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742724

Sigma-Aldrich

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:
90965-06-3
Molecular Weight:
192.11
Beilstein:
4247670
MDL number:
MFCD07368360
UNSPSC Code:
12352108
PubChem Substance ID:
329765588
NACRES:
NA.22

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

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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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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

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

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

Protocols

Bestmann-Ohira Reagent: Alkynes from Aldehydes

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

Bestmann-Ohira Reagent: Alkynes from Aldehydes

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

Bestmann-Ohira Reagent: Alkynes from Aldehydes

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

Bestmann-Ohira Reagent: Alkynes from Aldehydes

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

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