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| | 1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER Basic information |
| | 1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER Chemical Properties |
| Boiling point | 85-88 °C12 mm Hg(lit.) | | density | 1.279 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.471(lit.) | | Fp | 175 °F | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | color | Clear colorless | | Stability: | Light Sensitive | | InChI | 1S/C7H11BrO2/c1-2-10-6(9)7(8)4-3-5-7/h2-5H2,1H3 | | InChIKey | UTVNSHXHFRIXMM-UHFFFAOYSA-N | | SMILES | CCOC(=O)C1(Br)CCC1 | | CAS DataBase Reference | 35120-18-4 |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-27-36/37/39-45 | | RIDADR | UN 3265 8/PG 2 | | WGK Germany | 3 | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29162000 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1
Skin Corr. 1B |
| | 1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER Usage And Synthesis |
| Chemical Properties | Clear colorless liquid | | Uses | Ethyl 1-bromocyclobutanecarboxylate was used in the synthesis of 1aminocyclobutane carboxylic acid. | | Synthesis | To a solution of ethyl cyclobutanecarboxylate (10 g) in carbon tetrachloride (100 mL) was sequentially added N-bromosuccinimide (NBS, 20.83 g) and azobisisobutyronitrile (AIBN, 1.281 g). The reaction mixture was stirred at 80 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) and the mixture was extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with saturated sodium bicarbonate solution (50 mL), water (50 mL) and saturated saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100:1) to afford the target product ethyl 1-bromocyclobutanecarboxylate (10 g) as a yellow oil.1H NMR (400MHz, CDCl3) δ: 4.26 (q, J=14.4,7.2Hz, 2H), 2.95-2.88 (m, 2H), 2.67- 2.59 (m, 2H), 2.26-2.21 (m, 1H), 1.91-1.86 (m, 1H), 1.32 (t, J=7.2Hz, 3H). | | References | [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 11002 - 11005
[2] Chemical Communications, 2015, vol. 51, # 42, p. 8773 - 8776
[3] Organic Letters, 2016, vol. 18, # 9, p. 2040 - 2043
[4] Patent: WO2018/15411, 2018, A1. Location in patent: Paragraph 0165; 0166; 0167; 0168; 0169; 0170
[5] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 11, p. 988 - 993 |
| | 1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER Preparation Products And Raw materials |
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