4-氯-3-羟基苯甲醛 | 56962-12-0

• 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 - 有机氧化合物
• 中文名称: 4-氯-3-羟基苯甲醛
• 英文名称: 4-chloro-3-hydroxybenzaldehyde
• 英文别名: 4-Chlor-3-hydroxy-benzaldehyd
• CAS: 56962-12-0
• 化学式: C₇H₅ClO₂
• 分子量: 156.569
• InChiKey: UJAFGNAOINNEKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• 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：
  2913000090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  温度：2-8℃，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-Chloro-3-hydroxy-benzaldehyde
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-Chloro-3-hydroxy-benzaldehyde
CAS number: 56962-12-0

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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: C7H5ClO2
Molecular weight: 156.6

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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 chloride.

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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

用途

4-氯-3-羟基苯甲醛可用作医药合成中间体。

制备

4-氯-3-羟基苯甲醛的制备如下：将1克（10毫摩尔）3-羟基苯甲醛溶解于50毫升乙腈中，分批加入3.4克（20毫摩尔）对甲苯磺酸。混合物在室温下搅拌5分钟后，再加入1.33克（10毫摩尔）NCS，继续在室温下搅拌2小时。随后，使用硫代硫酸钠水溶液淬灭反应混合物，并用乙酸乙酯和盐水洗涤。分离有机层后进行干燥并浓缩，得到粗产物。通过硅胶色谱法纯化该粗产物，采用石油醚/乙酸乙酯（10:1至5:1）作为洗脱剂，最终获得4-氯-3-羟基苯甲醛（310毫克，产率19.7%），为黄色固体。

反应信息

• 作为反应物：
  描述：

  4-氯-3-羟基苯甲醛 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 nickel chloride hexahydrate 、 palladium hydroxide, 20 wt% on carbon 、 ammonium acetate 、 氢气 、 sodium hexamethyldisilazane 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~105.0 ℃ 、344.75 kPa 条件下， 反应 24.0h， 生成 tert-butyl (R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  用于研究小鼠脑中GABA B受体的新型18 F标签放射性示踪剂的合成与评价

  摘要：

  已经合成了新的GABA B激动剂，巴氯芬的氟吡啶醚类似物，作为潜在的PET放射性示踪剂。具有最高抑制结合亲和力和最大激动剂响应的化合物（R）-4-氨基-3-（4-氯-3-（（2-氟吡啶-4--4-基）甲氧基）苯基）丁酸（1b）用18 F放射性标记，具有良好的放射化学收率，较高的放射化学纯度和较高的摩尔放射性。放射性标记的（R）-4-氨基-3-（4-氯-3-（（2- [ 18 [ F]氟吡啶-4-基）甲氧基）苯基）丁酸[ 18 F] 1b的区域脑分布在CD-1雄性小鼠中进行了研究。研究表明[ 18F] 1b进入老鼠的大脑（1％ID / g组织）。预先注射GABA B激动剂1a抑制了[ 18 F] 1b在小鼠大脑中的蓄积（35％），表明放射性示踪剂脑的摄取部分由GABA B受体介导。提出的数据证明了在啮齿动物中对GABA B受体成像的可行性，并证明了进一步开发GABA B PET示踪剂具有改善

  DOI：

  10.1021/acschemneuro.8b00038
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium dithionite 、 水 作用下， 生成 4-氯-3-羟基苯甲醛
  参考文献：
  名称：

  Hodgson; Beard, Journal of the Chemical Society, 1927, p. 2381

  摘要：

  DOI：

文献信息

• [EN] DIHYDROQUINOLIZINONES AS ANTIVIRALS<br/>[FR] DIHYDROQUINOLIZINONES À UTILISER EN TANT QU'ANTIVIRAUX
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2018154466A1

  公开（公告）日：2018-08-30

  Compounds, specifically hepatitis B virus and/or hepatitis D virus inhibitors, more specifically compounds that inhibit HBe antigen and HBs antigen in a subject, for the treatment of viral infections, and methods of preparing and using such compounds. Formula (I):

  化合物，具体来说是乙型肝炎病毒和/或丙型肝炎病毒抑制剂，更具体地说是抑制受试者体内HBe抗原和HBs抗原的化合物，用于治疗病毒感染，并且涉及制备和使用这类化合物的方法。化学式（I）:
• [EN] PYRAZOLE MAGL INHIBITORS<br/>[FR] INHIBITEURS PYRAZOLE DE MAGL
  申请人：ABIDE THERAPEUTICS INC

  公开号：WO2018217805A1

  公开（公告）日：2018-11-29

  Provided herein are pyrazole compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of monoacylglycerol lipase (MAGL). Furthermore, the subject compounds and compositions are useful for the treatment of pain.

  本文提供了吡唑化合物和包含该化合物的药物组合物。这些化合物和组合物可用作单酰基甘油酶（MAGL）的调节剂。此外，这些化合物和组合物可用于治疗疼痛。
• 5,6-BISARYL-2-PYRIDINE-CARBOXAMIDE DERIVATIVES, PREPARATION AND APPLICATION THEREOF IN THERAPEUTICS AS UROTENSIN II RECEPTOR ANTAGONISTS
  申请人：Altenburger Jean-Michel

  公开号：US20090318473A1

  公开（公告）日：2009-12-24

  The present invention relates to derivatives of 5,6-bisaryl-2-pyridine-carboxamide, their preparation and their application in therapeutics as antagonists of urotensin II receptors.

  本发明涉及5,6-双芳基-2-吡啶甲酰胺衍生物，其制备以及其作为尿苷Ⅱ受体拮抗剂在治疗学中的应用。
• The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae (<i>sensu</i> APGII)
  作者：Sianne Schwikkard、Hannah Whitmore、Kamakshi Sishtla、Rania S. Sulaiman、Trupti Shetty、Halesha D. Basavarajappa、Catherine Waller、Alaa Alqahtani、Lennart Frankemoelle、Andy Chapman、Neil Crouch、Wolfgang Wetschnig、Walter Knirsch、Jacky Andriantiana、Eduard Mas-Claret、Moses K. Langat、Dulcie Mulholland、Timothy W. Corson

  DOI：10.1021/acs.jnatprod.8b00989

  日期：2019.5.24

  of a group of naturally occurring homoisoflavonoids isolated from the family Hyacinthaceae and related synthetic compounds, chosen for synthesis based on structure-activity relationship observations. Several compounds showed interesting antiproliferative and antiangiogenic activities in vitro on retinal microvascular endothelial cells, a disease-relevant cell type, with the synthetic chromane, 46,

  眼睛中过多的血管形成与湿性年龄相关性黄斑变性、增殖性糖尿病视网膜病变、新生血管性青光眼和早产儿视网膜病变有关，这些都是导致失明的主要原因。迫切需要小分子抗血管生成药物来补充现有的生物制剂。先前已证明同异黄酮类化合物在内皮细胞中比其他细胞类型具有更有效的抗增殖活性。此外，它们在体外和体内的眼新生血管动物模型中表现出强大的抗血管生成潜力。在这里，我们测试了一组从风信子科中分离出来的天然同型异黄酮类化合物和相关合成化合物的抗血管生成活性，这些化合物是根据结构-活性关系观察选择进行合成的。几种化合物在体外对视网膜微血管内皮细胞（一种与疾病相关的细胞类型）显示出有趣的抗增殖和抗血管生成活性，其中合成苯并二氢吡喃 46 显示出最佳活性（GI50 为 2.3 × 10-4 μM）。
• Synthesis and antirhinovirus activity of 6-(dimethylamino)-2-(trifluoromethyl)-9-(substituted benzyl)-9H-purines
  作者：James L. Kelley、James A. Linn、J. W. T. Selway

  DOI：10.1021/jm00128a016

  日期：1989.8

  A series of 6-(dimethylamino)-2-(trifluoromethyl)-9-(substituted benzyl)purines was synthesized and tested for antirhinovirus activity. Most of the compounds were synthesized by alkylation of 6-chloro-2-(trifluoromethyl)-9H-purine with the appropriate benzyl halide followed by displacement of the chloro group with dimethylamine. Alternatively, 6-(dimethylamino)-2-(trifluoromethyl)purine was alkylated

  合成了一系列6-（二甲基氨基）-2-（三氟甲基）-9-（取代的苄基）嘌呤，并测试了其抗鼻病毒的活性。大多数化合物是通过6-氯-2-（三氟甲基）-9H-嘌呤与适当的苄基卤化物烷基化，然后用二甲胺取代氯基而合成的。或者，用适当的苄基卤将6-（二甲基氨基）-2-（三氟甲基）嘌呤烷基化。尽管几种不同的芳基取代基提供了针对鼻病毒1B血清型的IC50 = 0.03 microM的化合物，但同系物没有比母体2活性高得多。测试了23种化合物针对其他18种血清型的化合物，但均未显示出均匀的活性分布。