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Sigma-Aldrich

烯丙基硼酸频哪醇酯

97%

同義詞:

2-烯丙基-4,4,5,5-四甲基-1,3,2-二氧环戊硼烷, 丙烯基硼酸频哪醇酯

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About This Item

線性公式:
((CH3)4C2O2)BCH2CH=CH2
CAS號碼:
分子量::
168.04
MDL號碼:
分類程式碼代碼:
12352103
PubChem物質ID:
NACRES:
NA.22
暫時無法取得訂價和供貨情況

品質等級

化驗

97%

折射率

n20/D 1.4268 (lit.)

bp

50-53 °C/5 mmHg (lit.)

密度

0.896 g/mL at 25 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

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

InChI

1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3

InChI 密鑰

YMHIEPNFCBNQQU-UHFFFAOYSA-N

一般說明

烯丙基硼酸季戊醇酯在简单酮亚胺的催化烯丙基化反应中被用作亲核试剂。 [1]

應用

作为试剂用于以下反应
  • 钯催化的铃木宫村交叉偶联反应和烯烃复分解[2]
  • 分子间自由基加成[3]
  • 手性螺二茚二醇(SPINOL)基磷酸催化醛烯丙基化[4]
  • 钴催化二烯与烯烃的区域选择性加氢乙烯基化[5]
  • 核酸模板能量转移导致光释放反应[6]
  • 立体选择性铟催化的Hosomi-Sakurai反应[7]

试剂用于制备
  • 环砜羟乙胺作为BACE1抑制剂减少淀粉样蛋白β-肽[8]
  • 碳烯碘化钌与银羧酸盐的金属转移,得到碳氢活化的钌碳烯配合物作为Z选择性烯烃复分解的催化剂[9]
  • 烯丙基硼化试剂,用于制备烯丙醇[10]和高烯丙基胺。[11]

象形圖

Flame

訊號詞

Warning

危險聲明

危險分類

Flam. Liq. 3

儲存類別代碼

3 - Flammable liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

114.8 °F - closed cup

閃點(°C)

46 °C - closed cup

個人防護裝備

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


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分析證明 (COA)

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Marion Arndt et al.
Organic letters, 13(23), 6236-6239 (2011-11-02)
The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates
Organometallics, 2, 230-230 (1983)
Asymmetric Allylboration of Aldehydes with Pinacol Allylboronates Catalyzed by 1,1'-Spirobiindane-7,7'-diol (SPINOL) Based Phosphoric Acids
Xing, C-H.; et al.
European Journal of Organic Chemistry, 6, 1115-1118 (2012)
A catalytic asymmetric borono variant of Hosomi-Sakurai reactions with N,O-aminals.
Yi-Yong Huang et al.
Angewandte Chemie (International ed. in English), 50(47), 11121-11124 (2011-10-07)
Catalytic enantioselective allylation of ketoimines
Reiko W et al.
Journal of the American Chemical Society, 128, 7687-7691 (2006)

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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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  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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