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| | ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE Basic information |
| | ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE Chemical Properties |
| 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) |
| Risk Statements | 36/37/38 | | Safety Statements | 26-37 | | WGK Germany | 3 | | TSCA | No | | HazardClass | IRRITANT | | HS Code | 2926907090 | | Storage Class | 10 - Combustible liquids |
| | ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE Usage And Synthesis |
| 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 |
| | ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE Preparation Products And Raw materials |
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