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安全信息

576638

Sigma-Aldrich

反丙烯硼酸

≥95.0%

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别名:
(E)-1-Propen-1-ylboronic acid, (E)-Prop-1-enylboronic acid, trans-1-Propeneboronic acid, trans-1-Propenylboronic acid, trans-Propenylboronic acid
线性分子式:
CH3CH=CHB(OH)2
CAS号:
7547-97-9
分子量:
85.90
MDL编号:
MFCD02179501
UNSPSC代码:
12352103
PubChem化学物质编号:
24880870
NACRES:
NA.22

质量水平

100

检测方案

≥95.0%

杂质

~10 wt. % cis-isomer

mp

123-127 °C (lit.)

储存温度

2-8°C

SMILES字符串

[H]\C(C)=C(\[H])B(O)O

InChI

1S/C3H7BO2/c1-2-3-4(5)6/h2-3,5-6H,1H3/b3-2+

InChI key

CBMCZKMIOZYAHS-NSCUHMNNSA-N

相关类别

应用

用于以下反应的反应物：
  • 钯膦催化的Suzuki-Miyaura偶联反应
  • Cu(II)介导的Ullmann偶联反应

作为反应物用于制备：
  • 炔基苯氧基乙酸，作为DP2受体拮抗剂，用于治疗过敏性炎症
  • 四氢苯并噻吩类化合物，通过涉及Suzuki偶联的Paal-Knorr合成，作为II型脱氢喹啉酶的构象限制烯醇模拟抑制剂
  • 通过二碘化钐介导的环化反应，生成高度取代的苯并环辛醇衍生物
  • 通过镍催化的与炔烃和烯酮的三组分还原偶联反应，生成立体定向性二烯
用作以下反应的反应物：
  • 钯膦催化的Suzuki-Miyaura偶联反应
  • Cu(II)介导的Ullmann偶联反应
  • 钯催化的Sonogashira交叉偶联反应

作为反应物用于制备：
  • 炔基苯氧基乙酸，作为DP2受体拮抗剂，用于治疗过敏性炎症
  • 四氢苯并噻吩类化合物，通过涉及Suzuki偶联的Paal-Knorr合成，作为II型脱氢喹啉酶的构象限制烯醇模拟抑制剂
  • 通过二碘化钐介导的环化反应，生成高度取代的苯并环辛醇衍生物
  • 通过镍催化的与炔烃和烯酮的三组分还原偶联反应，生成立体定向性二烯

其他说明

含有不定量的酸酐

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

新产品

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 576638, trans-1-Propen-1-ylboronic 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. Is the cis isomer present in Product 576638, trans-1-Propen-1-ylboronic acid?

    Product No. 576638 may contain up to 10 wt% of the cis isomer.

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

    Ask a Scientist here.

A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters
Fuwa, H.; et al.
Tetrahedron, 67, 4995-5010 (2011)
Ming-Bo Zhou et al.
The Journal of organic chemistry, 75(16), 5635-5642 (2010-08-14)
Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)(2) and Ag(2)O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding
Chun-Ming Yang et al.
Organic letters, 12(16), 3610-3613 (2010-08-14)
A highly regio- and stereoselective nickel-catalyzed three-component coupling of alkynes with enones and alkenyl boronic acids to afford highly substituted 1,3-dienes is described. The reaction can also be extended to cyclization of enynes with coupling to alkenyl boronic acids. A
Total synthesis of rodgersinol: a survey of the Cu(II)-mediated coupling of ortho-substituted phenols
Jung, J.-W.; et al.
Tetrahedron, 66, 6826-6831 (2010)
The preparation of substituted pyrazoles from β,β-dibromo-enones by a tandem condensation/Suzuki-Miyaura cross-coupling process
Beltran-Rodil, S.; et al.
Synlett, 4, 602-606 (2010)
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