| Identification | Back Directory | [Name]
2-BROMOPROPIONIC ACID TERT-BUTYL ESTER | [CAS]
39149-80-9 | [Synonyms]
TERT-BUTYL 2-BROMOPROPIONATE
Bromopropionicacidbutylester
tert-butyl 2-broMopropanoate
2-bromopropanoic acid tert-butyl ester
2-BROMOPROPIONIC ACID TERT-BUTYL ESTER
2-BROMOPROPIONIC ACID TERT-BUTYL ESTER 97+% | [EINECS(EC#)]
675-664-3 | [Molecular Formula]
C7H13BrO2 | [MDL Number]
MFCD00043897 | [MOL File]
39149-80-9.mol | [Molecular Weight]
209.08 |
| Chemical Properties | Back Directory | [Boiling point ]
90 °C / 60mmHg | [density ]
1,26 g/cm3 | [refractive index ]
1.4380-1.4410 | [storage temp. ]
Refrigerator | [form ]
clear liquid | [color ]
Colorless to Light yellow to Light orange | [InChI]
InChI=1S/C7H13BrO2/c1-5(8)6(9)10-7(2,3)4/h5H,1-4H3 | [InChIKey]
CVAWKJKISIPBOD-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)C(Br)C |
| Hazard Information | Back Directory | [Uses]
tert-Butyl 2-Bromopropanoate is a reactant used in the synthesis 3-(1-Aryl-1H-indol-5-yl)propanoic Acids as cytosolic phospholipase A2α inhibitors. | [Synthesis Reference(s)]
Tetrahedron Letters, 13, p. 4067, 1972 DOI: 10.1016/S0040-4039(01)94239-X | [Synthesis]
Step 1 Synthesis of tert-butyl 2-bromopropionate. Isobutene (2.4 g, 42.8 mmol) was condensed into a pressurized reaction flask at -15 °C. Dioxane (6 mL) and 2-bromopropionic acid (3.5 mL, 38.9 mmol) were then added and the mixture was stirred for 5 minutes. After slow warming to -10°C, concentrated sulfuric acid (250 μL) was added dropwise. The reaction vial was sealed and the reaction mixture was stirred at room temperature overnight. After the reaction was completed, the reaction vial was opened and the reaction mixture was poured into dichloromethane (50 mL). The organic phase was washed sequentially with 20% potassium carbonate solution (50 mL) and water (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give tert-butyl 2-bromopropionate (2.17 g, 27% yield). The product was characterized by 1H NMR (CDCl3, δ): 4.31 (1H, q, J=7.1Hz), 1.81 (3H, d, J=7.1Hz), 1.52 (9H, s). | [References]
[1] Journal of Medicinal Chemistry, 1986, vol. 29, # 5, p. 784 - 796
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 915 - 936
[3] Patent: US6399600, 2002, B1
[4] Journal fuer Praktische Chemie (Leipzig), 1974, vol. 316, p. 729 - 740
[5] Bulletin de la Societe Chimique de France, 1974, p. 2985 - 2986 |
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