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| | Mono-tert-butyl succinate Basic information |
| Product Name: | Mono-tert-butyl succinate | | Synonyms: | MONO-TERT-BUTYL SUCCINATE;mono-tert-Butyl succinate ,97%;MONO-TERT-BUTYL SUCCINATE 97％;Succiniccidono-tert-butylster;Butanedioic acid, 1-(1,1-diMethylethyl) ester;tert-Butyl hydrogen succinate;4-Tert-Butoxy-4-OxobutanoicAci;4-Tert-butoxy-4-oxobutanoic acid | | CAS: | 15026-17-2 | | MF: | C8H14O4 | | MW: | 174.19 | | EINECS: | | | Product Categories: | C8 to C9;Carbonyl Compounds;Esters | | Mol File: | 15026-17-2.mol |  |
| | Mono-tert-butyl succinate Chemical Properties |
| 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) | | pka | 4.46±0.17(Predicted) | | form | Solid | | color | Yellow-brown | | Water Solubility | Slightly soluble in water. | | InChI | 1S/C8H14O4/c1-8(2,3)12-7(11)5-4-6(9)10/h4-5H2,1-3H3,(H,9,10) | | InChIKey | PCOCFIOYWNCGBM-UHFFFAOYSA-N | | SMILES | CC(C)(C)OC(=O)CCC(O)=O | | CAS DataBase Reference | 15026-17-2 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2917198090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Mono-tert-butyl succinate Usage And Synthesis |
| 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 |
| | Mono-tert-butyl succinate Preparation Products And Raw materials |
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