2-羟基-[1,1-联苯]-4-甲醛 | 400744-38-9

• 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-羟基-[1,1-联苯]-4-甲醛
• 英文名称: 2'-hydroxy-[1,1'-biphenyl]-4-carbaldehyde
• 英文别名: 2-(4-Formylphenyl)phenol；4-(2-hydroxyphenyl)benzaldehyde
• CAS: 400744-38-9
• 化学式: C₁₃H₁₀O₂
• mdl: MFCD06801753
• 分子量: 198.221
• InChiKey: JSBVZTOUPUKBJG-UHFFFAOYSA-N

物化性质

• 沸点：
  361.1±25.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-(4-Formylphenyl)phenol
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-(4-Formylphenyl)phenol
CAS number: 400744-38-9

---

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: C13H10O2
Molecular weight: 198.2

---

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

反应信息

• 作为反应物：
  描述：

  1-碘-3-硝基苯 、 2-羟基-[1,1-联苯]-4-甲醛 在 palladium diacetate 、 溶剂黄146 、 silver(l) oxide 作用下， 反应 40.0h， 以80%的产率得到2-hydroxy-3''-nitro-1,1':2',1''-terphenyl-4'-carbaldehyde
  参考文献：
  名称：

  钯催化的羟基定向区域选择性单芳基化 2-羟基联苯为 2-羟基-邻三联苯

  摘要：

  提出了钯催化的羟基辅助区域选择性单芳基化 2-羟基联苯为 2-羟基-邻三联苯。目前的方法适用于范围广泛的 2-羟基联苯和碘芳烃，并以良好到优异的产率提供了各种 2-羟基邻三联苯。

  DOI：

  10.1002/ejoc.201801637
• 作为产物：
  描述：

  2-羟基苯硼酸 、 对溴苯甲醛 在 C₂₂H₃₂Cl₂N₄Pd 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以90%的产率得到2-羟基-[1,1-联苯]-4-甲醛
  参考文献：
  名称：

  苯并咪唑鎓-吡唑-钯（II）配合物：铃木，Heck和Sonogashira反应的新型高效催化剂

  摘要：

  已经方便地制备了三种不对称的苯并咪唑-吡唑NN配体2-（1-丙基苯并咪唑基甲基）-3，5-二-R-吡唑（R ＝ H，Me，t- Bu）并对其结构进行了分析。R = Me化合物在223 K处的固体晶格堆积显示出一维“ Z字形”水链，该水链通过N⋅⋅⋅HO和OH⋅⋅⋅O键被有机分子通道稳定化。这些杂化的配体加到钯（II）中，从而获得高收率的空气稳定复合物，该复合物已通过NMR，ESI和X射线单晶晶体学进行了全面表征。它们是室温下的活性Suzuki催化剂，可将未活化的芳基溴化物和5或6元杂芳基溴化物与芳基硼酸交叉偶联，其周转频率（TOF）高达60,000 h -1。它们的催化效率明显优于CN卡宾-咪唑类似物。这些催化剂在芳基溴化物的Heck和Sonogashira交叉偶联反应中也有活性，以高收率得到所需产物。这些结果表明，这些Pd（II）与N基杂化配体的配合物是适用于有氧条件下不同类型的交叉偶联反应的通用且有效的催化剂。

  DOI：

  10.1002/adsc.200800356

文献信息

• Synthesis of Dibenzopyranones through Palladium-Catalyzed Directed C-H Activation/Carbonylation of 2-Arylphenols
  作者：Shuang Luo、Fei-Xian Luo、Xi-Sha Zhang、Zhang-Jie Shi

  DOI：10.1002/anie.201304295

  日期：2013.9.27

  Dibenzopyranones were synthesized by a palladium‐catalyzed phenol‐directed C–H activation/carbonylation of 2‐phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air.

  二苯并吡喃酮是在CO存在下，通过钯催化的苯酚引导的2-苯基苯酚衍生物的C–H活化/羰基化反应合成的。Pd（OAc）2作为催化剂，Cu（OAc）2作为催化剂氧化剂。空气的存在。
• Visible-light-driven C(sp²)–H arylation of phenols with arylbromides enabled by electron donor–acceptor excitation
  作者：Da-Liang Zhu、Shan Jiang、David James Young、Qi Wu、Hai-Yan Li、Hong-Xi Li

  DOI：10.1039/d1cc07127k

  日期：——

  We herein reported an efficient, catalyst-free, and visible-light-induced C(sp²)–H arylation of unprotected phenols with aryl bromides enabled by in situ generated electron donor–acceptor complexes.

  我们在此报告了一种高效、无催化剂、可见光诱导的无保护酚与芳基溴化物的C(sp2)–H芳基化反应，该反应由原位生成的电子给体-受体复合物实现。
• 2-(Fluoromethoxy)-4′-(<i>S</i>-methanesulfonimidoyl)-1,1′-biphenyl (UCM-1306), an Orally Bioavailable Positive Allosteric Modulator of the Human Dopamine D₁ Receptor for Parkinson’s Disease
  作者：Javier García-Cárceles、Henar Vázquez-Villa、José Brea、David Ladron de Guevara-Miranda、Giovanni Cincilla、Melchor Sánchez-Martínez、Anabel Sánchez-Merino、Sergio Algar、María Teresa de los Frailes、Richard S. Roberts、Juan A. Ballesteros、Fernando Rodríguez de Fonseca、Bellinda Benhamú、María I. Loza、María L. López-Rodríguez

  DOI：10.1021/acs.jmedchem.2c00949

  日期：2022.9.22

  In search for selective modulators of the D1 receptor, the screening of a chemical library and subsequent medicinal chemistry program around an identified hit resulted in new synthetic compound 26 [UCM-1306, 2-(fluoromethoxy)-4′-(S-methanesulfonimidoyl)-1,1′-biphenyl] that increases the dopamine maximal effect in a dose-dependent manner in human and mouse D1 receptors, is inactive in the absence of dopamine

  用l - DOPA 替代多巴胺引起的耐受性发展和用正构激动剂激活多巴胺能受体后的治疗缺陷揭示了对安全和有效治疗帕金森病的重大未满足需求。为了寻找 D 1受体的选择性调节剂，化学文库的筛选和随后围绕已识别命中的药物化学程序产生了新的合成化合物26 [UCM-1306, 2-(fluoromethoxy)-4'-( S -methanesulfonimidoyl )-1,1'-联苯] 在人和小鼠中以剂量依赖性方式增加多巴胺的最大效应 D 1受体，在没有多巴胺的情况下是无活性的，调节多巴胺对受体的亲和力，表现出亚型选择性，并表现出与正构配体的低结合竞争。新的变构调节剂可增强可卡因诱导的运动并增强l- DOPA 恢复口服给药后再血平化小鼠运动活动降低的能力。化合物26的行为支持 D 1​​ 受体的正变构调节剂作为帕金森病的有希望的治疗方法的兴趣。
• Pd-catalyzed regioselective rollover dual C–H annulation cascade: facile approach to phenanthrene derivatives
  作者：Muniganti Naveen Kumar、Vavilapalli Suresh、Attunuri Nagireddy、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1039/d3cc02523c

  日期：——

  Annulations of unsaturated systems through C–H activation represent a powerful tool for producing multicyclic scaffolds. Having coordinating centers in both annulation partners (a dual coordination strategy) would afford remarkable selectivities in the outcomes. Along this concept, we report herein a Pd-catalyzed regioselective rollover cascade dual C–H annulation of o-arylphenols with alkynols for

  通过 C-H 活化形成不饱和系统是生产多环支架的有力工具。在两个环形合作伙伴中拥有协调中心（双重协调策略）将为结果提供显着的选择性。沿着这个概念，我们在此报道了一种钯催化的邻芳基酚与炔醇的区域选择性翻转级联双C-H环化，用于构建菲支架。进行对照、KIE 和氘化研究以确定反应机理，并进行下游转化和放大反应以评估转化的稳健性。
• Procédé de préparation de dérivés aromatiques hydroxylés par la réaction de Bayer-Villiger
  申请人：RHONE-POULENC CHIMIE

  公开号：EP0320346A2

  公开（公告）日：1989-06-14

  La présente invention concerne un procédé de préparation de dérivés aromatiques hydroxylés par la réaction de Baeyer-Villiger caractérisé en ce que dans une première étape on forme une solution d'acide percarboxylique, dans une deuxième étape on ajoute à la solution précédente une arylcétone ou un aldéhyde aromatique. Les dérivés hydroxylés obtenus sont utilisés dans toute l'industrie chimique des polymères, pharmaceutique ou phytosanitaire.

  本发明涉及一种通过 Baeyer-Villiger 反应制备羟基化芳香族衍生物的工艺，其特 点是 第一步，形成过羧酸溶液、 在第二步中，向前述溶液中加入芳基酮或芳香醛。 得到的羟基化衍生物可用于化学、聚合物、制药和植物检疫行业。