1-Chloro-N,N-2-trimethylpropenylamine
1-Chloro-N,N,2-trimethylprop-1-en-1-amine · 1-CHLORO-N,N,2-TRIMETHYL-1-PROPENYLAMINE · Ghosez′s reagent · TETRAMETHYL-ALPHA-CHLORENAMINE · 1-CHLORO-N,N,2-TRIMETHYLPROPENYLAMINE · 1-Chloro-N,N,2-trimethyl-1-propenylamin · (1-CHLORO-2-METHYLPROPENYL)DIMETHYLAMINE · 1-chloro-N,N,2-trimethyl-1-Propen-1-amine
Identifikatoren & physikalische Daten
| CAS No. | 26189-59-3 |
|---|---|
| Summenformel | C6H12ClN |
| Durchschnittliche Molmasse | 133,62 g/mol |
| Monoisotopische Masse | 133,06582706 g/mol |
| SMILES | CC(C)=C(Cl)N(C)C |
| InChIKey | GQIRIWDEZSKOCN-UHFFFAOYSA-N |
| PubChem CID | 640792 |
| EC No. | 629-420-8 |
| DTXSID | DTXSID30348806 |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 3,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 101 |
| Siedepunkt | 129-130 °C(lit.) |
| Dichte | 1.01 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.453(lit.) |
| Flammpunkt | 80 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Sparingly), Methanol (Slightly) |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 4.27±0.70(Predicted) |
| Farbe | Colorless to yellow |
| Stabilität | Hygroscopic, Moisture Sensitive, Unstable in Solution |
| InChI | 1S/C6H12ClN/c1-5(2)6(7)8(3)4/h1-4H3 |
| InChIKey | GQIRIWDEZSKOCN-UHFFFAOYSA-N |
| SMILES | CN(C)\C(Cl)=C(\C)C |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 72 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Flam. Liq. 3 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2734 8/PG 1 |
| Zollcode | 29211990 |
| R-Sätze (R) | 10-34 |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 16-26-36/37/39-45 |
| Gefahrenklasse | 8, 3Flam. Liq. 3Skin Corr. 1B |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
1-Chloro-N,N,2-trimethyl-1-propenylamine is an acid halogenation reagent developed by Ghosez, that enables the conversion of carboxylic acids into the corresponding chlorides under strictly neutral conditions. This method was successfully used in the total synthesis of caloporoside, roseophilin, (-)-enniatin B, (±)-epimeloscine and (±)-meloscine.
Herstellung & Synthese
synthetische
1-chloro-N,N,2-trimethylpropenylamine is conveniently prepared by the reaction of N,N,2- trimethylpropanamide with Phosgene followed by dehydrochlorination of the intermediate α-chloroiminium chloride (eq 1).[1,2] Recent unpublished results of our laboratory have shown that Phosphorus Oxychloride or dior triphosgene can also be used for the preparation of TMCE.