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742724

Sigma-Aldrich

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

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

Synonyme(s) :

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

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10 ML
441.00 CHF

441.00 CHF

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About This Item

Formule empirique (notation de Hill) :
C5H9N2O4P
Numéro CAS:
90965-06-3
Poids moléculaire :
192.11
Beilstein:
4247670
Numéro MDL:
MFCD07368360
Code UNSPSC :
12352108
ID de substance PubChem :
329765588
Nomenclature NACRES :
NA.22

441.00 CHF

Check Cart for Availability
Devis pour commande en gros

Niveau de qualité

100

Essai

≥96% (HPLC)

Forme

liquid

Capacité de réaction

reaction type: C-C Bond Formation

Concentration

~10% in acetonitrile (H-NMR)

Indice de réfraction

n20/D 1.352-1.354

Densité

0.800-0.850 g/mL at 20 °C

Groupe fonctionnel

ketone
phosphonate

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

SQHSJJGGWYIFCD-UHFFFAOYSA-N

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Catégories apparentées

Application

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]

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Classification des risques

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

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

35.6 °F

Point d'éclair (°C)

2 °C

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Certificats d'analyse (COA)

Lot/Batch Number
BCCL6520
BCCK8724
BCCH2811
BCCF3609
BCCC7436

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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)
An improved one-pot procedure for the synthesis of alkynes from aldehydes
Muller S, et al.
Synlett, 1996(06), 521-522 (1996)
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
Synthesis of New Pyrroline Nitroxides with Ethynyl Functional Group
{Ur Gyorgyi, et al.
Synthetic Communications, 45(18), 2122-2129 (2015)
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Protocoles

Bestmann-Ohira Reagent: Alkynes from Aldehydes

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

Questions

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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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