2-(苄氧基)-4-溴苯甲醛 | 142602-43-5

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(苄氧基)-4-溴苯甲醛
• 英文名称: 2-(benzyloxy)-4-bromobenzaldehyde
• 英文别名: 4-bromo-2-phenylmethoxybenzaldehyde
• CAS: 142602-43-5
• 化学式: C₁₄H₁₁BrO₂
• 分子量: 291.144
• InChiKey: MTCCBXXJEDZGIW-UHFFFAOYSA-N

物化性质

• 熔点：
  107-110 °C
• 沸点：
  404.5±35.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2913000090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Benzyloxy)-4-bromobenzaldehyde
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: 2-(Benzyloxy)-4-bromobenzaldehyde
CAS number: 142602-43-5

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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: C14H11BrO2
Molecular weight: 291.1

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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

2-(苄氧基)-4-溴苯甲醛是一种具有独特化学性质的苯甲醛类化合物，通常被应用于医学、环境和工业研究领域。

反应信息

• 作为反应物：
  描述：

  2-(苄氧基)-4-溴苯甲醛 在 caesium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.25h， 生成
  参考文献：
  名称：

  铜催化的[1,2]-Stevens型重排不对称二炔环化合成手性铬诺[3,4-c]吡咯

  摘要：

  公开了一种铜催化的不对称级联环化/[1,2]-Stevens 型重排，以通常中等至良好的产率和优异的对映选择性提供有价值的手性色烯并[3,4- c ]吡咯，其具有季碳立体中心。重要的是，该协议代表了第一个基于炔烃的催化不对称 [1,2]-史蒂文斯型重排和第一个不对称的形式卡宾插入 Si-O 键。

  DOI：

  10.1002/anie.202115554
• 作为产物：
  描述：

  间溴苯酚 在 potassium carbonate 、 三乙胺 、 magnesium chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-(苄氧基)-4-溴苯甲醛
  参考文献：
  名称：

  WO2006/102674

  摘要：

  公开号：

文献信息

• Ortho substituted aromatic compounds useful as antagonists of the pain
  申请人：Zeneca Limited

  公开号：US05811459A1

  公开（公告）日：1998-09-22

  The invention relates to compounds of the formula (I): ##STR1## wherein A, B and D are various ring systems such as phenyl, R.sup.1 includes carboxy, R.sup.3 is hydrogen or C.sub.1-4 alkyl and Z is a linking group such as --(CH(R.sup.5)).sub.m -- wherein m is 2, 3 or 4, and R.sub.5 includes hydrogen and methyl; and pharmaceutically acceptable salts and in vivo hydrolysable esters or amides thereof, processes for preparing these compounds, pharmaceutical compositions comprising them, and their use in the treatment of pain.

  该发明涉及以下式(I)的化合物：##STR1## 其中A、B和D是各种环系统，如苯基，R.sup.1包括羧基，R.sup.3是氢或C.sub.1-4烷基，Z是连接基，如--(CH(R.sup.5)).sub.m--其中m为2、3或4，R.sub.5包括氢和甲基；以及其药学上可接受的盐和体内可水解的酯或酰胺，制备这些化合物的方法，包含它们的药物组合物，以及它们在治疗疼痛中的用途。
• Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors
  作者：Kai Bao、Yi Dai、Zhi-Bin Zhu、Feng-Juan Tu、Wei-Ge Zhang、Xin-Sheng Yao

  DOI：10.1016/j.bmc.2010.07.062

  日期：2010.9

  of biphenyls, analogs of aglycone of natural product fortuneanoside E, were prepared using Suzuki–Miyaura cross-coupling and selective magnesium iodide demethylation/debenzylation, and their mushroom tyrosinase inhibitory activity was evaluated. Most of the 4-hydroxy-3,5-dimethoxyphenyl biphenyl compounds (series II, 20–36) were in general more active than 3,4,5-trimethoxyphenyl biphenyl compounds (series

  使用铃木-Miyaura交叉偶联和选择性碘化镁去甲基/去苄基作用，制备了两个新的联苯系列，即天然产物苦瓜子苷E糖苷配基类似物，并评估了其对蘑菇酪氨酸酶的抑制活性。通常，大多数4-羟基-3,5-二甲氧基苯基联苯化合物（II系列，20–36）比3,4,5-三甲氧基苯基联苯基化合物（I，1-19）更具活性。结构-活性关系研究表明，单糖取代基（例如葡萄糖）不是必需的，并且4-羟基-3,5-二甲氧基苯基部分的存在对于抑制活性至关重要。在合成的化合物中，化合物21（IC 50 = 0.02 mM）是活性最高的一种，其活性比金银花皂苷E（IC 50  = 0.14 mM）高7倍，比熊果苷（IC 50  = 0.21 mM）高10倍，被称为有效的酪氨酸酶抑制剂。通过Lineweaver-Burk图分析的抑制动力学表明，化合物21是竞争性抑制剂（K i  = 0.015 mM）。
• Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products
  作者：Kai Bao、Aixue Fan、Yi Dai、Liang Zhang、Weige Zhang、Maosheng Cheng、Xinsheng Yao

  DOI：10.1039/b916969e

  日期：——

  An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group

  一种使用芳基甲基/苄基醚的有效选择性脱甲基和脱苄基方法 碘化镁 在无溶剂条件下已开发并应用于天然的合成 黄酮和联苯糖苷。在反应条件下可以耐受包括糖苷在内的多种官能团。实验结果表明，无论它们是在羰基的间位还是对位，O-苄基的去除都比O-甲基的去除更容易。因此，对于同时带有苄氧基和甲氧基的底物可以实现选择性的脱苄基作用。
• Copper/B₂pin₂-Catalyzed Difluoroalkylation of Methylenecyclopropanes with Bromodifluorinated Acetates and Acetamides: One-Pot Synthesis of CF₂-Containing Dihydronaphthalene Derivatives
  作者：Chuang Liu、Yan-Jie Yang、Jun-Ying Dong、Ming-Dong Zhou、Lei Li、He Wang

  DOI：10.1021/acs.joc.9b01106

  日期：2019.8.16

  Novel copper/B2pin2-catalyzed difluoroalkylation of methylenecyclopropanes with bromodifluorinated acetates and acetamides via a tandem radical process involving ring-opening/intramolecular cyclization has been reported. This protocol is not only tolerated to a diverse range of substrates but also applicable to the synthesis of useful difluoromethylated compounds. Moreover, the reaction could be performed

  已经报道了经由涉及开环/分子内环化的串联自由基过程的新型铜/ B 2 pin 2催化的亚甲基环丙烷与溴代二氟乙酸盐和乙酰胺的二氟烷基化。该方案不仅可耐受多种底物，而且可用于合成有用的二氟甲基化化合物。此外，该反应可以以克的规模高产率地进行，这为实际应用开辟了可能性。
• Total Synthesis of Exiguamines A and B Inspired by Catecholamine Chemistry
  作者：Vladimir Sofiyev、Jean‐Philip Lumb、Matthew Volgraf、Dirk Trauner

  DOI：10.1002/chem.201103605

  日期：2012.4.16

  The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine‐2,3‐dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross‐coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary

  介绍了Exiguamines（两种结构异常的天然产物，它们是吲哚胺-2,3-Dioxygenase（IDO）的高活性抑制剂）的总合成过程。最终成功的策略涉及先进的交叉偶联方法，并具有潜在的生物合成互变异构/电环化反应，该反应形成两个杂环并在一个合成操作中安装季铵离子。