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597988

Sigma-Aldrich

环丙基硼酸

别名:

Cyclopropaneboronic acid

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About This Item

经验公式（希尔记法）:
C3H7BO2
CAS号:
411235-57-9
分子量:
85.90
MDL编号:
MFCD04038750
UNSPSC代码:
12352103
PubChem化学物质编号:
24881728
NACRES:
NA.22
价格与库存信息目前不能提供

表单

solid

mp

90-95 °C (lit.)

储存温度

−20°C

SMILES字符串

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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相关类别

应用

Cu-介导N-环丙烷化[1]
硼酸组分，Pd(II)、Ag(I)和苯醌环境中的碳氢键烷基化研究。[2]
试剂用于
  • 微波辅助铜 (II) 催化 N -环丙基化[3]
  • 镍和铜催化的 Suzuki-Miyaura 偶联反应[4]
  • Palladacycle 催化的卤代芳烃与环丙基硼酸的 Suzuki 偶联反应[5]
  • 钯催化的环丙烷 C-H 键功能化[6]
  • 钯催化脱羧偶联[7]
  • 钯催化环丙烷的配体导向氧化功能化[8]
  • 钯催化的 Suzuki 偶联反应[9]

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[10]
  • 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[11]

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
GHS08

警示用语：

Danger

危险声明

H360FD

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

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
SHBP2448
SHBM7576
SHBM6559
SHBL4069
SHBK2662

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Facile synthesis of aryl(het)cyclopropane catalyzed by palladacycle
Zhang, M.; et al.
Tetrahedron, 68, 900-905 (2012)
Chaoyang Dai et al.
Bioorganic & medicinal chemistry letters, 21(10), 3172-3176 (2011-04-05)
TNF-α converting enzyme (TACE) inhibitors are promising agents to treat inflammatory disorders and cancer. We have investigated novel tartrate diamide TACE inhibitors where the tartrate core binds to zinc in a unique tridentate fashion. Incorporating (R)-2-(2-N-alkylaminothiazol-4-yl)pyrrolidines into the left hand
A Mild Palladium-Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids
W. Li, et al.,
Advanced Synthesis & Catalysis, 353, 1671-1675 (2011)
Microwave-assisted N-cyclopropylation of pyridinols with cyclopropyl boronic acid
Tambe, Y. B.; et al.
Synthetic Communications, 42, 1341-1348 (2012)
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.
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Questions

1–8 of 8 Questions  

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

    1 answer

    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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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  3. What compounds are formed when boronic acids degrade?

    1 answer

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

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

    1 answer

    1. The pKa of most boronic acids is approximately 9.

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

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

    1 answer

    1. 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.

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

    1 answer

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

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