| Identification | More | [Name]
ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE | [CAS]
1558-81-2 | [Synonyms]
1-CYANO-CYCLOPROPANECARBOXYLIC ACIDETHYL ESTER
ETHYL 1-CYANO-1-CYCLOPROPANECARBOXYLATE
ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE | [Molecular Formula]
C7H9NO2 | [MDL Number]
MFCD00040159 | [Molecular Weight]
139.15 | [MOL File]
1558-81-2.mol |
| Chemical Properties | Back Directory | [Boiling point ]
217 °C (lit.) | [density ]
1.077 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.445(lit.)
| [Fp ]
211 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
liquid | [color ]
colorless | [InChI]
InChI=1S/C7H9NO2/c1-2-10-6(9)7(5-8)3-4-7/h2-4H2,1H3 | [InChIKey]
FDZLCIITHLSEQK-UHFFFAOYSA-N | [SMILES]
C1(C#N)(C(OCC)=O)CC1 | [CAS DataBase Reference]
1558-81-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Ethyl 1-cyano-1-cyclopropanecarboxylate may be used as a monomer in the preparation of poly(ethyl trimethylene-1-cyano-1-carboxylate)s. | [General Description]
Ethyl 1-cyano-1-cyclopropanecarboxylate (ethyl 1-cyanocyclopropanecarboxylate) is an alkyl 1-cyanocyclopanecarboxylate. It can be prepared by reacting ethyl cyanoacetate, 1,2-dibromoethane, potassium carbonate and DMSO. | [Synthesis]
The general procedure for the synthesis of ethyl 1-cyanocyclopropanecarboxylate from 1,2-dibromoethane and ethyl cyanoacetate was as follows: a suspension of ethyl cyanoacetate (11.3 g, 0.1 mol), 1,2-dibromoethane, tetrabutylammonium bromide (Na 4 (n-Bu)4Br) and potassium carbonate (K 2 CO 3 ) in N,N-dimethylformamide (DMF, 100 mL) was heated to 80 °C and reacted overnight. Upon completion of the reaction, the mixture was poured into water (600 mL) and extracted with ethyl acetate (EtOAc, 3 x 50 mL). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na 2 SO 4 ) and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1) to afford ethyl 1-cyanocyclopropanecarboxylate (10 g, yield: 72%).1H NMR (CDCl3, 400 MHz): δ 4.21 (q, J = 7.2 Hz, 2H), 1.65-1.61 (m, 2H), 1.58-1.55 (m, 2H) , 1.28 (t, J = 7.2 Hz, 3H). | [References]
[1] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 474 - 480
[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 541 - 548
[3] Synthetic Communications, 1996, vol. 26, # 3, p. 525 - 530
[4] Tetrahedron Letters, 2005, vol. 46, # 4, p. 635 - 638
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 420 - 422 |
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