5-氯-2-羟基苯基硼酸 | 89488-25-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-氯-2-羟基苯基硼酸
• 中文别名: 5-氯-2-羟基苯硼酸；2-羟基-5-氯苯硼酸
• 英文名称: 5-chloro-2-hydroxyphenylboronic acid
• 英文别名: 2-hydroxy-5-chlorophenylboronic acid；(5-chloranyl-2-oxidanyl-phenyl)boronic acid；(5-chloro-2-hydroxyphenyl)boronic acid
• CAS: 89488-25-5
• 化学式: C₆H₆BClO₃
• mdl: MFCD06659863
• 分子量: 172.376
• InChiKey: GGZASRFCRAZNPO-UHFFFAOYSA-N

物化性质

• 熔点：
  166-170
• 沸点：
  369.3±52.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S39
• 危险类别码：
  R41
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  存储条件为2-8°C，并需置于惰性气体环境中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
5-Chloro-2-hydroxyphenylboronic acid
Product Name:
Synonyms: 2-Borono-4-chlorophenol

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
5-Chloro-2-hydroxyphenylboronic acid
Ingredient name:
CAS number: 89488-25-5

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

---

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.
Storage: Store in closed vessels, refrigerated.

---

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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H6BClO3
Molecular weight: 172.4

---

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.

---

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

制备方法与用途

简介

5-氯-2-羟基苯基硼酸是一种有机中间体，有文献报道其可通过将5-氯-2-甲氧基苯基硼酸作为原料，在脱去甲基后得到。

制备

将10.0克（53.6毫摩尔）的5-氯-2-甲氧基苯基硼酸溶于100毫升二氯甲烷中，并冷却至5-10℃。随后，使用均压滴液漏斗在30分钟内逐滴滴加100毫升1M三溴化硼的二氯甲烷溶液。完成滴加后，在室温下搅拌反应混合物30分钟。

当反应完成后，将上述混合物缓慢滴入到600毫升冰冷的饱和碳酸氢钠溶液中，并在室温下继续搅拌1小时。分离出有机层（DCM），并将水层冷却至10-15℃。然后向该冷却后的水层加入1N稀盐酸溶液，形成沉淀。固体通过真空过滤收集并干燥，最终获得9克产物，产率为97%。

反应信息

• 作为反应物：
  描述：

  5-氯-2-羟基苯基硼酸 以 二甲基亚砜 为溶剂， 反应 18.0h， 以95%的产率得到对氯苯酚
  参考文献：
  名称：

  Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups

  摘要：

  The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by sigma-bond metathesis.

  DOI：

  10.1021/jo402174v
• 作为产物：
  描述：

  5-氯-2-甲氧基苯硼酸 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 5-氯-2-羟基苯基硼酸
  参考文献：
  名称：

  Rh / Pd催化与手性和非手性配体：氮杂二氢二苯并xepines的多米诺合成。

  摘要：

  多米诺骨牌游戏：通过在单个锅中将Rh催化的芳基化和Pd催化的C-O偶联相结合，描述了合成氮杂二氢二苯并xepinepines的合成途径。首次实现了将手性和非手性配体结合到两组分，两种金属的转化中的能力，从而使产品具有中等至良好的收率，并具有出色的对映选择性。

  DOI：

  10.1002/anie.201303659

文献信息

• Chemical Compounds
  申请人：Brown Alan Daniel

  公开号：US20120010182A1

  公开（公告）日：2012-01-12

  The invention relates to sulfonamide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to new sulfonamide Nav1.7 inhibitors of formula (I): or pharmaceutically acceptable salts thereof, wherein Z 1 , R a , R b , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the description. Nav 1.7 inhibitors are potentially useful in the treatment of a wide range of disorders, particularly pain.

  该发明涉及磺胺衍生物，其在医学上的应用，含有它们的组合物，其制备方法以及用于这些方法的中间体。 更具体地，该发明涉及公式（I）的新磺胺基Nav1.7抑制剂： 或其药学上可接受的盐，其中Z 1 ，R a ，R b ，R 1 ，R 2 ，R 3 ，R 4 和R 5 如描述中所定义。 Nav 1.7抑制剂在治疗各种疾病，特别是疼痛方面具有潜在用途。
• [EN] INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] INHIBITEURS DE RÉPLICATION DU VIRUS D'IMMUNODÉFICIENCE HUMAINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014028384A1

  公开（公告）日：2014-02-20

  The disclosure generally relates to compounds of formula (I), including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compounds, and methods for using these compounds in the treatment of HIV infection.

  该公开涉及到式(I)的化合物，包括用于治疗人类免疫缺陷病毒（HIV）感染的组合物和方法。该公开提供了HIV的新型抑制剂，包含这些化合物的药物组合物，以及使用这些化合物治疗HIV感染的方法。
• [EN] BIARYL ETHER SULFONAMIDES AND THEIR USE AS THERAPEUTIC AGENTS<br/>[FR] BIARYLÉTHERSULFONAMIDES ET LEUR UTILISATION EN TANT QU'AGENTS THÉRAPEUTIQUES
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2013064984A1

  公开（公告）日：2013-05-10

  This invention is directed to biaryl ether sulfonamides, or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.

  这项发明涉及联苯醚磺酰胺，或其药用可接受的盐、溶剂合物或前药，用于治疗和/或预防钠通道介导的疾病或症状，如疼痛。
• [EN] EIF4E-INHIBITING 4-OXO-3,4-DIHYDROPYRIDO[3,4-D]PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE 4-OXO-3,4-DIHYDROPYRIDO[3,4-D]PYRIMIDINE INHIBANT EIF4E
  申请人：EFFECTOR THERAPEUTICS INC

  公开号：WO2021003157A1

  公开（公告）日：2021-01-07

  The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X1, X2, X3, X4, X5, X6, Q, L1, L2, Y, R1, R2, R3, R4, R5, R6, R7, R8 and rings A, B and C are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4e and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

  本发明提供了根据式I合成的化合物、药用可接受的配方和用途，或其立体异构体、互变异构体或药用可接受的盐。对于式I化合物，X1、X2、X3、X4、X5、X6、Q、L1、L2、Y、R1、R2、R3、R4、R5、R6、R7、R8和环A、B和C的定义如规范中所述。创新的式I化合物是eIF4e的抑制剂，并在许多治疗应用中发挥作用，包括但不限于治疗炎症和各种癌症。
• [EN] BENZENESULFONAMIDES USEFUL AS SODIUM CHANNEL INHIBITORS<br/>[FR] BENZÈNESULFONAMIDES UTILES EN TANT QU'INHIBITEURS DES CANAUX SODIQUES
  申请人：PFIZER

  公开号：WO2015181797A1

  公开（公告）日：2015-12-03

  The invention relates to sulfonamide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to a new sulfonamide Nav1.7 inhibitors of formula (I), or a pharmaceutically acceptable salt thereof, wherein X, R1, R2, R3a, R3b and R4 are as defined in the description. Nav 1.7 inhibitors are potentially useful in the treatment of a wide range of disorders, particularly pain.

  本发明涉及磺酰胺衍生物，它们在医学中的应用，含有它们的组合物，它们的制备过程以及在这些过程中使用的中间体。更具体地说，本发明涉及一种新的磺酰胺Nav1.7抑制剂，其化学式为(I)或其药用可接受的盐，其中X、R1、R2、R3a、R3b和R4如描述中定义。Nav 1.7抑制剂在治疗广泛疾病，特别是疼痛方面具有潜在用途。