Merck
CN

597988

Sigma-Aldrich

环丙基硼酸

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别名:
Cyclopropaneboronic acid
经验公式(希尔记法):
C3H7BO2
分子量:
85.90
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

形式

solid

mp

90-95 °C (lit.)

储存温度

−20°C

SMILES string

OB(O)C1CC1

InChI

1S/C3H7BO2/c5-4(6)3-1-2-3/h3,5-6H,1-2H2

InChI key

WLVKDFJTYKELLQ-UHFFFAOYSA-N

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应用

Cu-介导N-环丙烷化
硼酸组分,Pd(II)、Ag(I)和苯醌环境中的碳氢键烷基化研究。
试剂用于
  • 微波辅助铜 (II) 催化 N -环丙基化
  • 镍和铜催化的 Suzuki-Miyaura 偶联反应
  • Palladacycle 催化的卤代芳烃与环丙基硼酸的 Suzuki 偶联反应
  • 钯催化的环丙烷 C-H 键功能化
  • 钯催化脱羧偶联
  • 钯催化环丙烷的配体导向氧化功能化
  • 钯催化的 Suzuki 偶联反应

试剂用于制备
  • Cu(OTf)2 和 Xantphos 催化芳基硼酸与芳香醛的芳基化反应合成二芳基酮
  • 基于氨基噻唑吡咯烷的酒石酸二酰胺作为 TACE 抑制剂治疗炎性疾病和癌症

其他说明

可能含有 3-5% 环丙醇
可能含有 5-10% 硼酸
含有不定量的酸酐

象形图

Health hazard

警示用语:

Danger

危险声明

危险分类

Repr. 1B

储存分类代码

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


分析证书(COA)

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  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. What is the pKa of Product 597988, Cyclopropylboronic acid?

    The pKa of most boronic acids is approximately 9.

  7. What is it about boronic acids that makes them acidic? 

    Boronic acids have a vacant p orbital. Therefore, despite the presence of two hydroxyl groups, the acidic character of most Boronic acids is that of a Lewis acid.

  8. What compounds are formed when boronic acids degrade?

    Boronic acids are typically very stable. However, if degradation occurs, boronic acid will degrade to corresponding alcohol and boric acid.

  9. What is the solubility for Product 597988, Cyclopropylboronic acid?

    Product No. 597988 should be soluble in methanol at 0.1g in 30 mL (approximately 3 mg/mL).

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Xiao Chen et al.
Journal of the American Chemical Society, 128(39), 12634-12635 (2006-09-28)
Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated.
A Mild Palladium-Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids
W. Li, et al.,
Advanced Synthesis & Catalysis, 353, 1671-1675 (2011)
Copper-catalyzed arylation of arylboronic acids with aldehydes
Zheng, H.; et al.
Synlett, 11, 1626-1630 (2011)
Ni- and Cu-catalyzed coupling reactions using 2-(4,5-dihydro-1H-imidazo-2-yl)phenol as a versatile phosphine-free ligand
Haneda, S.; Sudo, K.; Hayashi, M.
Heterocycles, 84, 569-575 (2012)
Facile synthesis of aryl(het)cyclopropane catalyzed by palladacycle
Zhang, M.; et al.
Tetrahedron, 68, 900-905 (2012)

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