| Identification | Back Directory | [Name]
2,2-DIMETHYLCYANOACETATE METHYL ESTER | [CAS]
72291-30-6 | [Synonyms]
MCYIB
methyl 2-cyano-2-methylpropanoate
Methyl 2-cyano-2,2-diMethylacetate
2,2-DIMETHYLCYANOACETATE METHYL ESTER
CYANODIMETHYLACETIC ACID METHYL ESTER
2-cyano-2-methyl-propionic acid methyl ester
Propanoic acid, 2-cyano-2-methyl-, methyl ester | [Molecular Formula]
C6H9NO2 | [MDL Number]
MFCD03428328 | [MOL File]
72291-30-6.mol | [Molecular Weight]
127.14 |
| Chemical Properties | Back Directory | [Boiling point ]
70-72 °C(Press: 17 Torr) | [density ]
1.021±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C6H9NO2/c1-6(2,4-7)5(8)9-3/h1-3H3 | [InChIKey]
TZPHOIMASXVLQZ-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C(C#N)(C)C |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to light yellow liquid | [Synthesis]
The general procedure for the synthesis of methyl 2-cyano-2-methylpropionate from methyl cyanoacetate and iodomethane is as follows:
1. In a dry reaction flask, methyl cyanoacetate (15 mL) and iodomethane (200 g) were added with potassium carbonate as base and acetone as solvent.
2. The reaction mixture was heated to reflux with continuous stirring for 4 days.
3. Upon completion of the reaction, insoluble potassium carbonate was removed by filtration.
4. The acetone in the filtrate was removed by distillation to obtain the crude product.
5. The crude product was purified by vacuum distillation (pressure: 16 mmHg, temperature: 76°C) to give methyl 2-cyano-2-methylpropionate (19.5 g, 73% yield).
Product characterization data:
1H NMR (270 MHz, CDCl3) δ: 1.62 (s, 6H), 3.83 (s, 3H).
13C NMR (67.5 MHz, CDCl3) δ: 24.6, 38.4, 121.0, 170.0. | [References]
[1] Patent: US5866592, 1999, A
[2] Patent: EP2533783, 2015, B1. Location in patent: Paragraph 0551-0552
[3] Acta Chemica Scandinavica (1947-1973), 1968, vol. 22, # 8, p. 2453 - 2461
[4] Phosphorus and Sulfur and the Related Elements, 1987, vol. 32, p. 153 - 162
[5] Patent: WO2013/134660, 2013, A1. Location in patent: Paragraph 0428 |
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