4-(2-氰基异丙基)苯基硼酸 | 850568-67-1

• 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-(2-氰基异丙基)苯基硼酸
• 中文别名: B-[4-(1-氰基-1-甲基乙基)苯基]-硼酸；4-(2-氰基-2-丙基)苯硼酸
• 英文名称: [4-(1-cyano-1-methylethyl)phenyl]boronic acid
• 英文别名: (4-(2-cyanopropan-2-yl)phenyl)boronic acid；2-(4-Boronophenyl)-2-methylpropanenitrile；[4-(2-cyanopropan-2-yl)phenyl]boronic acid
• CAS: 850568-67-1
• 化学式: C₁₀H₁₂BNO₂
• mdl: MFCD06659832
• 分子量: 189.022
• InChiKey: BNXBFDTWYHAEIR-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148
• 沸点：
  370.0±44.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.2
• 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
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(2-Cyanopropan-2-yl)phenylboronic acid
Synonyms: (4-boronophenyl)dimethylacetonitrile; 2-(4-Boronophenyl)-2-methylpropanenitrile

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(2-Cyanopropan-2-yl)phenylboronic acid
CAS number: 850568-67-1

---

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.

---

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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H12BNO2
Molecular weight: 189.0

---

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.

---

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：

  4-(2-氰基异丙基)苯基硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 16.0h， 生成 2-[4-(2-amino-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)-phenyl]-2-methyl-propionitrile
  参考文献：
  名称：

  [EN] TRIAZOLOPYRAZINE DERIVATIVES
  [FR] DÉRIVÉS DE TRIAZOLOPYRAZINE

  摘要：

  式(I)中R1、R2和R4具有权利要求1中所指示的含义的化合物是GCN2的抑制剂，可用于治疗癌症。

  公开号：

  WO2013131609A1
• 作为产物：
  描述：

  硼酸三甲酯 、 2-(4-溴苯基)-2-甲基丙腈 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 4-(2-氰基异丙基)苯基硼酸
  参考文献：
  名称：

  Metabolically Stable tert-Butyl Replacement

  摘要：

  Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.

  DOI：

  10.1021/ml400045j

文献信息

• PHARMACEUTICAL COMPOSITION AND THE USE THEREOF, AND APPLICATION REGIME OF SAID PHARMACEUTICAL COMPOSITION FOR ON-DEMAND CONTRACEPTION
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160089364A1

  公开（公告）日：2016-03-31

  The invention relates to a pharmaceutical composition for non-hormonal, on-demand contraception and to processes for preparing this pharmaceutical composition. The latter comprises 2H-indazole as novel EP2 receptor antagonists in combination with COX inhibitors. The invention furthermore provides a method for non-hormonal female-controlled on-demand contraception where a pharmaceutical composition comprising EP2 receptor antagonists in combination with COX inhibitors is taken on demand prior to expected sexual intercourse.

  这项发明涉及一种用于非激素、按需避孕的药物组合物，以及制备该药物组合物的方法。后者包括2H-吲哚唑作为新型EP2受体拮抗剂，与COX抑制剂结合使用。该发明还提供了一种非激素女性控制的按需避孕方法，其中在预期性交前按需服用含有EP2受体拮抗剂与COX抑制剂的药物组合物。
• Novel Selective Approach to Terminally Substituted [<i>n</i> ]Dendralenes
  作者：Peter Polák、Tomáš Tobrman

  DOI：10.1002/ejoc.201801522

  日期：2019.2.7

  A methodology for the synthesis of terminally substituted [3]‐ and [4]dendralenes, as well as 2,3‐disubstituted buta‐1,3‐dienes has been prepared. This involves the preparation of 1,2‐disubstituted cyclobutenes from readily available 2‐bromocyclobutanone and the subsequent thermal ring‐opening reactions.

  制备了末端取代的[3]-和[4]树枝状烯类以及2,3-二取代的buta-1,3-二烯的合成方法。这涉及从容易获得的2-溴环丁酮制备1,2-二取代的环丁烯，以及随后的热开环反应。
• CYANOINDAZOLE COMPOUNDS AND USES THEREOF
  申请人：Incyte Corporation

  公开号：US20190076401A1

  公开（公告）日：2019-03-14

  Disclosed are compounds of Formula (I), methods of using the compounds for inhibiting HPK1 activity and pharmaceutical compositions comprising such compounds. The compounds are useful in treating, preventing or ameliorating diseases or disorders associated with HPK1 activity such as cancer.

  揭示了式（I）的化合物，使用这些化合物抑制HPK1活性的方法以及包含这些化合物的药物组合物。这些化合物在治疗、预防或改善与HPK1活性相关的疾病或障碍，如癌症方面具有用处。
• Bench-Stable Sulfoxide-Based Boronates: Preparation and Application in a Tandem Suzuki Reaction
  作者：Marek Čubiňák、Václav Eigner、Tomáš Tobrman

  DOI：10.1002/adsc.201801000

  日期：2018.12.3

  A set of novel aromatic and heteroaromatic bench‐stable sulfoxide‐based boronates was prepared. The structure of the boronates was established by means of X‐ray crystallography, and the prepared boronates were successively used in Suzuki cross‐coupling reactions under different conditions. We also developed a tandem Suzuki reaction so that a base is generated during the nucleophilic addition of Grignard

  制备了一组新型的芳族和杂芳族台稳亚砜基硼酸盐。通过X射线晶体学确定硼酸盐的结构，并将所制备的硼酸盐依次用于不同条件下的Suzuki交叉偶联反应。我们还开发了串联Suzuki反应，以便在格氏试剂向4-溴苯甲醛的亲核加成过程中生成碱基。在外部无碱条件下，将形成的中间体与制备的硼酸盐和硼酸顺利偶联。
• The synthesis of polysubstituted indoles from 3-bromo-2-indolyl phosphates
  作者：Peter Polák、Tomáš Tobrman

  DOI：10.1039/c7ob01127j

  日期：——

  A novel methodology for the synthesis of functionalised indoles based on the cross-coupling reactions of 3-bromo-2-indolyl phosphates is described. The preparation involves the conversion of easily available 2-oxindoles to 3,3-dibromo-2-oxindoles followed by the Perkow reaction affording 3-bromo-2-indolyl phosphates. Then bromine atom is substituted regioselectively by the Suzuki coupling reaction

  描述了一种基于3-溴-2-吲哚磷酸酯的交叉偶联反应合成官能化吲哚的新方法。制备涉及将容易获得的2-氧吲哚转化为3，3-二溴-2-氧吲哚，然后进行Perkow反应，得到3-溴-2-吲哚基磷酸酯。然后通过Suzuki偶联反应将溴原子区域选择性地取代。我们观察到氯化铝促进了3-取代的-2-吲哚基磷酸与有机锌试剂的反应，最终提供了2,3-二取代的吲哚。由易于获得的物质合成生物活性分子证明了该方法的整体多样性和效率。