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/418/501/product-dating-information-06-25-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
Select a Size
| Pack Size | SKU | Availability | Price |
|---|---|---|---|
| 10 mL | Available to ship TODAYfromMILWAUKEE | $535.00 |
About This Item
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
Application
- Ethynyl compounds (alkynes) from aldehydes.
- Isoquinoline and pyridine N-oxides by cyclization with oximes in the presence of Rh catalyst.[1]
- Dimethyl(diazomethyl)phosphonate through methanolysis, which is further employed as a reagent in the synthesis of enol ethers or alkynes.
- Five-member heterocyclic scaffolds of pyrazoles, triazoles, and oxazoles via cycloaddition reaction and multicomponent reaction.
1 of 1
This Item | |||
|---|---|---|---|
| assay ≥96% (HPLC) | assay 96% | assay 95% | assay 80% |
| reaction suitability reaction type: C-C Bond Formation | reaction suitability reaction type: C-C Bond Formation | reaction suitability reaction type: C-C Bond Formation | reaction suitability reaction type: C-C Bond Formation |
| Quality Level 100 | Quality Level 200 | Quality Level 100 | Quality Level 100 |
| form liquid | form liquid | form powder | form liquid |
| density 0.800-0.850 g/mL at 20 °C | density 1.13 g/mL at 25 °C (lit.) | density - | density 1.089 g/mL at 25 °C (lit.) |
| refractive index n20/D 1.352-1.354 | refractive index n20/D 1.465 (lit.) | refractive index - | refractive index n20/D 1.46 (lit.) |
signalword
Danger
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2
Storage Class
3 - Flammable liquids
flash_point_f
35.6 °F
flash_point_c
2 °C
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Protocols
Acetylene chemistry's versatile applications from organic synthesis to bioorganic chemistry demand efficient synthesis methods.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 742724-10ML | 04061832888293 |
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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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