4-异丁基苯硼酸 | 153624-38-5

• 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 - 苯和取代衍生物
• 中文名称: 4-异丁基苯硼酸
• 中文别名: 异丁基苯硼酸；4-异丁基苯基硼酸；对异丁基苯硼酸
• 英文名称: 4-isobutyl-phenylboronic acid
• 英文别名: 4-Isobutylphenylboronic acid；[4-(2-methylpropyl)phenyl]boronic acid
• CAS: 153624-38-5
• 化学式: C₁₀H₁₅BO₂
• 分子量: 178.039
• InChiKey: YZSPHVWALUJQNK-UHFFFAOYSA-N

物化性质

• 熔点：
  117-120°C
• 沸点：
  306.5±35.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  29319090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Isobutylphenylboronic acid
Product Name:
Synonyms: 4-(2-Methylpropyl)phenylboronic acid

---

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.
4-Isobutylphenylboronic acid
Ingredient name:
CAS number: 153624-38-5

---

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:

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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.

---

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.

---

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: C10H15BO2
Molecular weight: 178.0

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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.

---

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.

---

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：

  4-异丁基苯硼酸 在 六氟异丙醇 、 N-nitrosaccharin 作用下， 反应 19.0h， 以84%的产率得到1-(2-甲基丙基)-4-硝基苯
  参考文献：
  名称：

  N-硝基杂环：用于芳基和杂芳基硼酸的催化Ipso硝化的稳定型有机试剂。

  摘要：

  光催化与通过不含金属的协议来访问各种芳族和杂芳族硝基化合物本位基于非金属使用被开发容易得到的硼酸衍生物的-nitration，长凳稳定的，并可回收硝化试剂。这些方法操作简便，温和，区域选择性，并且具有出色的官能团相容性，可提供高达99％的收率的所需产品。

  DOI：

  10.1021/acs.orglett.0c00671
• 作为产物：
  描述：

  硼酸三甲酯 、 (1-溴-2-甲基丙基)苯 在 盐酸 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以2.3 g (46%)的产率得到4-异丁基苯硼酸
  参考文献：
  名称：

  Phenyl sulfonamide endothelin antagonists

  摘要：

  式##STR1##的化合物抑制内皮素的活性。符号的定义如下：R.sup.1，R.sup.2和R.sup.3分别独立地是(a) 氢，除了R.sup.1不是氢；(b) 烷基，烯基，炔基，烷氧基，环烷基，环烷基烷基，环烯基，环烯基烷基，芳基，芳氧基，芳基烷基或芳基烷氧基，其中任何一个可能被Z.sup.1，Z.sup.2和Z.sup.3取代；(c) 卤素；(d) 羟基；(e) 氰基；(f) 硝基；(g) --C(O)H或--C(O)R.sup.6；(h) --CO.sub.2 H或--CO.sub.2 R.sup.6；(i) --SH，--S(O).sub.n R.sup.6，--S(O).sub.m --OH，--S(O).sub.m --OR.sup.6，--O--S(O).sub.m --R.sup.6，--O--S(O).sub.m --OH或--O--S(O).sub.m --OR.sup.6；(j) --Z.sup.4 --NR.sup.7 R.sup.8；或(k) --Z.sup.4 --N(R.sup.11 --Z.sup.5 --NR.sup.9 R.sup.10；其余符号如规范中定义。

  公开号：

  US05514696A1

文献信息

• Biphenylsulfonamide Endothelin Antagonists:  Structure−Activity Relationships of a Series of Mono- and Disubstituted Analogues and Pharmacology of the Orally Active Endothelin Antagonist 2‘-Amino-<i>N</i>- (3,4-dimethyl-5-isoxazolyl)-4‘-(2-methylpropyl)[1,1‘-biphenyl]-2-sulfonamide (BMS-187308)
  作者：Natesan Murugesan、Zhengxiang Gu、Philip D. Stein、Sharon Bisaha、Steve Spergel、Ravi Girotra、Ving G. Lee、John Lloyd、Raj N. Misra、Joan Schmidt、Arvind Mathur、Leslie Stratton、Yolanda F. Kelly、Eileen Bird、Tom Waldron、Eddie C.-K. Liu、Rongan Zhang、Helen Lee、Randy Serafino、Benoni Abboa-Offei、Parker Mathers、Mary Giancarli、Andrea Ann Seymour、Maria L. Webb、Suzanne Moreland、Joel C. Barrish、John T. Hunt

  DOI：10.1021/jm970872k

  日期：1998.12.1

  Substitution at the ortho position of N-(3,4-dimethyl-5-isoxazolyl) benzenesulfonamide led to the identification of the biphenylsulfonamides as a novel series of endothelin-A (ETA) selective antagonists. Appropriate substitutions on the pendant phenyl ring led to improved binding as well as functional activity. A hydrophobic group such as isobutyl or isopropoxyl was found to be optimal at the 4'-position

  N-（3,4-二甲基-5-异恶唑基）苯磺酰胺在邻位的取代导致将联苯磺酰胺鉴定为新型的内皮素-A（ETA）选择拮抗剂。苯环侧基上的适当取代导致改进的结合以及功能活性。发现疏水基团例如异丁基或异丙氧基在4'-位是最佳的。在2'-位引入氨基也导致改进的类似物。最佳的4'-异丁基取代基与2'-氨基官能团的结合提供了具有改善的ETA结合亲和力和功能活性的类似物（20，BMS-187308）。化合物20在抑制大鼠ET-1输注引起的升压作用方面也具有良好的口服活性。
• Identification and SAR exploration of a novel series of Legumain inhibitors
  作者：Sharon L. Eddie、Aaron Gregson、Emma Graham、Stephanie Burton、Timothy Harrison、Roberta Burden、Christopher J. Scott、Paul B. Mullan、Rich Williams

  DOI：10.1016/j.bmcl.2019.03.019

  日期：2019.6

  This letter describes the development of a series of potent and selective small molecule Legumain inhibitors suitable as chemical probes for in vitro experiments. Our previous research had identified a dipeptide inhibitor utilizing a semi-reversible cyano warhead that generated 2, a cell active inhibitor. This work explores an alternative P2-P3 linker and further SAR exploration of the P3 group which

  这封信描述了一系列有效的和选择性的小分子Legumain抑制剂的开发，这些抑制剂适合用作体外实验的化学探针。我们之前的研究已经确定了一种利用半可逆的氰基战斗部产生的二肽抑制剂，该头可产生2种细胞活性抑制剂。这项工作探索了另一种P2-P3连接子，并进一步探索了P3基团的SAR，从而鉴定了16i，这是一种具有出色的理化特性的高效抑制剂。
• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2017084630A1

  公开（公告）日：2017-05-26

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• Enantioselective Palladium‐Catalyzed Cross‐Coupling of α‐Bromo Carboxamides and Aryl Boronic Acids
  作者：Bowen Li、Tiejun Li、Muinat A. Aliyu、Zhen Hua Li、Wenjun Tang

  DOI：10.1002/anie.201905174

  日期：2019.8.12

  report an enantioselective palladium‐catalyzed cross‐coupling between α‐bromo carboxamides and aryl boronic acids, generating a series of chiral α‐aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium‐catalyzed coupling of α‐bromo carbonyl compounds

  我们在本文中报道了α-溴羧酰胺与芳基硼酸之间的对映选择性钯催化的交叉偶联，以高收率和优异的对映选择性产生了一系列手性α-芳基羧酰胺。手性P，P = O配体的发展对于克服第二个金属转移问题至关重要，并且可以实现α-溴代羰基化合物的第一个不对称钯催化偶联。
• Multicomponent Assembly of Boron-Based Dendritic Nanostructures
  作者：Nicolas Christinat、Rosario Scopelliti、Kay Severin

  DOI：10.1021/jo062607p

  日期：2007.3.1

  construction of boron-based macrocycles and dendrimers is described. Condensation of aryl- and alkylboronic acids with 3,4-dihydroxypyridine is shown to give pentameric macrocycles in which five boronate esters are connected by dative B−N bonds. Three macrocycles have been characterized crystallographically. The boron atoms of these assemblies represent chiral centers, and the assembly process is highly diastereoselective

  描述了一种用于构建基于硼的大环和树枝状大分子的新合成策略。芳基和烷基硼酸与3,4-二羟基吡啶的缩合显示出五聚体大环，其中五个硼酸酯通过B-N键连接。在晶体学上已经表征了三个大环。这些组装物中的硼原子代表手性中心，并且组装过程具有高度非对映选择性。氨基或醛基在芳基硼酸结构单元的间位上的连接不会干扰大环化。这允许分别在官能化的硼酸，二羟基吡啶配体和胺或醛之间进行多组分组装反应。3,5-二甲酰基苯基硼酸，3,4-二羟基吡啶和伯胺R-NH的反应图2（R ＝ Ph，Bn）给出了具有五聚体大环核和在其外围具有10个胺衍生的R基团的树枝状纳米结构。另一方面，将3，5-二甲酰基苯基硼酸与2，3-二羟基吡啶和树枝状的3，5-（苄氧基）苄基胺结合导致形成具有四聚体大环核和在其外围具有八个树枝状分子的树枝状聚合物。