3-羟基-4-甲氧基苯腈 | 52805-46-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-羟基-4-甲氧基苯腈
• 中文别名: 3-羟基-4-甲氧基苯甲腈；3-羟基-4-甲氧基苄腈
• 英文名称: 2-methoxy-5-cyanophenol
• 英文别名: 3-hydroxy-4-methoxy benzonitrile；3-Hydroxy-4-methoxybenzonitrile
• CAS: 52805-46-6
• 化学式: C₈H₇NO₂
• mdl: MFCD02258854
• 分子量: 149.149
• InChiKey: ASQHIJLQYYFUDN-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  300.8±27.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 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：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 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：
  存储条件：室温、干燥且密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Hydroxy-4-methoxybenzonitrile
Synonyms: 5-Cyano-2-methoxyphenol

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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: 3-Hydroxy-4-methoxybenzonitrile
CAS number: 52805-46-6

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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: C8H7NO2
Molecular weight: 149.1

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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, nitrogen oxides.

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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

反应信息

• 作为反应物：
  描述：

  3-羟基-4-甲氧基苯腈 在 正丁基锂 、 borane dimethyl sulphide complex 、 硼酸三甲酯 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 阿普斯特
  参考文献：
  名称：

  一种阿普斯特的制备方法

  摘要：

  本发明涉及一种阿普斯特的制备方法，包括：3‑羟基‑4‑甲氧基苯甲醛为起始原料，经与盐酸羟胺反应得3‑羟基‑4‑甲氧基苯甲腈，与溴乙烷反应得3‑乙氧基‑4‑甲氧基苯甲腈，而后在正丁基锂作用与二甲基砜反应并在盐酸水溶液中水解得1‑(3‑乙氧基‑4‑甲氧基苯基)‑2‑(甲磺酰基)乙酮)；最后以S‑(‑)‑α,α‑二苯基‑2‑吡咯烷甲醇为手性催化剂，硼烷二甲硫醚溶液为还原剂，得手性S‑3‑乙氧基‑4‑甲氧基‑α‑[(甲磺酰基)甲基]苯甲醇，然后在三苯基膦和偶氮二甲酸二乙酯作用下与3‑乙酰胺基邻苯二甲酰亚胺反应即得。本发明有效简化了工艺，而且反应条件温和，产品的收率和纯度都较高，有利于规模化工业生产。

  公开号：

  CN105330586B
• 作为产物：
  描述：

  异香兰素 在 甲酸 、 sodium formate 、 硫酸羟胺 作用下， 反应 8.0h， 以88%的产率得到3-羟基-4-甲氧基苯腈
  参考文献：
  名称：

  合成[11C] Iressa作为表皮生长因子受体酪氨酸激酶的新型潜在PET癌症显像剂。

  摘要：

  Iressa（吉非替尼）是一种表皮生长因子受体酪氨酸激酶（EGFR-TK）的口服活性抑制剂，参与对癌细胞增殖，凋亡，修复和血管生成至关重要的细胞信号转导过程。[11C] Iressa最初被设计和合成为EGFR-TK的新型潜在正电子发射断层扫描（PET）癌症成像剂，放射化学产率为30-40％，轰击结束时（EOB）的比活为4.0-6.0 Ci / micromol。

  DOI：

  10.1016/j.bmcl.2006.04.080
• 作为试剂：
  描述：

  2-[Methyl-(2,3,5,6-tetrafluoropyridin-4-yl)amino]acetamide 、 3-羟基-4-甲氧基苯腈 在 3-羟基-4-甲氧基苯腈 作用下， 生成
  参考文献：
  名称：

  Benzamidine derivatives and their use as anti-coagulants

  摘要：

  本发明涉及苯甲酰胺衍生物，其可用作抗凝剂。本发明还涉及含有本发明化合物的制药组合物，以及使用这些化合物治疗由血栓活性特征的疾病状态的方法。

  公开号：

  US05691364A1

文献信息

• Identification and Structure-Activity Relationship Studies of Small-Molecule Inhibitors of the Methyllysine Reader Protein Spindlin1
  作者：Dina Robaa、Tobias Wagner、Chiara Luise、Luca Carlino、Joel McMillan、Ralf Flaig、Roland Schüle、Manfred Jung、Wolfgang Sippl

  DOI：10.1002/cmdc.201600362

  日期：2016.10.19

  therapeutic target. Small‐molecule inhibitors of Spindlin1 should be valuable as chemical probes as well as potential new therapeutics. We applied an iterative virtual screening campaign, encompassing structure‐ and ligand‐based approaches, to identify potential Spindlin1 inhibitors from databases of commercially available compounds. Our in silico studies coupled with in vitro testing were successful in

  甲基赖氨酸阅读蛋白 Spindlin1 与多种癌症的肿瘤发生有关，可能是一个有吸引力的新治疗靶点。Spindlin1 的小分子抑制剂作为化学探针和潜在的新疗法应该很有价值。我们应用了一个迭代虚拟筛选活动，包括基于结构和配体的方法，从市售化合物的数据库中识别潜在的 Spindlin1 抑制剂。我们的计算机模拟研究与体外测试相结合，成功识别了新型 Spindlin1 抑制剂。几种 4-氨基喹唑啉和喹唑啉硫酮衍生物属于活性命中化合物，这表明这些支架代表了用于开发 Spindlin1 抑制剂的有前景的先导结构。因此进行了随后的铅优化研究，并合成了两种铅支架的许多衍生物。这导致发现了 Spindlin1 的新型抑制剂，并有助于探索这些抑制剂系列的构效关系。
• Structure–activity relationship studies of SETD8 inhibitors
  作者：Anqi Ma、Wenyu Yu、Yan Xiong、Kyle V. Butler、Peter J. Brown、Jian Jin

  DOI：10.1039/c4md00317a

  日期：——

  Comprehensive SAR studies of the first substrate-competitive SETD8 inhibitor led to the discovery of interesting SAR trends and novel analogs.

  对第一个底物竞争性SETD8抑制剂的全面SAR研究揭示了有趣的SAR趋势和新颖的类似物。
• Design and Optimization of an Acyclic Amine Series of TRPV4 Antagonists by Electronic Modulation of Hydrogen Bond Interactions
  作者：Jaclyn R. Patterson、Lamont R. Terrell、Carla A. Donatelli、Dennis A. Holt、Larry J. Jolivette、Ralph A. Rivero、Theresa J. Roethke、Arthur Shu、Patrick Stoy、Guosen Ye、Mark Youngman、Brian G. Lawhorn

  DOI：10.1021/acs.jmedchem.0c01303

  日期：2020.12.10

  heart failure generated a novel series of acyclic amine inhibitors displaying exceptional potency and PK properties. The series arose through a scaffold hopping approach, which relied on use of an internal H-bond to replace a saturated heterocyclic ring. Optimization of the lead through investigation of both aryl regions revealed approaches to increase potency through substituents believed to enhance separate

  TRPV4作为治疗与心力衰竭相关的肺水肿的潜在靶标的研究产生了一系列新的无环胺抑制剂，这些抑制剂显示出非凡的效能和PK特性。该系列是通过脚手架跳跃方法产生的，该方法依靠内部氢键的使用来取代饱和的杂环。通过研究两个芳基区域对铅进行优化，揭示了通过取代基提高效力的方法，这些取代基被认为可以增强单独的分子内和分子间H键相互作用。通过电子调节苯磺酰胺可稳定胺和相邻苯磺酰胺之间拟议的内部氢键。在芳基醚部分，对位的腈取代基显示出对TRPV4识别的电子作用。最后，
• NBS mediated nitriles synthesis through CC double bond cleavage
  作者：Xiaolin Zong、Qing-Zhong Zheng、Ning Jiao

  DOI：10.1039/c3ob42118j

  日期：——

  An NBS mediated nitriles synthesis through CC double bond cleavage has been developed. TMSN3 was employed as the nitrogen source for this Cu(OAc)2 promoted nitrogenation reaction. This transformation has a relatively high regio-selectivity to form aromatic nitriles.

  一种通过碳碳双键断裂进行氰基化合物的NBS介导合成方法已经开发出来。在该Cu(OAc)2促进的氰基化反应中，采用了TMSN3作为氮源。该转化过程具有较高的区域选择性，能形成芳香族氰化合物。
• Optimization of gefitinib analogues with potent anticancer activity
  作者：Kai-Hao Yin、Yi-Han Hsieh、Rohidas S. Sulake、Su-Pei Wang、Jui-I. Chao、Chinpiao Chen

  DOI：10.1016/j.bmcl.2014.09.056

  日期：2014.11

  The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant

  EGFR中吉非替尼（Iressa）的相互作用是氢键和通过喹唑啉和苯胺环的范德华力。但是，由于吉非替尼的吗啉代基团电子强度较弱，因此排列较差。设计并合成了一系列新的吉非替尼哌嗪子基类似物，其中吗啉代基团被各种哌嗪子基团取代。他们中的大多数表明对人类癌细胞系具有显着的抗癌活性。特别是，化合物52 – 54对癌细胞具有极好的效力。已经开发了用于合成吉非替尼中间体的会聚合成方法，该中间体可导致吉非替尼以及许多类似物。