1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& CAS 78269-85-9
1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& Basic information
| Product Name: | 1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& |
| Synonyms: | 1-({[2-(trimethylsilyl)ethoxy]carbonyl}oxy)pyrrolidine-2,5-dione;N-[2-(trimethylsilyl)ethoxycarbonyloxy]succinimide(Teoc-Osu);1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)&;N-[2-(Trimethylsilyl)ethoxycarbonyloxy]succinimide;Teoc-OSu;(TriMethylsilyl)ethoxycarbonyloxy]succiniMide;2,5-Dioxopyrrolidin-1-yl (2-(trimethylsilyl)-ethyl) carbonate;1-[[[2-(Trimethylsilyl)ethoxy]carbonyl]oxy]-2,5-pyrrolidinedione |
| CAS: | 78269-85-9 |
| MF: | C10H17NO5Si |
| MW: | 259.33 |
| EINECS: | |
| Product Categories: | Building Blocks;Heterocyclic Building Blocks;Pyrrolidines |
| Mol File: | 78269-85-9.mol |
1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& Chemical Properties
| Melting point | 83-88 °C(lit.) |
| Boiling point | 308.6±44.0 °C(Predicted) |
| density | 1.17±0.1 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | soluble in Methanol |
| form | powder to crystal |
| color | White to Almost white |
| Hydrolytic Sensitivity | 7: reacts slowly with moisture/water |
| InChI | InChI=1S/C10H17NO5Si/c1-17(2,3)7-6-15-10(14)16-11-8(12)4-5-9(11)13/h4-7H2,1-3H3 |
| InChIKey | FLDNDAMSCINJDX-UHFFFAOYSA-N |
| SMILES | C(OCC[Si](C)(C)C)(=O)ON1C(=O)CCC1=O |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HS Code | 2931.90.9010 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | White to off-white powder |
| Uses | 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]pyrrolidin-2,5-dione (Teoc-OSu) may be used as an acylating reagent to produce Teoc-amino acid derivatives. |
| General Description | 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]pyrrolidin-2,5-dione (Teoc-OSu) is a silicon-based reagent that can be prepared from 2-trimethylsilylethyl carbonochloridite and N-hydroxysuccinimide. |
| Synthesis | 6066-82-6 20160-60-5 78269-85-9 2-(Trimethylsilyl)ethyl chloroformate (S13) was dissolved in acetonitrile (105 mL) at 0 °C. Subsequently, N-hydroxybutanediimide (5.22 g, 45.4 mmol, 1.30 eq.) and triethylamine (4.59 g, 45.4 mmol, 1.30 eq.; dissolved in 11.0 mL acetonitrile) were added to the solution. The reaction mixture was kept stirred at 0 °C for 16 hours. After completion of the reaction, the mixture was poured into water. The aqueous layer was extracted with ether (6 times). The organic layers were combined and washed sequentially with water (2 times), 1.0 M hydrochloric acid and then with water, followed by drying with magnesium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give 1-[2-(trimethylmethylsilyl)ethoxycarbonyloxy]pyrrolidine-2,5-dione (S14, 7.72 g, 29.8 mmol, 85% yield in two steps) as a colorless solid. |
| References | [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 564 - 570 [2] Synthesis, 1987, # 4, p. 346 - 349 [3] Patent: US6627660, 2003, B1 [4] Patent: US2004/116391, 2004, A1 |
1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& Preparation Products And Raw materials
| Raw materials | (2-[(CHLOROCARBONYL)OXY]ETHYL)TRIMETHYLSILANE-->2-(Trimethylsilyl)ethanol-->N,N'-Disuccinimidyl carbonate-->N-Hydroxysuccinimide-->Acetonitrile-->Triphosgene-->Triethylamine |
