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CAS RN: 90965-06-3 | Product Number: D3546
Dimethyl (1-Diazo-2-oxopropyl)phosphonate
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Purity: >97.0%(HPLC)
Synonyms:
- (1-Diazo-2-oxopropyl)phosphonic Acid Dimethyl Ester
- Dimethyl 1-Diazoacetonylphosphonate
- 1-Diazoacetonylphosphonic Acid Dimethyl Ester
- Ohira-Bestmann Reagent
Product Documents:
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| 5G |
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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
|
Refrigerated (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:
| H.S.code* | 2931.49-000 |
Application
TCI Practical Example: Construction of the Terminal Alkyne Using Ohira-Bestmann Reagent
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Used Chemicals
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Procedure
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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).
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Experimenter’s Comments
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The reaction mixtures were monitored by 1H NMR (CDCl3).
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Analytical Data（1-Dodecyne (1)）
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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.
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Lead Reference
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- Further Improvements of the Synthesis of Alkynes from Aldehydes
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Other References
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- Methanolysis of Dimethyl (1-Diazo-2-oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl Compounds
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
- S. Ohira, Synth. Commun. 1989, 19, 561.
- S. Muller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521.
- H. D. Dickson, S. C. Smith, K. W. Hinkle, Tetrahedron Lett. 2004, 45, 5597.
- E. Quesada, R. J. K. Taylor, Tetrahedron Lett. 2005, 46, 6473.
PubMed Literature
Documents
Product Articles
[TCIMAIL No.137] One-pot Synthesis of Terminal Alkynes[TCI Practical Example] Construction of the Terminal Alkyne Using Ohira-Bestmann Reagent
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Related Products
Dimethyl (1-Diazo-2-oxopropyl)phosphonate (10% in Acetonitrile)
| Product # | D5048 |
| CAS RN | 90965-06-3 |
| Purity / Analysis Method: |