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Merck

742724

Sigma-Aldrich

(1-重氮-2-氧代丙基)膦酸二甲酯 溶液

~10% in acetonitrile (H-NMR), ≥96% (HPLC)

别名:

Bestmann-Ohira试剂, 二甲基(1-偶氮丙酮基)膦酸酯 溶液, 二甲基(乙酰基二甲基)膦酸酯 溶液

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10 ML
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About This Item

经验公式(希尔记法):
C5H9N2O4P
CAS号:
分子量:
192.11
Beilstein:
4247670
MDL编号:
UNSPSC代码:
12352108
PubChem化学物质编号:
NACRES:
NA.22

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质量水平

方案

≥96% (HPLC)

表单

liquid

反应适用性

reaction type: C-C Bond Formation

浓度

~10% in acetonitrile (H-NMR)

折射率

n20/D 1.352-1.354

密度

0.800-0.850 g/mL at 20 °C

官能团

ketone
phosphonate

储存温度

2-8°C

SMILES字符串

COP(=O)(OC)C(=[N+]=[N-])C(C)=O

InChI

1S/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3

InChI key

SQHSJJGGWYIFCD-UHFFFAOYSA-N

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应用

(1-重氮基-2-氧代丙基)膦酸二甲酯可用作合成以下物质的试剂:
  • 由醛合成乙炔基化合物(炔烃)[1]
  • 在存在铑催化剂的情况下通过与肟的环化反应生成异喹啉和吡啶N-氧化物。[2]
  • 通过甲醇水解生成 (重氮甲基)膦酸二甲酯,其可进一步用作合成烯醇醚或炔烃的试剂。[3]
  • 通过环加成反应和多组分反应生成吡唑、三唑和噁唑的五元杂环骨架。[4]

象形图

FlameExclamation mark

警示用语:

Danger

危险分类

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

35.6 °F

闪点(°C)

2 °C


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Further improvements of the synthesis of alkynes from aldehydes
Roth GJ, et al.
Synthesis, 2004(01), 59-62 (2004)
Methanolysis of dimethyl (1-diazo-2-oxopropyl) phosphonate: generation of dimethyl (diazomethyl) phosphonate and reaction with carbonyl compounds
Ohira S
Synthetic Communications, 19(3-4), 561-564 (1989)
Zhuangzhi Shi et al.
Journal of the American Chemical Society, 135(33), 12204-12207 (2013-07-31)
Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need
An improved one-pot procedure for the synthesis of alkynes from aldehydes
Muller S, et al.
Synlett, 1996(06), 521-522 (1996)
Synthesis of New Pyrroline Nitroxides with Ethynyl Functional Group
{Ur Gyorgyi, et al.
Synthetic Communications, 45(18), 2122-2129 (2015)

实验方案

乙炔化学一直是并且仍然是分子科学的重要组成部分。它的潜力和广泛的应用从有机合成到材料科学再到生物有机化学。一些例子是烯二炔(DNA切割剂),“点击化学”工具和构建块。 因此,它引发了对高效合成炔烃的需求。

Acetylene chemistry's versatile applications from organic synthesis to bioorganic chemistry demand efficient synthesis methods.

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

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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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