Skip to Content
Merck
CN

Key Documents

View All Documentation

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

Change View

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
Assay:
≥96% (HPLC)
Form:
liquid
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

100

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.

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
BCCF3609
BCCC7436
BCCC6353
BCBZ8954
BCBW9188

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

Protocols

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。

Bestmann-Ohira Reagent: Alkynes from Aldehydes

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

An improved one-pot procedure for the synthesis of alkynes from aldehydes
Muller S, et al.
Synlett, 1996(06), 521-522 (1996)
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)

Global Trade Item Number

SKUGTIN
742724-10ML04061832888293