2-氯-5-甲氧基苯硼酸 | 89694-46-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-氯-5-甲氧基苯硼酸
• 中文别名: 2-氯-5-甲氧基苯基硼酸
• 英文名称: 2-chloro-5-methoxyphenylboronic acid
• 英文别名: 2-chloro-5-methoxybenzeneboronic acid；(2-chloro-5-methoxyphenyl)boronic acid
• CAS: 89694-46-2
• 化学式: C₇H₈BClO₃
• 分子量: 186.403
• InChiKey: REFXAANPQCJZRY-UHFFFAOYSA-N

物化性质

• 熔点：
  106-110
• 沸点：
  354.8±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
2-Chloro-5-methoxyphenylboronic acid
Product Name:
Synonyms:

---

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.
2-Chloro-5-methoxyphenylboronic acid
Ingredient name:
CAS number: 89694-46-2

---

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: C7H8BClO3
Molecular weight: 186.4

---

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

反应信息

• 作为反应物：
  描述：

  2-氯-5-甲氧基苯硼酸 在 silver fluoride 、 C₄₁H₄₉I₂IrO₂ 、 copper(II) trifluoroacetate 、 calcium chloride 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (R)-(E)-7-(benzyloxy)-8-(2-chloro-5-methoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one O-(4-methylbenzyl) oxime
  参考文献：
  名称：

  铱（III）催化的阿托罗对映选择性氧化与芳基硼酯的 C−H 芳基化

  摘要：

  通过 C−H 键功能化进行的对映选择性联芳基偶合是一项新兴技术，允许直接构建轴向手性分子。这种方法很大程度上限于亲电偶联伙伴。我们报道了四氢萘酮衍生物与作为亲核组分的芳基硼酸酯配对的高度对映选择性 C−H 芳基化。该转化由手性环戊二烯基 (Cp x ) 铱 (III) 配合物催化，并通过高价环金属化铱物质的氧化增强还原消除来实现。

  DOI：

  10.1002/anie.202106403
• 作为产物：
  描述：

  3-甲氧基苯硼酸 在 N-氯代丁二酰亚胺 、 三苯基瞵硫 作用下， 以 氘代氯仿 、 氘代甲醇 为溶剂， 反应 0.33h， 以86%的产率得到2-氯-5-甲氧基苯硼酸
  参考文献：
  名称：

  实用的路易斯碱催化芳烃和杂环的亲电氯化反应

  摘要：

  公开了使用廉价且容易获得的N-卤代琥珀酰亚胺的温和的膦硫化物催化的芳烃和杂环的亲电子卤化。结果表明，该方法可以有效地氯化多种芳烃，包括简单的芳烃（如蒽）和杂环（如吲哚，吡咯并嘧啶和咪唑）。具有路易斯酸性部分的芳烃也被证明是可接受的，强调了该化学反应的温和性质。还发现路易斯碱催化可改善多种多样的芳族溴化反应和碘化反应。

  DOI：

  10.1021/acs.orglett.5b00186
• 作为试剂：
  描述：

  2,6-二氨基-3-碘吡啶 、 2-氯-5-甲氧基苯硼酸 在 2-氯-5-甲氧基苯硼酸 作用下， 以55的产率得到3-(2-chloro-5-methoxyphenyl)pyridine-2,6-diamine
  参考文献：
  名称：

  Pyridine derivatives

  摘要：

  本发明涉及式(I)的化合物及其药学上可接受的盐，制备这种化合物的过程中使用的中间体，含有这种化合物的组合物以及这种化合物用于治疗疼痛的用途。

  公开号：

  US08134007B2

文献信息

• [EN] ATROPISOMERISM FOR ENHANCED KINASE INHIBITOR SELECTIVITY<br/>[FR] ATROPISOMÉRISME POUR UNE SÉLECTIVITÉ AMÉLIORÉE DES INHIBITEURS DE KINASE
  申请人：SAN DIEGO STATE UNIV RESEARCH FOUNDATION

  公开号：WO2018237134A1

  公开（公告）日：2018-12-27

  The invention provides a series of conformationally stable and selective kinase inhibitors, and methods of using the kinase inhibitors. The effect of atropisomerism on kinase selectivity was assessed, finding improved selectivity compared to rapidly interconverting parent compounds. The compounds herein are atropisomers having increased kinase selectivity, and are for use in treating conditions that benefit from selective kinase inhibition.

  这项发明提供了一系列构象稳定且选择性激酶抑制剂，以及使用这些激酶抑制剂的方法。评估了扭曲异构体对激酶选择性的影响，发现与快速相互转化的母体化合物相比，选择性得到了改善。本文中的化合物是具有增强激酶选择性的扭曲异构体，用于治疗受益于选择性激酶抑制的疾病。
• Pyrimidine Derivatives As HSP90 Inhibitors
  申请人：Chessari Gianni

  公开号：US20090215777A1

  公开（公告）日：2009-08-27

  The invention provides a compound for use as an inhibitor of Hsp90, the compound having the formula (I): or salts, tautomers, solvates or N-oxides thereof; wherein: A is N or a group CR 3 ; R 1 is a monocyclic or bicyclic carbocyclic or heterocyclic ring of 5 to 10 ring members of which up to two ring members may be heteroatoms selected from N, O and S and the remainder are carbon atoms, the carbocyclic or heterocyclic ring being optionally substituted by one or more substituent groups independently selected from R 10 ; and R 2 , R 3 and R 10 are as defined in the claims.

  该发明提供了一种化合物，用作Hsp90的抑制剂，该化合物具有以下式（I）：或其盐、互变异构体、溶剂合物或N-氧化物；其中：A为N或CR基团；R1为由5至10个环成员组成的单环或双环碳环或杂环，其中最多两个环成员可以是从N、O和S中选择的杂原子，其余为碳原子，碳环或杂环可以选择地被一个或多个取代基独立地选择自R10的取代基取代；而R2、R3和R10如权利要求中所定义。
• [EN] DIBENZOTHIOPHENE DERIVATIVES AS DNA- PK INHIBITORS<br/>[FR] DÉRIVÉS DE DIBENZOTHIOPHÈNE EN TANT QU'INHIBITEURS D'ADN-PK
  申请人：KUDOS PHARM LTD

  公开号：WO2010136778A1

  公开（公告）日：2010-12-02

  Compound formula I: wherein: X1 and X2 may be either (a) C and O, (b) N and N, or (c) C and NH, where the dotted bonds represents a double bond in the appropriate location; R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; RN1 is selected from hydrogen and an optionally substituted C1-4 alkyl group; RC1 is selected from an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group; or RN1 and RC1 may together form an optionally substituted C2-4 alkylene group.

  化合物公式I：其中：X1和X2可以是（a）C和O，（b）N和N，或（c）C和NH，其中点线代表适当位置的双键；R1和R2分别从氢，可选择的取代的C1-7烷基基团，可选择的取代的C3-20杂环基团，或可选择的取代的C5-20芳基基团中独立选择，或者可以与它们附着的氮原子一起形成具有4至8个环原子的可选择取代的杂环环；RN1从氢和可选择的取代的C1-4烷基基团中选择；RC1从可选择的取代的C1-7烷基基团，可选择的取代的C3-20杂环基团，或可选择的取代的C5-20芳基基团中选择；或RN1和RC1可以一起形成一个可选择取代的C2-4烷基烃基团。
• A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls
  作者：Suzanne Willems、Georgios Toupalas、Julia C. Reisenbauer、Bill Morandi

  DOI：10.1039/d1cc00648g

  日期：——

  A cascade Suzuki–Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.

  已开发出可产生9,10-二氢菲的级联铃木-宫浦交叉偶联剂。使用具有不对称取代模式的联芳基，观察到全位点选择性。此外，烷基1,2-双硼烷频哪醇酯的这种交叉偶联通过具有完整立体保留的仲硼酸酯的挑战性偶联而进行。
• 10-(4-Phenylpiperazine-1-carbonyl)acridin-9(10H)-ones and related compounds: Synthesis, antiproliferative activity and inhibition of tubulin polymerization
  作者：Jana Waltemate、Igor Ivanov、Jahan B. Ghasemi、Elham Aghaee、Constantin Gabriel Daniliuc、Klaus Müller、Helge Prinz

  DOI：10.1016/j.bmcl.2020.127687

  日期：2021.1

  9(10H)-ones and N-benzoylated acridones were synthesized on the basis of a retrosynthetic approach. All newly synthesized compounds were tested for antiproliferative activity and interaction with tubulin. Several analogs potently inhibited tumor cell growth. Among the compounds tested, 10-(4-(3-methoxyphenyl)piperazine-1-carbonyl)acridin-9(10H)-one (17c) exhibited excellent growth inhibitory effects

  作为我们继续寻找微管蛋白聚合的有效抑制剂的一部分，基于 42 10-(4-苯基哌嗪-1-羰基)吖啶-9(10 H )-酮和N-苯甲酰化吖啶酮的两个新系列被合成逆合成方法。测试所有新合成的化合物的抗增殖活性和与微管蛋白的相互作用。几种类似物有效抑制肿瘤细胞生长。在测试的化合物中，10-（4-（3-甲氧基苯基）哌嗪-1-羰基）吖啶-9（10 H）-one ( 17c ) 对 93 种肿瘤细胞系表现出优异的生长抑制作用，平均 GI 50值 5.4 nM。我们能够证明强烈的细胞毒性作用是由微管蛋白聚合的破坏引起的，这得到了 EBI ( N , N'-亚乙基双（碘乙酰胺））测定以及癌细胞生长最有效的抑制剂被证明是最有效的微管蛋白聚合抑制剂这一事实。效力几乎可比或优于抗有丝分裂参考化合物的效力。与此密切相关的是，最活跃的类似物以低至 30 nM 的浓度抑制 G2/M 期的细胞循环并诱导 K562 白血