Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Advances in the Bestmann-Ohira Reagent-Assisted Regioselective Synthesis of Substituted Pyrazoles, Triazoles, and Oxazoles
Mohapatra S, et al.
Synthetic Communications, 43(15), 1993-2007 (2013)
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
Synthesis of New Pyrroline Nitroxides with Ethynyl Functional Group
{Ur Gyorgyi, et al.
Synthetic Communications, 45(18), 2122-2129 (2015)
An improved one-pot procedure for the synthesis of alkynes from aldehydes
Muller S, et al.
Synlett, 1996(06), 521-522 (1996)
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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service