4-溴-2,6-二甲氧基苯甲醛 | 1354050-38-6

• 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: 4-溴-2,6-二甲氧基苯甲醛
• 英文名称: 4-bromo-2,6-dimethoxybenzaldehyde
• CAS: 1354050-38-6
• 化学式: C₉H₉BrO₃
• 分子量: 245.073
• InChiKey: HNUALSDMDHKUEH-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±42.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2913000090
• 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：
  温度：2-8°C，保持在惰性气体氛围中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2,6-dimethoxybenzaldehyde
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: 4-Bromo-2,6-dimethoxybenzaldehyde
CAS number: 1354050-38-6

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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: C9H9BrO3
Molecular weight: 245.1

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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, hydrogen bromide.

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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

应用领域广泛，4-溴-2,6-二甲氧基苯甲醛可用作有机合成中间体和医药中间体，在实验室研发和化工生产过程中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  4-溴-2,6-二甲氧基苯甲醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium tert-butylate 、 氢气 、 RuCl₂(R-Xyl-Garphos)(R-Daipen) 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 、 甲苯 、 乙腈 为溶剂， -78.0~60.0 ℃ 、3.04 MPa 条件下， 反应 47.16h， 生成 2-(2,6-dimethoxy-4-pentylphenyl)-4-methyl-cyclohex-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  [EN] CANNABINOID DERIVATIVES AND PRECURSORS, AND ASYMMETRIC SYNTHESIS FOR SAME
  [FR] DÉRIVÉS ET PRÉCURSEURS DE CANNABINOÏDES, ET SYNTHÈSE ASYMÉTRIQUE S'Y RAPPORTANT

  摘要：

  本公开涉及新的大麻素衍生物和前体，以及它们的制备的催化不对称过程。该公开还涉及新的大麻素衍生物的药物组合物以及药用和分析用途。例如，该公开涉及新前体的制备，以及利用这种前体化合物利用手性和无手性催化剂和催化过程制备同位素标记的大麻素产品。可以在转化为所需的个别氘代大麻素产品之前制备和纯化含氘、碳-13和碳-14的化合物。

  公开号：

  WO2021046640A1
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 、 N,N-二甲基甲酰胺 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 4-溴-2,6-二甲氧基苯甲醛
  参考文献：
  名称：

  7-Alkyl-3-benzylcoumarins: A Versatile Scaffold for the Development of Potent and Selective Cannabinoid Receptor Agonists and Antagonists

  摘要：

  A series of 7-alkyl-3-benzylcoumarins was designed, synthesized, and tested at cannabinoid CB1 and CB2 receptors in radioligand binding and cAMP accumulation studies. 7-Alkyl-3-benzylcoumarins were found to constitute a versatile scaffold for obtaining potent CB receptor ligands with high potency at either CB1 or CB2 and a broad spectrum of efficacies. Fine-tuning of compound properties was achieved by small modifications of the substitution pattern. The most potent compounds of the present series include 5-methoxy-3-(2-methylbenzyl)-7-pentyl-2H-chromen-2-one (19a, PSB-SB-1201), a selective CB1 antagonist (K-i CB1 0.022 mu M), 5-methoxy-3-(2-methoxybenzyl)-7-pentyl-2H-chromen-2-one (21a, PSB-SB-1202), a dual CB1/CB2 agonist (CB1 K-i 0.032 mu M, EC50 0.056 mu M; CB2 K-i 0.049 mu M, EC50 0.014 mu M), 5-hydroxy-3-(2-hydroxybenzyl)-7-(2-methyloct-2-yl)-2H-chromen-2-one (25b, PSB-SB-1203), a dual CB1/CB2 ligand that blocks CB1 but activates CB2 receptors (CB1 K-i 0.244 mu M; CB2 K-i 0.210 mu M, EC50 0.054 mu M), and 7-(1-butylcyclopentyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one (27b, PSB-SB-1204), a selective CB2 receptor agonist (CB1 K-i 1.59 mu M; CB2 K-i 0.068 mu M, EC50 0.048 mu M).

  DOI：

  10.1021/jm3008213

文献信息

• Computational discovery, structural optimization and biological evaluation of novel inhibitors targeting transient receptor potential vanilloid type 3 (TRPV3)
  作者：Fang Zhang、Yiyu Lin、Wenjian Min、Yi Hou、Kai Yuan、Jin Wang、Peng Yang

  DOI：10.1016/j.bioorg.2021.105093

  日期：2021.9

  few reports of TRPV3 inhibitors exist at present besides some patents. Therefore, TRPV3 research has always been fraught with challenges. Through a combination of virtual screening and biological evaluation, compound P1 (10 μM) was identified as a top hit with 34.5% inhibitory effect on 2-APB (1 mM)-evoked currents of mTRPV3-WT. Further structural optimization provided the inhibitor PC5 with the best

  瞬时受体电位香草素类型 3 (TRPV3) 是一种 Ca 2+可渗透的非选择性阳离子通道，在皮肤角质形成细胞中大量表达。TRPV3 成为治疗瘙痒、炎症、疼痛和皮肤相关疾病的有吸引力的靶点。然而，除了部分专利外，目前关于TRPV3抑制剂的报道寥寥无几。因此，TRPV3的研究一直充满挑战。通过虚拟筛选和生物学评估的组合，化合物P1 (10 μM) 被鉴定为对 mTRPV3-WT 的 2-APB (1 mM) 诱发电流具有 34.5% 抑制作用的最佳化合物。进一步的结构优化为抑制剂PC5提供了最佳活性 (IC 50 = 2.63 ± 0.28 μM)，点突变分析表明氨基酸 V629 和 F633 对PC5和 TRPV3的结合至关重要。总之，这些新发现的抑制剂可以作为未来开发TRPV3抑制剂的有前途的先导化合物。
• [EN] HERBICIDAL PROPYNYL-PHENYL COMPOUNDS<br/>[FR] COMPOSÉS PROPYNYLE-PHÉNYLE HERBICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2015197468A1

  公开（公告）日：2015-12-30

  The present invention relates to a compound of formula (I) wherein: R1 is C1-C3alkoxy, C1-C2alkoxy-C1-C3alkoxy, C1-C2fluoroalkoxy, ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl; R2 is hydrogen, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, C1-C3alkoxy, C1-C3fluoroalkyl, C1-C2fluoroalkoxy, C1-C2alkoxy-C1-C3alkoxy-, or C1fluoroalkoxy-C1-C3alkoxy-; provided that when R1 is ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl, then R2 is hydrogen, ethyl, n-propyl, cyclopropyl, vinyl or ethynyl; and Y is O, S, S(O), S(O)2, N(C1-C2alkyl), N(C1-C2alkoxy), C(O), CR8R9 or -CR10R11CR12R13-; and and G, R3, R4, R5 and R6 are as defined herein; wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are suitable for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledonous weeds, in crops of useful plants, comprising applying a compound of formula (I), or a herbicidal composition comprising such a compound, to the plants or to the locus thereof.

  本发明涉及一种具有以下结构的化合物（I）：其中：R1为C1-C3烷氧基，C1-C2烷氧基-C1-C3烷氧基，C1-C2氟烷氧基，乙基，正丙基，正丁基，环丙基或乙炔基；R2为氢，乙基，正丙基，环丙基，乙烯基，乙炔基，C1-C3烷氧基，C1-C3氟烷基，C1-C2氟烷氧基，C1-C2烷氧基-C1-C3烷氧基，或C1氟烷氧基-C1-C3烷氧基-；但是当R1为乙基，正丙基，正丁基，环丙基或乙炔基时，R2为氢，乙基，正丙基，环丙基，乙烯基或乙炔基；Y为O，S，S(O)，S(O)2，N(C1-C2烷基)，N(C1-C2烷氧基)，C(O)，CR8R9或-CR10R11CR12R13-；以及G，R3，R4，R5和R6如本文所定义；其中化合物（I）可作为农药中可接受的盐存在。这些化合物适用于用作除草剂。因此，本发明还涉及一种控制杂草，特别是草本单子叶杂草，在有用植物作物中的方法，包括将化合物（I）或含有这种化合物的除草剂组合物施用于植物或其生长地点。
• [EN] METHODS AND COMPOUNDS FOR TREATING DISORDERS<br/>[FR] PROCÉDÉS ET COMPOSÉS POUR TRAITER DES TROUBLES
  申请人：FOGHORN THERAPEUTICS INC

  公开号：WO2019152440A1

  公开（公告）日：2019-08-08

  The present invention relates to methods and compositions for the treatment of BAF-related disorders such as cancers and viral infections.

  本发明涉及用于治疗与BAF相关的疾病，如癌症和病毒感染的方法和组合物。
• New Pyridinones and Isoquinolinones as Inhibitors of the Bromodomain BRD9
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20180044335A1

  公开（公告）日：2018-02-15

  The present invention encompasses compounds of general formula (I) wherein the groups R 1 to R 9 , X 1 and X 2 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation, e.g. cancer, pharmaceutical preparations containing such compounds and their uses as a medicament.

  本发明涵盖了一般式（I）的化合物，其中基团R1至R9，X1和X2的含义如权利要求和说明书中所述。本发明的化合物适用于治疗由细胞过度或异常增殖所特征化的疾病，例如癌症，含有这种化合物的制药制剂以及它们作为药物的用途。
• Efficient synthesis of polymethoxyselenoflavones via regioselective direct C–H arylation of selenochromones
  作者：Woo-Ram Yang、Yong-Sung Choi、Jin-Hyun Jeong

  DOI：10.1039/c7ob00118e

  日期：——

  changes, the development of a generally applicable synthetic method was a key. Until now, an efficient pathway for palladium-catalyzed direct arylation with the selenocyclic enone systems is not known in the literature. We herein introduce a simple direct C–H arylation of two difficult coupling partners, selenochromones and electron-rich aryl bromide, affording diverse polymethoxyselenoflavones with

  大量研究表明，黄酮类化合物的构型和官能团总数会影响其生物活性。为了研究硒黄酮的生物活性与结构变化的关系，开发一种通用的合成方法是关键。迄今为止，文献中尚不知道钯催化与硒环烯酮体系直接芳基化的有效途径。我们在这里介绍了两个困难的偶合伙伴硒代色酮和富电子芳基溴的简单直接C–H芳基化反应，可高效高效地提供多种聚甲氧基硒代黄酮。