2-甲基-4-羟基苯甲醛 | 41438-18-0

• 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 - 有机氧化合物
• 中文名称: 2-甲基-4-羟基苯甲醛
• 中文别名: 4-羟基-2-甲基苯甲醛
• 英文名称: 4-hydroxy-2-methyl-benzaldehyde
• 英文别名: 2-methyl-4-hydroxybenzaldehyde；4-Hydroxy-2-methylbenzaldehyde
• CAS: 41438-18-0
• 化学式: C₈H₈O₂
• mdl: MFCD04037443
• 分子量: 136.15
• InChiKey: JDWWIEFMFPWBST-UHFFFAOYSA-N

物化性质

• 熔点：
  104-107°C
• 沸点：
  205-207 °C(Press: 18 Torr)
• 密度：
  1.175±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R36/37/38
• 海关编码：
  2912499000
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Hydroxy-2-methylbenzaldehyde
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
H412: Harmful to aquatic life with long lasting effects
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P273: Avoid release to the environment
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
4-Hydroxy-2-methylbenzaldehyde
Ingredient name:
CAS number: 41438-18-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8O2
Molecular weight: 136.1

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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

化学性质

2-甲基-4-羟基苯甲醛呈现为白色至淡黄色结晶性粉末，稍溶于水，并可溶于油。

用途

该化合物主要用于有机合成，并作为对照品用于复方雪莲胶囊的分析检测。

合成方法

将14.4克（0.6摩尔）镁粉加入200毫升甲醇中，开启电动搅拌，瓶内产生大量气泡，温度上升至61℃。两小时后，溶液变为乳白色悬浊液。随后，加入108克（1.0摩尔）对甲基苯酚，在50分钟后开始蒸出甲醇。待反应液变稠时，补充200毫升甲苯，并升高温度直至内温达到95℃。分批加入3.0摩尔的多聚甲醛（90克），改为蒸馏装置以蒸除低沸点物质。约30分钟后几乎无馏分蒸出，撤去蒸馏装置并继续反应2.5小时。使用薄层色谱跟踪，确认对甲基苯酚已完全反应。停止加热，待内温降至65℃时，用18.5%的盐酸调节pH值至1。静置后分液，有机层用70毫升甲苯萃取两次，合并有机层并用水洗三次以调至接近中性pH值。最终得到2-甲基-4-羟基苯甲醛。

反应信息

• 作为反应物：
  描述：

  2-甲基-4-羟基苯甲醛 在 哌啶 、 吡啶 、 palladium on activated charcoal 、 乙醇 、 乙酸乙酯 作用下， 生成 3-(4-hydroxy-2-methylphenyl)propionic acid
  参考文献：
  名称：

  Ring Size in the Dienone-Phenol Rearrangement

  摘要：

  DOI：

  10.1021/ja01526a069
• 作为产物：
  描述：

  间甲基苯甲醚 在 溴 、 吡啶盐酸盐 、 magnesium 作用下， 以 四氯化碳 为溶剂， 生成 2-甲基-4-羟基苯甲醛
  参考文献：
  名称：

  取代基对邻甲苯甲醛光化学的影响

  摘要：

  研究了4-氧基和4,5-二氧基取代基对2-甲基苯甲醛向邻喹啉二甲烷（o-QDMs）的光化学转化的影响。4-甲氧基或4和5-甲氧基取代基的存在阻止了o-QDM的光化学形成，而4-乙酰氧基和4,5-二乙酰氧基-2-甲基苯甲醛以及相应的甲磺酸酯和甲苯磺酸酯则成功转化为o-QDM。

  DOI：

  10.1016/s0040-4039(00)80821-7

文献信息

• BORON-CONTAINING SMALL MOLECULES
  申请人：Xia Yi

  公开号：US20100256092A1

  公开（公告）日：2010-10-07

  This invention relates to, among other items, 6-substituted benzoxaborole compounds and their use for treating bacterial infections.

  这项发明涉及6-取代苯硼酯化合物等物品，以及它们用于治疗细菌感染的用途。
• [EN] IMIDAZO [2, 1-F] [1, 2, 4] TRIAZIN-4-AMINE DERIVATIVES AS TLR7 AGONIST<br/>[FR] DÉRIVÉS D'IMIDAZO[2,1-F] [1, 2, 4] TRIAZIN-4-AMINE UTILISÉS EN TANT QU'AGONISTES DE TLR7
  申请人：BEIGENE LTD

  公开号：WO2020160711A1

  公开（公告）日：2020-08-13

  Disclosed herein is an imidazo [2, 1-f] [1, 2, 4] triazin-4-amine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as a TLR7 agonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the imidazo [2, 1-f] [1, 2, 4] triazin-4-amine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as TLR7 agonist.

  披露的是一种咪唑[2,1-f][1,2,4]三嗪-4-胺衍生物或其立体异构体，或其药用可接受盐，用作TLR7激动剂，以及包含该化合物的药物组合物。还披露了一种使用咪唑[2,1-f][1,2,4]三嗪-4-胺衍生物或其立体异构体，或其药用可接受盐作为TLR7激动剂来治疗癌症的方法。
• Formylation of Electron-Rich Aromatic Rings Mediated by Dichloromethyl Methyl Ether and TiCl4: Scope and Limitations
  作者：Iván Ramos-Tomillero、Marta Paradís-Bas、Ibério de Pinho Ribeiro Moreira、Josep Bofill、Ernesto Nicolás、Fernando Albericio

  DOI：10.3390/molecules20045409

  日期：——

  Here the aromatic formylation mediated by TiCl4 and dichloromethyl methyl ether previously described by our group has been explored for a wide range of aromatic rings, including phenols, methoxy- and methylbenzenes, as an excellent way to produce aromatic aldehydes. Here we determine that the regioselectivity of this process is highly promoted by the coordination between the atoms present in the aromatic moiety and those in the metal core.

  在这里，我们探索了我们小组之前描述的由TiCl4和二氯甲基甲醚介导的芳香环的甲酰化反应，适用于广泛类型的芳香环，包括酚、甲氧基苯和甲基苯，作为生成芳香醛的一种优秀方法。在此，我们确定该过程的区域选择性高度受到芳香部分中存在的原子与金属核中原子之间的配位作用促进。
• [EN] BIARYL COMPOUNDS USEFUL AS IMMUNOMODULATORS<br/>[FR] COMPOSÉS BIARYLES UTILES EN TANT QU'IMMUNOMODULATEURS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018044963A1

  公开（公告）日：2018-03-08

  The present disclosure generally relates to compounds useful as immunomodulators. Provided herein are compounds, compositions comprising such compounds, and methods of their use. The disclosure further pertains to pharmaceutical compositions comprising at least one compound according to the disclosure that are useful for the treatment of various diseases, including cancer and infectious diseases.

  本公开涉及通常用作免疫调节剂的化合物。本文提供了包含这些化合物的组合物，以及它们的使用方法。该公开进一步涉及包含至少一种根据本公开的化合物的药物组合物，用于治疗各种疾病，包括癌症和传染病。
• Oxazole derivatives
  申请人：——

  公开号：US20030055265A1

  公开（公告）日：2003-03-20

  The present invention relates to novel oxazole compounds which act as PPAR&agr; and PPAR&ggr; agonists and are accordingly useful for the treatment of diseases modulated by PPAR&agr; and PPAR&ggr; such as diabetes.

  本发明涉及新型噁唑化合物，其作为PPAR&agr;和PPAR&ggr;激动剂，并因此可用于治疗由PPAR&agr;和PPAR&ggr;调节的疾病，如糖尿病。

表征谱图