2-溴-5-甲氧基苄醇 | 150192-39-5

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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-溴-5-甲氧基苄醇
• 中文别名: 2-溴-5-甲氧基苯甲醇
• 英文名称: 2-Bromo-5-methoxybenzyl alcohol
• 英文别名: (2-bromo-5-methoxyphenyl)methanol
• CAS: 150192-39-5
• 化学式: C₈H₉BrO₂
• 分子量: 217.062
• InChiKey: NRDAKNCVXNJCGB-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  308.2±27.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8°C，干燥密封。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: (2-Bromo-5-methoxyphenyl)methanol
Synonyms: 2-Bromo-5-methoxybenzyl alcohol

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: (2-Bromo-5-methoxyphenyl)methanol
CAS number: 150192-39-5

---

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.
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: C8H9BrO2
Molecular weight: 217.1

---

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.

---

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

反应信息

• 作为反应物：
  描述：

  2-溴-5-甲氧基苄醇 在 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以72%的产率得到间甲氧基苯甲醇
  参考文献：
  名称：

  通过钯催化的取代控制的邻溴苄醇的官能化：二甲苯和茚基的合成

  摘要：

  提出了一种有效的多米诺骨牌钯催化的简单的邻溴苄苄基叔醇向色烯的转化。据信它们的形成是通过形成五元的palladacycle来进行的，而该五元的palladacycle又与第二邻位分子发生了分子间的均质偶联。-溴苄基叔醇产生均联-芳基键，然后形成分子内C-O键。有趣的是，当苄基碳原子上存在一个烯丙基取代基时，观察到化学选择性开关，其优选分子内Heck偶联并得到茚基。此外，已经证实叔醇官能团对于提供偶联产物必不可少，而伯/仲苄醇的使用则通过可能的还原脱溴和随后的氧化作用提供了简单的羰基产物，这归因于β-氢的存在（ s）。

  DOI：

  10.1021/jo402763m
• 作为产物：
  描述：

  间甲氧基苯甲醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 以94%的产率得到2-溴-5-甲氧基苄醇
  参考文献：
  名称：

  改良的Hoveyda-Grubbs复分解催化剂中含有螯合的碘代亚苄基配体的有趣的取代基作用†

  摘要：

  制备并表征了一系列改性的结合了碘代亚苄基配体的Hoveyda-Grubbs催化剂。发现在碘化物对位的吸电子环取代基会降低催化活性，这表明Ru⋯I–Ar键的解离不是决定速率的步骤。

  DOI：

  10.1039/c2dt32422a

文献信息

• Enantioselective Allylation of Selected<i>ortho</i>-Substituted Benzaldehydes: A Comparative Study
  作者：Filip Hessler、Robert Betík、Aneta Kadlčíková、Roman Belle、Martin Kotora

  DOI：10.1002/ejoc.201403034

  日期：2014.11

  Lewis base catalysis proved to be more efficient, and the highest asymmetric induction for allylation of ortho-fluorobenzaldehyde reached 82 % ee, which is comparable to other used catalytic conditions. In cases of ortho-vinylbenzaldehyde, the Keck allylation provided the product in 88 % ee. An enantioenriched homoallylic alcohol was used as the starting material for the synthesis of a sertraline

  我们报告了在路易斯碱（N，N-二氧化物）、路易斯酸（凯克烯丙基化）和布朗斯台德酸催化下邻位取代苯甲醛烯丙基化的系统研究。邻-卤代苯甲醛被用作醛底物，并特别关注邻-乙烯基和炔基苯甲醛，它们可能作为有趣的合成子用于制备更复杂的手性化合物。在催化条件下实现了类似的对映选择性。在邻卤苯甲醛的情况下，路易斯碱催化被证明更有效，邻氟苯甲醛烯丙基化的最高不对称诱导达到 82% ee，与其他使用的催化条件相当。在邻乙烯基苯甲醛的情况下，Keck 烯丙基化提供 88% ee 的产物。
• Fe(III)-catalyzed trityl benzyl ether formation and disproportionation cascade reactions to yield benzaldehydes
  作者：Xiaoyu Wang、Chuan Du、Hui Shi、Yadong Pang、Shengfei Jin、Yuqian Hou、Yanshi Wang、Xiaoshi Peng、Jianyong Xiao、Yang Liu、Yongxiang Liu、Maosheng Cheng

  DOI：10.1016/j.tet.2015.07.040

  日期：2015.9

  During investigating water-compatible Lewis acids catalyzed etherifications using alcohols as alkylating reagents directly, we developed Fe(III)-catalyzed trityl benzyl ether formations irradiated by microwave. Then an in situ trityl benzyl ether formation and disproportionation cascade reaction was achieved to yield the benzaldehyde products with good functional group tolerances under neat conditions

  在直接使用醇作为烷基化试剂研究与水相容的路易斯酸催化的醚化过程中，我们开发了Fe（III）催化的微波辐照的三苯甲基苄基醚形成。然后，在相对较高的温度下，在纯净条件下，实现了原位三苯甲基苄基醚的形成和歧化级联反应，从而得到具有良好官能团耐受性的苯甲醛产物。通过使用化学动力学图方法改变苄醇和三芳基甲醇上的取代基，探讨了底物对醚化和歧化的取代作用，并通过交叉实验研究了转化机理。醚化和歧化级联过程可以在实验室中方便地扩大规模，而不会损失很多效率。
• Asymmetric conjugate addition reaction
  申请人：Merck & Co., Inc.

  公开号：US06353110B1

  公开（公告）日：2002-03-05

  This invention relates to a key intermediate in the synthesis of an endothelin antagonist the synthesis of this key intermediate via an asymmetric conjugate addition reaction.

  这项发明涉及一种内皮素拮抗剂合成中的关键中间体，通过不对称共轭加成反应合成这种关键中间体。
• Cyclopropenium Enhanced Thiourea Catalysis
  作者：Ivor Smajlagic、Rocio Durán、Melanie Pilkington、Travis Dudding

  DOI：10.1021/acs.joc.8b02321

  日期：2018.11.16

  The addition of benzoic acid as a co-catalyst facilitating cooperative Brønsted acid catalysis was found to be valuable for reactions involving phenols and higher substituted alcohols. Mechanistic investigations, including kinetic and 1H NMR binding studies in conjunction with density function theory calculations, are described that collectively support a Brønsted acid mode of catalysis.

  现代有机催化的一个组成部分是硫脲催化剂的开发和应用。在此，作为我们旨在开发环丙烯催化剂的计划的一部分，已报道了同时具有阳离子氢键供体和静电特性的硫脲-环丙烯有机催化剂的合成。该硫脲有机催化剂的用途在使用苯酚，伯醇，仲醇和叔醇的吡喃酰化反应中，在操作简单，温和的反应条件下，可在较宽的底物范围内进行应用。发现添加苯甲酸作为促进协同布朗斯台德酸催化的助催化剂对于涉及酚和高级取代的醇的反应是有价值的。机械研究，包括动力学和1结合密度泛函理论计算的H NMR结合研究被描述为共同支持布朗斯台德酸催化模式。
• [EN] MACROCYCLIC INDOLE DERIVATIVES FOR THE TREATMENT OF HEPATITIS C INFECTIONS<br/>[FR] DÉRIVÉS MACROCYCLIQUES D'INDOLE POUR LE TRAITEMENT DES INFECTIONS D'HÉPATITE C
  申请人：ANGELETTI P IST RICHERCHE BIO

  公开号：WO2009010783A1

  公开（公告）日：2009-01-22

  A class of macrocyclic compounds of formula (I), wherein R7, R9, B, F, M, Q, W, Y and Z are defined herein, that are useful as inhibitors of viral proteases, particularly the hepatitis C virus (HCV) NS3 protease, are provided. Also provided are processes for the synthesis and use of such 5 macrocyclic compounds for treating or preventing HCV infection.

  提供一类宏环化合物的化学式(I)，其中R7、R9、B、F、M、Q、W、Y和Z的定义如下，这些化合物可用作病毒蛋白酶抑制剂，特别是对乙型肝炎病毒（HCV）NS3蛋白酶的抑制剂。还提供了合成和使用这些5种宏环化合物的方法，用于治疗或预防HCV感染。