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78181

Sigma-Aldrich

苯基硼酸

purum, ≥97.0% (HPLC)

别名:

NSC 66487, 二羟基苯硼烷, 苯基硼酸, 苯硼酸

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About This Item

线性分子式:
C6H5B(OH)2
CAS号:
98-80-6
分子量:
121.93
Beilstein:
970972
EC 号:
202-701-9
MDL编号:
MFCD00002103
UNSPSC代码:
12352103
PubChem化学物质编号:
329768124
NACRES:
NA.22
价格与库存信息目前不能提供

等级

purum

质量水平

200

方案

≥97.0% (HPLC)

表单

crystals

mp

216-219 °C (lit.)
218-222 °C

SMILES字符串

OB(O)c1ccccc1

InChI

1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H

InChI key

HXITXNWTGFUOAU-UHFFFAOYSA-N

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相关类别

一般描述

苯硼酸是高度稳定的受体配体，可用于交联反应和药物递送。[1]

苯硼酸(Phenylboronic acid, PBA)是一种有机硼酸。[2]用作分子受体，可结合到含顺式二醇基团的化合物上。[3]苯硼酸可与芳基氯化物一起在Pd/C（催化剂）和水（溶剂）的存在下进行微波辅助的Suzuki偶联反应。[4]苯硼酸可与卤芳烃通过钯催化的交叉偶联反应合成联芳基化合物。[5]

应用

苯硼酸可用于下列反应：
  • 铑催化的分子内胺化。[6]
  • 钯催化的直接芳基化。[7]
  • 钯纳米粒子催化的 Mizoroki-Heck 和 Suzuki-Miyaura 偶联反应。[8]
  • 钯催化的立体选择性 Heck 型反应。[9]
  • 高效钯催化芳基化 Suzuki-Miyaura 在水中交叉偶联。[10]

苯硼酸可用作试剂制备：
  • Ni (II) 钳形配合物和 Pd (II) 吡哆醛腙类金属化合物作为 Suzuki-Miyaura 交叉偶联反应的催化剂。[11][12]
  • 用于全聚合物太阳能电池的 N 型聚合物。[13]
  • 新型系列强效和选择性 mTOR 激酶抑制剂。[14]
  • 乳酸脱氢酶抑制剂抑制癌细胞增殖。[15]

其他说明

含有不定量的苯硼酸酐

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H302

危险分类

Acute Tox. 4 Oral

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
WXBF4507V
WXBF1935V
WXBD9259V
WXBD2122V
WXBD5283V

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Phenylboronic-acid-based functional chemical materials for fluorescence imaging and tumor therapy
Li S, et al.
ACS Omega, 7, 2520-2532 (2022)
Synthesis of polyfunctional glycerol esters: lipase-catalyzed esterification of glycerol with diesters.
Villeneuve P, et al.
Journal of the American Oil Chemists' Society, 75(11), 1545-1549 (1998)
Riina K Arvela et al.
Organic letters, 7(11), 2101-2104 (2005-05-20)
[reaction: see text]. We present here a methodology for the Suzuki coupling of aryl chlorides with phenylboronic acid using Pd/C as a catalyst, water as a solvent, and microwave heating. We show that simultaneous cooling in conjunction with microwave heating
Peng-Cheng Chen et al.
Langmuir : the ACS journal of surfaces and colloids, 27(20), 12597-12605 (2011-09-09)
Phenylboronic acid (PBA)-functionalized materials have attracted considerable attention because of their potential applications in many fields. In this paper, we report a PBA-segregated honeycomb-patterned porous film (HPPF) for glucose sensing. Polystyrene-block-poly(acrylic acid-co-acrylamidophenylboronic acid) with different contents of PBA pendants was
Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors
Mortensen, D. S.; et al.
Bioorganic & Medicinal Chemistry, 21, 6793-6799 (2011)
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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