Tert-butyl 2,2,2-trichloroethanimidate
TBTA · FMOC-NH2 · Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine · tert-Butyl trichloroacetiMidate · tert-Butyl 2,2,2-trichloroethanimidate · tert-butyl 2,2,2-trichloroethanecarboximidate · T-BUTYL TRICHLOROACETIMIDATE · 9-(FLUORENYLMETHYLCARBONYL) AMIDE
Identifikatoren & physikalische Daten
| CAS No. | 98946-18-0 |
|---|---|
| Summenformel | C6H10Cl3NO |
| Durchschnittliche Molmasse | 218,5 g/mol |
| Monoisotopische Masse | 216,982797 g/mol |
| SMILES | CC(C)(C)OC(=N)C(Cl)(Cl)Cl |
| InChIKey | CQXDYHPBXDZWBA-UHFFFAOYSA-N |
| PubChem CID | 2734700 |
| EC No. | 629-631-5 |
| DTXSID | DTXSID40370451 |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 33,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 156 |
| Schmelzpunkt | 21 °C(lit.) |
| Siedepunkt | 65 °C11 mm Hg(lit.) |
| Dichte | 1.222 |
| Brechungsindex | n20/D 1.456(lit.) |
| Flammpunkt | 131 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in organic solvents, cyclo hexane. |
| Aggregatzustand | Liquid or Low Melting Crystalline Mass |
| pKa (Säurekonstante) | 2.49±0.70(Predicted) |
| Wichte | 1.222 |
| Farbe | Clear colorless to pale yellow |
| BRN | 1770049 |
| Stabilität | Hygroscopic |
| InChI | 1S/C6H10Cl3NO/c1-5(2,3)11-4(10)6(7,8)9/h10H,1-3H3 |
| InChIKey | CQXDYHPBXDZWBA-UHFFFAOYSA-N |
| SMILES | CC(C)(C)OC(=N)C(Cl)(Cl)Cl |
| CAS Datenbank | 98946-18-0(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226 (98%): Flammable liquid and vapor [Warning Flammable liquids]H302 (88%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (98%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Flam. Liq. 3 (98%)Acute Tox. 4 (88%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (98%) |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | No |
| UN-Transportnummer | UN 1993 3/PG 3 |
| Zollcode | 29252900 |
| R-Sätze (R) | 10-22-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant/Moisture Sensitive |
| Sicherheitshinweise (S) | 26-37/39-16-36/37-24/25 |
| Gefahrenklasse | 3.2Acute Tox. 4 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
tert-Butyl 2,2,2-trichloroacetimidate is used to produce di-tert-butyl peroxide at temperature of -5°C. It may be used in the synthesis of N-α-Fmoc-phospho(1-nitrophenylethyl-2-cyanoethyl)-L-serine, caged building block. It may be used in the conversion of alcohols and carboxylic acids to their respective ethers and esters.
Herstellung & Synthese
synthetische
Potassium t-Butoxide (1.68 g, 15 mmol) was dissolved in t-butanol (30 mL) and this solution was added over 15 min to a stirred solution of Trichloroacetonitrile (21.6 g, 15 mL, 15 mmol) in dry diethyl ether (30 mL) cooled to 0 °C under nitrogen. The yellow mixture was allowed to warm to 20 °C over 1 h, and then heated to reflux for 1 h. After the reaction mixture had been cooled to rt, volatiles were removed on the rotary evaporator and the residual oil was dissolved in pentane (30 mL). The solution was filtered and the pentane was removed on the rotary evaporator. The residue was then distilled to yield 23 g (70%), bp 65-69 °C/12 mmHg, which solidified on storage.