Dimethyl (1-Diazo-2-oxopropyl)phosphonate
Dimethyl (1-Diazo-2-oxopropyl)phosphonate Basic information
- Product Name:
- Dimethyl (1-Diazo-2-oxopropyl)phosphonate
- Synonyms:
-
- dimethyl 1-(1-diazo-2-oxopropyl)phosphonate
- DIMETHYL (1-DIAZO-2-OXOPROPYL)PHOSPHONATE
- (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER
- (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER BESTMANN OHIRA REAGENT
- 1-Diazoacetonylphosphonic Acid Dimethyl Ester
- Dimethyl 1-Diazoacetonylphosphonate
- Ohira-Bestmann reagent
- diMethyl(1-diazo-2-oxopropyl)phosphanate
- CAS:
- 90965-06-3
- MF:
- C5H9N2O4P
- MW:
- 192.11
- Mol File:
- 90965-06-3.mol
Dimethyl (1-Diazo-2-oxopropyl)phosphonate Chemical Properties
- Density
- 1.28
- refractive index
- n20/D1.352-1.354
- Flash point:
- 2℃
- storage temp.
- 2-8°C
- solubility
- Chloroform, Methanol (Slightly)
- form
- Oil
- color
- Pale Yellow to Yellow
- Merck
- 14,1177
- BRN
- 4247670
- Stability:
- Light Sensitive
Safety Information
- Hazard Codes
- F,Xn
- Risk Statements
- 11-20/21/22-36
- Safety Statements
- 16-26-36/37
- RIDADR
- UN 1648 3 / PGII
- WGK Germany
- 3
- HazardClass
- 3
- PackingGroup
- II
- HS Code
- 29319090
Dimethyl (1-Diazo-2-oxopropyl)phosphonate Usage And Synthesis
Description
Dimethyl (1-diazido-2-oxopropyl)phosphonate is a liquid-added organophosphorus flame retardant with good solubility with water, common organic solvents, and inorganic salts flame retardants, with excellent flame retardant properties, low price and low additive amount and other advantages.
Chemical Properties
Light yellow liquid
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.
Uses
Reagent for transformation of aldehydes to terminal alkynes and ketones to methyl enol ethers.
Synthesis
Dissolve NaH (0.67 g, 60% w/w, 16.75 mmol) in benzene (45 mL) and dry THF (15 mL). Cool the mixture on ice. A solution of dimethyl (2-oxopropyl) phosphonate (15.3 mmol) in dry benzene (15 mL) was added. A white solid was formed. The reaction mixture was stirred at room temperature for 1 hour. To the mixture was added a solution of toluidic acid hydrazide (16.23 mmol) in dry benzene (7.5 mL). The mixture was stirred at room temperature overnight. The mixture was filtered with Hyflo. The mixture was concentrated in a vacuum to give dimethyl (1-diazido-2-oxopropyl)phosphonate.
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