4-(正丙基氨甲酰基)苯硼酸 | 171922-46-6

• 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-(正丙基氨甲酰基)苯硼酸
• 中文别名: 4-(N-丙基甲酰氨)苯基硼酸
• 英文名称: 4-(propylcarbamoyl)phenylboronic acid
• 英文别名: (4-(Propylcarbamoyl)phenyl)boronic acid；[4-(propylcarbamoyl)phenyl]boronic acid
• CAS: 171922-46-6
• 化学式: C₁₀H₁₄BNO₃
• mdl: MFCD06656015
• 分子量: 207.037
• InChiKey: KWJCBWYHJKWCRD-UHFFFAOYSA-N

物化性质

• 熔点：
  210-214°C
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
4-(N-Propylaminocarbonyl)phenylboronic acid
Product Name:
Synonyms: N-Propyl 4-boronobenzamide

---

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-(N-Propylaminocarbonyl)phenylboronic acid
Ingredient name:
CAS number: 171922-46-6

---

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.

---

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: C10H14BNO3
Molecular weight: 207.0

---

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：

  (2,4-dibromo-thiophen-3-yl)-acetic acid methyl ester 、 4-(正丙基氨甲酰基)苯硼酸 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Thiophene substituted acylguanidines as BACE1 inhibitors

  摘要：

  A series of thiophene-substituted acylguanidines were designed from a pyrrole substituted acylguanidine HTS lead. This template allowed a greater flexibility, through differential Suzuki couplings, to explore the binding site of BACE1 and to enhance the inhibitory potencies. This exploration provided a 25-fold enhancement in potency to yield compound 10a, which was 150 nM in a BACE1 FRET assay.

  DOI：

  10.1016/j.bmcl.2007.08.010

文献信息

• Exploring a cascade Heck–Suzuki reaction based route to kinase inhibitors using design of experiments
  作者：Andreas Ekebergh、Christine Lingblom、Peter Sandin、Christine Wennerås、Jerker Mårtensson

  DOI：10.1039/c4ob02694b

  日期：——

  A fused tricyclic system with kinase inhibiting properties was assembledviaa palladium catalyzed tandem reaction. The reaction was optimized using statistical experimental design.

  通过钯催化串联反应组装了具有激酶抑制特性的融合三环系统。该反应使用统计实验设计进行了优化。
• Photoreduction of Anthracenes Catalyzed by <i>peri</i>‐Xanthenoxanthene: a Scalable and Sustainable Birch‐Type Alternative
  作者：Cristian De Luca、Davide Zanetti、Tommaso Battisti、Rúben R. Ferreira、Sofia Lopez、Alexander H. McMillan、Sasha Cai Lesher‐Pérez、Laura Maggini、Davide Bonifazi

  DOI：10.1002/chem.202302129

  日期：2023.11.13

  The typical Birch reduction transforms arenes into cyclohexa‐1,4‐dienes by using alkali metals, an alcohol as a proton source, and an amine as solvent. Capitalizing on the strong photoreductive properties of peri‐xanthenoxanthene (PXX), herein we report the photocatalyzed “Birch‐type” reduction of acenes by employing visible blue light irradiation at room temperature in the presence of air. Upon excitation at 405 or 460 nm in the presence of a mixture of N,N‐diisopropylethylamine (DIPEA) and trifluoromethanesulfonimide (HNTf₂) in DMSO, PXX photocatalyzes the selective reduction of full‐carbon acene derivatives (24–75 %). Immobilization of PXX onto polydimethylsiloxane (PDMS) beads (PXX‐PDMS) allowed the use of the catalyst in heterogeneous batch reactions, giving 9‐phenyl‐9,10‐dihydroanthracene in high yield (68 %). The catalyst could easily be recovered and reused, with no notable drop in performance observed after five reaction cycles. Integration of the PXX‐PDMS beads into a microreactor enabled the reduction of acenes under continuous‐flow conditions, thereby validating the sustainability and scalability of this heterogeneous‐phase approach.

  摘要典型的 Birch 还原法是利用碱金属、作为质子源的醇和作为溶剂的胺将烯烃转化为环己-1,4-二烯。利用过呫吨呫吨（PXX）的强光电还原性，我们在此报告了在室温、空气存在的情况下，利用可见蓝光照射光催化 "桦树型 "还原烯的情况。在 N,N-二异丙基乙胺（DIPEA）和三氟甲烷磺酰亚胺（HNTf2）在二甲基亚砜（DMSO）中的混合物存在下，PXX 在 405 或 460 纳米波长的激发下，光催化全碳烯衍生物的选择性还原（24-75%）。将 PXX 固定在聚二甲基硅氧烷（PDMS）珠（PXX-PDMS）上可将催化剂用于异相批量反应，从而获得高产率（68%）的 9-苯基-9,10-二氢蒽。催化剂很容易回收和重复使用，经过五个反应周期后，性能没有明显下降。将 PXX-PDMS 珠子集成到微反应器中，可在连续流动条件下还原烯烃，从而验证了这种异相方法的可持续性和可扩展性。
• Discovery of Sibiriline derivatives as novel receptor-interacting protein kinase 1 inhibitors
  作者：Ningjie Cui、Shang Li、Yonglei Zhang、Fucheng Yin、Xinye Chen、Zhongwen Luo、Siyuan Wan、Xinxin Li、Lingyi Kong、Xiaobing Wang

  DOI：10.1016/j.ejmech.2023.115190

  日期：2023.3
• Thiophene substituted acylguanidines as BACE1 inhibitors
  作者：William F. Fobare、William R. Solvibile、Albert J. Robichaud、Michael S. Malamas、Eric Manas、Jim Turner、Yun Hu、Erik Wagner、Rajiv Chopra、Rebecca Cowling、Guixan Jin、Jonathan Bard

  DOI：10.1016/j.bmcl.2007.08.010

  日期：2007.10

  A series of thiophene-substituted acylguanidines were designed from a pyrrole substituted acylguanidine HTS lead. This template allowed a greater flexibility, through differential Suzuki couplings, to explore the binding site of BACE1 and to enhance the inhibitory potencies. This exploration provided a 25-fold enhancement in potency to yield compound 10a, which was 150 nM in a BACE1 FRET assay.