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CAS RN: 90965-06-3 | Product Number: D3546

Dimethyl (1-Diazo-2-oxopropyl)phosphonate


Purity: >97.0%(HPLC)
Synonyms:
  • (1-Diazo-2-oxopropyl)phosphonic Acid Dimethyl Ester
  • Dimethyl 1-Diazoacetonylphosphonate
  • 1-Diazoacetonylphosphonic Acid Dimethyl Ester
  • Ohira-Bestmann Reagent
Documents:
1G
€88.00
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5G
€390.00
5   ≥20 

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Product Number D3546
Purity / Analysis Method >97.0%(HPLC)
Molecular Formula / Molecular Weight C__5H__9N__2O__4P = 192.11  
Physical State (20 deg.C) Liquid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Heat Sensitive
CAS RN 90965-06-3
Reaxys Registry Number 4247670
PubChem Substance ID 87559944
Merck Index (14) 1177
MDL Number

MFCD07368360

Specifications
Appearance Light yellow to Brown clear liquid
Purity(HPLC) min. 97.0 area%
Properties (reference)
Specific Gravity (20/20) 1.28
Refractive Index 1.48
GHS
Related Laws:
Transport Information:
HS Number 2931499090
Application
TCI Practical Example: Construction of the Terminal Alkyne Using Ohira-Bestmann Reagent

Used Chemicals

Procedure

To a methanol (10 mL) solution of undecanal (0.20 g, 1.2 mmol) was added potassium carbonate (0.32 g,2.4 mmol) and Ohira-Bestmann reagent (0.27 g, 1.4 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, then diluted with diethyl ether and washed with saturated aqueous sodium bicarbonate, and dried by sodium sulfate. The organic layer was concentrated under reduced pressure. The resulting crude product was purified by column chromatography (hexane:toluene = 3:1 on silica gel) to give 1 as a colorless liquid (0.11 g, 56% yield).

Experimenter’s Comments

The reaction mixtures were monitored by 1H NMR (CDCl3).

Analytical Data(1-Dodecyne (1))

1H NMR (400 MHz, CDCl3); δ 2.18 (t, 2H, J = 7.1 Hz), 1.94 (s, 1H), 1.57-1.46 (m, 2H), 1.44-1.33 (m, 2H), 1.33-1.19 (m, 12H), 0.88 (t, 3H, J = 6.4 Hz).

13C NMR (101 MHz, CDCl3); δ 85.0, 68.2, 32.0, 29.7, 29.7, 29.5, 29.3, 28.9, 28.6, 22.8, 18.5, 14.3.

Lead Reference

Other References


Application
Synthesis of Phosphonyl Pyrazoles

Typical Procedure: To a stirred solution of aldehyde (1 mmol), cyanoacid derivative (1.2 mmol) and Ohira-Bestmann reagent (1.5 mmol) in distilled MeOH (4 mL), is added molecular sieves followed by powdered KOH (2 mmol). The reaction mixture is stirred at room temperature for one hour. After the completion of the reaction (TLC monitoring), methanol is distilled off under reduced pressure. The crude residue is dissolved in ethyl acetate (50 mL) and washed with saturated ammonium chloride (2×20 mL). Finally the organic layer is washed with saturated brine (20 mL) and dried over anhydrous sodium sulphate. After removal of the solvent, column chromatographic purification is carried out using acetone-dichloromethane as eluent to afford the products.

References


Application
One-pot Synthesis of Terminal Alkynes

References


PubMed Literature


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