Skip to Content
Merck
CN

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C5H9N2O4P
CAS Number:
90965-06-3
Molecular Weight:
192.11
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
329765588
MDL number:
MFCD07368360
Beilstein/REAXYS Number:
4247670

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Dimethyl (1-diazo-2-oxopropyl)phosphonate solution, ~10% in acetonitrile (H-NMR), ≥96% (HPLC)

InChI

1S/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3

SMILES string

COP(=O)(OC)C(=[N+]=[N-])C(C)=O

InChI key

SQHSJJGGWYIFCD-UHFFFAOYSA-N

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

Quality Level

100

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

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

wgk

WGK 3

flash_point_f

35.6 °F

flash_point_c

2 °C

Regulatory Information

危险化学品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCL6520
BCCK8724
BCCH2811
BCCF3609
BCCC7436

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

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)
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)
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 试剂：从醛类协议合成炔烃

乙炔化学一直是并且仍然是分子科学的重要组成部分。它的潜力和广泛的应用从有机合成到材料科学再到生物有机化学。一些例子是烯二炔（DNA切割剂），“点击化学”工具和构建块。 因此，它引发了对高效合成炔烃的需求。

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