2-甲氧基-6-甲基苯甲醛 | 54884-55-8

• 物质功能分类: 有机原料 - 醛类化合物
• 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-甲氧基-6-甲基苯甲醛
• 中文别名: 2-甲基-6-甲氧基苯甲醛
• 英文名称: 2-methoxy-6-methyl-benzaldehyde
• 英文别名: 2-Methoxy-6-methylbenzaldehyde
• CAS: 54884-55-8
• 化学式: C₉H₁₀O₂
• mdl: MFCD08235006
• 分子量: 150.177
• InChiKey: QLUHWZADTAIBKK-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41℃
• 沸点：
  256℃
• 密度：
  1.062
• 闪点：
  113℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2912499000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  温度：2-8°C，保持在惰性气体氛围中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Methoxy-6-methylbenzaldehyde
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Methoxy-6-methylbenzaldehyde
CAS number: 54884-55-8

---

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.

---

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.

---

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.

---

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, refrigerated.
Storage:

---

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.

---

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: C9H10O2
Molecular weight: 150.2

---

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

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-羟基-6-甲基苯甲醛	2-hydroxy-6-methylbenzaldehyde	18362-36-2	C8H8O2	136.15
  2,3-二甲基苯甲醚	2,3-dimethylanisole	2944-49-2	C9H12O	136.194
  2-甲氧基-6-甲基苯甲酸	2-methoxy-6-methyl-benzoic acid	6161-65-5	C9H10O3	166.177
  2-甲氧基-6-甲基苯甲酸甲酯	methyl 2-methyl-6-methoxybenzoate	79383-44-1	C10H12O3	180.203
  ——	(2-methoxy-6-methylphenyl)methanol	89244-39-3	C9H12O2	152.193
  ——	3-(Bromomethyl)-2-methylanisole	70264-73-2	C9H11BrO	215.09
  2-(溴甲基)-1-甲氧基-3-甲基苯	2-(Bromomethyl)-3-methylanisole	89244-40-6	C9H11BrO	215.09
  2-甲氧基-6-甲基苯甲酸乙酯	ethyl 2-methoxy-6-methylbenzoate	6520-83-8	C11H14O3	194.23
  二甲酚	2,3-Dimethylphenol	526-75-0	C8H10O	122.167

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2-羟基-6-甲基苯甲醛	2-hydroxy-6-methylbenzaldehyde	18362-36-2	C8H8O2	136.15
  2-甲氧基-6-甲基苯甲酸	2-methoxy-6-methyl-benzoic acid	6161-65-5	C9H10O3	166.177
  3-溴-6-甲氧基-2-甲基苯甲醛	3-bromo-6-methoxy-2-methylbenzaldehyde	137644-93-0	C9H9BrO2	229.073
  1-(2-甲氧基-6-甲基苯基)乙酮	2'-methoxy-6'-methylacetophenone	6161-64-4	C10H12O2	164.204
  ——	4-((2-formyl-3-methylphenoxy)methyl)benzoic acid	1360618-29-6	C16H14O4	270.285
  ——	methyl 4-((2-formyl-3-methylphenoxy)methyl)benzoate	1360618-17-2	C17H16O4	284.312
  2-甲氧基-6-甲基苯甲酸甲酯	methyl 2-methyl-6-methoxybenzoate	79383-44-1	C10H12O3	180.203
  ——	2-bromo-1-(2-methoxy-6-methylphenyl)ethanone	126524-09-2	C10H11BrO2	243.1
  ——	2-methoxy-6-methylbenzoyl cyanide	71687-95-1	C10H9NO2	175.187
  ——	coahuilensol, methyl ether	72473-09-7	C10H12O	148.205

反应信息

• 作为反应物：
  描述：

  2-甲氧基-6-甲基苯甲醛 在 盐酸羟胺 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-甲氧基-6-甲基苯甲腈
  参考文献：
  名称：

  NOVEL COMPOUNDS AS MODULATORS OF PROTEIN KINASES

  摘要：

  本发明提供了PI3K蛋白激酶调节剂，其制备方法，含有它们的药物组合物，以及使用它们进行治疗、预防和/或改善激酶介导的疾病或紊乱的方法。

  公开号：

  US20120289496A1
• 作为产物：
  描述：

  5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以99%的产率得到2-甲氧基-6-甲基苯甲醛
  参考文献：
  名称：

  芳炔[2+2]环加成和苯并环丁烯醇开环合成氧化邻甲基苯甲醛

  摘要：

  本文描述了从市售溴代芳烃开始制备氧化邻甲基苯甲醛衍生物的两步程序。该合成的特点是通过与乙醛烯醇锂的苯炔[2+2]环加成反应，将甲基和甲酰基同时且高度区域选择性地安装到苯核上，以高产率得到相应的苯并环丁烯醇。苯并环丁烯醇在碱性条件下在甲醇中进行键选择性开环，得到标题化合物。

  DOI：

  10.2533/chimia.2018.870

文献信息

• Chemoselective Reduction of Sterically Demanding <i>N</i>,<i>N</i>-Diisopropylamides to Aldehydes
  作者：Peihong Xiao、Zhixing Tang、Kai Wang、Hua Chen、Qianyou Guo、Yang Chu、Lu Gao、Zhenlei Song

  DOI：10.1021/acs.joc.7b02868

  日期：2018.2.16

  EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed

  已经开发出一种用于化学选择性地将空间上需要的N，N-二异丙基酰胺还原成醛的顺序一锅法。在该反应中，酰胺用EtOTf活化形成酰亚胺，然后用LiAlH（OR）3 [R = t- Bu，Et]还原，通过水解所得到的半缩醛产生醛。非亲核碱基2,6-DTBMP显着提高了反应效率。发现EtOTf / 2，6-DTBMP和LiAlH（O- t- Bu）3的组合对于还原烷基，烯基，炔基和2-单取代的芳基N，N-二异丙基酰胺是最佳的。相反，EtOTf和LiAlH（OEt）3在没有碱的情况下，发现其对于还原空间上要求极高的2，6-二取代的N，N-二异丙基苯甲酰胺是最佳的。该反应可耐受各种可还原的官能团，包括醛和酮。1 H NMR研究证实了在水中稳定形成的酰亚胺。这种方法的综合实用性通过N，N-二异丙基酰胺定向的邻位金属化和CH键的活化得到了证明。
• Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
  作者：Xue Li、Fang Bai、Chaogan Liu、Xiaowei Ma、Chengzhi Gu、Bin Dai

  DOI：10.1021/acs.orglett.1c02651

  日期：2021.10.1

  An efficient electrochemical method for benzylic C(sp3)–H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry

  已经开发了一种用于苄基 C(sp 3 )-H 键氧化的有效电化学方法。各种甲基芳烃、甲基杂芳烃和苄基（杂）亚甲基可以在未分割的电池中以中等至极好的收率转化为所需的芳醛和芳酮，使用 O 2作为氧源，高氯酸镥作为电解质。在循环伏安法研究、18 O 标记实验和自由基捕获实验的基础上，提出了一种可能的单电子转移机制用于电氧化反应。
• Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
  作者：Hao Liang、Xiaobo He、Yaqi Zhang、Bin Chen、Jia-sheng Ouyang、Yongsu Li、Bendu Pan、Chitreddy V. Subba Reddy、Wesley Ting Kwok Chan、Liqin Qiu

  DOI：10.1039/d0cc04373g

  日期：——

  The copper(II)-catalyzed (4+1) cyclizations and copper(I)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionalized dimethyl (E)-3-benzylideneindoline-2,2-dicarboxylates and methyl 5-(2-hydroxyphenyl)-2-methoxy-4-phenylfuran-3-carboxylates were conveniently prepared

  通过使用高效，安全的碘鎓碘化物代替传统的重氮化合物，成功开发了铜（II）催化的（4 + 1）环化反应和铜（I）催化的碘化碘化物和炔烃的环加成反应。方便地以中等至优异的产率制备高度官能化的二甲基（E）-3-亚苄基吲哚啉-2，2-二羧酸酯和5-（2-羟基苯基）-2-甲氧基-4-苯基呋喃-3-羧酸甲酯。还讨论了可能的反应机理。
• Synthesis of (+)-Varitriol Analogues via Novel and Versatile Building Blocks Based on Julia Olefination
  作者：Annamalai Senthilmurugan、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.200901012

  日期：2010.1

  The synthesis of (+)-varitriol (1) analogues was achieved through the use of Julia olefination. The potential anticancer properties of 1 coupled with our interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of our research project. Efforts are aimed at the synthesis of building blocks 2 and 3 and to explore their use towards the synthesis

  (+)-varitriol (1) 类似物的合成是通过使用 Julia 烯化实现的。1 的潜在抗癌特性加上我们对开发能够在 Julia 协议下形成烯烃的构建模块的兴趣构成了我们研究项目的基础。努力旨在合成构件 2 和 3，并探索它们在合成 (+)-varitriol 类似物方面的用途。在此，我们想展示构建块 3 的合成及其与各种取代的芳族、杂环和碳水化合物衍生的醛反应以中等至良好收率生成烯烃 ​​6 的能力，其中 E 作为主要异构体。2与（呋喃糖苷部分）醛5k的成功偶联，
• Benzofurane, benzothiophene, benzothiazol derivatives as FXR modulators
  申请人：Merck Sante

  公开号：EP2110374A1

  公开（公告）日：2009-10-21

  The present invention relates to compounds of formula (I) wherein the substituents are as defined in the claims, including pharmaceutical compositions thereof and for their use in the treatment and/or prevention and/or amelioration of one or more symptoms of disease or disorders related to the activity of FXR. The invention is also directed to intermediates and to a method of preparation of compounds of formula (I).

  本发明涉及式(I)的化合物，其中取代基如权利要求中定义的那样，包括其药物组合物及其用于治疗和/或预防及/或改善与FXR活性相关的疾病或障碍的一个或多个症状。本发明还涉及中间体以及化合物式(I)的制备方法。

表征谱图