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633348

Sigma-Aldrich

乙烯基硼酸频哪醇酯

contains phenothiazine as stabilizer, 95%

同義詞:

2-乙烯基-4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷

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About This Item

經驗公式（希爾表示法）:
C8H15BO2
CAS號碼:
75927-49-0
分子量：:
154.01
MDL號碼:
MFCD00192492
分類程式碼代碼:
12352103
PubChem物質ID:
24882546
NACRES:
NA.22
暫時無法取得訂價和供貨情況

品質等級

100

化驗

95%

包含

phenothiazine as stabilizer

折射率

n20/D 1.4300 (lit.)

密度

0.908 g/mL at 25 °C (lit.)

儲存溫度

−20°C

SMILES 字串

CC1(C)OB(OC1(C)C)C=C

InChI

1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3

InChI 密鑰

DPGSPRJLAZGUBQ-UHFFFAOYSA-N

相關類別

應用

在“双”Heck-Mizoroki芳基化的使用中，生成β, β-二芳基化乙烯基硼酸盐，并与额外芳基卤化物反应形成Π-扩展系统。这种方法用于制备共轭树枝状化合物。[1] 也用于通过光诱导黄原酸酯的添加制备γ羰基乙烯基硼酸盐。[2]
试剂用于
  • Suzuki-Miyaura 偶联反应[3]
  • Mizoroki-Heck 反应（级联反应）[3]
  • 分子内 Nozaki-Hiyama-Kishi 反应[4]
  • 立体选择性铜催化 γ-选择性和立体定向偶联[5]
  • 分子内 (4 + 1) 环加成反应的立体选择性控制及机理描述[6]
  • 金 (I) 催化卤代炔烃的氢磷氧基化反应和钯催化的连续交叉偶联反应合成三取代烯烃的区域和立体选择性[7]
  • 不对称桦木还原性烷基化[8]

制备过程中使用的试剂
  • 脂类感应分子管[9]
  • 酶抑制剂、抗生素、受体类似物和其他具有生物学意义的化合物（包括全合成）[10][11][12][4]

訊號詞

Warning

危險聲明

H226,H317,H411

危險分類

Aquatic Chronic 2 - Flam. Liq. 3 - Skin Sens. 1

儲存類別代碼

3 - Flammable liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

93.2 °F

閃點（°C）

34 °C

個人防護裝備

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
MKCW2120
0000202873
0000201611
0000202873
0000201611

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Christopher A Leclair et al.
Tetrahedron letters, 51(52), 6852-6855 (2011-04-26)
A total synthesis of LL-Z1640-2 (2), a potent and selective kinase inhibitor, has been completed. The key step of the convergent synthesis utilized a late-stage intramolecular Nozaki-Hiyama-Kishi (NHK) reaction to close the macrocycle at the C6'-C7' bond.
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Chemical communications (Cambridge, England), 47(27), 7851-7853 (2011-06-07)
A new stereoselective synthesis of trisubstituted alkenes is developed. Hydrophosphoryloxylation of haloalkynes provides Z-alkenyl halophosphates, which undergo Pd-catalyzed consecutive cross-coupling reactions to afford regio- and stereodefined trisubstituted alkenes.
Markus R Heinrich et al.
Chemical communications (Cambridge, England), (24), 3077-3079 (2005-06-17)
Gamma-carbonyl vinyl boronates can be prepared by a visible light induced radical chain addition of an S-acyl dithiocarbonate (xanthate) to the pinacol ester of vinyl boronic acid, followed by treatment with base.
Mingyu Yang et al.
Organic letters, 14(3), 816-819 (2012-01-20)
A Cu-catalyzed γ-selective coupling reaction between propargylic phosphates and aryl- or alkenylboronates afforded aryl- or alkenyl-conjugated allenes. The reaction showed excellent functional group compatibility in both the propargylic substrates and the boronates. The reaction of an enantioenriched propargylic phosphate proceeded
A forgotten olefin: a convenient one-pot cascade reaction involving Suzuki-Miyaura and Mizoroki-Heck couplings to form (E)-1,2-di(1-pyrenyl)ethylene
Yamashita, K.; et al.
Chemistry Letters (Jpn), 40, 1459-1461 (2011)
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  1. 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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  2. 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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