucleophilic Grignard addition to nitriles using continuous flow chemistry
  作者：Carlos Mateos、Juan A. Rincón、José Villanueva

  DOI：10.1016/j.tetlet.2013.02.069

  日期：2013.5

  In the present Letter we report the development of efficient continuous flow chemistry conditions for the scalable preparation of ketones. This transformation is achieved via nucleophilic addition of Grignard reagents to the corresponding nitriles and imine hydrolysis by means of in-series plug flow reactors.

  在本函中，我们报告了可扩展制备酮的有效连续流化学条件的发展。这种转化是通过将Grignard试剂亲核加成到相应的腈中并通过串联活塞流反应器进行亚胺水解来实现的。
• Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier
  作者：Nidhi Garg、Soumen Paira、Basker Sundararaju

  DOI：10.1002/cctc.202000228

  日期：2020.7.6

  an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron‐rich/electron‐poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence

  在这里，我们证明了在Ir（III）催化下，使用甲醇作为实用和有用的液态有机氢载体（LOHC）转移酮氢化的有效方案。各种酮，包括富电子/贫电子的芳族酮，杂芳族和脂族酮，已被有效地还原为相应的醇。在温和条件下，在存在各种其他可还原官能团的情况下，确定了酮的化学选择性还原。
• Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products
  作者：Louis K. M. Chan、Darren L. Poole、Di Shen、Mark P. Healy、Timothy J. Donohoe

  DOI：10.1002/anie.201307950

  日期：2014.1.13

  The rhodium‐catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and the hydrogen‐borrowing method. The sequence is notable for the relatively low temperatures that are required and for the ability of the reaction system to form α‐branched products with ease. Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a

  使用甲醇作为甲基化剂和借氢方法完成了铑催化的酮的甲基化。该序列的显着之处在于所需的温度相对较低，并且反应系统能够轻松形成 α 支化产物。双烷基化酮可以通过使用连续的一锅铱和铑催化工艺由甲基酮和两种不同的醇制备。
• Catalytic C₁  Alkylation with Methanol and Isotope-Labeled Methanol
  作者：Jan Sklyaruk、Jannik C. Borghs、Osama El-Sepelgy、Magnus Rueping

  DOI：10.1002/anie.201810885

  日期：2019.1.14

  A metal‐catalyzed methylation process has been developed. By employing an air‐ and moisture‐stable manganese catalyst together with isotopically labeled methanol, a series of D‐, CD3‐, and 13C‐labeled products were obtained in good yields under mild reaction conditions with water as the only byproduct.

  已经开发了一种金属催化的甲基化方法。通过将空气和水分稳定的锰催化剂与同位素标记的甲醇一起使用，在温和的反应条件下，以水为唯一副产物，可以高收率获得一系列D-，CD 3-和13 C-标记的产品。