| Identification | Back Directory | [Name]
Mono-tert-butyl succinate | [CAS]
15026-17-2 | [Synonyms]
MONO-TERT-BUTYL SUCCINATE
Succiniccidono-tert-butylster
tert-Butyl hydrogen succinate
4-Tert-Butoxy-4-OxobutanoicAci
mono-tert-Butyl succinate ,97%
MONO-TERT-BUTYL SUCCINATE 97％
4-Tert-butoxy-4-oxobutanoic acid
SUCCINIC ACID MONO-TERT-BUTYL ESTER
Butanedioic acid, 1-(1,1-diMethylethyl) ester | [Molecular Formula]
C8H14O4 | [MDL Number]
MFCD00273441 | [MOL File]
15026-17-2.mol | [Molecular Weight]
174.19 |
| Chemical Properties | Back Directory | [Melting point ]
51-54 °C(lit.)
| [Boiling point ]
92°C/1.5mmHg(lit.) | [density ]
1.097±0.06 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Sparingly) | [form ]
Solid | [pka]
4.46±0.17(Predicted) | [color ]
Yellow-brown | [Water Solubility ]
Slightly soluble in water. | [InChIKey]
PCOCFIOYWNCGBM-UHFFFAOYSA-N | [CAS DataBase Reference]
15026-17-2 |
| Hazard Information | Back Directory | [Uses]
Mono-tert-butyl Succinate is a reagent used for the synthesis of fluorinated β2- and β3-amino acids, an inhibitor of α-chymotrypsin. | [Synthesis Reference(s)]
Tetrahedron Letters, 32, p. 4239, 1991 DOI: 10.1016/S0040-4039(00)92137-3 | [General Description]
mono-tert-Butyl succinate can be prepared by refluxing a mixture of succinic anhydride and N-hydroxyl succinimide in the presence of dimethylaminopyridine and triethylamine in tert-butanol and toluene. | [Synthesis]
Tert-butanol (10 mL) was added to a solution of toluene (100 mL) containing succinic anhydride (6.04 g, 60.40 mmol), N-hydroxysuccinimide (2.53 g, 22.01 mmol) and 4-dimethylaminopyridine (DMAP, 0.88 g, 7.23 mmol). The reaction mixture was heated under reflux conditions for 48 hours. Upon completion of the reaction, it was cooled to room temperature and two layers (brown oil and a clarified colorless solution) were observed to form in the reaction vessel. The crude product solution was diluted with ethyl acetate (EtOAc, 50 mL) and washed sequentially with 10% aqueous citric acid (2 x 50 mL) and saturated saline. The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and the solvent was evaporated under reduced pressure. The crude product was recrystallized with a solvent mixture of ethyl ether/petroleum ether (1:3, 25 mL) to obtain mono-tert-butyl succinate in quantitative yield. | [References]
[1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2428 - 2441
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10460 - 10474
[3] Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6679 - 6684
[4] Organic Letters, 2006, vol. 8, # 4, p. 713 - 716
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1643 - 1647 |
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