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
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About This Item
Empirical Formula (Hill Notation):
C5H9N2O4P
CAS Number:
Molecular Weight:
192.11
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4247670
Assay:
≥96% (HPLC)
Form:
liquid
Quality Segment
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
Dimethyl (1-diazo-2-oxopropyl)phosphonate can be used as a reagent for the synthesis of:
- Ethynyl compounds (alkynes) from aldehydes.
- Isoquinoline and pyridine N-oxides by cyclization with oximes in the presence of Rh catalyst.
- 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.
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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