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742724

Sigma-Aldrich

Dimethyl (1-diazo-2-oxopropyl)phosphonate solution

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

Sinonimo/i:

Bestmann-Ohira Reagent, Dimethyl (1-azoacetonyl)phosphonate solution, Dimethyl (acetyldiazomethyl)phosphonate solution

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10 ML
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10 ML
410,00 €

About This Item

Formula empirica (notazione di Hill):
C5H9N2O4P
Numero CAS:
Peso molecolare:
192.11
Beilstein:
4247670
Numero MDL:
Codice UNSPSC:
12352108
ID PubChem:
NACRES:
NA.22

410,00 €


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Saggio

≥96% (HPLC)

Stato

liquid

Impiego in reazioni chimiche

reaction type: C-C Bond Formation

Concentrazione

~10% in acetonitrile (H-NMR)

Indice di rifrazione

n20/D 1.352-1.354

Densità

0.800-0.850 g/mL at 20 °C

Gruppo funzionale

ketone
phosphonate

Temperatura di conservazione

2-8°C

Stringa SMILE

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
SQHSJJGGWYIFCD-UHFFFAOYSA-N

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Applicazioni

Dimethyl (1-diazo-2-oxopropyl)phosphonate can be used as a reagent for the synthesis of:
  • Ethynyl compounds (alkynes) from aldehydes.[1]
  • Isoquinoline and pyridine N-oxides by cyclization with oximes in the presence of Rh catalyst.[2]
  • Dimethyl(diazomethyl)phosphonate through methanolysis, which is further employed as a reagent in the synthesis of enol ethers or alkynes.[3]
  • Five-member heterocyclic scaffolds of pyrazoles, triazoles, and oxazoles via cycloaddition reaction and multicomponent reaction.[4]

Pittogrammi

FlameExclamation mark

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

35.6 °F

Punto d’infiammabilità (°C)

2 °C


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Certificati d'analisi (COA)

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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)
Advances in the Bestmann-Ohira Reagent-Assisted Regioselective Synthesis of Substituted Pyrazoles, Triazoles, and Oxazoles
Mohapatra S, et al.
Synthetic Communications, 43(15), 1993-2007 (2013)
Synthesis of New Pyrroline Nitroxides with Ethynyl Functional Group
{Ur Gyorgyi, et al.
Synthetic Communications, 45(18), 2122-2129 (2015)
An improved one-pot procedure for the synthesis of alkynes from aldehydes
Muller S, et al.
Synlett, 1996(06), 521-522 (1996)

Protocolli

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

Domande

1–2 di 2 domande  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 risposta
    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

      Utile?

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

    1 risposta
    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

      Utile?

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