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| | tert-Butyl cyanoacetate Basic information |
| Product Name: | tert-Butyl cyanoacetate | | Synonyms: | TERT-BUTYL CYANOACETATE;aceticacid,cyano-,1,1-dimethylethylester;Cyanoaceticacidbutylester;3-Oxo-3-tert-butoxypropanenitrile;Cyanoacetic acid 1,1-dimethylethyl ester;Tert-butyl cyanoacet;2-cyanoacetic acid tert-butyl ester;tert-butyl 2-cyanoethanoate | | CAS: | 1116-98-9 | | MF: | C7H11NO2 | | MW: | 141.17 | | EINECS: | 214-243-7 | | Product Categories: | C6 to C7;Carbonyl Compounds;Esters;1 | | Mol File: | 1116-98-9.mol |  |
| | tert-Butyl cyanoacetate Chemical Properties |
| Boiling point | 40-42 °C/0.1 mmHg (lit.) | | density | 0.988 g/mL at 20 °C (lit.) | | refractive index | n20/D 1.420 | | Fp | 91°C | | storage temp. | 2-8°C | | solubility | Difficult to mix. | | pka | 3.21±0.10(Predicted) | | form | Oil | | color | Clear Colorless | | BRN | 1755933 | | InChI | InChI=1S/C7H11NO2/c1-7(2,3)10-6(9)4-5-8/h4H2,1-3H3 | | InChIKey | BFNYNEMRWHFIMR-UHFFFAOYSA-N | | SMILES | C(OC(C)(C)C)(=O)CC#N | | CAS DataBase Reference | 1116-98-9(CAS DataBase Reference) | | EPA Substance Registry System | Acetic acid, cyano-, 1,1-dimethylethyl ester (1116-98-9) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 24/25 | | WGK Germany | 3 | | F | 10-21 | | TSCA | TSCA listed | | HS Code | 29269090 | | Storage Class | 10 - Combustible liquids |
| | tert-Butyl cyanoacetate Usage And Synthesis |
| Chemical Properties | Yellow liquid | | Uses | tert-Butyl cyanoacetate is used in the synthesis of vinylogous urea and tert-butyl phenylcyanoacrylates. It is also used as a new additive for the sugar nucleoside base coupling step en route to DAPD with improved β-selectivity. | | General Description | tert-Butyl cyanoacetate undergoes functionalization and decarboxylation to form 3-amino-4-alkyl isoquinolines. | | Synthesis | tert-butyl cyanoacetate synthesis: 2-Cyanoacetic acid (1.701 g, 20 mmol) was suspended in a cetonitrile (20 ml) and tert-butanol (2.391 ml, 25.00 mmol). To this, a solution of N,N′-Dicyclohexylcarbodiimide (4.54 g, 22.00 mmol) in DCM (22 ml) was added under stirring at RT. The reaction mixture was stirred for 30 minutes, then filtered through Celite, and the solvents were evaporated. Proton NMR analysis of the residue showed complete conversion to the product. The product, tert-butyl cyanoacetate was not purified, but was taken straight through to the next reaction.
1H NMR (400 MHz, CDCl 3 ) δ 3.37 (s, 2H), 1.50 (s, 9H). | | Purification Methods | The IR spectrum of a film should have bands at 1742 (ester CO) and 2273 (CN), but no band at ca 3500 broad (OH) cm-1 . If it does not have the last-named band, then fractionally distil; otherwise dissolve in Et2O, wash with saturated aqueous NaHCO3, dry over K2CO3, evaporate Et2O, and distil the residue under a vacuum (see tert-butyl ethyl malonate for precautions to avoid decomposition during distillation). [Beech & Piggott J Chem Soc 423 1955, Dahn & Hauth Helv Chim Acta 42 1214 1959, Beilstein 2 I 255.] | | References | [1] Patent: US2015/38466, 2015, A1. Location in patent: Paragraph 0500-0501
[2] Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 272, p. 58 - 64
[3] Organic Letters, 2001, vol. 3, # 23, p. 3733 - 3735
[4] Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 8975 - 8982
[5] Patent: TWI525093, 2016, B. Location in patent: Page/Page column 182; 183; 184 |
| | tert-Butyl cyanoacetate Preparation Products And Raw materials |
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