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.
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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
742724
Dimethyl (1-diazo-2-oxopropyl)phosphonate solution
~10% in acetonitrile (H-NMR), ≥96% (HPLC)
Synonym(s):
Bestmann-Ohira Reagent, Dimethyl (1-azoacetonyl)phosphonate solution, Dimethyl (acetyldiazomethyl)phosphonate solution
About This Item
Recommended Products
Quality Level
Assay
≥96% (HPLC)
form
liquid
reaction suitability
reaction type: C-C Bond Formation
concentration
~10% in acetonitrile (H-NMR)
refractive index
n20/D 1.352-1.354
density
0.800-0.850 g/mL at 20 °C
functional group
ketone
phosphonate
storage temp.
2-8°C
SMILES string
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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Related Categories
Application
- 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]
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
35.6 °F
Flash Point(C)
2 °C
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Acetylene chemistry's versatile applications from organic synthesis to bioorganic chemistry demand efficient synthesis methods.
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How is shipping temperature determined? And how is it related to the product storage temperature?
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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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